Triterpenoids from Viburnum suspensum

Three triterpenoids, 3-oxo-11,13(18)-oleanadien-28-oic acid, 24-hydroxy-3-oxo-11,13(18)-oleanadien-28-oic acid, 6β-hydroxy-3-oxo-11,13(18)-oleanadien-28-oic acid have been isolated together with the previously known virgatic acid, vibsanin B and 3-hydroxyvibsanin E from the leaves of Viburnum suspensum. Their structures were determined by spectroscopic methods and by comparison of their NMR spectral data with those of the previously known 11,13(18)-oleanadien-3β-ol.     

Triterpenoids from Viburnum suspensum

Three triterpenoids, 3-oxo-11,13(18)-oleanadien-28-oic acid, 24-hydroxy-3-oxo-11,13(18)-oleanadien-28-oic acid, 6β-hydroxy-3-oxo-11,13(18)-oleanadien-28-oic acid have been isolated together with the previously known virgatic acid, vibsanin B and 3-hydroxyvibsanin E from the leaves of Viburnum suspensum. Their structures were determined by spectroscopic methods and by comparison of their NMR spectral data with those of the previously known 11,13(18)-oleanadien-3β-ol.     

A-seco-oleane-type triterpenes from Phomopsis sp. (strain HKI0458) isolated from the mangrove plant Hibiscus tiliaceus

From the fermentation broth of an unidentified Phomopsis sp. (strain HKI0458) isolated from the mangrove plant Hibiscus tiliaceus, four A-seco-oleane-type triterpenes, namely 3,4-seco-olean-11,13-dien-4,15alpha, 22beta,24-tetraol-3-oic acid (1), 3,4-seco-olean-11,13-dien-4,7beta,22beta,24-tetraol-3-oic acid (2), 3,4-seco- olean-13-en-4,7,15,22,24-pentaol-3-oic acid (3), and 3,4-seco-olean-13-en-4,15,22,24-tetraol-3-oic acid (4) were obtained. Their structures were elucidated by extensive spectroscopic (UV, IR, FABMS, and 2D NMR) data analyses.     

Cytotoxic triterpenes from the aerial roots of Ficus microcarpa

Six triterpenes, 3beta-acetoxy-12,19-dioxo-13(18)-oleanene (1), 3beta-acetoxy-19(29)-taraxasten-20alpha-ol (2), 3beta-acetoxy-21alpha,22alpha-epoxytaraxastan-20alpha-ol (3), 3,22-dioxo-20-taraxastene (4), 3beta-acetoxy-11alpha,12alpha-epoxy-16-oxo-14-taraxerene (5), 3beta-acetoxy-25-methoxylanosta-8,23-diene (6) along with nine known triterpenes, 3beta-acetoxy-11alpha,12alpha-epoxy-14-taraxerene (7), 3beta-acetoxy-25-hydroxylanosta-8,23-diene (8), oleanonic acid (9), acetylbetulinic acid (10), betulonic acid (11), acetylursolic acid (12), ursonic acid (13), ursolic acid (14), and 3-oxofriedelan-28-oic acid (15) were isolated from the aerial roots of Ficus microcarpa, and their structures elucidated by spectroscopic methods. The in vitro cytotoxic efficacy of these triterpenes was investigated using three human cancer cell lines, namely, HONE-1 nasopharyngeal carcinoma, KB oral epidermoid carcinoma, and HT29 colorectal carcinoma cells. Compound 8 and pentacyclic triterpenes 9-15 possessing a carboxylic acid functionality at C-28 showed significant cytotoxic activities against the aforementioned cell lines and gave IC50 values in the range 4.0-9.4 microM.     

Triterpenoids from Sanguisorba officinalis

Seven triterpenoids, i.e., 3beta-[(alpha-L-arabinopyranosyl)oxy]-19beta-hydroxyurs-12,20(30)-dien-28-oic acid (1), 3beta-[(alpha-L-arabinopyranosyl)oxy]-urs-11,13(18)-dien-28-oic acid beta-D-glucopyranosyl ester (2), 2alpha,3alpha,23-trihydroxyurs-12-en-24,28-dioic acid 28-beta-D-glucopyranosyl ester (3), 3beta-[(alpha-L-arabinopyranosyl)oxy]-urs-12,19(20)-dien-28-oic acid (4), 3beta-[(alpha-L-arabinopyranosyl)oxy]-urs-12,19(29)-dien-28-oic acid (5), 3beta-[(alpha-L-arabinopyranosyl)oxy]-19alpha-hydroxyolean-12-en-28-oic acid (6), 2alpha,3beta-dihydroxy-28-norurs-12,17,19(20),21-tetraen-23-oic cid (7), together with three known ones (8-10), were isolated from the roots of Sanguisorba officinalis. Their structures were determined by spectroscopic and chemical methods. Compounds 7 and 10 showed marginal inhibition activity against the growth of tumor cell lines.     

黄棉木中两个新的三萜类化合物

从黄棉木（Metadina trichotoma（Zoll．et．Mor．）Bakn．）树皮中分离得到2个新的三萜类化合物：3-oxo-29-hydroxy-urs-12-en-27,28-dioicacid（黄棉木素A,1）和3-oxo-21β-hydroxy-urs-12-en-27,28-dioicacid（黄棉木素B,2）。其结构主要通过MS,1D以及2DNMR等波谱方法鉴定。     

Production of bioactive triterpenes by Eriobotrya japonica calli

Callus tissue cultures induced from an axenic leaf of Eriobotrya japonica (Rosaceae) produced triterpenes in large amounts (ca. 50 mg/g dry wt). Nine triterpenes were characterized as ursolic acid, oleanolic acid, 2alpha-hydoxyursolic acid, maslinic acid, tormentic acid, 2alpha, 19alpha-dihydroxy-3-oxo-urs-12-en-28-oic acid, hyptadienic acid and a mixture of 3-O-cis-p-coumaroyltormentic acid and 3-O-trans-p-coumaroyltormentic acid. The triterpene composition in the callus tissues was noticeably different from that in intact leaves. The contents of tormentic acid with antidiabetic action, and 2alpha, 19alpha-dihydroxy-3-oxo-urs-12-en-28-oic acid with anti-HIV activity, were much larger than those in the intact leaves. All of the triterpenes isolated from the callus tissues showed an inhibitory effect comparable to (-)-epigallocatechin gallate (EGCG) of green tea on the activation of Epstein-Barr virus early antigen (EBV-EA) induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). 2alpha, 19alpha-Dihydroxy-3-oxo-urs-12-en-28-oic acid was the most potent inhibitor among them and caused a significant delay of two-stage carcinogenesis on mouse skin.     

Triterpenoids from enkianthus campanulatus

From the leaves of Enkianthus campanulatus were isolated three new triterpenes, 3-oxo-19,23,24-trihydroxyurs-12-en-28-oic acid, 3β,6β, 19,23-tetrahydroxyurs-12-en-28-oic acid and 3β,6β,23-trihydroxyurs-12-en-28-oic acid.     

Terpenes with antimicrobial activity from Cretan propolis

Five terpenes, the diterpenes: 14,15-dinor-13-oxo-8(17)-labden-19-oic acid and a mixture of labda-8(17),13E-dien-19-carboxy-15-yl oleate and palmitate as well as the triterpenes, 3,4-seco-cycloart-12-hydroxy-4(28),24-dien-3-oic acid and cycloart-3,7-dihydroxy-24-en-28-oic acid were isolated from Cretan propolis. Moreover, 18 known compounds were also isolated, seven of them for the first time as propolis components. All structures were established on the basis of spectroscopic analysis and chemical evidence. All isolated compounds were tested for antimicrobial activity against some Gram-positive and Gram-negative bacteria as well as against some human pathogenic fungi showing a broad spectrum of antimicrobial activity.     

飞龙掌血中三萜酸成分研究

从芸香科植物飞龙掌血中提取分离出4个新三萜酸,经波谱数据分析,分别鉴定为2α,3α,19α-trihydroxy11-oxo-urs-12-en-28-oic acid（1）,2α,3α,11α,19α-tetrahydroxy-urs-12-en-28-oic acid（2）,2α,3α-dillydroxy-19-oxo-18,19-seco-urs-11,13（18）-diene-28-oic acid（3）和2α,3α,19α-trihydroxy-olean-11,13（18）-dien-28-oic acid（4）。还分离鉴定出已知成分野鸭春酸（5）、arjunic acid（6）、飞龙掌血素、勒钩内脂和β-谷甾醇。     

Sterols and triterpenes in cell culture of Hyssopus officinalis L

Cell suspension cultures from hypocotyl-derived callus of Hyssopus officinalis were found to produce two sterols i. e. beta-sitosterol (1) and stigmasterol (2), as well as several known pentacyclic triterpenes with an oleanene and ursene skeleton. The triterpenes were identified as oleanolic acid (3), ursolic acid (4), 2alpha,3beta-dihydroxyolean-12-en-28-oic acid (5), 2alpha,3beta-dihydroxyurs-12-en-28-oic acid (6), 2alpha,3beta,24-trihydroxyolean-12-en-28-oic acid (7), and 2alpha,3beta,24-trihydroxyurs-12-en-28-oic acid (8). Compounds 5-8 were isolated as their acetates (6, 8) or bromolactone acetates (5, 7).     

Triterpenes from Periandra dulcis roots

Three oleanane triterpenes were isolated from the roots of Periandra dulcis,and identified as 3β-hydroxy-25-al-olean-18-en-30-oic acid (periandric acid I), 3β-hydroxy-25-al-olean-12-en-30-oic acid (periandric acid II) and 3-oxo-25-hydroxy-olean-12-en-30-oic acid. The former two compounds (periandric acids I and II) were identical with the aglycones obtained by hydrolysis of periandrin I and II, respectively and the latter one was a new triterpene.     

3β-hydroxy-21β-e-cinnamoyloxyolean-12-en-28-oic acid,a triterpenoid from enterolobium contorstisiliquum

The triterpenes 3β-hydroxy-21β-E-cinnamoyloxyolean-12-en-20-oic acid, 3β,21β-dihydroxyolean-12-en-28-oic acid (machaerinic acid) and its lactone (3β-hydroxyolean-12-en-21β→28-lactone) were isolated from the fruits of Enterolobium contorstisiliquum. Methyl and ethyl esters of 3β,21β-dihydroxyolean-12-en-oic acid were isolated and characterized as artifacts. The structures of these triterpenes have been established by a study of their chemical and spectroscopic (IR, MS and NMR) data.     

Anti-HIV-1 protease triterpenoids from Stauntonia obovatifoliola Hayata subsp. intermedia

Three triterpenoids, 16beta-hydroxy-2,3-seco-lup-20(29)-ene-2,3-dioic acid (1), 3beta,21beta,24-trihydroxy-30-noroleana-12,20(29)-dien-28-oic acid (2) and 16beta-hydroxylupane-1,20(29)-dien-3-one (3), along with eleven known triterpenes were isolated from stems of Stauntonia obovatifoliola Hayata subsp. intermedia (Y.C. Wu) T. Chen. Their structures were determined by analysis of HR-EI/FAB-MS and 1D and 2D NMR spectroscopic data and comparison with those in the literature. Ten of the compounds showed inhibitory activity against HIV-1 protease.     

Biotransformation of betulinic and betulonic acids by fungi

Betulinic acid (1), a triterpenoid found in many plant species, has attracted attention due to its important pharmacological properties, such as anti-cancer and anti-HIV activities. The closely related, betulonic acid (2) also has similar properties. In order to obtain derivatives potentially useful for detailed pharmacological studies, both compounds were submitted to incubations with selected microorganisms. In this work, both were individually metabolized by the fungi Arthrobotrys, Chaetophoma and Dematium, isolated from the bark of Platanus orientalis as well as with Colletotrichum, obtained from corn leaves; such fungal transformations are quite rare in the scientific literature. Biotransformations with Arthrobotrys converted betulonic acid (2) into 3-oxo-7beta-hydroxylup-20(29)-en-28-oic acid (3), 3-oxo-7beta,15alpha-dihydroxylup-20(29)-en-28-oic acid (4) and 3-oxo-7beta,30-dihydroxylup-20(29)-en-28-oic acid (5); Colletotrichum converted betulinic acid (1) into 3-oxo-15alpha-hydroxylup-20(29)-en-28-oic (6) acid whereas betulonic acid (2) was converted into the same product and 3-oxo-7beta,15alpha-dihydroxylup-20(29)-en-28-oic acid (4); Chaetophoma converted betulonic acid (2) into 3-oxo-25-hydroxylup-20(29)-en-28-oic acid (7) and both Chaetophoma and Dematium converted betulinic acid (1) into betulonic acid (2). Those fungi, therefore, are useful for mild, selective oxidations of lupane substrates at positions C-3, C-7, C-15, C-25 and C-30.     

Alisolide, alisols O and P from the rhizome of Alisma orientale

A nor-protostane, alisolide (1), a rearranged protostane, alisol O (2), and a 2,3-seco-protostane triterpene, alisol P (3), were isolated from the rhizomes of Alisma orientale, along with eight known protostane triterpenes. The structures were elucidated to be (17S)-3,11-dioxo-23-nor-protost-12-en-23(17)-olide, 3-oxo-11beta,23-dihydroxy-24,24-dimethyl-26,27-dinorprotost-13(17)-en-25-oic acid, and (20R,23S,24R)-23,24,25-trihydroxy-2,3-seco-protost-13(17)-en-3-oic acid 2,11beta-lactone, respectively, by interpretation of spectroscopic data.     

6-Methylcryptoacetalide, 6-methyl-epicryptoacetalide and 6-methylcryptotanshinone from Salvia aegyptiaca

From the whole plant of Salvia aegyptiaca, 6-methylcryptoacetalide, 6-methyl-epicryptoacetalide and 6-methylcryptotanshinone have been isolated and characterized, mainly by spectroscopic means. In addition to these novel diterpenoids, the known compounds 3beta-hydroxy-olean-12-en-28-oic acid, 3beta-hydroxy-oleana-11,13(18)-dien-28-oic acid, sitosterol-3beta-glucoside, sitosterol, stigmasterol, 5-hydroxy-7,3',4'-trimethoxyflavone and 5, 6-dihydroxy-7,3',4'-trimethoxyflavone were isolated.     

Minor triterpenes from Orthopterygium huancuy

Two new triterpenes, 3-oxo-20-hydroxy-lupan-28-oic and 3β,6β-dihydroxy-olean-18-en-28-oic acids, along with oleanonic, morolic and sumaresinolic acids have been isolated from Orthopterygium huancuy. The structure of the first new terpene was determined by single crystal X-ray analysis.     

Triterpenoid saponins from Oreopanax guatemalensis

Seven oleanane-type saponins were isolated from the leaves and stems of Oreopanax guatemalensis, together with ten known saponins of lupane and oleanane types. The new saponins were respectively characterized as 3-O-alpha-L-arabinopyranosyl echinocystic acid 28-O-[alpha- L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester, 3-O-beta-D-glucopyranosyl 3beta-hydroxy olean-11,13(18)-dien-28-oic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta- D-glucopyranosyl]ester, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl]3beta-hydroxy olean-11,13(18)-dien-28-oic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl]3beta, 23 dihydroxy olean-18-en-28-oic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-6-O-acetyl glucopyranosyl-(1-->6)-beta-D-glucopyranosyl]ester, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl] hederagenin 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-[beta-D-xylopyranosyl-(1-->2 )-]beta-D-glucopyranosyl]ester, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl]hederagenin 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-[beta-D-glucopyranosyl-(1-->2)-]beta-D-glucopyranosyl] ester and 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl] hederagenin 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-[alpha-L-arabinofuranosyl-(1-->2)]-beta-D-glucopyranosyl] ester. The structures were determined by spectral analyses. The NMR assignments were made by means of HOHAHA, 1H-1H COSY, HMQC, HMBC spectra and NOE difference studies.     

nor-Oleanene type triterpene glycosides from the leaves of Acanthopanax japonicus

Three new (1-3) and two known (4-5) triterpene glycosides were isolated from the leaves of Acanthopanax japonicus (Araliaceae) and elucidated structurally by mass, 1D, and 2D NMR spectroscopy. All the compounds possessed a nor-oleanene triterpene skeleton as the aglycone. The structures of 1-5 were established as 28-O-alpha-L-rhamno-pyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester of 3beta-hydroxy- 30-nor-olean-12,20(29)-diene-23,28-dioic acid, designated as acanjaposide A, 3beta- hydroxy-23-oxo-30-nor-olean-12,20(29)-diene-28-oic acid, named acanjaposide B, 3beta,20alpha-dihydroxy-23-oxo-30-nor-olean-12-en-28-oic acid, named acanjaposide C, and nipponoside E, a known saponin, respectively.