A new triterpenoid saponin from Abrus precatorius Linn

A new triterpenoid saponin, 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl subprogenin D (1), together with six known triterpenoids: subprogenin D (2), abrusgenic acid (3), triptotriterpenic acid B (4), abruslactone A (5), abrusogenin (6) and abrusoside C (7) were isolated from the leaves and stems of Abrus precatorius. Their structures were elucidated on the basis of physical and NMR analysis, respectively. Compounds 5 and 6 showed moderate cytotoxicity against MCF-7, SW1990, Hela, and Du-145 cell lines. Compounds 1, 2 and 4 were isolated from this plant for the first time.     

Structure elucidation of sweet-tasting cycloartane-type saponins from ginseng oolong tea and Abrus precatorius L. leaves

The composition of ginseng oolong a widely used tea product was investigated. A new sweet-tasting cycloartane-type saponin 3β-O-[β-D-glucuronopyranosyl(1→2)]-β-D-6-acetylglucopyranosyl)-(20S,22S)-3β,22-dihydroxy-9,19-cyclolanost-24-en-26,29-oic acid (9), along with five new compounds, was identified in the methanolic extract of the ginseng oolong tea. Structural elucidation was conducted by spectroscopic methods, including 1D- and 2D-NMR, HR-MS, HPLC-LITMS/MS. It was shown that these compounds have different sugar chains connected to the abrusogenin molecule. Then saponin profiles of four commercially available ginseng oolong samples and Abrus precatorius L. leaves were compared and the presence of three known abrusosides and six new acetyl and malonyl abrusogenin derivatives was proved. The original ginsenosides were not detected in the extract, therefore, abrusosides could serve as a replacement responsible for the sweet taste of the tea.     

Activity-directed-fractionation and isolation of four antibacterial compounds from Abrus precatorius L., roots

Root extracts of the plant Abrus precatorius L., was tested for antibacterial activity. Various solvent fractions exhibited inhibitory activity against 13 gram-positive and gram-negative bacteria. Root extracts were analyzed by thin layer chromatography (TLC). The antibacterial activity was localized to specific chromatophores in the chloroform fraction through a bioautography assay. It was found localized to four chromatophores out of seven. The chromatophores were isolated from the TLC plates and rechecked for activity against Slaphylococcus aureus A, using a disc diffusion assay. Among the four active principles isolated, AP 3 (Rf 0.87) exhibited maximum activity i.e. 56% inhibition of growth of S. aureus A, in disc diffusion assay compared to the standard antibiotic Ampicillin. Results of this study suggest that chloroform extractable phytochemicals in A. precatorius L. may yield promising molecules with antibiotic activity.     

Activity-directed fractionation and isolation of four antibacterial compounds from Abrus precatorius L. roots

Root extracts of the plant Abrus precatorius L. was tested for antibacterial activity. Various solvent fractions exhibited inhibitory activity against 13 gram-positive and gram-negative bacteria. Root extracts were analyzed by thin layer chromatography. The antibacterial activity was localized to specific chromatophores in the chloroform fraction through a bioautography assay. It was found localized to 4 chromatophores out of 7. The chromatophores were isolated from the TLC plates and rechecked for activity against Staphylococcus aureus A, using a disc diffusion assay. Among the four active principles isolated, AP 3 (Rf 0.87) exhibited maximum activity, i.e., 56% inhibition of growth of S. aureus A, in disc diffusion assay compared to the standard antibiotic Ampicillin. Results of this study suggest that chloroform extractable phytochemicals in A. precatorius L. may yield promising molecules with antibiotic activity.     

Pentacyclic triterpenoids from leaves of Excoecaria agallocha

A new oleanane-type triterpenoid (1) and five known pentacyclic triterpenoids (2-6) were isolated from the leaves of Excoecaria agallocha. Their structures were elucidated by spectroscopic analyses. The new compound was characterized as 3beta-[(2E,4E)-5-oxo-decadienoyloxy]-olean-12-ene (1). Compounds 1-6 were found inactive in vitro against several human cancer cell lines.     

Antibacterial triterpenoids from the leaves of Ilex hainanensis Merr.

One new triterpenoid (1) and seven known analogues (2–8) were isolated from the leaves of Ilex hainanensis Merr.. Their structures were established by analysis of their MS, 1D and 2D NMR spectroscopic data and comparison with those in the literature. The antibacterial activity of compounds 1–8 were evaluated by determination of minimum inhibitory concentration using twofold microdilution broth method against Streptococcus mutans ATCC 25175 (Gram-positive) and Fusobacterium nucleatum ATCC 10953 (Gram-negative). Compounds 3 and 5 showed significant antibacterial activity against S. mutans in concentration of 9.7 μg/mL, while showed little antibacterial activity against F. nucleatum. On the contrary, the inhibitory activity of compounds 1, 2 and 6 against F. nucleatum were higher than them against S. mutans.     

New triterpenoids from Tricholoma saponaceum

Six new triterpenes, saponaceolides E (1), F (2), and G (3), and saponaceoic acids I (4), II (5), and III (6) were isolated from the fruiting body of the fungus Tricholoma saponaceum, and their structures were elucidated on the base of extensive NMR experiments. Compounds 1 and 2 exhibited inhibitor activity against B16 and L929 cells.     

New triterpenoids from Gentiana lutea

Three new triterpenoids, 2,3-seco-3-oxours-12-en-2-oic acid, 2,3-seco-3-oxoolean-12-en-2-oic acid, and betulin 3-O-palmitate, have been isolated from the rhizomes and roots of Gentiana lutea, together with five known ones. The structures of the new compounds were determined by spectral and chemical methods.     

New triterpenoids from Corchorus trilocularis

Two new tetracyclic triterpenoid trilocularol A and trilocularol A 3-glucoside and one pentacyclic triterpenoid tirlocularoside A were isolated from Corchorus trilocularis L., their structure were elucidated as 3beta,6alpha,16alpha,20(S),27-pentahydroxydammar-24(Z)-ene (1), 3beta-D-glucopyranosyloxy-6alpha,16alpha,20(S),27-tetrahydroxydammar-24(Z)-ene (2) and 2alpha,3beta,19alpha,30-tetrahydroxyurs-12-en-24,28-dioic acid 28-O-beta-D-glucopyranosyl ester (3). respectively, on the basis of detailed spectroscopic studies.     

Tetracyclic triterpenoids from the leaves of Azadirachta indica and their insecticidal activities

A new tetranortriterpenoid, meliatetraolenone [24,25,26,27-tetranor-apotirucalla-(apoeupha)-6alpha-O-methyl, 7alpha-senecioyl(7-deacetyl)-11alpha,12alpha,21,23-tetrahydroxy-21,23-epoxy-2,14,20(22)-trien-1,16-dione] (1) was isolated from the methanolic extract of fresh leaves of Azadirachta indica along with the known compound odoratone (3) which was hitherto unreported from this source. Their structures have been elucidated by spectral studies including 2D NMR. The insecticidal activities of 1 as well as those of odoratone (3) are reported. 1 and odoratone both showed mortality on fourth instar larvae of mosquitoes (Anopheles stephensi) with LC(50) values of 16 and 154 ppm, respectively.     

New triterpenoids from the stem barks of Drypetes tessmanniana

The MeOH extract of the stem barks of Drypetes tessmanniana (Euphorbiaceae) afforded two new triterpene derivatives characterized as 3beta-O-(E)-3,5-dihydroxycinnamoyl-11-oxo-olean-12-ene and 3beta,6alpha-dihydroxylup-20(29)-ene together with seven known compounds. Their structures were established on the basis of spectral analysis.     

New sesquiterpenoid and triterpenoids from the fruits of Rhizophora mucronata

A new sesquiterpene (1) and two new pentacyclic triterpenoid esters (2, 3) together with three known compounds (4-6) were isolated from the fruits of Rhizophora mucronata. Their structures were elucidated by analysis of their spectroscopic data. The new compounds were characterized as 3-hydroxy-3,7,11-trimethyl-9-oxododeca-1,10-diene (mucronatone, 1), 3beta-E-caffeoyltaraxerol (2) and 3beta-Z-caffeoyltaraxerol (3).     

Three novel tetracyclic triterpenoids of biogenetic interest from the leaves of Azadirachta indica

From the methanolic extract of Azadirachta indica leaves, we have isolated three new tetracyclic triterpenoids of biogenetic interest, namely, melianol 1, desfurano-desacetylnimbin-17-one 2 and meliatetraone 3. The structure elucidation is based on extensive spectral studies including ¹H–¹H-COSY, NOESY, HMQC, and HMBC experiments.     

New sterols and triterpenoids from four edible mushrooms

Four edible mushrooms, Panellus serotinus, Lepista nuda, Tricholoma matsutake and Naematoloma sublateritium, have been investigated chemically. Two new sterols, 5alpha,9alpha-epidioxy-(22E)-ergosta-7,22-diene-3beta,6alpha-diol (1) and 5alpha,9alpha-epidioxy-(22E)-ergosta-7,22-diene-3beta,6beta-diol (2), have been isolated from Panellus serotinus. Compound 2 was also isolated from Lepista nuda. A new sterol, 3beta,5alpha,9alpha,14beta-tetrahydroxy-(22E)-ergosta-7,22-dien-6-one (3), and compound 2 have been isolated from Tricholoma matsutake. Three new triterpenoids, sublateriols A-C (4-6), have been isolated from Naematoloma sublateritium. The structures of the new compounds were elucidated on the basis of their spectral data.     

New triterpenoids from the orchids Scaphyglottis livida and Nidema boothii

Two new triterpenoids, nidemin (1), a modified lanostane, and 9,19-cyclolanosta-24,24-dimethyl-25-en-3beta-yl trans-p-hydroxycinnamate (2) have been isolated from the orchids Nidema boothii and Scaphyglottis livida, respectively. The isolates were characterized by spectral methods. The structure of nidemin (1) was unambiguously confirmed by X-ray analysis.     

New triterpenoids isolated from the root bark of Ulmus pumila L

Three new triterpenoids, 1-3, were isolated from the dried root bark of Ulmus pumila. Along with the three new compounds, six known triterpenoids, epifriedelanol (4), friedelin (5), oleanolic acid (6), maslinic acid (7), camaldulenic acid (8), and arjunolic acid (9) were also isolated. The structures of new compounds were established as ulmudiol (bauer-7-ene-1alpha,3beta-diol, 1), dehydroulmudiol [bauer-7,9(11)-diene-1alpha,3beta-diol, 2], and ulmuestone [3alpha-hydroxy-11alpha-(4'-hydroxy-3'-methoxy)benzoyloxybauer-1-one, 3], on the basis of extensive 1D and 2D NMR spectroscopic data interpretation. In addition, the cytotoxic activities of these compounds are also reported.     

Qingqianliusus A-N, 3,4-seco-dammarane triterpenoids from the leaves of Cyclocarya paliurus and their biological activities

Fourteen previously unreported 3,4-seco-dammarane triterpenoids named Qingqianliusus A-N (1–14), along with four known 3,4-seco-dammarane triterpenoid derivatives (15–18) were isolated from the 95 % ethanol extract of the Cyclocarya paliurus leaves. Compounds 1 and 2 possess a rare 3,11-heptacyclic lactone as natural product, and several pairs of the 3,4-seco-dammarane triterpenoid epimers with R/S configuration at C-24 were investigated and determined in detail for the first time. Compounds 8, 11, and 14 showed good α-glucosidase inhibitory effects with IC₅₀ values of 4.97 ± 0.63, 7.08 ± 0.53, and 3.76 ± 0.77 μM, respectively. Meanwhile, compound 11 was also found potent inhibition rate of 35.83 % against COX-2, as compared with the positive control celecoxib (70.28 %). In addition, compounds 3, 7, 10, and 13 exhibited outstanding cytotoxicities against human gastric cancer cell lines (BGC-823) with IC₅₀ values of 7.69 ± 0.21, 8.47 ± 0.41, 9.04 ± 0.61, and 8.86 ± 0.38 μM, respectively. Compounds 13 and 3 had modest activities on human colon cancer cell lines (HCT-116) with IC₅₀ values of 8.80 ± 0.36 and 9.45 ± 0.93 μM, respectively.     

New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana

Chromatographic separation ofn-hexane and ethyl acetate fraction of a crude methanol extract obtained from aerial parts of theScorzonera aucherianaDC collected from Sivas province of Turkey yielded nine natural compounds; two new 3-caffeoyl-quinic acid analogs (1-2), one new taraxasterol oleate (3), and six known triterpenoids taraxasterol (4), taraxasterol acetate (5), ptiloepoxide (6), lupeol (7), lupeol acetate (8), andβ-sitosterol (9) were characterized. The structures of the isolated compounds were elucidated on the basis of NMR (¹H,¹³C, COSY, HMBC, HSQC, and TOCSY), UV, FT-IR and LC-Q-TOF-MS spectrometric data.     

New cardenolides from the leaves ofGomphocarpus fruticosus

Two new glycosides, gomphotin (1) and gomphotoxin (13), and also the known gomphoside (9) have been isolated from the leaves ofGomophocarpus fruticosus. Compounds (1) and (9) contain a 4,6-dideoxyhexosulose residue as the sugar component, and (13) a 6-deoxyhexosulose, which are attached to glycolic OH groups of the aglycons by 3-O-1,2-O-2 (9, 13) and 3-O-1,4-O-2 (1) acetal-ketal bonds. The structures of the new compounds are represented by the names (3-O-1,4-O-2)-(2,3-dihydroxy-4, 6dideoxyhexulosido)-14-hydroxy-5-card-20(22)-enolide* (1) and (3-O-1,2-O-2)-(2,3,4-trihydroxy-6-deoxyhexulosido)-14-hydroxy-5-card-20(22)-enolide* (13).State Scientific Center for Drugs of the Ministry of Health and the National Academy of Sciences of the Ukraine, Kharkov, fax 441118. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 824–832, November–December, 1995. Original article submitted May 22, 1995.     

New nor-oleanane triterpenoids from the fruits of Stauntonia brachyanthera with potential anti-inflammation activity

Abstract

The continuing studies on the fruits of Stauntonia brachyanthera led to the isolations of 6 normal and nor-oleanane triterpenoids, including two new compounds, brachyantheoraside B10 (1) and brachyantheraside C1 (2). Compounds 1–3 showed inhibitory activity on lipopolysaccharide (LPS)-induced nitric oxide production in RAW 264.7 macrophages with the IC₅₀ values of 27.04, 26.22, and 21.41?μM, respectively, which were all stronger than that of indomethacin. The study not only revealed a new type of nor-oleanane triterpenoids, but also confirmed the anti-inflammation abilities of three type nor-oleanane triterpenoids as the inhibitors of NO production.