Schistosoma, is a neglected tropical disease that afflicts over 230 million people worldwide. Currently, treatment is achieved with only one drug, praziquantel (PZQ). In this regard, the roots of Solidago microglossa (Asteraceae) and Aristolochia cymbifera (Aristolochiaceae) are popularly used as anthelmintic. Despite their medicinal use against helminthiasis, such as schistosomiasis, A. cymbifera, and S. microglossa have not been evaluated against S. mansoni. Then, in this work, the in vitro antischistosomal activity of the crude extracts of A. cymbifera (Ac) and S. microglossa (Sm) and their isolated compounds were investigated against S. mansoni adult worms. Sm (200 μg/mL) and Ac (100–200 μg/mL) were lethal to all male and female worms at the 24 h incubation. In addition, Sm (10–50 μg/mL) and Ac (10 μg/mL) caused significant reduction in the parasite's movements, showing no significant cytotoxicity to Vero cells at the same range of schistosomicidal concentrations. Confocal laser scanning microscopy revealed that Sm and Ac caused tegumental damages and reduced the numbers of tubercles of male schistosomes. Chromatographic fractionation of Sm leads to isolation of bauerenol, α-amirin, and spinasterol, while populifolic acid, cubebin, 2-oxopopulifolic acid methyl ester, and 2-oxopopulifolic acid were isolated from Ac. At concentrations of 25–100 μM, bauerenol, α-amirin, spinasterol, populifolic acid, and cubebin showed significant impact on motor activity of S. mansoni. 2-oxopopulifolic acid methyl ester and 2-oxopopulifolic acid caused 100% mortality and decreased the motor activity of adult schistosomes at 100 μM. This study has reported, for the first time, the in vitro antischistosomal effects of S. microglossa and A. cymbifera extracts, also showing promising compounds against adult schistosomes.Schistosomiasis, caused by helminth flatworms of the genus  Schistosoma, afflicts over 250 million people worldwide [Schistosomiasis, a chronic parasitic disease caused by helminth flatworms of the genus orldwide –3, beingorldwide , 4. Therorldwide . Therefoorldwide . As a reSolidago (Asteraceae) species are used in folk medicines of all over the world for many medicinal purposes, including as antiparasitic and antiseptic [Solidago microglossa De Candolle (Asteraceae), synonymy S. chilensis Meyen, is a medicinal plant known as “arnica-do-campo” and “erva-lanceta” that possess a very widely popular therapeutic applications in South America, including as anti-inflammatory [S. microglossa is included in the National List of Medicinal Plants of Interest to the Brazilian Unified Health System (RENISUS) [In this regard, several tiseptic , 9. Soliammatory , 11 and ammatory , 13. DueRENISUS) , 11, 13.S. microglossa are popularly used as anthelmintic for the complementary and alternative treatment of some parasitic diseases [S. microglossa roots are employed for the treatment of helminthiasis, this popular indication against helminths, such as Schistosoma, which arise from the traditional knowledge, has not been supported by any scientific evidence so far.Also, in Brazil, mainly in the South States, the roots decoctions of diseases –16. AlthAristolochia species known as “cipó-mil-homens,” such as A. triangularis and A. cymbifera, with suggested oral doses varying of 0.1 to 2 mL up to three times daily, have been used in the traditional medicine of South America as anthelmintic and for the treatment of malaria and general infectious [A. cymbifera Mart. & Zucc (Aristolochiaceae), synonymy A. esperanzae Kuntze, is a medicinal plant used in Brazilian folk medicine for the treatment of infectious diseases, malaria, wounds, fever, diarrhea, snakebite, and as anthelmintic [A. cymbifera extracts [A. cymbifera is included in the first edition of the Brazilian Official Pharmacopoeia [A. cymbifera are sold in several Brazilian markets, either alone or in combination with other plants, as herbal remedies for the treatment of helminthiasis, such as schistosomiasis and general infections [A. cymbifera have not been evaluated against Schistosoma.In addition, studies have shown that the roots decoctions of some fectious , 14–19. elmintic –19. Prevextracts –22. Due acopoeia . Nowadayfections , 19. HowS. microglossa and A. cymbifera and their isolated compounds possess effects against S. mansoni. Thus, in this work, we evaluated the in vitro antischistosomal effects of the crude extracts and isolated compounds from the roots of S. microglossa and A. cymbifera.Then, based on their traditional use as anthelmintic, we wondered whether the roots of S. microglossa (650 g) and A. cymbifera (1300 g) were collected at Faculty of Pharmacy's garden from the Federal University of Juiz de Fora. Exsiccates of the plant species were deposited in the Herbarium Leopoldo Krieger of the Federal University of Juiz de Fora, MG, Brazil, under the numbers #64488 (S. microglossa) and #50054 (A. cymbifera). After collected, roots were dried at 40°C, pulverized, and extracted, by maceration, using ethanol : water (8 : 2 v/v) as solvent. Next, the solvent was removed under reduced pressure to yield 15 g of the crude hydroalcoholic extract of the roots of S. microglossa (Sm) and 40 g of the hydroalcoholic extract from the roots of A. cymbifera (Ac).This study was developed in line with Brazilian Federal Law number 13.123/2015 on Access to Genetic Heritage, registered under number AE32DB3. Roots of 1 (0.23 g), 2 (0.20 g), and 3 (0.05 g).The crude extract Sm (10 g) was chromatographed over silica gel  under the vacuum liquid chromatography system , using hexane: EtOAc mixtures in increasing proportions as eluent, furnishing nine fractions. The resulting fraction IV  was submitted to classic column chromatography over silica gel, using hexane: EtOAc in increasing proportions as eluent, furnishing the compounds 4 . Also, fraction V was submitted to flash chromatography using DCM: EtOAc  as eluent, furnishing the compound 5 (0.07 g). Fraction VI was submitted to semipreparative reverse-phase HPLC purification (HPLC-DAD Waters 2998), binary HPLC pump, column ODS 250 × 10 mm, 5 μm, UV-DAD detector at 220 nm) using MeOH-H2O 75 : 25 v/v as mobile phase, affording 6 (0.02 g) and 7 (0.01 g).In addition, the crude extract Ac (35 g) was firstly chromatographed over silica gel  using hexane: EtOAc mixtures to furnish 8 fractions. Next, fraction II  was additionally chromatographed over VLC system with silica gel with hexane: EtOAc mixtures as eluent, giving 6 subfractions, affording 1H- and 13C-NMR analysis in comparison with the literature. 1H- and 13C- NMR spectra were recorded in CDCl3 solutions on a Bruker 500 Advance spectrometer (500 MHz for 1H NMR and 125 MHz for 13C NMR) with chemical shifts (δ) reported in parts per million (ppm) relative to trimethylsilane (TMS) as internal standard and coupling constants (J) in Hertz (Hz). The purity of all isolated compounds was predicted to be higher than 95% by 13C- and 1H-NMR data analysis.Chemical structures of all compounds were established by 1 (baurenol): the NMR spectroscopic data are according to the literature [1H NMR  δ (ppm): 3.24 ; 5.40 . 13C NMR  δ (ppm): 37.0 (C-1); 27.8 (C-2); 79.4 (C-3); 39.0 (C-4); 50.5 (C-5); 24.3 (C-6); 116.5 (C-7); 145.4 (C-8); 48.3 (C-9); 35.3 (C-10); 16.9 (C-11); 32.5 (C-12); 37.8 (C-13); 41.3 (C-14); 28.9 (C-15); 37.8 (C-16); 32.1 (C-17); 55.0 (C-18); 35.4 (C-19); 32.1 (C-20); 29.3 (C-21); 31.6 (C-22); 27.6 (C-23); 14.8 (C-24); 13.1 (C-25); 23.5 (C-26); 22.8 (C-27); 39.7 (C-28); 25.7 (C-29); 22.7 (C-30).Compound terature . 1H NMR 2 (α-amirin): the NMR spectroscopic data are according to the literature [1H NMR  δ (ppm): 4.5 ; 5.12 . 13C NMR  δ (ppm): 38.1 (C-1); 27.8 (C-2); 79.4 (C-3); 39.0 (C-4); 55.0 (C-5); 18.5 (C-6); 32.5 (C-7); 41.3 (C-8); 48.3 (C-9); 37.0 (C-10); 23.8 (C-11); 124.5 (C-12); 139.7 (C-13); 41.6 (C-14); 28.2 (C-15); 26.3 (C-16); 33.8 (C-17); 59.2 (C-18); 38.9 (C-19); 39.8 (C-20); 31.4 (C-21); 41.6 (C-22); 29.0 (C-23); 15.7 (C-24); 15.8 (C-25); 16.9 (C-26); 23.5 (C-27); 28.8 (C-28); 16.9 (C-29); 21.5 (C-30).Compound terature . 1H NMR 3 (spinasterol): the NMR spectroscopic data are according to the literature [1H NMR  δ (ppm): 3.60 ; 5.02 ; 5.15 . 13C NMR  δ (ppm): 37.2 (C-1); 31.6 (C-2); 71.2 (C-3); 38.1 (C-4); 40.4 (C-5); 29.7 (C-6); 117.6 (C-7); 139.7 (C-8); 49.5 (C-9); 34.3 (C-10); 21.5 (C-11); 39.6 (C1-2); 43.4 (C-13); 55.2 (C-14); 23.1 (C-15); 28.6 (C-16); 56.0 (C-17); 12.2 (C-18); 13.1 (C-19); 40.9 (C-20); 21.5 (C-21); 138.3 (C-22); 129.5 (C-23); 51.4 (C-24); 32.0 (C-25); 21.2 (C-26); 21.2 (C-27); 25.5 (C-28); 12.4 (C-29).Compound terature . 1H NMR 4 (populifolic acid): the NMR spectroscopic data are according to the literature [1H NMR  δ (ppm): 0.71 ; 0.79 ; 0.98 ; 1.00 ; 1.57 ; 5.18 . 13C NMR  δ (ppm): 18.2 (C-1); 26.8 (C-2); 120.3 (C-3); 144.4 (C-4); 38.1 (C-5); 36.8 (C-6); 27.5 (C-7); 36.2 (C-8); 38.5 (C-9); 46,4 (C-10); 35.4 (C-11); 29.4 (C-12); 30.8 (C-13); 41.4 (C-14); 179.2 ; 19.9 (C-16); 15.9 (C-17); 19.8 (C-18); 17.9 (C-19); 18.4 (C-20).Compound terature . 1H NMR 5 (cubebin): the NMR spectroscopic data are according to the literature [1H NMR  δ (ppm): 2.01 ; 2.43 ; 2.69 ; 4.11 ; 3.59 ; 5.24 ; 5.94 ; 6.63 . 13C NMR  δ (ppm): 133.2 (C-1); 108.9 (C-2); 147.6 (C-3); 145.7 (C-4); 108.2 (C-5); 121.4 (C-6); 38.4 (C-7); 53.0 (C-8); 103.3 (C-9); 134.1 (C-1′); 109.1 (C-2′); 147.5 (C-3′); 145.9 (C-4′); 108.0 (C-5′); 121.7 (C-6′); 39.2 (C-7′); 45.8 (C-8′); 72.1 (C-9′); 100.8 (2 x OCH2O).Compound terature . 1H NMR 6 (2-oxopopulifolic acid methyl ester): the NMR spectroscopic data are according to the literature [1H NMR  δ (ppm): 0.65 ; 0.96 ; 1.06 ; 1.80 ; 3.67 ; 5.65 . 13C NMR  δ (ppm): 35.4 (C-1); 188.9 ; 137.2 (C-3); 172.2 (C-4); 38.1 (C-5); 35.2 (C-6); 26.3 (C-7); 37.5 (C-8); 38.8 (C-9); 50.9 (C-10); 35.1 (C-11); 32.2 (C-12); 30.9 (C-13); 38.1 (C-14); 178.6 ; 19.9 (C-16); 15.2 (C-17); 18.4 (C-18); 19.6 (C-19); 17.3 (C-20); 26.3 (OCH3).Compound terature –31. 1H N7 (2-oxopopulifolic acid): the NMR spectroscopic data are according to the literature [1H NMR  δ (ppm): 0.80 ; 0.96 ; 1.10 ; 1.87 ; 5.70 ; 7.60 . 13C NMR  δ (ppm): 34.2 (C-1); 189.0 ; 137.3 (C-3); 172.2 (C-4); 41.5 (C-5); 37.3 (C-6); 26.2 (C-7); 37.2 (C-8); 37.9 (C-9); 50.0 (C-10); 34.2 (C-11); 35.2 (C-12); 31.0 (C-13); 41.5 (C-14); 172.2 ; 20.0 (C-16); 15.4 (C-17); 17.8 (C-18); 18.3 (C-19); 17.3 (C-20).Compound terature –31. 1H NSchistosoma mansoni (BH strain) was maintained by passage through Biomphalaria glabrata, as the intermediate host and Swiss female mice  as definitive host as previously described [escribed . Both miS. mansoni were removed from the hepatic portal system and cultured in RPMI 1640 culture medium  at 37°C in an atmosphere of 5% CO2 until usage. For the determination of activity against adult schistosomes, all samples were initially tested at the concentration of 100 μM (compounds) or 100 μg/mL (extracts), using DMSO stock solutions (10 mM) diluted in supplemented RPMI 1640 medium within 24 flat bottom well plates  with a final volume of 2 mL per well [μM) served as positive control. Parasites were kept for 48 h , and their viability was assessed via microscopic readout  [Seven weeks after infection, per well . SamplesGermany) . Next, sGermany) .μm) using a confocal laser scanning microscope . For confocal studies, after the occurrence of death, helminths were fixed in a formalin-acetic acid-alcohol solution and analyzed under a confocal microscope with autofluorescence excited at 488 nm and emitted light at 505 nm [Adult schistosomes were monitored by light microscopy using a Leica Microsystems EZ4E  , 36. AlsSexual fitness of adult worms exposed to nonlethal concentrations of samples and parasites were monitored in order to determine the schistosome egg output by counting the number of eggs for five days using an inverted microscope, as previously described . After 4All experiments were conducted in conformity with the Brazilian law for Guidelines for Care and Use of Laboratory Animals (Law 11790/2008). The protocol for experimental design was approved by the Comissão de Ética no Uso de Animais (CEUA), Brazil . Animal studies are reported in compliance with the ARRIVE guidelines.50) were obtained using GraFit Version 5 software.Mammalian Vero cells (African green monkey kidney fibroblast) used in this study were obtained from the American Type Culture Collection  and provided by Instituto Butantan . Cytotoxicity of the samples was determined using the MTT assay . The valP < 0.05.The statistical tests were performed with using Graph Pad Prism software 5.0 . Significant differences were determined by one-way analysis of variance (ANOVA) and applying Tukey's test for multiple comparisons with a level of significance set at S. mansoni [Schistosomiasis is a neglected disease with a huge impact in public health. Also, there is only one available drug to treat schistosomiasis, and due to the urgent need to identify new drugs, several natural compounds have been recently investigated against  mansoni , 38. In  mansoni , 40.S. microglossa and A. cymbifera extracts and their isolated compounds against S. mansoni, which have not been reported in the literature.In this context, we have highlighted the in vitro antischistosomal activity of S. mansoni. Effects on mortality rate and motor activity of parasites after incubation with Sm and Ac, at concentrations of 10–200 μg/mL, are shown in μg/mL) and Ac (100–200 μg/mL) were lethal to all male and female worms at the 24 h incubation, while Sm (100 μg/mL) and Ac (25–50 μg/mL) caused death in half of adult worms and significant reduction in motor activity together with tegumental alterations. In addition, concentrations of 10–50 μg/mL of Sm and 10 μg/mL of Ac were not lethal to schistosomes but caused significant reduction in the parasite's movements  and Ac (100–200 μg/mL) (μg/mL) and Ac (200 μg/mL) showed apparent rupture and/or disintegration of tubercles, which appeared eroded and deformed along the surface of worms, while nontreated adult worms showed intact surface   also cau0 μg/mL) . Additio surface .Schistosoma' tegument of is well-recognized as an important drug target and model of study in schistosomiasis [Schistosoma not only because it is one of the major route for nutrient absorption, but also because it is important for the protection of schistosomes, since tegumental changes might result in exposure of parasite antigens to the host immune system [somiasis . In thise system , 42.μg/mL of Sm (P < 0.001), while PZQ (5 μM) and Ac (50 μg/mL) caused 71.1% (P < 0.001) and 64.4% (P < 0.001) of reduction.Furthermore, a quantitative analysis of the number of intact tubercles on male parasites was performed . ResultsmL of Sm  a reductS. mansoni was monitored for 120 hours  and after 120 hours with Ac (10 μg/mL) (μg/mL) and Ac (10 μg/mL), egg laying was decreased significantly in 65.9% and 27.5% in comparison to the negative control group. Results showed a suppression of egg laying in all sublethal concentrations of Sm and Ac. These are important observed antischistosomal effects, since the pathology of human schistosomiasis is directly associated to the large number of eggs, which become trapped in the hosts tissues, resulting in immunopathological lesions that are characterized by inflammation and fibrosis in the target organs [Clerodendrum umbellatum (Verbenaceae) [Zingiber officinale (Zingiberaceae) [In addition, the schistosomicidal activity can also be assessed by the ability of samples in suppressing female oviposition . Regardi20 hours . The egg0 μg/mL) . Followit organs . Other penaceae)  and fromeraceae) .13C- and 1H- NMR data analysis in comparison to those in the literature as follows: baurenol (1) [α-amirin (2) [3) [4) [5) [6) [7) [13C- and 1H- NMR data analysis.Additionally, Sm was submitted to chromatographic fractionation, yielding three isolated compounds , which wenol (1) , α-amiriirin (2) , and spi (2) [3) . Similar [3) [4) , cubebin [4) [5) , 2-oxopo [5) [6) –31, and  [6) [7) –31 were μM) were also evaluated against S. mansoni adult worms (1), α-amirin (2), and spinasterol (3) were able to decrease the motor activity of adult schistosomes in a dose-dependent manner (μM. Although bauerenol (1), α-amirin (2), and spinasterol (3) were not lethal to schistosomes, they showed significant impact on worm motor activity of S. mansoni, like the crude Sm extract.All isolated compounds  and cubebin (5) were not lethal at concentrations of 25–100 μM but caused significant reduction in motor activity and movements of parasites (4) and cubebin (5) have been previously isolated from A. cymbifera [4) is a diterpene widely found in Aristolochia species [5) is a lignan previously evaluated against S. mansoni. Recently, Parreira et al., showed that cubebin (5) (at 100 μM) can separate adult worm pairs and reduce egg laying, without causing death in adult schistosomes [μM) was lethal to 100% of the worms after 24 h of incubation, while all worms incubated in RPMI-1640 stayed alive until the end of the experiment.Furthermore, along with the isolated compounds from Ac, populifolic acid  and 2-oxopopulifolic acid (7) showed the best in vitro antischistosomal activity, causing death and decrease of motor activity in all adult schistosomes at 100 μM after 24 h of incubation (6) and 2-oxopopulifolic acid (7) on the mortality rate of schistosomes (6) and 2-oxopopulifolic acid (7) have been previously isolated from Aristolochia species [7) isolated from A. cymbifera showed antimicrobial activity against Staphylococcus sp and Pseudomonas aeruginosa [On the other hand, 2-oxopopulifolic acid methyl ester  and 7-ceto-sempervirol, obtained from Lycium chinense [S. mansoni, such as the diterpene phytol [Copaiba species [Diterpenes are a class of plant-derived compounds that display a broad spectrum of biological activities, including antiparasitic effects against parasites of neglected tropical diseases . Previou mansoni , such as mansoni , isolatechinense . Also, ae phytol  and othe species .6) and 2-oxopopulifolic acid (7) suggest that these diterpenes may be important candidates for further antischistosomal investigations.The schistosomicidal results of methyl-2-oxopopulifoloate (S. microglossa and A. cymbifera extracts, with no cytotoxicity on mammalian cells. Also, we have isolated and identified compounds from these active extracts that demonstrate in vitro properties against adult schistosomes. Finally, our findings identified some diterpenes as promising lead antischistosomal compounds to further antiparasitic investigations.In this study, we have reported, for the first time, the in vitro antischistosomal effects of


S)-2-Me-CBS-catalysed reduction of alnustone with BH3SMe2 gave (R)(-)-1,7-diphenylhepta-4,6-dien-3-ol, a natural product. Reduction of alnustone with Na int-BuOH at –15 °C under N3 atm gave (E)-1,7-diphenylhept-5- en-3-one as a Birch-type reduction product. t-BuOK catalysed condensation of benzalacetone with propionyl chloride gave -5-hydroxy-1,7-diphenylhepta-4,6-dien-3-one, a natural product. -5-Hydroxy-4-phenethyl-1,7-diphenylhepta-1,4,6-trien-3-one, a curcuminoid, was synthesized starting from pentan-2,4-dione in 3 steps. The synthesized chemical compounds were applied against 2 gram-positive bacteria (Bacillus cereusandArthrobacter agilis), 4 gram-negative bacteria , and 1 yeast  by the disc diffusion method. All of the synthesized compound exhibited different degrees of antimicrobial activity at concentrations between 20–100 μg/disc against the test organisms.Four linear nonphenolic diarylheptanoids were synthesized and their antibacterial activities were studied. ( Diarylheptanoids are classified into 4 categories:i)phenolic or nonphenolic linear diarylheptanoids,ii)macrocyclic diarylheptanoids,iii)macrocyclic diaryl ether heptanoids, andiv)C7 chain-cyclized diarylheptanoids [1]. Nonphenolic diarylheptanoids constitute a special group of linear diarylheptanoids. Alnustone (1) is one of the first examples of nonphenolic diarylheptanoids . The first isolation of alnustone was performed fromAlnus pendulaby Suga et al. . Several studies showed that alnustone (1) is a bioactive molecule in a broad spectrum. On this basis, it has been reported to have antihepatotoxic [4], anti-inflammatory [5], antibacterial [6], antiemetic [7], and estrogenic activity [8].Diarylheptanoids, a special class of natural products, are compounds with the structure of Ar-CE,6E)-1,7-Diphenylhepta-4,6-dien-3-ol (-) (2), a natural diarylheptanoid, was first isolated fromCurcuma xanthorrhizaby Claeson et al. [5] and was reported to exhibit significant antiinflammatory activity. Jurgens et al. [9] isolated compound2fromCurcuma comosa. The following isolation of (R)-2was performed by Suksamrarn et al. [8] and was reported to exhibit a good level of phytoestrogenic activity. In further studies, Tantikanlayaporn et al.  isolated (R)-2fromCurcuma comosaand reported its very strong phytoestrogenic activity.(4E)-1,7-diphenyl-5-hepten-3-one (3) and compound 5 as new natural diarylheptanoids with strong antibacterial activity againstHelicobacter pylori.Zhang et al. [12] reported  -5-hydroxy-1,7-diphenyl-4,6-heptadien-3-one, the  isomer of 4, to have strong neuraminidase inhibitory activity.Compounds1) itself was synthesized from several starting materials using different synthetic methods [18–21]. In our previous studies we described an efficient method for the preparation of alnustone (1) itself [22] and alnustone-like compounds [23], and their antitumor activities against estrogen receptor alpha-positive human breast cancer.Alnustone (4was first synthesized by thermolysis of ethyl 3-oxo-5-phenyl-2-(cinnamoyl)pentanoate by Borsche and Lewinsohn [24]. Kato et al. [21] synthesized compounds2and4starting from 3-phenylpropanoic acid in many steps. A semisynthetic procedure for the preparation of (R/S)-2was described by Yang et al. [25] via NaBH4 reduction of alnustone (1).Compound2) and total synthesis of compound3are not known in the literature. In this study we report the first enantioselective synthesis of compound R-(2), its enantiomerS-(2), and^3via chemoselective reduction of alnustone (1). Moreover, we report an efficient one-pot synthesis of compound4and an attempted synthesis of compound5.To the best of our knowledge, the enantioselective synthesis of R-(R)-2, (S)-2, and3were based on reduction of alnustone (1). As mentioned above, efficient synthesis of alnustone (1) was previously reported by our research group . If one considers the relationship between alnustone (1) and (R)-2or (S)-2, it can be readily seen that (R)-2and (S)-2could be obtained from enantioselective reduction of the carbonyl group of alnustone (1). Chiral oxazaborolidines have been used as reagents or catalysts (with borane sources) for enantioselective reduction of prochiral ketones [26]. In this manner, Corey et al. [27] efficiently used (S)-2-methyl-CBS-oxazaborolidine as a catalyst with BH3 in the enantioselective reduction of aryl ketones to give the corresponding chiral alcohols with predominant R configuration (ee ~84-96.7%). We proposed that alnustone (1) itself may be successively reduced to give the corresponding alcohol (R)-2by following this methodology. Indeed, while (S)-2-Me-CBS-catalysed reduction of alnustone (1) gave alcohol (R)-2(ee 90%), (R)-2-Me-CBS-catalysed reduction gave alcohol (S)-2(ee 90%) in good yield (80%) where the ee values were determined by chiral HPLC. The absolute configuration of alcohol (R)-2was determined by agreement of its specific rotation with data given in the literature for natural (R)-2[8]. The opposite specific rotation obtained for alcohol (S)-2also confirmed its structure. The NaBH4 reduction [25] of alnustone (1) also gave racemic-2 in 80% yield .In our synthetic strategy, syntheses of compounds (R)-2or (S)-2, the 1H-NMR spectrum of the C7 chain showed 2 AB systems belonging to the olefinic HC(6)-HC(7) at δ 6.79 and δ 6.57 and to HC (4)- HC (5) at δ 5.86 and δ 6.40, a quartet belonging to HC (3) at δ 4.24, and multiplets belonging to H2C(1) at δ 2.81-2.68 and H2C(2) at δ 2.05- 1.80. The absence of a carbonyl peak and the 3 aliphatic carbons at 72.2 (C(3)), 38.9 (C(1)), and 31.9 (C(2)) confirmed the reduction of the carbonyl group. Both 1H-NMR and 13C-NMR spectra of (S)-2and (R)-2were in agreement with the data given for (R)-2in the literature . Thus, we easily synthesized enantioselectively the natural compound (R)-2and its enantiomer (S)-2.For the structure of (R)-2and (S)-2is in good agreement with the results reported by Corey et al. [27]. As seen in Figure 3, both the ethyl phenyl ketone and alnustone (1) are reduced by hydride transformation fromsifaces.Mechanistically, the enantioselective formation of  could be performed by a Birch reaction, which reduces 1,3-butadienes to 2-butenes. However, classical Birch reduction of alnustone (1) with metallic lithium in liquid N3 yielded a mixture with many undesirable reduction products. Therefore, instead of the classical Birch reduction conditions, the modification by Menzek et al.  was applied to obtain 3. This modification successfully allowed reduction to the conjugated 1,3-diene moiety of aromatic compounds using metallic lithium or sodium as the reducing agent in Et2O andt-BuOH under N3 (gas). Thus, reduction of alnustone (1) with 2.5 molar eq. Na as a reducing agent afforded compound3in a yield of 85% via Menzek’s method .We proposed that synthesis of compound1H-NMR spectrum of compound3was in exact agreement with its structure, in which olefinic hydrogens HC (5) at δ 5.67 and HC (6) at δ 5.74 arose as an AB system splitting into triplets . In this context, H2C(4) at δ 3.17 and H2C(7) at δ 3.43 also resonated as doublets. The spectral values belonging to H2C(4) and H2C(7) of compound3are in good agreement with allylbenzene and 4-penten-2-one, 2 similar structures. In the structures, the CH2 of 4-penten-2-one resonates at δ 3.19 ppm with J = 6.9 Hz [30], and the CH2 of allylbenzene resonates at δ 3.33 ppm with J = 6.7 Hz [31] . In double-resonance experiments, irradiation of both olefinic protons together, HC(5) and HC(6), converted doublets of H2C(4) and H2C(7) to singlets, which supports the CH2-CH=CH-CH2 structure. H2C(1) at δ 2.96 and H2C(2) at δ 2.81 also resonated as triplets. The HR-ESI-MS spectrum of compound3was also in good agreement with the structure of compound3(C19H20NaO: 287.1418). HMBC correlations of compound3are given in Figure 6.The 1H-NMR data of the heptenone part of compound3were in full disagreement with the reported data of Zhang et al. [12]. H/C assignments of the heptenone skeleton for synthetic compound3compared with data of the isolated 3 are given in Table 1. For example, they reported 1H-NMR data for H2C(4) at δ 2.74  and H2C(7) at δ 2.77 , which are also in disagreement with 4-penten-2-one and allylbenzene.However, the 3isolated by Zhang et al. [12], the presence of 2 phenyl rings, 1 carbonyl, 4 CH2, 1 CH=CH, and especially the HRMS results are in agreement with C19H20O which implies a structural isomer of compound3.Nonetheless, for compound3starting from alnustone (1) in a 1-step reaction, which is the first reported synthetic method for compound3.Thus, we synthesized compound4, we modelled a reaction described by Krishnamurty and Ghosh [32] for synthesis of dihydrocurcumin, in which they synthesized dihydrocurcumin via C-acylation of O-protected vanillylidene acetone with O-protected dihydroferuloyl chloride. We applied this methodology with a few modifications by treatment of benzalacetone (6) with KOBut at 0 °C and reacting with 3-phenylpropanoyl chloride to give compound4in a yield of 60% .For the simple synthesis of compound1H-NMR spectrum of compound4the C7 chain has an AB system belonging to HC(7) at δ 7.60 and HC(6) at δ 6.46, a singlet belonging to HC(4) at δ 5.64, and an A2 B2 system belonging to H2C(2) at δ 2.74 and H2C(1) at δ 3.00. The 1H-NMR and 13C-NMR spectra are in agreement with the data given for natural product 4 [13].In the 4. Therefore, we proposed that we could readily obtain 5 by alkylating 4 with 2- phenylethylbromide. However, alkylation of 4 to give 5 with bases such as LDA, NaH, and KOBut was not successful. In another attempted synthesis, we proposed that an alkylation of 6 with PhCH2CH2 Br and then acylation with 3-phenylpropanoyl chloride could give compound 5. However, the first step of this attempted synthesis afforded styrene, an elimination product, instead of the expected (E)-1,6-diphenylhex-1-en-3-one.If we consider the similarity between compounds 4 and 5, we readily see that 5 is the alkylated derivative of compound2O3-mediated condensation of 2,4-pentanedione with benzaldehydes in the presence of morpholine and AcOH. Applying this methodology to 9 with benzaldehyde gave curcuminoid 10.Therefore, we decided to apply a different strategy, where 2,4-pentanedione was first condensed with 2- phenylacetaldehyde in the presence of AcOH and pyrrolidine to give 8 as a sole compound . Catalytic hydrogenation of 8 gave 9 as a keto-enol tautomer. Nichols et al. [33] developed a practical methodology for solvent-free microwave-assisted synthesis of curcumin analogues based on B2 formed in situ in the reaction medium. Indeed, an independent reaction performed with Zn(OAc)2 supported this hypothesis with the formation of 11 from 10 in good yield (70%) . However, attempted selective reduction of compound 10 with Na or Mg to give 5, failed.Curcuminoid 10 and natural product 5 differ from each other with a hydrogenated double bond. Therefore, we applied selective reduction of the double bonds of compound 10. Changtam et al. [34] reported an easy procedure for preparing dihydrocurcumin by reduction of curcumin with Zn in AcOH. However, applying this methodology to curcuminoid 10 gave cyclic compound 11. We proposed that this cyclization might occur with Zn(OAc)R)-2, (S)-2, (R/S) -2, 3, 4, 10, and 11 were applied against 2 gram-positive bacteria (Bacillus cereusandArthrobacter agilis), 4 gram-negative bacteria , and 1 yeast  by disc diffusion method. The antimicrobial activity of the chemicals was variable, as seen in Table 2. All the synthesized chemicals showed different degrees of antimicrobial activity at concentrations of 30–90 μg/disc against the test organisms.The synthesized chemical compounds 1, . Inhibition zone was greater than 7 mm. These evaluations were carried out by diffusion disc tests.3was highly antibacterial againstK. oxytoca,A. agilis,B. cereus, andH. pylori. Additionally, 3 and 1 were observed to have stronger inhibitory effects against C. albicans. Among the compounds, 4 was determined as the least effective against the microorganisms. Ofloxacin and nystatin are well known as antibacterial and antifungal substances, respectively. The average inhibition zones of ofloxacin and nystatin were found to be 22 and 20 mm, respectively.CompoundR)-2and (S)-2, 3, and 4. An attempted synthesis of compound 5 gave a cyclocurcumin derivative (11).In conclusion, we developed an easy synthesis of diarylheptanoids (1) and dihydroalnustone (3) structures can be developed for new antibiotic drugs.The results of this study indicate that the synthesized chemicals showed dose-dependent inhibition against the tested microorganisms. This result may suggest that alnustone (1H- and 13C-NMR spectra were recorded with 400 (100) MHz Bruker and Varian instruments. Interchangeable hydrogens or carbons were shown with the same letters. Elemental analyses were performed with a LECO CHNS-932. HRMS spectra were recorded with an Agilent 6530 LC-MS QTOF. Enantiomeric excesses were determined by HPLC analysis using a chiral column eluting n-hexane–i-PrOH (90:10), and detection was performed at 210–254 nm. Optical rotations were measured on a Bellingham Stanley ADP220 589-nm spectropolarimeter. All percent yields were calculated from isolated compounds.THF was used by distillation over Na. Compound1was synthesized as described in our previous studies .2 atmosphere, 2 M BH3SMe2 in THF  was dissolved in THF (2 mL), cooled to 0 °C, and 1 M (S)-2-Me-CBS in toluene  was added. After the reaction mixture was stirred at the same temperature for 1 h, alnustone (1)  was added to the reaction mixture. The resulting mixture was stirred for 4 h at 0 °C and MeOH (3 mL) was added, stirred for 15 min, and warmed to room temperature. The solvent was evaporated in vacuo, and a solution of saturated NH4Cl (2 mL) was added. The organic solution was extracted with AcOEt (3×25 mL) and dried (Na2SO4). The solvent was removed and the residue was purified by silica gel column chromatography with AcOEt/hexane (20:80) to give compound (R)-2as a light-yellow oil . Enantiomeric excess: 90%. Rf (AcOEt/hexanes 2:8): 0.4. [α]27D = –53.3°. Lit [8]: [α]27D = –64.2°. 1H-NMR  : δ 7.41–7.19 , 6.79 , J6,7 = 15.7, J5,6 = 10.6 Hz), 6.57 , J6,7 = 15.7 Hz), 6.40 , J4,5 = 15.2, J5,6 = 10.6 Hz), 5.86 , J4,5 = 15.2, J3,4 = 7.0 Hz), 4.24 , J = 6.4 Hz), 2.81–2.68 ), 2.05–1.80 ) ppm; 13C-NMR  : δ 142.0 (C(1”)), 137.3 (C(1’)), 136.5 (C(4)), 133.0 (C(7)), 131.2 (C(5)), 128.8 (C(3’/5’)), 128.7 (C(2”/6”)), 128.6 (C(2’/6’)), 128.4 (C(4’)), 127.8 (C(4”)), 126.6 (C(3”/5”)), 126.1 (C(6)), 72.2 (C(3)), 38.9 (C(1)), 31.9 (C(2)) ppm; Anal. Calcd. for C19H20 O.1.3 H2O (MW 264.37): C, 79.3; H, 7.92%. Found: C, 78.94; H, 7.43%.Under N1H-NMR and 13C-NMR data are in agreement with data given in the literature .The S)-2was applied using (R)-2-Me-CBS to give compound (S)-2. Rf (AcOEt/hexanes 2:8): 0.4. Enantiomeric excess: 90%. [α]27D = +53.3°. ee: 0.90. Anal. Calcd. for C19H20 O.1.05 H2O (MW 264.37): C, 80.56; H, 7.86%. Found: C, 80.35; H, 7.63%.The procedure given above for synthesis of (1)  was dissolved in EtOH and NaBH4  was added, and the mixture was stirred for 4 h, monitored by TLC. The reaction mixture was cooled down to 0 °C and saturated aq. NH4Cl solution (2 mL) was added. The resulting aqueous solution was extracted with AcOEt (3×75 mL), and the organic phase was dried (Na2SO4). The solvent was removed and the residue was purified by silica gel column chromatography eluting with AcOEt/hexane (20:80) to give (R/S)-2 . Rf (AcOEt/hexanes 2:8): 0.5.Alnustone (1)  dissolved in dry Et2O (20 mL) was put into a 50-mL double-necked flask. A plastic balloon was connected to 1 neck of the flask and the other neck was fastened to a supply of N3 (gas). The solution was deoxygenated by the passing of 15 L of N3 (gas) and kept under N3 atmosphere by the filled balloon. The mixture was cooled to –15 °C, and then metallic Na  was added. At the same temperature, the reaction mixture was stirred for approximately 4 min, and then t-BuOH  was added and the reaction mixture was stirred for 16 min. At this stage, the colour of the reaction mixture changed to dark green as monitored by TLC and the completion of the reaction was observed. EtOH (15 mL) was added to quench the reaction mixture and then all solvents were removed under reduced pressure. The residue was dissolved in H2O (5 mL) and extracted with AcOEt (4 ×15 mL). The combined organic phase was dried on Na2SO4 and filtered. Evaporation of the solvent gave a crude product, which was then chromatographed on a silica gel column eluting with 95:5 AcOEt/hexane solvent mixture to give light yellow oily compound3. Rf (AcOEt/hexanes 1:9): 0.64. 1H-NMR  : δ 7.37–7.23 , 5.74 , J5,6 = 15.4 Hz, J6,7 = 6.2 Hz), 5.67 , J5,6 = 15.4 Hz, J4,5 = 6.3 Hz), 3.43 , J6,7 = 6.2 Hz), 3.17 , J4,5 = 6.3 Hz), 2.96 , J = 7.5 Hz), 2.81 , J = 7.5 Hz) ppm; 13C-NMR  : δ 208.4 (C(3)), 141.3 (C(1’)), 140.4 (C(1”)), 134.0 (C(6)), 128.80 (C(3’/5’)), 128.78 (C(3”/5”)), 128.6 (C(2’/6’)), 128.4 (C(2”/6”)), 126.4 (C(4’/4”)), 123.6 (C(5)), 47.1 (C(4)), 44.0 (C(2)), 39.3 (C(7)), 30.0 (C(1)) ppm; Anal. Calcd. for C19H20 O (MW 264.37): C, 86.32; H, 7.63%. Found: C, 86.96; H, 7.80%. HR-ESI-MS: 287.1418 [M+Na]+; calc. 287.1406.Alnustone  in anhydrous THF (15 mL) was cooled to 0 °C and (E)-4-phenylbut-3-en-2-one (6)  in anhydrous THF (20 mL) was added to the solution. The mixture was stirred for 30 min, and then 3-phenylpropanoyl chloride  was added. The mixture was stirred at room temperature for 12 h. An aq. sat. NH4Cl solution (3 mL) was added to the mixture at 0 °C. THF was evaporated, and the organic phase was extracted with AcOEt (2 ×50 mL) and dried over Na2SO4 . Evaporation of the solvent and silica gel column chromatography of the residue with hexane/AcOEt 95:5 gave 4 as light-yellow crystals . Rf (AcOEt/hexanes 1:9): 0.80. Mp 67–68 °C (Lit13 : 74–75 °C from hexane). 4: 1H-NMR  : δ 15.3 , 7.60 , J = 15.7 Hz), 7.42–7.20 , 6.46 , J = 15.7 Hz), 5.64 ), 3.00 , J = 7.8 Hz), 2.74 , J = 7.8 Hz) ppm; 13C-NMR  : δ 199.9 (C(3)), 176.7 (C(5)), 140.8 (C(1”)), 139.8 (C(7)), 135.1 (C(1’)), 129.9 (C(4’)), 128.9 (C(3’/5’a)) , 128.5 (C(2’/6’a)) , 128.3 (C(3”/5”a)) , 127.9 (C(2”/6”a)) , 126.2 (C(4”)), 122.7 (C(6)), 100.8 (C(4)), 41.9 (C(2)), 31.2 (C(1)) ppm. The 1H-NMR and 13C-NMR data are in agreement with the data given for isolated natural product 4 [13]. Anal. Calcd. for C19 H18 O2 (MW 278.35): C, 81.99; H, 6.52%. Found: C, 82.13; H: 6.53%.Under N2O (50 mL) and H2O (25 mL). The organic layer was separated and washed with H2O (25 mL), 1 M HCl (2 ×25 mL), and a saturated solution of NaHCO3 (10 mL). The organic layer was dried over Na2SO4 . Evaporation of the solvent and column chromatography of the residue with hexane/AcOEt 9:5 gave 8 as a dark yellow oil . Rf (AcOEt/hexanes 1:9): 0.60. 1H-NMR  : δ 16.74 , 7.44–7.34 , 6.75 , 6.42 , 2.22  ppm; 13C-NMR  : δ 191.4 (C(2/4)), 137.4 ), 134.5 styryl (C(1)), 128.9 ), 128.0 ), 126.4 ), 123.1 styryl (C(2)), 111.6 (C(3)), 24.5 (C(1/5)) ppm. The 1H-NMR and 13C-NMR data are in agreement with data given in the literature [35].To pentan-2,4-dione (7)  in benzene (50 mL) was added 2-phenylacetaldehyde , a catalytic amount of anhydrous AcOH (0.35 mL), and pyrrolidine (0.56 mL). Using a Dean-Stark apparatus the reaction mixture was refluxed for 18 h with monitoring by TLC. After cooling to ambient temperature, the mixture was diluted with EtE)-styryl)pent-3-en-2-one (8)  in AcOEt (20 mL) was added to the 100-mL double-necked flask. A balloon filled with H2 gas (3 L) was fitted to the flask. The mixture was deoxygenated by flushing with H2 and then hydrogenated for 3 h at room temperature. When TLC analyses indicated the disappearance of the starting material, the catalyst was removed by filtration. Removal of the solvent under reduced pressure gave 9 as a keto-enol tautomer and light-yellow oil ((9a):(9b) = 2:1) . 9a: 1H-NMR  : δ 7.31–7.15 , 3.63 , J = 7.3 Hz), 2.70 , 2.22–2.12 (CHCH2CH2 Ph), 2.14  ppm; 13C-NMR  : δ 204.3 (C(2/4)), 141.2 (C(1” of Ph)), 128.8 (C(3”/5” of Ph)), 128.8 (C(2”/6” of Ph)), 126.6 (C(4” of Ph)), 68.1 (C(3)); 33.7 (PhCH2CH2), 29.9 (PhCH2CH2), 29.4 (C(1/5)) ppm.9b: 1H-NMR  : δ 16.83 , 7.31-7.15 , 2.59–2.52  , 2.03  ppm; 13C-NMR  : δ 191.6 (C(2/4)), 140.8 (C(1” of Ph)), 128.8 (C(3”/5” of Ph)), 128.7 (C(2”/6” of Ph)), 126.5 (C(4” of Ph)), 109.6 (C(3)), 37.0 (PhCH2CH2), 29.9 (PhCH2CH2) , 22.9 (C(1/5)), 2.81 , J = 7.5 Hz), 5.74 , J5,6 = 15.4 Hz, J6,7 = 6.2 Hz).Pd/C (10%) (69 mg) was added to EtOAc (50 mL) cooled to 0 °C and then (Z)-4-hydroxy-3- was mixed with boric anhydride  in a 250-mL Erlenmeyer flask. Benzaldehyde , morpholine , and acetic acid  were then added to the mixture. The reaction was irradiated in a kitchen-type microwave (2450 MHz) for 1 min. The flask was cooled and then MeOH (30 mL) was added. This mixture was then sonicated in a sonicator for 10 min. The suspended mixture was taken onto filter paper and washed with MeOH cooled to 0 °C, and then the MeOH-soluble part was removed. The solid part remaining on the paper was dried in air. Thus, compound10was obtained as a sole enol form . Yellow crystal. Mp 151–152 °C. 1H-NMR  : δ 17.60 , 7.73 , J = 15.4 Hz), 7.53–7.17 , 6.98 , J = 15.4 Hz), 2.88  ppm; 13C-NMR  : δ 183.4 (C(3/5)), 141.8 (C(1/7)), 141.0 (C(1”’)), 135.6 (C(1’/1”)), 130.2 (C(2”’/6”’)), 129.1 (C(2’/6’ and 2”/6”)), 128.9 (C(3”’/5”’)), 128.8 (C(4’/4”)), 128.4 (C(3’/5’ and C-3”/5”)), 126.6 (C(4”’)), 120.6 (C(2/6)), 110.9 (C(4)), 38.6 (PhCH2CH2), 28.4 (PhCH2CH2) ppm. Anal. Calcd. for C27H24O2 (MW 380.49): C, 85.23; H, 6.36%. Found: C, 84.96; H, 6.60%.Compound2O (25 mL) was added. The organic phase was extracted with AcOEt (2 ×25 mL) and washed with H2O (20 mL). The organic layer was dried (Na2SO4), and evaporation of the solvent and silica gel column chromatography of the residue with hexane/AcOEt 95:5 gave 11 as a colourless oil . Rf (AcOEt/hexanes 5:95): 0.6. 1H-NMR  : δ 7.52–7.16 , 6.75 , 5.41 , J = 13.9, J = 3.3 Hz), 2.94 ), J = 17.0, J = 13.9 Hz), 2.81–2.72 ); 13C-NMR  : δ 192.6 (C(4)), 164.6 (C(6)); 142.0 (C(1”)), 139.2 (C(1’)), 137.4 (PhCH=CH), 136.0 (C(1”’)), 129.63 (1 arom. C), 129.04 (4 arom. C), 128.95 (2 arom. C), 128.88 (1 arom. C), 128.62 (2 arom. C), 127.9 (2 arom. C), 126.3 (2 arom. C), 126.29 (1 arom. C), 119.0 (PhCH=CH), 116.2 (C(5)), 79.6 (C(2)), 43.7 (C(3)), 36.4 (PhCH2CH2) , 26.2 (PhCH2CH2) ppm; Anal. Calcd. for C27H24O2 (MW 380.49): C, 85.23; H, 6.36%. Found: C, 85.46; H, 6.53%.Compound 10  was dissolved in AcOH (10 mL). Zn  was added to this solution, and the reaction mixture was refluxed for 12 h. After the mixture was cooled to room temperature, HBacillus cereusBC-On [36],Arthrobacter agilisA17 [37],Pseudomonas aeruginosaOG1 [38],Xanthomonas campestrisMO-03 [39], Candida albicans,Klebsiella oxytoca, andHelicobacter pylori[40] (ATCC 43629). For this purpose, a suspension of the tested microorganism (0.1 mL of 108 cells per mL) was spread on the agar plates. Mueller-Hinton agar with 5% sheep blood plates forH. pyloriand tryptic soy agar (TSA) for the other bacteria were used for testing antibacterial activities.H. pyloriplates were incubated under microaerophilic conditions in anaerobic jars [40]. Discs made of Whatman qualitative filter paper, grade 1 (6 mm diameter), containing 20–100 μg/disc of the synthesized chemicals were placed on the plates. The plates were incubated at 37 °C for 24 h. At the end of the incubation period, a zone of inhibition of diameter ≥7 mm was considered positive. DMSO was used as the negative control. Ofloxacin and nystatin  were used as positive standards for antimicrobial activities.The synthesized chemicals were dissolved in dimethyl sulfoxide  at a final concentration of 10 mg/mL. Antimicrobial activities of the synthesized chemicals were tested by disc diffusion method against


The chemical structures of these compounds were identified by 1D and 2D NMR and HRESIMS spectroscopic analyses. Configurations of new compounds were determined by ROESY correlations and comparison of their 13C NMR data with literature reported values. All compounds were evaluated for their inhibition against α-glucosidase, in which compounds 2, 5, 7, 8, 9 showed moderate inhibitory activities with IC50 values ranging from 28.40 to 63.26 μM comparing with the positive control .Ten cucurbitane-type triterpene glycosides, including five new compounds named charantosides H (The online version of this article (10.1007/s13659-020-00241-5) contains supplementary material, which is available to authorized users. Momordica charantia (Cucurbitaceae) was very popular and had an incredible hypoglycemic effect. Therefore, M. charantia has great research potential in reducing blood sugar and is a hot spot in modern phytochemical research.Diabetes mellitus (DM) is a type of metabolic disorder caused by insufficient insulin secretion or insulin utilization disorder, and is marked by persistent hyperglycemia . The latMomordica charantia is a traditional medicinal and edible plant, which has a long history of use in developing countries. Modern phytochemistry research shows that both crude extracts and secondary metabolites  of M. charantia possess anti-diabetic activity +), indicated eight degrees of unsaturation. The 1H NMR spectrum of 1 , 5.48 , 5.22 ], and an anomeric proton [δH 5.36 ]. The 13C NMR -5β,19-epoxy-19,23-dimethoxycucurbita-6,24-dien-3β-ol 3-O-β-d-allopyranoside (charantoside II) [δC values [δC (charantoside II) − δC (1)] for the relevant signals were calculated as 1.7 (C-5), − 7.3 (C-8), − 0.7 (C- 9), 2.8 (C-10), 1.6 (C-11) and -1.4 (C-19) from the 13C NMR data of charantoside II and 1, which were feckly consistent with the ΔδC values [δC (19R) − δC (19S)] of 1.8 (C-5), − 7.8 (C-8), − 0.7 (C-9), 2.6 (C-10), 1.8 (C-11) and -2.6 (C-19) calculated from the 13C NMR data of 5β,(19R)- and 5β,(19S)-epoxy-19,23-dimethoxycucurbita-6,24-dien-3β-ol +) in the HRESIMS (positive-ion mode) spectrum and had the same molecular formula C38H62O9 as 1, which also possessed eight degrees of unsaturation. Detailed analysis of the 1H, 13C NMR, and DEPT spectra -5β,19-epoxy-19,23-dimethoxycucurbita-6,24-dien-3β-ol 3-O-β-d-allopyranoside  except that d-allose of 1 were replaced by d-glucose in 2. In the 13C NMR spectrum of compound 2, an anomeric carbon atom (δC 105.2) and a series of oxygenated carbon signals  were in line with 5, confirmed the presence of a β-d-glucopyranosyl residue +) in the HRESIMS (positive-ion mode) spectrum and had the same molecular formula C38H62O9 as 1. According to the 1H, 13C NMR, and DEPT spectra  except for the signals due to the stereochemistry at C-23. Compound 3 exhibited 1H NMR signals , 1.69 and 1.73 , 3.29 , 4.10 , and 5.15 . Detailed comparisons of its 13C NMR data  − ΔδC (3)] for the side-chain signals were calculated as − 1.1 (C-20), − 1.0 (C-21), + 0.3 (C-22), − 1.7 (C-23), + 0.5 (C-24), − 1.6 (C-25), − 0.0 (C-26), and − 0.3 (C-27), which were almost in line with the ΔδC values [ΔδC (23R) − ΔδC (23S)] of − 0.9 (C-20), − 0.9 (C-21), + 0.4 (C-22), − 1.6 (C-23), + 0.5 (C-24), − 1.4 (C-25), − 0.1 (C-26), and − 0.4 (C-27) calculated from the 13C NMR data of charantoside II (23R) and charantoside VI (23S) +), indicating nine degrees of unsaturation. The absorption at 238 nm in the UV spectrum exhibited a conjugated double bond group. The 1H NMR spectrum of 4 , 6.17 , 5.91 , 5.53 , 5.48 ], and a β-allopyranoside moiety [δH 5.38 ]  implied that a conjugated double bond existed in the side chain. This was further confirmed via the 1H-1H COSY correlations of H-21/H-20/H-22/H-23/H-24 and the key HMBC correlations Me-21/C-17, C-20, C-22, H-22/C-21, C-24, H-24/C-22, C-23, H-26/C-24, C-25, C-27, and H-27/C-24, C-25, C-26 ] . After a5 was obtained as white amorphous powder and assigned a molecular formula of C37H60O9, (HRESIMS m/z 671.4136 [M + Na]+), indicating eight degrees of unsaturation. The 1H NMR spectrum of 5 , 5.92 , 5.92 , 5.48 ], and a β-glucopyanosyl moiety [δH 4.92 ]  for the relevant signals were feckly consistent with those reported in the literature  , 21. TheM. charantia, all of which were cucurbitane-type triterpene glycosides. All compounds were evaluated for their α-glucosidase inhibitory activities with acarbose as a positive control. Compounds 2, 5, 7, 8, and 9 showed moderate inhibitory activities with IC50 values of 63.26 ± 3.04, 59.13 ± 4.67, 35.08 ± 4.15, 36.38 ± 3.03, 28.40 ± 2.08 μM, respectively. The IC50 value of positive control (acarbose) was 87.65 ± 6.51 μM  as internal standard . Column chromatography (CC) was performed on macroporous resin , Lichroprep RP-18 , sephadex LH-20 , silica gel , and Semi-preparative HPLC was performed on an Agilent 1260 liquid chromatography system equipped with a ZORBAX SB-C18 column  and a DAD detector. Fractions were detected by TLC, and spots were visualized by spraying with 10% H2SO4 in EtOH, followed by heating. α-glucosidase inhibitory activity was evaluated on the basis of the ability of the compounds to decrease glucosidase activity and then inhibit the breaking of glycosidic bonds in p-nitrophenyl-α-d-glucopyranoside (PNPG). Water was purchased from wahaha group co. LTD. Acetonitrile (chromatographic grade) was purchased from OCEANPAK (Sweden). Common organic solvents are industrial grade, used after re-distillation. PNPG was obtained from Sigma Chemical Co. . α-glucosidase was purchased from Shanghai yuanye biotechnology Co., Ltd. Potassium phosphate buffer solution (PPBS) was obtained from Shanghai Yidian Scientific Instrument Co., Ltd. 96-well plates was purchased from Nest biotechnology co., LTD.UV spectra were recorded on a UV-2401PC spectrometer . Optical rotations were measured in methanol on JASCO P-1020 digital polarimeter . IR spectra were scanned on a Bruker Tensor-27 Fourier transform infrared spectrometer with KBr pellets . High-resolution (HR) ESI mass spectra data were measured on a Waters API QSTAR Pulsar spectrometer. 1D and 2D NMR spectra were obtained in pyridine-M. charantia were purchased from the Luosiwan Chinese Herbal Medicine Market in Kunming, Yunnan Province, China, in February 2017. The material was identified by associate Prof. Jian-Chao Cheng from Kunming Institute of Botany (KIB), Chinese Academy of Science (CAS). A specimen was deposited in the State Key Laboratory of Phytochemistry and Plant Resource in West China, Kunming Institute of Botany, Kunming, China.Dried slices of M. charantia (40.0 kg) were sliced and extracted with MeOH. The solution was concentrated under reduced pressure to obtain a crude extract (25 kg), which was then successfully partitioned with petroleum ether (PE), EtOAc (EA), and n-butanol, respectively. The EtOAc fraction (2.0 kg) was subjected to the D101 macroporous resin, eluting with gradient system of MeOH/H2O  to afford five fractions. The fraction  was chromatographed on a silica gel column, eluting with gradient system of CHCl3/MeOH (100:1–1:1) to give four fractions (Fr.1–Fr.4). Fr.2 (16.8 g) was applied to ODS column, eluting with MeOH/H2O to give six sub fractions (Fr.2.1–Fr.2.6). Fr.2.5 (4.2 g) was separated over silica gel column (PE/EA) followed by semi-preparative HPLC (CH3CN/H2O), to yield compounds 1 (1.0 mg), 2 (1.0 mg), 3 (2.5 mg), and 10 (4.0 mg), respectively. Fr.2.6 (2.1 g) was successively purified by open column CC (CHCl3/MeOH) and semi-preparative HPLC (CH3CN/H2O), respectively, to afford compounds 4 (28.0 mg), 6 (6.0 mg), 7 (5.0 mg), 8 (1 mg), and 9 (30.0 mg). Similarly, Fr.3 (643 mg) was purified by RP-HPLC with CH3CN /H2O as eluent to obtain compounds 5 (10.0 mg).The dried fruits of α]D19 − 49.62 ; UV (MeOH) λmax (log ε) 196 (4.22) nm; IR (KBr) νmax 3426, 3027, 2926, 2875, 2815, 1736, 1634, 1465, 1447, 1380, 1320, 1292, 1260, 1218, 1182, 1154, 1108, 1084, 1049, 1033, 986, 953, 926, 882, 843, 801, 775, 747, 721, 696, 557, 529, 513, 467, 440, 411, 402 cm−1; For 1H NMR and 13C NMR (pyridine-d5) spectroscopic data, see Tables + .White amorphous powder; [α]D20 − 88.78 ; UV (MeOH) λmax (log ε) 196 (4.33) nm; IR (KBr) νmax 3424, 3026, 2928, 2875, 2815, 1736, 1636, 1465, 1446, 1383, 1320, 1292, 1260, 1218, 1183, 1153, 1110, 1086, 1050, 1033, 987, 952, 919, 817, 801, 775, 747, 721, 695, 618, 582, 557, 529, 513, 466, 411, 402 cm−1; For 1H NMR and 13C NMR (pyridine-d5) spectroscopic data, see Table + .White solid;  − 35.77 ; UV (MeOH) λmax (log ε) 196 (4.15) nm; IR (KBr) ν23Dmax 3428, 3028, 2925, 2874, 1736, 1630, 1465, 1448, 1377, 1307, 1287, 1260, 1212, 1197, 1180, 1155, 1108, 1082, 1049, 1033, 985, 953, 941, 926, 882, 843, 803, 778, 755, 731, 691, 550, 522, 496, 467, 449, 440, 411, 402 cm−1; For 1H NMR and 13C NMR (pyridine-d5) spectroscopic data, see Tables + .White amorphous powder; D24 − 53.88 ; UV (MeOH) λmax (log ε) 238 (4.02), 196 (4.07), 211(3.73) nm; IR (KBr) νmax 3391, 3124, 2949, 2873, 2387, 2318, 1637, 1592, 1469, 1397, 1377, 1348, 1310, 1085, 1034, 1000, 777, 749, 684, 661, 628, 586, 531, 493, 410 cm−1; For 1H NMR and 13C NMR (pyridine-d5) spectroscopic data, see Tables + .White amorphous powder; [α]D20 − 71.96 ; UV (MeOH) λmax (log ε) 196 (4.21) nm; IR (KBr) νmax 3427, 3027, 2970, 2947, 2927, 2873, 1735, 1632, 1464, 1449, 1377, 1312, 1288, 1256, 1199, 1158, 1138, 1112, 1078, 1050, 980, 950, 941, 925, 844, 803, 778, 753, 733, 695, 579, 549, 529, 491, 466, 450, 439, 429, 412 cm−1; For 1H NMR and 13C NMR (pyridine-d5) spectroscopic data, see Tables + .White amorphous powder;  and specific rotation compared with the authentic samples, All: Rf = 0.47, [α]D21 =  + 24.4; Glc: Rf = 0.51, [α]D21 =  + 51.9.Compounds α-glucosidase inhibition assay was performed according to the method adapted from the literature with slight modifications  × 100.The ications . α-glucoSupplementary file1 (DOCX 120873 kb)Below is the link to the electronic supplementary material.


Arthropoda, Hexapoda, Collembola) are small arthropods commonly found in soil, litter and other habitats all around the Globe. More than 9,000 species have been described worldwide, but knowledge about their diversity and distribution remains far from complete. Reports of springtail diversity in the Antilles are uneven, some islands are relatively well known, whereas others have not been explored at all. The fauna of Puerto Rico is reasonably well known, but many recent reports are scattered in published literature and unpublished theses.Springtails (Entomobryidae, but this possibly reflects the taxonomic expertise of specialists working in Puerto Rico rather than a real bias in the distribution of higher taxa in the islands. In addition to the new records, the database provides information on the world and local distribution of species listed. The dataset, presented here, is work in progress and will be updated as ongoing taxonomic inventories are completed.Here, we present a summary of all springtail species identified from the Bank of Puerto Rico, including unpublished records. As a result, we list 146 species including 43 unnamed, included in 65 genera and 17 families. Most species, 33, belong to  The main island accounts for approximately 8746 km2 of that area, whereas the islands of Vieques and Culebra account for 131 km2 and 26 km2, respectively. In the main island, the altitude varies between sea level and 1300 m a.s.l. Temperatures tend to decrease towards higher elevations along the centre of the main island (Puerto Rico is an archipelago located in the north-eastern part of the Caribbean and has an area of approximately 8900 kmn island  and the n island .Collembola in Puerto Rico was made by Rhizophoramangle) around the Island. The first report of Collembola of Puerto Rico published by Collembola from Puerto Rico, we include a list of species, historical reports and world and local distribution.The present work updates the list of The list of species recorded from Puerto Rico Fig.  is basedBiogeographical distribution regions according to https://doi.org/10.2737/RDS-2018-0063 are: Family, genus, species, world distribution and Neotropical distribution, historical reports in Puerto Rico, life zone in P.R, location  and habitat F5B1C268-F9FD-528E-A482-7923799CB13ECosmopolitan; Puerto Rico.Hypogastruradenticulata.Reported by 463EF932-F3DE-5BAD-814D-B5B71EDE5264Endemic; Puerto Rico: Luquillo.Reported by 69B65246-77A8-54FE-B4BB-05398B987F73Cosmopolitan; Puerto Rico: Ceiba, Guayama, Naguabo, Santa Isabel.Reported by Axelson, 19009A965CD5-5787-58C8-9DD9-6194CD65F551Boreal, Neotropical, Austral; Puerto Rico.Reported by Salmon, 1951CC1240DF-6DBB-5BD5-A3BA-39A6B55D2A5FNeotropical, Paleartic; Puerto Rico: Mayagüez.Reported by da Gama, 19763005AB3A-83E0-5F9A-89A6-85F44B8EA8E2Endemic; Puerto Rico.Reported by Folsom, 1916A00A99D9-E483-5E9B-9E09-EFBE2CD3C98ECosmopolitan; Puerto Rico: San Juan.Reported by Mills, 1938A364FC86-2B92-5757-840E-4AC29E183242Cosmopolitan; Puerto Rico.Reported by BC3B3396-0486-5A4D-8AFB-3A4DCE39344AEndemic; Puerto Rico: Luquillo.Reported by 154E60C5-9A6E-59B9-843A-F97F3B92C2ADEndemic; Puerto Rico: Luquillo.Reported by 2CE45F80-AEDC-5B76-9E37-C9E64B2AF14FMari Mutt, 1977481149DF-E830-5BC0-90EE-EB1A61A594A6Cosmopolitan; Puerto Rico: Cayey, Luquillo.Reported by Mills, 193491C5FE60-9BCF-5283-9C07-5B93739FC2E9Cosmopolitan; Puerto Rico: Luquillo.Reported by F45807F6-4D07-524C-AD93-FC9EF24AD709Wray, 1953EA41CD0C-89D2-5EA3-9837-925F29C2BE1DNeotropical; Puerto Rico: Luquillo, Mayagüez.Reported by Gruia, 19838A550CC7-FBC6-5D2F-B878-469A6678D805Neotropical; Puerto Rico: Cabo Rojo, Guánica.Reported by 2FC4C5CD-0BEF-5802-AE30-5638E7FCCC1FEndemic; Puerto Rico: Luquillo.Reported by Soto-Adames (unpublished data), new record.FFB4A7D1-CDE1-587F-9FAB-C1677B3B2383Endemic; Puerto Rico: Luquillo.Reported by 90D01416-E82A-5E01-BE50-2FD73C68EADBEndemic; Puerto Rico: Luquillo.Reported by 7DA24243-48B6-5919-A929-B3CAC3C757FFMari Mutt, 1976F1559C6C-8C74-5D5A-956B-78D34A064893Cosmopolitan; Puerto Rico.Reported by Palacios-Vargas, 19860C756A26-BDFD-5539-8F6C-1F90FC9C2D82Neotropical; Puerto Rico.Reported by Denis, 1931595A475A-13AC-5F62-B5DB-1B752510A615Neotropical; Puerto Rico: Luquillo.Reported by Cassagnau & Palacios-Vargas, 19833D90DC4E-20E7-54A9-BA68-D5B352BD9758Neotropical; Puerto Rico: Mayagüez.Reported by Folsom, 1927090D350F-3E43-55A9-AF39-40323E447270Neotropical; Puerto Rico: Mayagüez.Portachorutesmambatus, Reported by 783D260F-4765-52F3-A698-6BDA7BA28F9DEndemic; Puerto Rico: Luquillo.Reported by Soto-Adames (unpublished data), new record.B2C74B9E-41DA-5B18-99D6-D1EBC079D127Endemic; Puerto Rico: Luquillo.Reported by 6160F4D0-5711-5A44-9B8E-D2BED7E51FC0Neotropical; Puerto Rico: Cayey, Luquillo, Maricao, Mayagüez.Reported by 08A0F850-F2DA-5D87-95BB-D70B8352FCCFNeotropical; Puerto Rico: Luquillo.Reported by Soto-Adames (unpublished data), new record.Ospina-Sánchez, Palacios-Vargas & González, 2020B322BCB7-740A-54F0-BC31-6D19325E2047Endemic; Puerto Rico: Luquillo.Reported by ADA789EC-18D3-5D5C-A2C1-D34126C1007FEndemic; Puerto Rico: Luquillo.Reported by Arlé, 1966E0CEC7CE-3D79-546A-A142-895111CA48CFNeotropical; Puerto Rico: Luquillo.Reported by 122F3D1E-8FC3-5E1C-8FDB-BDE6CB958A09Endemic; Puerto Rico: Luquillo.Reported by FC9BB18E-8643-5671-9911-565CB591FDC5Neotropical; Puerto Rico: Luquillo.Micranuridawladimiri n. subsp. caribeña".Reported by Börner, 19015D2E0733-D196-550C-8849-5E631E11CCEBNeotropical, Paleartic; Puerto Rico: Mayagüez.Reported by 2D3B61D5-24EE-52B9-9BBB-A0CDAF228C88Endemic; Puerto Rico: Luquillo.Reported by Soto-Adames (unpublished data), new record.9A50A179-3F46-5ADD-9354-DF2538C31FD1Endemic; Puerto Rico: Luquillo.Reported by 676D0AED-AAA1-5DEA-8F18-11B1B5FEFE7AEndemic; Puerto Rico: Luquillo.Reported by Schuster, 1965D5ECE55F-066C-550C-8DA3-0B85885D7C43Neotropical, Paleartic; Puerto Rico: Aguadilla.Reported by Mari Mutt, 19770FDCDAD6-ACB7-57C3-8364-1841F8BAAFE1Holartic, Paleartic, Neotropical; Puerto Rico: Cayey, Guajacata, Luquillo, Quebradillas, San Sebastián.Reported by Christiansen & Bellinger, 198019DD7A85-29F2-5D52-B3DF-B0092A1AEF94Paleartic; Puerto Rico.Reported by Hammer, 19533DFECF84-AEE1-5C75-AE73-FF9B17CB1B6EHolartic; Puerto Rico.Reported by Palacios-Vargas & Soto-Adames, 2017D2B1FF23-FE04-56BE-924A-D338D70082B0Endemic; Puerto Rico: Luquillo, Maricao.Reported by BD1A7B1B-B4CA-503F-A3F1-131284F3BD8FNearctic; Puerto Rico.Neanuranr.illina.Reported by D9D2A23D-5087-5C46-BA82-044B367B7091Reported by Soto-Adames (unpublished data), new record.230318CA-74C2-5F31-A01F-CB80FCE8BF0D085B9CD5-15DA-5048-9443-F3F57B2C7236Neotropical; Puerto Rico: Arecibo.Reported by 894D8FA6-2A6E-58EB-8C90-973C40D9128DNeotropical; Puerto Rico: Maricao, Mayagüez.Onychiurusfimetarius.Reported by B73C3AEB-13BD-5561-8B84-19B0BA4D5595Paleartic; Puerto Rico: Luquillo, Mayagüez.Reported by 768497E7-8FF5-50EA-897A-456AA9871064Cosmopolitan; Puerto Rico: Luquillo.Protaphoruranr.encarpata.Reported by A52BD976-F634-566E-B145-7EFA375821A3Endemic; Puerto Rico: Luquillo.Reported by 24C341C5-F466-5498-BCFC-6411DB9451C0Cosmopolitan; Puerto RicoProtaphoruranr.hera.Reported by FCF93DAA-D48F-5A9D-B067-FE848EFE929C13217400-65BE-5FD5-8890-107C724834EFCosmopolitan; Puerto Rico.Reported by 882C2E59-C3D0-50C6-A03B-324AABCADD03Cosmopolitan; Puerto Rico: Mayagüez.Reported by Christiansen & Bellinger, 198003BBF93C-F328-5279-A9A0-D4285491BC63Cosmopolitan; Puerto Rico: Luquillo.Reported by 785A7C24-024F-500D-8072-7ECE937742CFThibaud, 199377CCCAD6-F335-546A-9202-615C133A19A9Neotropical; Puerto Rico.A.interstitialis, Reported by Delamare Deboutteville, 1953B5F84ADF-FDC3-5F7E-B082-F08EA8B911ADCosmopolitan; Puerto Rico.Reported by Strenzke, 19583E11B8E4-DD56-55C1-AB0A-CC2A54BEF9D9Neotropical; Puerto Rico: Guánica, Guayama, Lajas, Patillas, Salinas, Santa Isabel.Reported by 98F8CC9C-61A9-5F8C-9D70-4694DBA5DC96Cosmopolitan; Puerto Rico: Aguadilla, Arecibo, Cabo Rojo, Cayey, Ceiba, Guayama, Las Marias, Luquillo, Maricao, Mayagüez, Morovis, Río Grande, Toa Baja.ryptophygus thermophilus, Reported by 4A90534C-10DE-5FB3-B01C-07F8F024791CCosmopolitan; Puerto Rico.Reported by Denis, 1931F1903C0F-48B6-5A01-8BEA-3A40A9A5758ECosmopolitan; Puerto Rico: Mayagüez.Reported by Willem, 1902652602E1-D413-5E69-8E3E-418D64219334Cosmopolitan; Puerto Rico.Reported by Wray, 195340C922C2-9A0A-56CF-A6D4-25E97E0BC024Neotropical; Puerto Rico.Reported by Denis, 193176A79071-00D5-594C-9745-FEDCE126E6F4Tropical; Puerto Rico: Luquillo.Reported by Soto-Adames (unpublished data), new record.DAD521DF-A02D-54A9-AD32-9A0B658B6404Neotropical, Austral, Paleartic; Puerto Rico: Arecibo, Cabo Rojo, Humacao, Mayagüez, Toa Baja.Reported by Stach, 19229CC963BD-4350-5809-9BC6-44123532B32ECosmopolitan; Puerto Rico: Arecibo, Mayagüez, Moca, San Juan, Toa Baja.Folsomidesamericanus, Reported by 212E7DC7-5626-5EDD-9F07-E1D05DE8C810Cosmopolitan; Puerto Rico: Mayagüez.Reported by F10C6E14-A0D8-5163-933C-E30FBEDEA85FCosmopolitan; Puerto Rico: Arecibo, Cabo Rojo, Humacao, Luquillo, Mayagüez, San Juan Toa Baja.Reported by B7259822-08D6-56E0-A68B-5076420C6890Reported by 82CC5674-D182-5F6D-B535-FD88BCE03159Cosmopolitan; Puerto Rico: Luquillo, Mayagüez.Reported by 37F108A1-337C-5CE9-8E08-1CB3254AD2EFEndemic; Puerto Rico: Luquillo.Reported by 8B0DBC24-6948-5B6C-8D66-87F26691FBCDNeotropical; Puerto Rico: Cabo Rojo, Ceiba, Toa Baja.Reported by B49FD005-0D82-5451-82E2-E65D0583BB15Soto-Adames, 1988C52CDE92-C319-550C-A4B3-343776CD0F00Endemic; Puerto Rico: Isla Mona.Reported by Soto-Adames, 19888B87F230-FC86-5858-A5F8-159CE69BFC65Endemic; Puerto Rico: Guánica, Vieques.Reported by Soto-Adames, 1988057C0024-D253-5F4F-A531-5570A1B3A3A5Endemic; Puerto Rico: Aguadilla, Guajataca, Isla Mona, Vega Baja.Reported by Soto-Adames, 1988053BE56A-EDC1-5109-98B9-5AB7C5617932Endemic; Puerto Rico: Guánica, Vieques, Yabucoa.Reported by 807F9098-E5DD-5242-8150-AC33819DAD55Mari Mutt, 198509D57104-5442-557D-9DC0-F18E19C2246EEndemic; Puerto Rico.Reported by Wray, 1953977A24DA-7C74-522E-8414-54C5F3E8445DEndemic; Puerto Rico: Mayagüez.Reported by D2153588-8379-58C5-BDD5-C8457AB5B42AEndemic; Puerto Rico: Maricao, Mayagüez.Reported by 2317468E-6AAC-51AE-AB61-D3D07A758248Endemic; Puerto Rico: Mayagüez.Reported by B233020F-69B1-5968-8A8F-AAEE792A0026Neotropical; Puerto Rico: Luquillo.Reported by Soto-Adames (unpublished data), new record.9CC835A4-03E9-5DEC-9281-8432199A522EC2258673-F86A-51F8-9694-91552DB570D1Neotropical, Holartic; Puerto Rico: Fajardo.Reported by B1EAC128-006A-5482-9713-A5A35E3E047ENeotropical; Puerto Rico.Entomobyacubensis, Reported by Soto-Adames, 200277525943-BA84-56FB-8B61-82491D176DFFNeotropical; Puerto Rico: Humacao, Toa Baja.Reported by Soto-Adames, 20028ACF627B-28E4-5759-9AFC-60F9EC12BF5DNeotropical; Puerto Rico: Mayagüez, Luquillo, Orocovis.Reported by C95B178F-6FAC-5E28-9852-3D0F6E84B530Endemic; Puerto Rico: Luquillo.Reported by 3ED221CD-BB3F-5C90-8A00-3088EAB9FE9BNeotropical, Paleartic, Austral; Puerto Rico: Fajardo, Salinas.Reported by Mari Mutt, 19862C7BCA04-820E-5A57-A9BF-C8FC6C5A9120Endemic; Puerto Rico: Carolina, Cabo Rojo, Fajardo, Humacao, Río Grande.Reported by B70C55FF-0337-5757-94D1-B388C73707F9Neotropical, Holartic; Puerto Rico: Cabo Rojo, Carolina, Ceiba, Guayama, Peñuelas, Salinas, San Juan, Santa Isabel.Reported by Soto-Adames, 20028E9A3A7D-7A87-5226-AC4E-61C02AA44746Endemic; Puerto Rico.Reported by CB81DD41-BFF0-583B-A985-1785ACBC376ANeotropical, Holartic; Puerto Rico: Guánica, Luquillo.Reported by 1C7C0ABB-EF74-5A82-9FDD-D9DFF2B91D8BNeotropical, Holartic; Puerto Rico: Bayamón, Guánica, Mayagüez.Seiradistincta.Reported by Wray, 1953BA4518C3-F83D-599F-A32F-0DCA21A7C29DNeotropical; Puerto Rico: Arecibo, Cayey, Guayama, Isabela, Las Marias, Luquillo, Manatí, Maricao, Mayagüez, Moca, Orocovis, Quebradillas, Río Grande, Utuado.Reported by Mari Mutt, 19863C992F7F-3103-5F43-93C2-9C003333EBFBEndemic; Puerto Rico: Aibonito, Aguadilla, Arecibo, Cabo Rojo, Cayey, Coamo, Guánica, Manatí, Moca, Utuado, Villalba.Reported by Mari Mutt, 1986CF6BEB03-DC06-52EE-A937-E03EA8B46011Endemic; Puerto Rico: Cabo Rojo, Guánica, Mayagüez, Quebradillas.Reported by Mari Mutt, 1986C8527B1F-3D17-5641-9333-6AD4D2DBC253Endemic; Puerto Rico: Aguadilla, Cayey, Isabela, Luquillo, Manatí, Maricao, Mayagüez, Moca, Quebradillas, Río Grande, Utuado.Reported by Mari Mutt, 1986D92F7C42-5918-546D-983F-CCA9DAD023F2Endemic; Puerto Rico: Mayagüez.Reported by Mari Mutt, 19881B99E82E-D5CD-560B-9BE3-6EAF5C2B7333Endemic; Puerto Rico: Aguadilla, Vieques.Reported by Mari Mutt, 198672020E7B-4114-5EC7-B95A-4E3DECB93039Endemic; Puerto Rico: Guánica, Mayagüez, Utuado.Reported by Mari Mutt, 19869E9D90AE-CA0F-546F-B56B-9B3DEE8BDC7DNeotropical; Puerto Rico: Cayey.Reported by Mari Mutt, 198673218575-4317-58ED-A5C8-1BAD262565BCEndemic; Puerto Rico: Cabo Rojo, Guánica, Toa Baja.Reported by Mari Mutt, 19866D7C5BB2-346A-5444-9DFF-798F86C1BDE7Neotropical; Puerto Rico: Carite, Luquillo, Orocovis, Salinas, Villalba.Reported by Folsom, 192711878589-B841-5616-9FF0-B90A24BB273DNeotropical; Puerto Rico: Adjuntas, Aguadilla, Arecibo, Barranquitas, Cabo Rojo, Caguas, Cayey, Ceiba, Coamo, Fajardo, Guayama, Humacao, Isabela, Manatí, Mayagüez, Morovis, Orocovis, Río Grande, Salinas, San Juan, San Sebastián, Toa Baja, Vega Baja.Reported by Mari Mutt, 1988F8DEFCE9-1F49-53B7-B64A-1D577BF04EBAEndemic; Puerto Rico: Luquillo.Reported by Mari Mutt, 1988E66E8964-C44C-5C1A-9E8C-66BFCC246489Endemic; Puerto Rico: Aguadilla, Añasco, Arecibo, Caguas.Reported by Mari Mutt, 1986E2C25D8C-AE3B-518A-B023-BEC2E7BB91ADEndemic; Puerto Rico: Aguadilla, Mayagüez, San Sebastián.Reported by Ellis, 1967C29003EE-9B9B-58FE-83FB-E51CC2E535E2Neotropical; Puerto Rico: Aguadilla, Caguas, Manatí, Mayagüez, Utuado, Villalba.Reported by Christiansen & Luther, 1986455CE984-03F2-5329-8ABF-D1D6173C4DF8Neotropical; Puerto Rico: Arecibo.Reported by Mari Mutt, 19868CC0BDD2-8D89-55F6-B64E-3D74CB048B0DEndemic; Puerto Rico: Arecibo, Cayey, Ceiba, Guayama, Isabela, Las Marias, Luquillo, Mayagüez, Orocovis, Río Grande, Toa Baja.Reported by Mari Mutt & Gruia, 19831994087A-15DC-5C3B-9444-66AB12BF09B4Endemic; Puerto Rico.Reported by Mari Mutt & Gruia, 19831154D03F-3AD9-58BE-B13B-34F7F8B67AF0Endemic; Puerto Rico.Reported by Massoud & Gruia, 1973973358F7-82A1-52A2-8FF7-08084B3F6B08Endemic; Puerto Rico.Metasinellarapoporti, Reported by Bonet, 1944C6941A76-07C7-58DC-A198-B08299625031Endemic; Puerto Rico.Metasinellatopotyca.Reported by FE22CF98-2D83-5EFB-B2D9-1F6ABF1A3CDDEndemic; Puerto Rico.Reported by 31A3639F-D739-5D89-B212-B86A5081A77A Mitra, 197511802DDB-D91D-537E-AAB1-3F56A59D66B6Endemic; Puerto Rico: Luquillo, Mayagüez, Toa Baja.Gampylothoraxsabanus, Reported by BFA291FE-E813-5DED-AB89-566E02054D20Neotropical, Afrotropical; Puerto Rico: Luquillo.Reported by 27A180B3-27E6-5B17-B5DC-70F86FA866C5Neotropical; Puerto Rico: Mayagüez.Reported by 7D6C998D-1858-5A2E-971F-37E5923753D4Neotropical; Puerto Rico: Mayagüez.Dicranocentrugajataca, Reported by 27931F87-FC3E-539B-9C26-9E5589E14308Neotropical; Puerto Rico: Luquillo.Reported by 90FA48E1-A262-5387-A2B3-D18C7A4F3643Neotropical; Puerto Rico: San Juan.Reported by 4DF1CD1C-E70F-502A-9615-A2C265A62ACCEndemic; Puerto Rico.Reported by Soto-Adames & Bellini, 2015F532DB21-7DA0-531C-9018-51AB0EDFE5D9Neotropical; Puerto Rico.Microparonellaincerta, Reported by Denis, 19318FFF02CA-EF42-5531-B11D-DAB0BD42EDD5Neotropical; Puerto Rico: Aguadilla, Arecibo, Cabo Rojo, Luquillo, Mayagüez, Río Grande, Toa Baja.Reported by Folsom, 19277344ECBC-FBD9-5694-88DA-93F704156480Endemic; Puerto Rico: Bayamón, Isabela, Peñuelas San Juan.Reported by Folsom, 19276EFBB619-61CD-57D0-9D62-86731025A8FCNeotropical; Puerto Rico: Mayagüez.Reported by Folsom, 192721A02917-46E1-5B8B-B0BF-6337C8C24E85Paleartic, Boreal, Neotropical; Puerto Rico: Arecibo, Cabo Rojo, Ceiba, Mayagüez, Toa Baja, Vega Baja.Reported by 52E84939-3671-53B6-9A0F-6591EAF1C4E9Endemic; Puerto Rico: Luquillo.Reported by F2B7547F-E823-5E19-907E-D1102B7AB75CMari Mutt, 19849620B819-CB6C-5CC3-80BF-C7568929958CEndemic; Puerto Rico: Arecibo, Luquillo.Reported by D5B6E143-942E-59EF-B99D-29D5EDBA6F0BFB2359E8-DE42-5D96-B031-6250FA15CD0BReported by Denis, 1933CB471663-A37D-5D3D-A082-45F8CB169CBCNeotropical, Paleartic; Puerto Rico: Adjuntas, Humacao, Mayagüez, San Sebastián.Reported by D1540D98-4928-52AF-B642-7E5350A8F464Soto-Adames, 1988AC8CA1A9-547D-5669-88E3-F8401169E56FEndemic; Puerto Rico: Aibonito, Arecibo, Cayey, Las Marias, Mayagüez, Luquillo, Utuado, Villalba.Reported by Soto-Adames, 1988469A153E-0013-5152-87D2-A2124A2A3DE2Endemic; Puerto Rico: Aguadilla.Reported by  Betsch, 198096367E68-A35D-58E9-8685-6EFD20D96E11Boreal, Neotropical, Paleartic; Puerto Rico: Aguadilla, Mayagüez.Reported by Soto-Adames, 19889D1ED20A-33A7-56C0-91EB-BEB79021617CEndemic; Puerto Rico: Aguadilla, Arecibo, Guayama, Cabo Rojo, Coamo, Mayagüez, San Juan, Toa Baja.Reported by  Betsch, 198030C09E7B-645E-54FC-B19D-B0FC857D44CFBoreal, Neotropical, Paleartic; Puerto Rico: Luquillo, Mayagüez.Reported by 207E5A0F-3661-5F58-8922-1E550BA04AA5Neotropical; Puerto Rico: Mayagüez, Toa Baja.Reported by 1337902F-D6F4-5850-9EBF-B37CE45757FCNeotropical; Puerto Rico: Ceiba, Humacao, Mayagüez, Naguabo, Río Grande, San Juan, Toa Baja, Vega Baja.Reported by 318AD05E-13B5-5E24-A467-4A4588DCCD16Neotropical; Puerto Rico: Mayagüez, Toa Baja.Reported by 02616D44-F5F6-5CCC-8253-5F86C5D8D618Neotropical; Puerto Rico: Mayagüez.Reported by 916AF289-9F35-5997-A86A-3BA6076A96B6Neotropical; Puerto Rico: Mayagüez.Reported by 36D37377-F3CE-51F8-9F8B-AA111C87F4F1DADD79BD-174C-5764-9AD3-265A69C5F5D8Neotropical; Puerto Rico: Arecibo, Guayama, Lajas, Patillas.Reported by A062862C-DB07-5BAD-B8A4-3E442ACBE58ANeotropical; Puerto Rico: Arecibo, Vega Baja.Reported by 1E2739F8-1155-5699-8374-35E443FF288DNeotropical; Puerto Rico: Arecibo, Guayama, Lajas, Patillas.Reported by B8839830-2CAD-5ADA-8017-1FD2A5A4494CNeotropical; Puerto Rico: Luquillo.Reported by Soto-Adames (unpublished data), new record.3F1C8FE3-C8E6-5A68-B413-FFBA202F90BCWray, 1953982FE70B-05AF-51DD-9DDE-7D8D80700B28Endemic; Puerto Rico: Luquillo.Reported by B77F5957-4950-502D-95FE-91C5D88E7A9CB2B14E35-9EB3-5B90-9396-072E30F278AANeotropical, Paleartic; Puerto Rico: Cabo Rojo, Ceiba.Reported by 60BBD986-5291-5E67-A243-463AF0E6D158Cosmopolitan; Puerto Rico: Isabela, Luquillo.Reported by EA1E7B93-0277-57F4-BB66-404AFC6FF2ED Bonet, 194757991AFA-C60B-5BDB-B582-814607787C0DBoreal, Neotropical, Paleartic; Puerto Rico: Luquillo.Reported by Najt, 1971D5132ACC-2953-5044-84FD-2EF1C8A7A078Cosmopolitan; Puerto Rico: Luquillo; Puerto Rico: Luquillo.Reported by Folsom, 1896FF6AAA2E-B369-5200-80B0-4BAEA4D32D24Austral, Boreal, Neotropical, Paleartic; Puerto Rico: Luquillo, Mayagüez.Reported by Tomoceridae is not represented in the islands. Most small families, not reported from Greater Puerto Rico , represent divergent lineages endemic to geographical regions distant from the Caribbean and are unlikely to be found here. Sturmiidae is a Neotropical family of the small order Symphypleona that typically occur on epiphytic mosses. Mosses have not been widely sampled for springtails in Greater Puerto Rico and it is possible that Sturmius Bretfeld, 1994 may still be found in the Islands. Isotogastruridae, Coenaletidae are known from other Antilles  and they might likely occur in Greater Puerto Rico, although none has been recorded yet.Of the 33 families of springtails recognised worldwide . Archisotomagourbaultae, A.interstitialis, S.aebianus, S.bellingeri. S.calcalectoris and S.myoptesimus are reported from littorals habitats. Sulcuncustopotypica, O.arecibena, T.subterranea and C.quadrioculata were reported in caves. Amongst the listed species from Puerto Rico, 58 have Neotropical distribution, 54 are Endemic and 24 are present in more than three world regions.Politically, the Island is divided into 78 municipalities, 45 of them covered in this database Fig. . AccordiEntomobryomorpha with 73 species. Amongst Entomobryomorpha, the family with the largest number of species is Entomobryidae (33); followed by Isotomidae (17). Poduromorpha with 51, the families Neanuridae (25) and Hypogastruridae (10) have the largest number of species , is the genus best represented in the islands, with 14 species, followed by Calvatomina Yosii, 1966 (Dicyrtomidae) represented by 8 spp. (Fig. In the present dataset, we report that the most abundant order is anuridae 5 and Hypanuridae 5 and Hypanuridae 5 and Hyp


Correction to: J Genet Eng Biotechnol (2019) 17:8https://doi.org/10.1186/s43141-019-0008-1In the publication of this article , the titThe error:Fig. 6 (1) AgNPs sample formed at pH 6.0, (2) at pH 8.0, (3) at pH 10.0, (4) at pH 12.0, and (5) cell free filtrateIt should instead read:A. fumigatus CFF mediation. (1) AgNPs sample formed at pH 6.0, (2) at pH 8.0, (3) at pH 10.0, (4) at pH 12.0, and (5) cell free filtrateFig. 6 Antimicrobial activity of the AgNPs biosynthesized by means of


Scientific Reportshttps://doi.org/10.1038/s41598-020-66131-5, published online: 17 June 2020.Correction to: The original Supplementary Information file published with this Article was incorrect. This version did not include Figure S1, Figure S2, Figure S3, Figure S4, Figure S5, Figure S6, Figure S7, Figure S8, Figure S9, Figure S10, Figure S11, Figure S12, Figure S13, Figure S14 or Figure S15. The correct Supplementary Information file now accompanies the Article.