New Triterpenes from the Heartwood of Melaleuca leucadendron L.

Fourteen chemical constituents were isolated from the CHCl₃ soluble portion of the heartwood of Melaleuca leucadendron L. These compounds include β-sitosterol (1) , β-sitostenone (2) , 6-hydroxy-4,6-dimethyl-3-hepten-2-one (3) , naphthalene (4) , squalene (5) , 2α3β-dihydroxyurs-12-en-28-oic acid (6) , 3β-hydroxylup-20(29)-en-27,28-dioic acid (7) , 2α,3β-dihydroxyolean-12-en-28-oic acid (8) , 3β,23-dihydroxyolean-12-en-28-oic acid (9) , 2α,3β,23-trihydroxyolean-12-en-28-oic acid (10) , 3β-trans-p-coumaroyloxy-2α,23-dihydroxyolean-12-en-28-oic acid (11) , and three novel oleanane derivatives 23-trans-p-coumaroyloxy-2α,3β-dihydroxyotean-12-en-28-oic acid (12), 3β-trans-caffeoyloxy-2α,23-dihydroxyolean-12-en-28-oic acid (13) , and its isomer 3β-cis-caffeoyloxy-2α,23-dihydroxyolean-12-en-28-oic acid (14) , The three novel compounds were characterized as the two and three O-methylated derivatives, respectively.     

Terpene glycosides from the roots of Sanguisorba officinalis L. and their hemostatic activities

Guided by a hemostasis bioassay, seven terpene glycosides were isolated from the roots of Sanguisorba officinalis L. by silica gel column chromatography and preparative HPLC. On the grounds of chemical and spectroscopic methods, their structures were identified as citronellol-1-O-α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside (1), geraniol-1-O-α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside (2), geraniol-1-O-α-Larabinopyranosyl-(1→6)-β-D-glucopyranoside (3), 3β-[(α-L-arabinopyranosyl)oxy]-19α-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranoside (4), 3β-[(α-L-arabinopyranosyl)-oxy]-19α-hydroxyurs-12-en-28-oic acid 28-β-D-glucopyranoside (ziyu-glycoside I, 5), 3β,19α-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranoside (6) and 3β,19α-dihydroxyurs-12-en-28-oic acid 28-β-D-glucopyranoside (7). Compound 1 is a new mono-terpene glycoside and compounds 2, 3 and 5 were isolated from the Sanguisorba genus for the first time. Compounds 1–7 were assayed for their hemostatic activities with a Goat Anti-Human α2-plasmin inhibitor ELISA kit, and ziyu-glycoside I (5) showed the strongest hemostatic activity among the seven terpene glycosides. This is the first report that ziyu-glycoside Ι has strong hemostatic activity.     

A new triterpene from the plant of uncaria macrophylla

Our ongoing investigations on the stem bark of Uncaria macrophylla afforded a new ursolic triterpene, 3β,6β,19α-trihydroxy-urs-12-en-28-oic acid-24-carboxylic acid methyl ester (1), named uncariursanic acid, and three known ursolic triterpenes including 3β,6β,19α-trihydroxy-23-oxo-urs-12-en-28-oic acid (2), 3β,6β,19α-trihydroxy-urs-12-en-28-oic acid (3) and ursolic acid (4). Their structures were elucidated by extensive spectral methods, including 1D and 2D NMR and HR-ESI-MS. The cytotoxicities of the four compounds were evaluated against two cancer cell lines (MCF-7 and HepG2) by the MTT method, and only compound 4 exhibited potent activity.     

Microbial hydroxylation and glycosidation of oleanolic acid by Circinella muscae and their anti-inflammatory activities

Biotransformation of oleanolic acid (OA) by Circinella muscae AS 3.2695 was investigated. Nine hydroxylated and glycosylated metabolites (1–9) were obtained. Their structures were elucidated as 3β,7β-dihydroxyolean-12-en-28-oic acid (1), 3β,7β,21β-trihydroxyolean-12-en-28-oic acid (2), 3β,7α,21β-trihydroxyolean-12-en- 28-oic acid (3), 3β,7β,15α-trihydroxyolean-12-en-28-oic acid (4), 7β,15α-dihydroxy- 3-oxo-olean-12-en-28-oic acid (5), 7β-hydroxy-3-oxo-olean-12-en-28-oic acid (6), oleanolic acid-28-O-β-D-glucopyranosyl ester (7), 3β,21β-dihydroxyolean-12-en-28- oic acid-28-O-β-D-glucopyranosyl ester (8), and 3β,7β,15α-trihydroxyolean-12-en- 28-oic acid-28-O-β-D-glucopyranosyl ester (9) by spectroscopic analysis. Among them, compounds 4 and 9 were new compounds. In addition, anti-inflammatory activities were assayed and evaluated for the isolated metabolites. Most of the metabolites exhibited significant inhibitory activities on lipopolysaccharides-induced NO production in RAW 264.7 cells.     

Two oleananes from Ammannia auriculata Willd

Two new compounds: 3-β,15-α,23,28-tetrahydroxyolean-12-en-3-O-arabinopyaranoside and 3-β,23,28-trihydroxy-olean-12-en-3-O-β-D-glucopyranoside were isolated from the aerial parts of Ammania auriculata along with the known compounds kaempferol, β-sitosterol-3-O-β- D-glucoside, 2-α,3-β,23-trihydroxyolean-12-en-28-oic acid-28-O-β-D-glucopyranoside, quercetin, kaempferol-3-O-α-L-arabinofuranoside, kaempferol-3-O-β-D-xylopyranoside and ellagic acid. Structures of these compounds were elucidated on the basis of their spectroscopic data (NMR, UV, MS and IR spectra). The antioxidant activities of the total extract, the fractions CH(2)Cl(2), EtOAc and the remaining aqueous together with the compounds 1, 6 and 9 were comparable with that of the standard antioxidant, ascorbic acid.     

五叶木通中一个新的三萜成分

对五叶木通藤茎进行了较为系统的研究, 从其体积分数为80%的乙醇提取物的正丁醇部分分离得到3个三萜成分, 通过理化性质和波谱分析鉴定为: 3α,24-二羟基-30-去甲齐墩果烷-12,20(29)-双烯-28-酸(Ⅰ); 3α,24,29-三羟基齐墩果烷-12-烯-28-酸(Ⅱ); 2α,3β,23-三羟基齐墩果烷-12-烯-28-酸(Ⅲ). 其中化合物Ⅱ为新化合物, 命名为木通茎酸(Quinatic stem acid).     

Platycoside N: a new oleanane-type triterpenoid saponin from the roots of Platycodon grandiflorum

A new oleanane-type triterpenoid saponin, named platycoside N (1), together with six known saponins, was isolated from the roots of Platycodon grandiflorum. On the basis of acid hydrolysis, comprehensive spectroscopic data analyses and comparison with the spectral data of the known compounds, its structure was elucidated as 3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-28-oic acid 28-O-β-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside. The six known compounds were platycodin D (2), deapioplatycodin D (3), platycodin D3 (4), deapioplatycodin D3 (5), platycoside E (6) and deapioplatycoside E (7).     

Two new triterpenoids from the seeds of blackberry (Rubus fructicosus)

Two new ursane-type triterpenoids (1, 2) attached to isopropylidenedioxy group were isolated from the seeds of blackberry (Rubus fructicosus L., Rosaceae) along with two known ursane-type triterpenoids, 2,3-O-isopropylidenyl-2α,3α,19α-trihydroxyurs-12-en-28-oic acid (3) and 1β-hydroxyeuscaphic acid (4). The chemical structures of 1 and 2 were determined to be 2,3-O-isopropylidene-1β,2β,3β,19α-tetrahydroxyurs-12-en-28-oic acid and 1,2-O-isopropylidene-1β,2α,3α,19α-tetrahydroxyurs-12-en-28-oic acid, respectively, based on spectroscopic data. Additionally, their cytotoxic activity towards HL-60 human leukaemia cells was evaluated. Among them, 3 demonstrated a clear cytotoxic activity with 72.8 μM of IC₅₀ value.     

New triterpene glucosides from the roots of Rosa laevigata Michx

Two new ursane-type triterpene glucosides, 2alpha,3alpha,24-trihydroxyurs-12,18-dien-28-oic acid beta-D-glucopyranosyl ester (1) and 2alpha,3alpha,23-trihydroxyurs-12,19(29)-dien-28-oic acid beta-D-glucopyranosyl ester (2), were isolated from the roots of Rosa laevigata, together with three known compounds: 2alpha,3beta,19alpha-trihydroxyurs-12-en-28-oic acid beta-Dglucopyranosyl ester (3), 2alpha,3alpha,19alpha-trihydroxyurs-12-en-28-oic acid beta-D-glucopyranosyl ester (4) and 2alpha,3beta,19alpha,23-tetrahydroxyurs-12-en-28-oic acid beta-D-glucopyranosyl ester (5). The structures of new compounds were established on the basis of detailed 1D and 2D NMR spectroscopic analyses. Compounds 2 and 5 exhibited modest in vitro antifungal activities against Candida albicans and C. krusei.     

Triterpenoids from the roots of Sanguisorba tenuifolia var. Alba

The ethyl acetate soluble fraction from the roots of Sanguisorba tenuifolia was found to have a hypoglucemic effect in alloxan-induced diabetic rats. Two new triterpenoids, identified as 2-oxo-3β,19α-dihydroxyolean-12-en-28-oic acid β-D-gluco-pyranosyl ester (1) and 2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid β-D-glucopyranosyl ester (4) were isolated from this fraction, along with thirteen known triterpenoids. Their structures were elucidated by chemical and spectroscopic methods. All these compounds demonstrated inhibitory activities against α-glucosidase with IC?? values in the 0.62-3.62 mM range.     

Two new lupene-type triterpenoids from the roots of Liquidambar formosana

Two new lupene-type triterpenoids, 3β,6β-dihydroxylup-20(29)-en-28-oic acid β-glucopyranosyl ester (1) and 2α-acetoxyl-3β,6β-dihydroxylup-20(29)-en-28-oic acid β-glucopyranosyl ester (2), along with 18 known compounds, were isolated from Liquidambar formosana. The structures were elucidated on the basis of spectroscopic methods, including UV, IR, ESIMS, 1D- and 2D-NMR experiments, as well as by comparison of the spectral data with those of related compounds.     

Platycoside O, a new triterpenoid saponin from the roots of Platycodon grandiflorum

A new unusual minor triterpenoid saponin, platycoside O (1), was isolated from the 75% EtOH extract obtained from the roots of Platycodon grandiflorum, together with four known saponins: platycoside M-3 (2), platycoside J (3), platycoside F (4) and platycoside B (5). The structure of 1 was determined as 3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-24-methoxyl, 24-oxo-28-oic acid 28-O-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside on the basis of spectral analysis and chemical evidence.     

Two antifungal active triterpenoid saponins from the seeds of Lathyrus plants

Two novel triterpenoid glycosides have been isolated from butanolic seeds extract of two varieties of Lathyrus plants, i.e. Lathyrus ratan and Lathyrus aphaca. Their structures were elucidated as 3-O-[β-D-glucuronopyranosyl-(1?→?4)-α-L-arabinopyranosyl-(1?→?2)-α-L-arabinopyranosyl]-olean-11,13(18)-dien-28-oic acid (1) and 3-O-{β-D-xylopyranosyl-(1 → 2)-β-D-glcopyranosyl-(1?→?4)-[β-D-glucopyranosyl-(1?→?2)]-β-D-xylopyranosyl}-2,16α-dihydroxy-4-hydroxymethyl urs-12-en-28-oic acid (2) on the basis of spectral evidences, i.e. FTIR, (1)H-NMR, (13)C-NMR, ESI-MS and FAB-MS data. The isolated saponins were tested for their antifungal activity. Compound 1 showed maximum inhibition against Colletotrichum dematium (77.8%), whereas compound 2 showed maximum inhibition against Alternaria alternata (53.9%).     

A new triterpene and a saponin from Centella asiatica

A new triterpene and a saponin,named 2α,3β,23-trihydroxyurs-20-en-28-oic acid(1)and 2α,3β,23-trihydroxyurs-20-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester(2),have been isolated from the aerial part of Centella asiatica.Their structures were elucidated by spectral methods,including 2D-NMR spectra.     

Two new triterpenes from Duchesnea indica

Two new triterpenes,2α,3β-dihydroxyurs-12-en-18,19-epoxy-28-oic acid(1)and 18,19-seco,2α,3α-dihydroxyl-19-oxo-urs-11, 13(18)-dien-28-oic acid(2)were isolated from the herbaceous part of Duchesnea indica.Their structures were elucidated by spectroscopic analysis,including 2D NMR technique.The isolated compounds exhibited moderate cytotoxic activities against HeLa and L929 cell lines.     

A new polyoxygenated triterpene and two new aeginetic acid quinovosides from the roots of Rehmannia glutinosa

A new minor polyoxygenated triterpene named glutinolic acid (1) and two new aeginetic acid quinovosides (2, 3) were isolated from the roots of Rehmannia glutinosa LIBOSCH. (Scrophulariaceae) cultivated in Gunwi-gun, Korea. The structures of these compounds were established as 3α,19α,20β,24,30-pentahydroxyurs-12-en-28-oic acid (1, glutinolic acid), aeginetic acid 5-O-β-D-quinovoside (2) and aeginetoyl ajugol 5″-O-β-D-quinovoside (3) on the basis of chemical and spectroscopic evidence.     

Two new labdane diterpenoids from the rhizomes of Isodon yuennanensis

Two new labdane diterpenoids, s-trans-8(17),12E,14-labdatrien-20-oic acid (1), s-trans-12E,14-labdadien-20,8β-olide (2), along with 10 known compounds, hinokiol (3), ursonic acid (4), 2α,3α-dihydroxyolean-12-en-28-oic acid (5), 2α,3β,23-trihydroxyolean-12-en-28-oic acid (6), ethyl 3-(3,4-dihydroxyphenyl)lactate (7), ethyl rosmarinate (8), (Z,E)-2-(3,4-dihydroxyphenyl)ethenyl caffeic ester (9), tridecanoic acid (10), β-sitosterol (11) and daucosterol (12), were isolated from the 70% acetone extract of the rhizomes of Isodon yuennanensis. Their structures were elucidated based on the analyses of extensive spectroscopic data and physicochemical properties.     

Saponins from Amaranthus hypochondriacus.

Four triterpenoid saponins were isolated from Amaranthus hypochondriacus which are grain crops in the Nepal, Mexico and South America. Their structures were elucidated based on spectral evidence to be: (1) 3-O-alpha-L-rhamnopyranosyl(1----3)-beta-D-glucuronopyranosyl-2 beta,3 beta-dihydroxyolean-12-en-28-oic acid 28-O-beta-D-glucopyranosyl ester. (2) 3-O-alpha-L-rhamnopyranosyl(1----3)-beta-D-glucuronopyranosyl-2 beta,3 beta- dihydroxyolean-12-en-23-al-28-oic acid 28-O-beta-D-glucopyranosyl ester; (3) 3-O-alpha-L-rhamnopyranosyl(1----3)-beta-D-glucuronopyranosyl-2 beta, 3 beta-dihydroxy-30-norolean-12,20(29)-dien-28-oic acid 28-O-beta-D-glucopyranosyl ester. (4) 3-O-alpha-L-rhamnopyranosyl (1----3)-beta-D-glucuronopyranosyl-2 beta, 3 beta-dihydroxy-30-norolean-12, 20(29)-dien-23-al-28-oic acid 28-O-beta-D-glucopyranosyl ester.     

中药白头翁的皂素III.配基结构的研究

The structure of anemosapogenin 1 has been proved to be 3β, 23-dihydroxylup-20 (29)-en-28-oic acid on the basis of spectroscopic (IR, ^1H NMR, C-13 NMR, MS) evidences and chemical transformations, namely, the formation of acetonide 3 from 6, the acid catalysed rearrangement of 1 and 2 into 18 (α)-oleanan-28, 19β-olide derivatives 4 and 5 respectively and finally, the conversion of 7 through LiAiH4 reduction into the known compound, lup-20(29)-ene- 3β, 23, 28-triol. The third sugar component of the saponin is shown to be arabinose.     

The Terpenoids of Maytenus boaria MOL. (Celastraceae)

The known triterpenoids β-amyrin (= olean-12-en-3β-ol; 22 ), lupeol (= lup-20(29)-en-3β-ol; 17 ), betulin (= lup-20(29)-ene-3β,28-diol; 18 ), lup-20(29)-ene-3β,30-diol ( 20 ), oleanolic acid (= 3β-hydroxyolean-12-en-28-oic acid; 21 ), and betulonic acid (= 3-oxolup-20(29)-en-28-oic acid; 19 ), together with epicatechol (= cis-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol; 23 ), 5′-O-methylgallocatechol (= trans-2-(3,4-dihydroxy-5-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol; 24 ), and 4-hydroxybenzaldehyde were isolated from the aerial parts of Maytenus boaria (MOL. ). Additonally, the eight 4,C⁴-dihydro-β-agarofuran sesquiterpenoids 1–8 , one of them a diol with a (4R)-configuration, and compound 9 were present in the extract. The structures of these compounds were established by spectroscopic and chemical means.