Showing papers on "Triterpene published in 1997"
TL;DR: 22 beta-Acetoxylantic acid showed antimicrobial activity against Staphylococcus aureus and Salmonella typhi and this compound and 22 beta-dimethylacryloyloxy lantanolic acid also showed antimutagenic activity.
133 citations
TL;DR: Gymnemoside b and gymnemic acids III, V, and VII were found to exhibit a little inhibitory activity against glucose absorption, but the principal constituents, gymnemic acid I and gymnemasaponin V, lacked this activity.
Abstract: Although the glycosidic fraction from the dried leaves of Gymnema sylvestre R. BR., gymnemic acid, was reported to be effective for diabetes, it showed little inhibitory activity on the increase of serum glucose level in oral glucose-loaded rats. From the glycosidic fraction, six triterpene glycosides, gymnemosides a, b, c, d, e, and f, were isolated together with nine known triterpene glycosides. The structures of gymnemosides a and b were determined on the basis of chemical and physicochemical evidence as 21-O-tigloyl-22-O-acetylgymnemagenin 3-O-beta-D-glucopyranosiduronic acid and 16-O-acetyl-21-O-tigloylgymnemagenin 3-O-beta-D-glucopyranosiduronic acid, respectively. In addition, an acetyl group linked to the 16- or 22-hydroxyl group in gymnemosides a and b was found to migrate easily to the primary 28-hydroxyl group, while the acyl migration from the 28-position was rarely observed. The inhibitory activity of each triterpene glycoside from gymnemic acid was examined to determine its impact on the increase of serum glucose level in oral glucose-loaded rats. Gymnemoside b and gymnemic acids III, V, and VII were found to exhibit a little inhibitory activity against glucose absorption, but the principal constituents, gymnemic acid I and gymnemasaponin V, lacked this activity.
77 citations
TL;DR: From the roots of Astragalus melanophrurius eight known saponins were isolated and found to be inactive, but Modest antibacterial activity was observed, as was immunomodulatory activity, as indicated by stimulation of isolated human lymphocytes.
Abstract: From the roots of Astragalus melanophrurius eight known saponins (1-8) were isolated Based on spectral data (IR, 1H- and 13C-NMR, and FABMS), the structures were established as astrasieversianins II (1) and X (4), astragalosides I (2), II (3), IV (5) and VI (7), and cyclocanthosides E (6) and G (8) The isolates were evaluated in a broad range of bioassay systems and found to be inactive Modest antibacterial activity was observed, however, as was immunomodulatory activity, as indicated by stimulation of isolated human lymphocytes
72 citations
TL;DR: This is the first report of triterpenoids, which is a new triterpene assigned as 11α, 12α-epoxy-3β, 23-dihydroxy-30-norolean-20(29)-en-28,13 β-olide, from this plant.
64 citations
TL;DR: The chloroform extract of the leaves of Momordica foetida has yielded 3β, 7β, 23ξ-trihydroxycucurbita-5,24-dien-19-al and the novel compounds.
62 citations
TL;DR: In this paper, five new compounds have been isolated from the fresh fruits of Momordica charantia and their structures elucidated through spectroscopic studies, including three pentacyclic triterpenes and a monocyclic alcohol.
59 citations
TL;DR: The aerial parts of Melilotus messanensis (sweet clover) afforded, from moderately and polar bioactive fractions, 11 triterpenes and five steroids and seven sterols, which had an important stimulatory effect on H. vulgare germination and growth.
Abstract: The aerial parts of Melilotus messanensis (sweet clover) afforded, from moderately and polar bioactive fractions, 11 triterpenes and five steroids. A series of aqueous solutions at 10−4–10−9 M of five steroids and nine triterpenes was monitored to test their effects on germination and growth of the monocots Hordeum vulgare and Allium cepa, and the dicots Lactuca sativa (var. nigra and var. romana) and Lycopersicon esculentum. An important stimulatory effect on H. vulgare germination (between 40% and 80% for almost all tested compounds) was observed. Some considerations about the ecological role of triterpenes on M. messanensis are made. In addition to known lupane triterpenes (platanic acid and 3β,28,30-lup-20(29)-enetriol), oleanane triterpenes (soyasapogenol B, soyasapogenol G, and messagenolide), a gammacerane triterpene (gammacer-16-en-3-one), five new lupane triterpenes (messagenic acids A–E: (27-cis-4-hydroxycinnamoyloxy)-betulinic acid; 27-(trans-4-hydroxycinnamoyloxy)betulinic acid; 20(S)-3β-hydroxy-29-oxolupan-28-oic acid; 3β,30-dihydroxylup-20(29)-en-28-oic acid; and 3β,20-dihydroxylup-18(19)-en-28-oic acid, respectively), and sterols (β-sitosterol, ergosterol peroxide, 7α-hydroxysitosterol, 7β-hydroxysitosterol, and 7-oxositosterol) were isolated and chemically characterized. Their structures and stereochemistry were elucidated by spectroscopic methods (one- and two-dimensional 1H and 13C NMR, IR, MS).
58 citations
TL;DR: Eight known triterpene alcohols isolated in this study were evaluated in ear inflammation in mice induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) and the 50% inhibitory dose of these triterpenes for TPA-induced inflammation was 0.2-0.9 mg/ear.
Abstract: The nonsaponifiable lipids of camellia and sasanqua oils from the seeds of Camellia japonica L. and C. sasanqua THUNB., respectively, were investigated for their triterpene alcohol constituents. This led to the isolation of twenty-seven triterpene alcohols of which seven were novel naturally occurring compunds, tirucalla-5, 7, 24-trien-3β-ol (1), lemmaphylla-7, 21-dien-3β-ol (2), isoeuphol (3), isotirucallol (4), (24R)-24, 25-epoxybutyrospermol (5) and its 24S-epimer (6), and isoaglaiol (7). The structures were determined by spectroscopic and chemical methods. The inhibitory effects of 3, 4, a mixture of 5 and 6, a mixture of 7 and its 24S-epimer (aglaiol), and eight known triterpene alcohols isolated in this study were evaluated in ear inflammation in mice induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). The 50% inhibitory dose of these triterpenes for TPA-induced inflammation (1 μg per ear) was 0.2-0.9 mg/ear.
56 citations
TL;DR: The inhibitory effects of gymnemosides-c, -d, -e, and -f and principal triterpene glycosides from G. sylvestre on glucose uptake in rat small intestinal fragments were examined, and gymnemic acids II, III, and IV, gymnemasaponin V, and gymnemoside-f were found to exhibit the inhibitory activity.
Abstract: Following the characterization of gymnemosides-a and -b, new triterpene glycosides, gymnemosides-c, -d, -e, and -f, were isolated from the leaves of Gymnema (G) sylvestre R BR Their chemical structures were elucidated on the basis of chemical and physicochemical evidence as follows : 21-O-benzoyl-28-O-acetylgymnemagenin 3-O-β-D-glycopyranosiduronic acid (gymnemoside-c), 23-O-[β-D-xylopyranosyl (1→6)-β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl] gymnestrogenin (gymnemoside-d), 23-O-[β-D-xylopyranosyl (1→6)β-D-glopyranosyl (1→6)-β-D-glucopyranosyl]-28-O-[β-D-glucopyranosyl (1→6)-β-D-glyucopyranosyl] 23-hydoxylongispinogenin (gymnemoside-e), 23-O-[β-D-xylopyranosyl (1→6)-β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl]-28-O-[β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl] 3β, 16β, 23, 28-tetrahydroxyolean-18-ene (gymnemoside-f) The inhibitory effects of gymnemosides-c, -d, -e, and -f and principal triterpene glycosides from G sylvestre on glucose uptake in rat small intestinal fragments were examined, and glymnemic acids II, III, and IV, gymnemasaponin V, and gymnemoside-f were found to exhibit the inhibitory activity
55 citations
TL;DR: Three new polyoxygenated triterpenes and six new quinovic acid glycosides have been isolated from Uncaria tomentosa by spectral methods.
51 citations
TL;DR: ChEN et al. as mentioned in this paper characterized dammarane-type triterpene oligoglycosides, including notoginsenosides, and a novel acetylenic fatty acid glycoside, β-sophoroside.
Abstract: Following the characterization of notoginsenosides-A, -B, -C, and -D, new dammarane-type triterpene oligoglycosides, notoginsenosides-E, -G, -H, -I, and -J, and a novel acetylenic fatty acid glycoside, notoginsenic acid β-sophoroside, were isolated from the glycoside fraction with hepatoprotecting activity obtained from the dried roots of Panax notoginseng (BURK.) F. H. CHEN. Their chemical structures were elucidated on the basis of chemical and physicochemical evidence as follows : notoginsenoside E; 3-O-[β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl]-20-O-(β-D-glucopyranosyl)-3β, 12β, 20(S)-trihydroxy-25-hydroperoxydammar-23-ene, G; 3-O-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl]-20-O-(β-D-glucopyranosyl)-3β, 7β, 20(S)-trihydroxydammar-5, 24-diene, H; 6-O-[β-D-xylopyranosyl(1→2)-β-D-glucopyranosyl]-20-O-(β-D-glucopyranosyl)-3β, 6α, 12β, 20(S), 25-pentahydroxydammar-23-ene, I; 3-O-[β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl]-20-O-[β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl]-3β, 20(S)-dihydroxydammar-24-ene, J; 6-O-(β-D-glucopyranosyl)-20-O-(β-D-glucopyranosyl)-3β, 6α, 12β, 20(S), 24ζ, 25-hexahydroxydammarane, and notoginsenic acid β-sophoroside; 10-hydroxydaca-4, 6-diynoic acid 10-O-β-D-glucopyranosyl (1→2)-β-D-glucopyranoside, respectively.
TL;DR: A validated method using the acetate derivatives of sterols instead of their silyl ethers is presented, and GC/mass spectrometric structure of the assigned retention times was confirmed for the sterols and triterpene diols.
Abstract: Alkaline hydrolysis was performed on a series of different vegetable oils. The unsaponifiable lipid matter was extracted with ethyl ether, and the class of 4,4-desmethylsterols (sterols) plus the triterpene diols (diols) erythrodiol, uvaol, and betulinol were isolated by thin-layer chromatography. A validated method using the acetate derivatives of sterols instead of their silyl ethers is presented. The acetate derivatives were analyzed by high resolution gas chromatography (HRGC). Retention time, precision, recovery studies, and absolute response factors were calculated for these esters, and GC/mass spectrometric structure of the assigned retention times was confirmed for the sterols and triterpene diols.
TL;DR: Two new triterpenoid saponins, 3-O]-beta-D-2-O-sulphonylglucopyranosyl]-quinovic acid-28-O-[beta- D-glucanalyst] ester (zygophyloside G), and seven known sapon Ins have been isolated by NMR spectroscopy.
TL;DR: Four new taraxastane triterpene glycosides, named eclalbasaponins VII–X were isolated from the dried whole plants of Eclipta alba, and the structures were characterized as 3β,20β,16β- and 3 β,20 β,28-trihydroxytaraxastanes glycoside and their sulphated saponins on the basis of spectral data.
TL;DR: The methanol extract of the outer bark of Tripterygium hypoglaucum (Levl) has been found to yield five new triterpenes: 2,3-seco 2,24-epoxy-D:A-friedoolenane-2, 24-olide-29-oic acid named celastolide, 2,23-dihydroxy-3-methoxy-6-oxoxo-1,3,5(10), 8-tetraene-24-nor,D:
TL;DR: Eighteen dammarane-type triterpenes were obtained from the whole plant of Cleome africana by means of cytotoxic bioassay-directed fractionation, twelve of them were novel compounds whose structures were elucidated by various spectroscopic methods.
TL;DR: The characterization of taxifolin, alpha-spinasterol glucoside, Mi-glycoside 1, and two new triterpenoid saponins mimusopside A and B were isolated from the seeds of Mimusops elengi by a combination of LSIMS, FABMS, 1H and 13C NMR and some strategic chemical transformations.
TL;DR: Two novel triterpenoid saponins, named mussaendosides U and V, together with one known saponin and four known triter penes were isolated from the aerial parts of Mussaenda pubescens (Rubiaceae).
TL;DR: In this article, two cycloartane-type triterpenoids were isolated from the leaves of Aglaia harmsiana using 1H, 13C and 2D NMR techniques.
TL;DR: Six saponins, cyclaminorin (1), deglucocyclamin (2), cyclacoumin (3), cyclamin (4), isocyclam (5), and mirabilin (6) were isolated from the tubers of Cyclamen mirabile and the structure elucidation of this compound was accomplished using both spectral and chemical methods.
Abstract: Six saponins, cyclaminorin (1), deglucocyclamin (2), cyclacoumin (3), cyclamin (4), isocyclamin (5), and mirabilin (6) were isolated from the tubers of Cyclamen mirabile. Compound 6 is a new natural compound, and its structure was established as 3-{O-β-[[β-d-xylopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→6)]-β-d-glucopyranosyl-(1→4)]-[β-d-glucopyranosyl-(1→2)]-α-l-arabinopyranosyl}-3β,16α,28-trihydroxyolean-12-en-30-oic acid (6). The structure elucidation of this compound was accomplished using both spectral and chemical methods. Antimicrobial and uterocontractile activities of the saponins were also investigated.
TL;DR: Akaterpin (1), an inhibitor of phosphatidylinositol-specific phospholipase C, was isolated from an acetone extract of the marine sponge Callyspongia sp. Structural determination by 2D-NMR spectroscopy revealed that it was a novel triterpene with the hydroquinone disulfate.
TL;DR: In this paper, three pregnanes and two known cycloartane-type triterpenoid hydroperoxides were isolated from the leaves of Aglaia grandis and their structures were determined using 1 H, 13 C and 2D NMR techniques.
TL;DR: Extracts from the aerial parts of Sanicula europaea L. were investigated for their anti-HIV activity, and the 50% ethanolic extract was shown to exhibit the highest activity.
Abstract: Extracts from the aerial parts of Sanicula europaea L. were investigated for their anti-HIV activity, and the 50% ethanolic extract was shown to exhibit the highest activity. A new triterpene saponin glycoside, 21β-(angeloyloxy)-3-O-[β-d-arabinopyranosyl(1→4)-β-d-glucopyranosyl(1→3)-β-d-glucuronopyranosyl propyl ester]-3β,15,16,22α,28β-pentahydroxy-Δ12-oleanene, saniculoside N (1), in addition to the known phenolic acids, rosmarinic acid (2), and caffeic acid (3) were isolated as major components. Rosmarinic acid was established as the principal active substance.
TL;DR: Four new oleanane-type triterpene glycosides, pithedulosides H-K (1-4), were isolated from the seeds of Pithecellobium dulce by extensive NMR experiments and chemical methods.
Abstract: Four new oleanane-type triterpene glycosides, pithedulosides H−K (1−4), were isolated from the seeds of Pithecellobium dulce. Their structures were established by extensive NMR experiments and chemical methods. Compounds 1−3 comprised acacic acid as the aglycon and either monoterpene carboxylic acid and its xyloside or monoterpene carboxylic acid as the acyl moiety at C-21. The oligosaccharide moieties linked to C-3 and C-28 were determined as α-l-arabinopyranosyl-(l→2)-α-l-arabinopyranosyl-(1→6)-[β-d-glucopyranosyl-(l→2)]-β-d-glucopyranosyl and α-l-arabinofuranosyl-(l→4)-[β-d-glucopyranosyl-(l→3)]-α-l-rhamnopyranosyl-(l→2)-β-d-glucopyranosyl ester, respectively. Compound 4 was established as an echinocystic acid 3-O-glycoside having the same sugar sequences as 1−3. Also obtained in this investigation was the known compound 5, which was identified as echinocystic acid 3-O-β-d-xylopyranosyl-(l→2)-α-l-arabinopyranosyl-(1→6)-[β-d-glucopyranosyl-(l→2)]-β-d-glucopyranoside.
TL;DR: Nine new triterpene glucosides, named cumingianosides G-O (4-7, 9, 12-15), containing a 14,18-cycloapotirucallane-type skeleton were isolated from a cytotoxic fraction of the leaves of Dysoxylumcumingianum, showing significant cytotoxicity against leukemia and melanoma cell lines.
Abstract: Nine new triterpene glucosides, named cumingianosides G-O (4-7, 9, 12-15), containing a 14,18-cycloapotirucallane-type skeleton were isolated from a cytotoxic fraction of the leaves of Dysoxylum cumingianum. The structures of the new compounds were established on the basis of chemical and spectral examinations. Evaluation of the cytotoxic activity of cumingianosides G-O showed that cumingianoside M exhibited significant (< 4 microM) cytotoxicity, especially against leukemia and melanoma cell lines.
TL;DR: In this article, the first report of the isolation of 2-oxygenated 3-O-acylated triterpenoids from Eucalyptus genus was made.
Abstract: Ten pentacyclic triterpenoids including two new constituents, eucalyptic acid and eucalyptolic acid, and eight known compounds (ursolic acid lactone, betulinic acid, oleanolic acid, ursolic acid, 3β-O-cis-p-coumaroylalphitolic acid, alphitolic acid, 3β-O-trans-p-coumaroylalphitolic acid, and 3β-O-trans-p-coumaroylmaslinic acid) have been isolated from the fresh and uncrushed leaves of Eucalyptus camaldulensis var. obtusa. Their structures were elucidated through detailed 1D and 2D NMR studies. The new natural products were characterized as 2α-hydroxy-3β-E-feruloyloxy-lup-20(29)-en-28-oic acid and 2α-hydroxy-3β-E-feruloyloxy-olean-12-en-28-oic acid, respectively. Except for oleanolic acid, all the known compounds are hitherto unreported from this plant. This is the first report of the isolation of 2-oxygenated 3-O-acylated triterpenoids from Eucalyptus genus.
TL;DR: In this paper, triterpenoid saponins latifolosides A-E were isolated from the leaves of Ilex latifolia, along with a known compound, and their chemical structures have been elucidated on the basis of the chemical and spectral methods.
TL;DR: The callus of T. wilfordii var. regelii afforded three pentacyclic triterpenes as discussed by the authors, named triptocallic acid C, D, and Triptocalline A, which were determined by spectroscopic analyses.
TL;DR: Compounds 1 and 2 showed good inhibitory activity against DNA synthesis in human leukemia HL-60 cells with IC50 values of 8.8 and 6.1 microM, respectively.
Abstract: A further investigation of Aster lingulatus has led to the isolation of two additional novel triterpene saponins, asterlingulatoside C [3-O-β-d-glucopyranosyl-3β,16α-dihydroxyolean-12-en-28-oic acid 28-O-β-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside] (1) and asterlingulatoside D [3-O-β-d-glucopyranosyl-3β,16α-dihydroxyolean-12-en-28-oic acid 28-O-β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside] (2). Elucidation of the structures of 1 and 2 was mainly based on FABMS and 1D and 2D homonuclear and heteronuclear NMR techniques. Compounds 1 and 2 showed good inhibitory activity against DNA synthesis in human leukemia HL-60 cells with IC50 values of 8.8 and 6.1 μM, respectively.
TL;DR: In this paper, the structure of four triterpene dimers, cangorosins, isolated from Maytenus ilicifolia Mart, were reported to consist of two tritene units joined by an ether bond formed between the two units.
Abstract: Structures of four triterpene dimers, cangorosins, isolated from Maytenus ilicifolia Mart., were previously reported to consist of two triterpene units joined by an ether bond formed between the tw...