Showing papers on "Triterpene published in 2000"
TL;DR: Six novel feruloyl esters of triterpene alcohols and sterols, besides five known trans-ferulates, showed marked inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice, and eight free sterols examined showed weaker activity than their corresponding ferulates.
Abstract: Six novel feruloyl esters of triterpene alcohols and sterols, viz., two trans-ferulates, cycloeucalenol and 24-methylenecholesterol trans-ferulates, and four cis-ferulates, cycloartenol, 24-methyelenecycloartanol, 24-methylcholesterol, and sitosterol cis-ferulates, besides five known trans-ferulates, cycloartenol (CAR), 24-methylenecycloartanol (24-MCA), 24-methylcholesterol, sitosterol, and stigmastanol trans-ferulates, and one known cis-ferulate, stigmastanol cis-ferulate, were isolated from the methanol extract of edible rice bran. These and eight other synthetic trans- and cis-ferulates of triterpene alcohols and sterols, along with the corresponding free alcohols, were evaluated with respect to their anti-inflammatory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg per ear) in mice. All of the ferulates showed marked inhibitory activity, and their 50% inhibitory dose (ID(50)) was 0. 1-0.8 mg per ear. On the other hand, whereas two free triterpene alcohols, CAR and 24-MCA, showed strong inhibition (ID(50) 0.2-0.3 mg/ear), eight free sterols examined showed weaker activity (ID(50) 0.7-2.7 mg/ear) than their corresponding ferulates.
289 citations
TL;DR: Although animal studies have enhanced the understanding of the possible action of squalene in decreasing carcinogenesis, one must apply caution in extrapolating the information obtained in animal studies to humans, because of possible species differences.
Abstract: Squalene is a triterpene that is an intermediate of the cholesterol biosynthesis pathway and it can be obtained from the diet. Olive oil contains 0.2 - 0.7% squalene. The average intake of squalene is 30 mg/day in the United States, however, when consumption of olive oil is high, the intake of squalene can reach 200 - 400 mg/day as observed in Mediterranean countries. The decreased risk for various cancers associated with high olive oil consumption may be due to the presence of squalene. Experimental studies have shown that squalene can effectively inhibit chemically-induced colon, lung and skin tumourigenesis in rodents. The protective effect is observed when squalene is given before and/or during carcinogen treatment. The mechanisms involved for the chemopreventive activity of squalene may include inhibition of Ras farnesylation, modulation of carcinogen activation and anti-oxidative activities. However, several factors must be taken into consideration when the evidence for the inhibition of carcinogene...
277 citations
TL;DR: New semi-synthetic analogs were developed that have the adjuvanticity of quillaja saponins, yet with less toxicity and greater stability in aqueous solutions, as well as CTL production against exogenous antigens.
200 citations
TL;DR: It is clear that certain structural features are required for immunostimulation of cycloartane-type triterpene glycosides.
Abstract: In the course of our research on the oligoglycosidic constitutents of Turkish Astragalus species, we have isolated a number of cycloartane-type triterpene glycosides. The current study examines the immunostimulatory effects of nineteen of these cycloartane-type compounds using a transcription-based bioassay for Nuclear Factor kappa B (NF-κB) activation in a human macrophage/monocyte cell line, THP-1. All compounds were inactive at 100 μg/ml except astragaloside I which increased NF-κB directed luciferase expression to levels about 65% as compared with maximal stimulation by E. coli lipopolysaccharide (LPS) at 10 μg/ml. None of the compounds were active at low dosage levels (0.1 μg/ml) in combination with 50 ng/ml LPS. Astragaloside I also increased mRNA expression of the inflammatory cytokines interleukin-1β(IL-1β) and tumor necrosis factor-α (TNF-α) as measured using reverse transcriptase-polymerase chain reaction (RT)-PCR. Based on these results it is clear that certain structural features are required for immunostimulation of cycloartane-type triterpene glycosides.
167 citations
TL;DR: In this paper, homology based PCRs with degenerate primers designed from the conserved sequences found in the known beta-amyrin synthases have resulted in cloning of two triterpene synthase cDNAs from immature seeds of P. sativum.
Abstract: Ursane type triterpene is one of the most widespread triterpene aglycones found in plants, together with oleanane type, and these two types often occur together in the same plant. Pisum sativum is known to produce both types of triterpenes. Homology based PCRs with degenerate primers designed from the conserved sequences found in the known beta-amyrin synthases have resulted in cloning of two triterpene synthase cDNAs from immature seeds of P. sativum. They show high sequence identities to each other (78%) and also to the known beta-amyrin synthases (70-90%). ORFs of the full-length clones named as PSY (2277 bp, codes for 759 amino acids) and PSM (2295 bp, codes for 765 amino acids) were ligated into the yeast expression vector pYES2 under the control of GAL1 promoter. Heterologous expression in yeast revealed PSY to be a P. sativum beta-amyrin synthase. Surprisingly, however, PSM turned out to be a novel mixed amyrin synthase producing both alpha- and beta-amyrin. Several minor triterpenes were also identified as the PSM byproducts. The presence of such multifunctional triterpene synthase would account for the co-occurence of ursane and oleanane type triterpenes in plants.
142 citations
TL;DR: Eight new triterpene glycosides named cimiracemosides A-H, respectively, and eight known triterPene Glycosides were isolated from the rhizome extracts of black cohosh (Cimicifuga racemosa).
Abstract: Eight new triterpene glycosides named cimiracemosides A-H, respectively, and eight known triterpene glycosides were isolated from the rhizome extracts of black cohosh (Cimicifuga racemosa). The new compounds were determined by spectral data to be 21-hydroxycimigenol-3-O-alpha-L-arabinopyranoside (1), 21-hydroxycimigenol-3-O-beta-D-xylopyranoside (2), cimigenol-3-O-alpha-L-arabinopyranoside (3), 12beta-acetoxycimigenol-3-O-alpha-L-arabinopyranoside (4), 24-acetylisodahurinol-3-O-beta-D-xylopyranoside (5), 20(S),22(R), 23(S),24(R)-16beta:23;22:25-diepoxy-12beta-acetoxy-3be ta,23, 24-trihydroxy-9,19-cycloanost-7-ene-3-O-beta-D-xylopyranoside (6), 20(S),22(R),23(S),24(R)-16beta:23;22:25-diepoxy-12beta -acetoxy-3beta, 23,24-trihydroxy-9,19-cycloanost-7-en-3-O-alpha-L-arabinopyrano side (7), and 20(S),22(R),23(S), 24(R)-16beta:23;22:25-diepoxy-12beta-acetoxy-3beta,23, 24-trihydroxy-9,19-cycloanostane-3-O-beta-D-xylopyranoside (8).
97 citations
TL;DR: Seven triterpenes were isolated from the stem bark extract of P. intermedius as active principles responsible for the cytotoxicity against five cultured human tumor cell lines, i.e., A549, SK-OV-3 (ovary), SK-MEL-2 (melanoma), XF498 (central nerve system) and HCT-15 (colon), in vitro.
Abstract: Seven triterpenes (1-7), i.e., betulinic acid 1, ursolic acid 2, oleanolic acid 3, 3-O-caffeoyloleanolic acid 4, euscaphic acid 5, 2 alpha-hydroxyursolic acid 6 and maslinic acid 7 were isolated from the stem bark extract of P. intermedius as active principles responsible for the cytotoxicity against five cultured human tumor cell lines, i.e., A549 (non small cell lung), SK-OV-3 (ovary), SK-MEL-2 (melanoma), XF498 (central nerve system) and HCT-15 (colon), in vitro.
86 citations
01 Jan 2000
TL;DR: This work describes the analysis and isolation of saponins from plant material, and the chemical and pharmacological studies on triterpenoidal saponin and other new constituents from Terminalia alata and some Sri Lankan plants, as well as their applications in human and animal nutrition and bioassays.
Abstract: Preface. 1. Analysis and isolation of saponins from plant material A. Marston, et al. 2. Bioactive saponins from some plants used in Indian traditional medicine S.B. Mahato. 3. Micro-extraction and characterization of saponins in peanut meal and soybean flour using HPLC and FAB mass spectrometry J.A. Singleton, et al. 4. LC-MS and LC-MS/MS analysis of saponins and sapogenins - comparison of ionization techniques and their usefulness in compound identification A.D. Muir, et al. 5. Separation of alfalfa (Medicago sativa L.) saponins as their borate complexes by capillary electrophoresis A. Tava, et al. 6. Single run HPLC separation of escins Ia and IIa by means of a Waters symmetry shield C8 column S. Apers, et al. 7. Polyhydroxylated steroidal saponins from Asteroidea (starfish) A.A. Kicha, et al. 8. Production of a diverse library of plant natural products for bioassays M. Steward, et al. 9. Structure determination of saponins with cardiotonic activity by circular dichroism J.-G. Dong, et al. 10. Non-NMR methods for structure elucidation of saponins T. Schopke. 11. A triterpenoidal saponin and other new constituents from Terminalia alata S.K. Srivastava, et al. 12. Chemistry and bioactivity of saponins from some Sri Lankan plants U.L.B. Jayasinghe, et al. 14. Oat root saponins and root-infecting fungi A. Osbourn, et al. 14. Chemo-ecological role of spirostanol saponins in the interaction between plants and insects J. Harmatha. 15. Localizations of saponins,furanocoumarins and other phenolics in fruits and shoots of some Rutaceae, Umbelliferae, Caprifoliaceae and Leguminosae A.M. Zobel, et al. 16. Triterpene glycosides from sea cucumbers (Holothurioidea): structure, function and evolution V.I. Kalinin, et al. 17. Production of ginseng saponins by cell suspension cultures of Panax notoginseng in bioreactors J.J. Zhong. 18. Saponin production by cell/callus cultures of Panax species A. Mathur, et al. 19. Use of 14C-labeled alfalfa saponins for monitoring their fate in soil M. Okumura, et al. 20. Chemical and pharmacological studies on triterpene saponins, escins, from horse chestnut seeds M. Yoshikawa, H. Matsuda. 21. Biologically and pharmacologically active saponins from plants: recent advances M.A. Lacaille-Dubois. 22. Physicochemical characteristics of interaction of saponins from Holothurians (sea cucumbers) with cell membranes I.A. Gorshkova, et al. 23. Biological activity of deltoside from Allium nutans L. L.S. Akhov, et al. 24. Glycoside based adjuvants F. Ferreira, J. Llodra. 25. Actual and potential applications of Yucca schidigera and Quillaja saponaria saponins in human and animal nutrition P.R. Cheeke. 26. Dietary saponins and human health A.V. Rao, D.M. Gurfinkel. 27. Sustainable production of Quillaja saponaria Mol. Saponins R. San Martin. 28. Beneficial effects of saponins on animal production H.P.S. Makkar, K. Becker.
81 citations
TL;DR: Investigation of Arabidopsis thaliana LUP1 gene encodes an enzyme that converts oxidosqualene to pentacyclic triterpenes uncovered the additional products germanicol, taraxasterol, psi-taraxastersol, and 3,20-dihydroxylupane, which suggest that the 80 known C(30)H(50)O compounds that are structurally consistent with being oxidosQualene cyclase products may be derived from
68 citations
TL;DR: These experiments indicated that the triterpenes once biosynthesized in the leaves are translocated to the root bark and further transformed to the antitumoral quinonemethide triter penoids.
68 citations
TL;DR: The Arabidopsis thaliana genome sequencing project has identified several triterpene synthase homologues, including extensively migrated triterpenes, multiflorenol and bauerenol as discussed by the authors.
TL;DR: Thirteen novel cycloartane-type triterpenes were isolated from Combretum quadrangulare, a Vietnamese medicinal plant by spectroscopic methods as well as by chemical transformations, and among those compounds, quadrangularic acids F, G, and H and 24-epiquadrangularic acid G are the first examples of cycloartsic acids bearing carboxylic acid groups at both C-4 and C-20.
Abstract: Thirteen novel cycloartane-type triterpenes were isolated from Combretum quadrangulare, a Vietnamese medicinal plant. The structures of the novel triterpenes were determined by spectroscopic methods as well as by chemical transformations. Among those compounds, quadrangularic acids F (1), G (2), and H (4) and 24-epiquadrangularic acid G (3) are the first examples of cycloartane-type triterpenes bearing carboxylic acid groups at both C-4 and C-20. Furthermore, norquadrangularic acid A (13) is the first example of a trinorcycloartane-type triterpene isolated from the genus Combretum.
TL;DR: Three of these compounds, namely uncarinic acids C, D, and E, are newly reported as natural products, showed dose-dependent inhibitory activities against PLCgamma1 in vitro and inhibited the proliferation of human cancer cells with IC(50) values of 0.5-6.5 microg/mL.
Abstract: Investigation of the hooks of Uncaria rhynchophylla resulted in isolation of six phospholipase Cgamma1 (PLCgamma1) inhibitors (1-6). The structures of these compounds were elucidated as pentacyclic triterpene esters by spectroscopic and chemical analysis. Three of them, namely uncarinic acids C (1), D (2), and E (3), are newly reported as natural products. All the compounds showed dose-dependent inhibitory activities against PLCgamma1 in vitro with IC(50) values of 9.5-44.6 microM and inhibited the proliferation of human cancer cells with IC(50) values of 0.5-6.5 microg/mL.
TL;DR: Six oleanane-type saponins, along with two known triterpene saponine glycosides, were isolated from the leaves of Gymnema sylvestre on the basis of hydrolysis and spectral evidence.
TL;DR: The new 3,4-secotriterpene acid 20-epi-koetjapic acid (5) potently inhibited rat neonatal brain microglia phorbol ester-stimulated thromboxane B(2) and superoxide anion (IC(50) = 1.9 microM) generation.
Abstract: The aerial parts of Maytenus undata yielded four new 12-oleanene and 3,4-seco-12-oleanene triterpene acids, namely, 3-oxo-11α-methoxyolean-12-ene-30-oic acid (1), 3-oxo-11α-hydroxyolean-12-ene-30-o...
TL;DR: Three olean-12-ene type triterpenoid saponins were isolated as methyl esters from tea roots after treatment with diazomethane by extensive 1D and 2D-NMR as well as FABMS and HR-MS analyses.
TL;DR: As a mixture, the triterpene glycosides protect E. formosus from predatory reef fishes, but when these compounds were separated into fractions some failed to deter feeding at natural concentrations, suggesting that terpene Glycosides may have important ecological functions, just as a defensive role has been ascribed to similar compounds in sea stars, sea cucumbers, and ter- restrial plants.
Abstract: The reef sponge Erylus formosus (Demospongiae: Geodiidae) from the Bahamas and southern Florida contains a suite of triterpene glycosides that, at a natural volumetric concentration, deters predation by the fish Thalassoma bifasciatum in laboratory assays, and a natural assemblage of reef fishes in field assays. Antifeedant metabolites were isolated by bioassay-guided fractionation of extracts of E. formosus using standard chromatographic methods and identified by nuclear mag- netic resonance (NMR) spectroscopy and mass spectrometry. Included in the deterrent mixture from E. formosus collected in the Bahamas and Florida were at least 6 related triterpene glycosides pos- sessing identical aglycones but with different sugar residues. Two additional compounds with a penasterol triterpene core (formoside, and an N-acetyl galactosamine derivative, formoside B) were found in specimens from the Bahamas but not Florida. Formoside, while being the major deterrent metabolite of E. formosus from the Bahamas, is less potent than the other triterpene glycosides on a weight per volume basis. As a mixture, the triterpene glycosides protect E. formosus from predatory reef fishes, but when these compounds were separated into fractions some failed to deter feeding at natural concentrations. As compounds of this type are beginning to be recognized as prevalent sponge metabolites, we suggest that terpene glycosides may have important ecological functions, just as a defensive role has been ascribed to similar compounds in sea stars, sea cucumbers, and ter- restrial plants.
TL;DR: In this paper, five new triterpene glucosides, quadranosides I−V (1−5), have been isolated from a MeOH extract of the seeds of Combretum quadrangulare, together with 13 known compounds.
Abstract: Five new triterpene glucosides, quadranosides I−V (1−5), have been isolated from a MeOH extract of the seeds of Combretum quadrangulare, together with 13 known compounds. The structures of compounds 1−5 were elucidated on the basis of spectroscopic analysis. Among the new triterpene glucosides, three compounds (1, 2, 5) showed significant hepatoprotective effects against d-galactosamine (d-GalN)/tumor necrosis factor-α (TNF-α)-induced cell death in primary cultured mouse hepatocytes.
TL;DR: Eight new triterpenoid saponins were isolated from a bark extract of Quillaja saponaria Molina by silica and reverse phase chromatography and characterized by spectroscopic data and chemical methods as phytolaccagenic acid, 22beta-hydroxy-quillaic acids, and echinocystic acid substituted with different oligosaccharides at C-3 and C-28.
TL;DR: Bioactivity-directed fractionation of the CHCl3-MeOH extract of the leaves of Celaenodendron mexicanum by means of the brine shrimp lethality test and chromatographic techniques led to the isolation of three carboxylic acid triterpenes, the new tirucalla-type triterpene, and four non-active compounds.
Abstract: Bioactivity-directed fractionation of the CHCl3-MeOH extract of the leaves of Celaenodendron mexicanum by means of the brine shrimp lethality test and chromatographic techniques led to the isolation of three carboxylic acid triterpenes, the new tirucalla-type triterpene, 3 alpha-hydroxytirucalla-7,24Z-dien-26-oic acid, 3-oxotirucalla-7,24Z-dien-26-oic acid, and epi-oleanolic acid, and three biflavonoids amentoflavone, podocarpusflavone A, and podocarpusflavone B. Four non-active compounds friedelin, maytensifolin B, 3 beta-hydroxyfriedelan-16-one, and celaenodendrolide were also obtained. epi-Oleanolic acid was the most active against brine shrimps with LC50 value of 23.3 microM. In addition, all isolates were tested for in vitro antiprotozoal and cytotoxic activities. 3-Oxotirucalla-7,24Z-dien-26-oic acid and epi-oleanolic acid showed the highest activity against Leishmania donovani promastigotes with IC50 values of 13.7 and 18.8 microM, respectively. Only 3-oxotirucalla-7,24Z-dien-26-oic acid showed activity against Trypanosoma brucei brucei bloodstream forms with IC50 value of 16.8 microM.
TL;DR: The method can be used to distinguish black cohosh products from among different plant species for quality control purposes and can specifically serve as indicators for species identification.
Abstract: A method to directly identify triterpene glycosides using reversed-phase liquid chromatography with positive atmospheric pressure chemical ionization mass spectrometry (LC/(+)APCIMS) was developed Based on the analysis of the molecular weight, fragment ions, selected ion chromatograms, a number of triterpene glycosides, including actein, 27-deoxyactein, cimicfugoside M, and cimicifugoside, from Cimicifuga racemosa were studied A chromone, cimifugin, from C foetida was also identified Cimicifugoside M and cimifugin can specifically serve as indicators for species identification The method can, therefore, be used to distinguish black cohosh products from among different plant species for quality control purposes
TL;DR: The minimum inhibitory concentrations of these compounds against Mycobacterium tuberculosis are reported and it is concluded that they are responsible for antitubercular activity originally observed in the crude plant extract.
Abstract: Three novel triterpenes, 3,4-seco-olean-12-ene-3,28-dioic acid (4), 3alpha-hydroxyolean-11-en-28,13beta-olide (5), and 3alpha-hydroxyoleane-11:13(18)-dien-28-oic acid (6), were isolated from the aerial parts of the Argentinean shrub, Junellia tridens. Another five compounds-oleanolic (1), oleanonic (2), and epioleanolic acids (3), all biosynthetically related to the three new oleananes, and epibetulinic acid (7) and sitosterol (8)-were also isolated. Structures were elucidated primarily by 1D and 2D NMR and mass spectrometry, and all protons and carbons of the three novel compounds were fully assigned by NMR. We report the minimum inhibitory concentrations of these compounds against Mycobacterium tuberculosis and conclude that they are responsible for antitubercular activity originally observed in the crude plant extract. LC-MS data is provided on the occurrence of triterpenes 1-6 in six other species of Junellia.
TL;DR: Six new triterpene glucosides, quadranosides VI-XI (1-6) have been isolated from a MeOH extract of the seeds of Combretum quadrangulare KURZ (Combretaceae), together with nine known compounds.
Abstract: Six new triterpene glucosides, quadranosides VI-XI (1-6), belonging to three different [ursane- (1-4), oleanane- (5) and lupane-type (6)] triterpene classes, have been isolated from a MeOH extract of the seeds of Combretum quadrangulare KURZ (Combretaceae), together with nine known compounds, rosamutin (7), 28-O-beta-D-glucopyranosyl-6beta,23-dihydroxytormentic acid (8), arjunetin (9), arjunglucoside II (10), combreglucoside (11), chebuloside II (12), vitexin (13), (+)-catechin (14) and (-)-epigallocatechin (15). The structures of these compounds were elucidated by spectroscopic analysis.
TL;DR: Four new 3,4-seco-lupane-type triterpene glycosides (1-4) were isolated from the leaves of Acanthopanax senticosus forma inermis by (HMBC, HMQC) methods and FABMS.
Abstract: Four new 3,4-seco-lupane-type triterpene glycosides (1−4) were isolated from the leaves of Acanthopanax senticosus forma inermis. The structures of 1−4 were established as 11α-hydroxy-3,4-seco-lup-4(23),20(30)-dien-3-oic acid methyl ester 28-oic acid 28-O-α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside, designated as inermoside (1); 1-deoxychiisanoside (2); 24-hydroxychiisanoside (3); and 11-deoxyisochiisanoside (4) by 1H−1H COSY and 1H−13C COSY(HMBC, HMQC) methods and FABMS.
TL;DR: In this article, 19 compounds were isolated from the CHCl3 soluble portion of the heartwood of Eucalyptus citriodora and the structures of these compounds were elucidated on the basis of spectroscopic evidence.
Abstract: Nineteen compounds were isolated from the CHCl3 soluble portion of the heartwood of Eucalyptus citriodora. These compounds included trans-calamenene (1), T-muurolol (2), α-cadinol (3), 2β-hydroxy-α-cadinol (4), 4-hydroxy-3,5-dimethoxybenzaldehyde (5), 4-hydroxy-3,5-dimethoxybenzoic acid (6), linoleic acid (7), squalene (8), α-tocopherol (9), erythrodiol (10), morolic acid (11), betulonic acid (12), cycloeucalenol (13), cycloeucalenol vernolitate (14), β-sitosterol (15), β-sitosteryl-β-D-glucopyranoside (16), β-sitostenone (17), yangambin (18), sesamin (19). Among them, 14 is a new compound. The structures of these compounds were elucidated on the basis of spectroscopic evidence.
TL;DR: In this article, the structures of cycloartane triterpenes, cyclopassifloic acids, and six related saponins were determined from the leaves and stems of Passiflora edulis, and their structures were elucidated on the base of extensive NMR experiments and chemical methods.
Abstract: Four cycloartane triterpenes, cyclopassifloic acids A (1), B (2), C (3), and D (4), and six related saponins, cyclopassiflosides I (5), II (6), III (7), IV (8), V (9), and VI (10), were isolated from the leaves and stems of Passiflora edulis, and their structures were elucidated on the base of extensive NMR experiments and chemical methods. Cyclopassifloic acids A−D were assigned as 22(R),24(S)-1α,3β,22,24,31-pentahydroxy-24-methylcycloartan-28-oic acid; 24(S)-1α,3β,24,31-tetrahydroxy-24-methylcycloartan-28-oic acid; 20(S),24(S)-1α,3β,21,24,31-pentahydroxy-24-methylcycloartan-28-oic acid; and 22(R)-1α,3β,22-trihydroxy-24-oxocycloartan-28-oic acid, respectively. Cyclopassiflosides I−VI, in turn, were established as the 28-O-β-d-glucopyranosides of cyclopassifloic acids A−D. Finally, cyclopassiflosides III and V were demonstrated as the 28,31-bis-O-β-d-glucopyranosides of cyclopassifloic acids B and C, respectively. Also obtained in this investigation were the known compounds passiflorin (11) and passiflori...
TL;DR: Six triterpene saponins, including two new compounds, were isolated from the fruits of Hedera helix L. (Araliaceae) on the basis of chemical and spectral data.
TL;DR: The extract of Tripterygium wilfordii Hook f.
TL;DR: The antiproliferative activity of compounds 1-8 and of their prosapogenins (2a-7a) prepared by alkaline hydrolysis, was evaluated using three continuous culture cell lines.
Abstract: During the course of a study of plants of the family Araliaceae, antiproliferative activity was demonstrated by the crude saponin fraction of Trevesia palmata. After chromatographic purification, s...
TL;DR: Enfumafungin (1) is a hemiacetal, triterpene glycoside that was isolated from a fermentation of Hormonema sp. as a mixture of two interconverting forms.
Abstract: Enfumafungin (1) is a hemiacetal, triterpene glycoside that was isolated from a fermentation of Hormonema sp. as a mixture of two interconverting forms. The primary structure of the major component of the mixture was determined as part of the mixture, mainly via NMR and comparison with hyalodendroside A (2), a related hemiacetal, triterpene glycoside that exists in a single form. The primary structure was confirmed, and the relative stereochemistry determined, based on a pair of methylacetal derivatives (3 and 4). Enfumafungin is an antifungal agent that acts as a specific inhibitor of glucan synthesis in cells and in vitro, and leads to morphological changes in yeasts and molds.