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PubMed2002

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.

Animals↗
PubMed1999

Triterpenoid saponins from Fagonia indica.

Two new triterpenoid saponins, 3-O-{[beta-D-glucopyranosyl-(1-->2)]-[alpha-L-arabinopyranosyl-(1- ->3)]- alpha-L-arabinopyranosyl}-ursolic acid-28-O-[beta-D-glucopyranosyl] ester (indicasaponin A), 3-O-{[beta-D-glucopyranosyl-(1-->2)]-[alpha-L-arabinopyranosyl-(1- ->3)]- alpha-L-arabinopyranosyl}-oleanolic acid-28-O-[beta-D-glucopyranosyl] ester (indicasaponin B) and two known triterpenoid saponins, 3-O-[beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl]-ur solic acid-28-O-[beta-D-glucopyranosyl] ester, 3-O-[beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl]-olean olic acid-28-O-[beta-D-glucopyranosyl] ester have been isolated from Fagonia indica. The structures were determined primarily by NMR spectroscopy. The assignment of NMR signals was performed by means of 1H-1H COSY, NOESY, ROESY, TOCSY, HMQC and HMBC experiments.

Carbohydrate Conformation↗
PubMed2000

Growth characteristics and chemical analysis of Psychotria carthagenensis cell suspension cultures.

Callus and cell suspension cultures of Psychotria carthagenensis have been established in Gamborg's B5 medium supplemented, respectively, with 3% sucrose, 0.2 mg/l kinetin, and 1.0 mg/l 2,4-D and 2% sucrose, 2.0 mg/l 2,4-D, 0.2 mg/l kinetin, and 50 mg/l cysteine. Suspension culture presented a typical growth curve with the complete cycle of ca. 18 days and the maximum specific growth rate (µ) was 0.0099 day. The presence of different secondary metabolite pathways was determined by measuring the enzyme activity of phenylalanine ammonia lyase (PAL), tryptophan decarboxylase (TDC), strictosidine synthase (STR), strictosidine-beta-glucosidase (SG), and geraniol-10-hydroxylase (G10H). Activity could only be measured for SG (14.55 pkatal/mg protein) and G10H (0.3 pkatal/mg protein). Analysis of extracts from leaves, callus and cell suspension cultures demonstrated the presence of two major triterpenes: beta-sitosterol and ursolic acid.(2)

Journal Article↗
PubMed2000

A new ent-kaurane diterpenoid from Isodon phyllostachys.

A new ent-kaurane diterpenoid, phyllostachysin C (1), together with five known compounds, sculponeatins B and C, nodosin, ursolic acid and 2 alpha-hydroxyursolic acid, were isolated from the leaves of Isodon phyllostachys. The structure of 1 was elucidated on the basis of its spectral properties.

Diterpenes↗
PubMed2002

Constituents of Gnetum montanum.

A new stilbene, gnetifolin M (1), was isolated from the lianas of Gnetum montanum, together with seven known compounds, resveratrol (2), gnetol (3), 4', 5,7-trihydroxy-3'-methoxyflavone, beta-sitosterol, daucosterol, ursolic acid, and tetracosanoic acid. The structure of 1 was determined to be 2-(5'-methoxy-3'-hydroxyphenyl)-4-hydroxybenzofuran on the basis of spectroscopic evidence.

Benzofurans↗
PubMed2001

Antimicrobial activity of Alstonia macrophylla: a folklore of bay islands.

The methanolic crude and methanol-aqueous extract of Alstonia macrophylla leaves and n-butanol part of the crude extract showed antimicrobial activity against various strains of Staphylococcus aureus, Staphylococcus saprophyticus, Streptococcus faecalis, Escherichia coli, Proteus mirabilis, Trichophyton rubrum, Trichophyton mentagrophytes var. mentagrophytes and Microsporum gypseum. The minimum inhibitory concentration (MIC) values ranges from 64 to 1000 microg/ml for bacteria and 32-128 mg/ml for dermatophytes. However, the strains of Pseudomonas aeruginosa, Klebsiella sp. and Vibrio cholerae showed resistance against in vitro treatment of the extracts up to 2000 microg/ml concentration, while the two yeast species were resistant even at 128 mg/ml concentration. The stem bark extract prepared similarly was found to be less active compared to the leaves. Phytochemical study indicates that the crude extract contains tannins, flavonoids, saponins, sterols, triterpene and reducing sugars. Further fractionation and purification of n-butanol part of the extract showed the presence of beta-sitosterol, ursolic acid, beta-sitosterol glucoside and a mixture of minor compounds only detected in TLC.

Anti-Bacterial Agents↗
PubMed2003

CNS activity of the methanol extract of Mallotus peltatus (Geist) Muell Arg. leaf: an ethnomedicine of Onge.

The aim of the present study was to investigate several neuropharmacological effects of the methanol extract and different fractions of Mallotus peltatus (Geist) Muell Arg. var acuminatus (Euphorbiaceae) leaves in Wistar albino rats and Swiss albino mice. General behavior, exploratory behavior, muscle relaxant activity and phenobarbitone sodium-induced sleeping time were studied. The results revealed that the crude extract at 200-300 mg kg(-1) p.o. and its fractions A and B at 50 mg kg(-1) caused a significant reduction in spontaneous activity (general behavioral profile), remarkable decrease in exploratory behavioral pattern (Y-maze and head dip tests), a reduction in muscle relaxant activity (rotarod, 30 degrees inclined screen and traction tests), and also significantly potentiated phenobarbitone sodium-induced sleeping time. The phytochemical study of crude leaf extract revealed the presence of tannin, triterpenoid, flavonoid, sterol, alkaloid and reducing sugar. Further fractionation and purification yielded two major fractions A (ursolic acid) and B (beta-sitosterol) with some fatty acids as the major compounds. The psychopharmacological activity of the crude leaf extracts appeared to be either due to fraction A (50 mg kg(-1)) or a combination of fractions A and B (50 mg kg(-1)) along with some fatty acids present in the n-butanol part of methanol extract of M. peltatus leaf (MEMPL).

Analgesics↗
PubMed2003

Identification of triterpene hydroxycinnamates with in vitro antitumor activity from whole cranberry fruit (Vaccinium macrocarpon).

Bioactivity-guided fractionation of cranberry fruit was used to determine the identity of triterpenoid esters from Vaccinium macrocarpon, which inhibit tumor cell growth and may play a role in cancer prevention. In our previous study, a fraction from whole fruit exhibited tumor cell growth inhibition in vitro. The major components of this fraction were isolated by chromatographic separation of ethyl acetate extracts, purified by semipreparative HPLC, and identified by NMR as cis- (1) and trans- (2) isomers of 3-O-p-hydroxycinnamoyl ursolic acid. These triterpenoid esters have not been previously reported in Vaccinium fruit. Bioassay of the purified triterpene cinnamates in tumor cell lines in vitro showed slightly greater activity of compound 1 in most cell lines, with GI(50) values of approximately 20 microM in MCF-7 breast, ME180 cervical and PC3 prostate tumor cell lines. Quercetin was slightly less active than 1, while cyanidin-3-galactoside exhibited much lower cytotoxicity, with GI(50) greater than 250 microM in all cell lines. Phenylboronic acid (3) was also isolated from the fruit but showed insignificant antitumor activity.

Antineoplastic Agents, Phytogenic↗
PubMed2005

Phenolic and triterpenoid antioxidants from Origanum majorana L. herb and extracts obtained with different solvents.

Antioxidant properties of marjoram (Origanum majorana L.) herb and extracts obtained with ethanol, n-hexane, and supercritical CO2 extraction are presented. Individual antioxidants, ursolic acid, carnosic acid, and carnosol, were quantified with high-performance liquid chromatography. The effects of different parameters (temperature and pressure) of high-pressure extraction on the yield of carnosol were studied. Furthermore, two marjoram herbs from Hungary and Egypt were compared measuring hydrogen-donating abilities with 1,1-diphenyl-2-picrylhydrazyl by spectrophotometric and the total scavenger capacities by chemiluminometric methods from the aqueous extracts of the herbs. The antioxidant activities of the solvent extracts were performed using the Rancimat method. The Egyptian herb and its extracts possessed better antioxidant activities than Hungarian ones. Applying supercritical CO2 extraction, the highest value of carnosol was obtained at 400 bar and 60 degrees C.

Antioxidants↗
PubMed2003

Saponins from Cussonia bancoensis and their inhibitory effects on nitric oxide production.

Two new triterpenoid saponins (1 and 2) were isolated from the stem bark of Cussonia bancoensis together with the known stigmasterol, ursolic acid, 23-hydroxyursolic acid (3), and 3beta-hydroxylup-20(29)-en-28-oic acid. On the basis of their spectroscopic data and on chemical transformations, the structures of the new saponins have been established as 3-O-(alpha-Ll-arabinopyranosyl)-23-hydroxyursolic acid (1) and 3-O-(beta-D-glucopyranosyl)-23-hydroxyursolic acid (2). In a nitric oxide (NO)-production bioassay, compound 3 exhibited significant NO inhibitory activity, while compounds 1 and 2 were less potent than 3.

Animals↗
PubMed1994

Cytotoxic constituents of Baccharis gaudichaudiana.

Three new labdane diterpenes, gaudichaudols A-C [1-3], a new clerodane diterpenoid, gaudichaudone [4], and the known clerodane, articulin acetate [5] have been isolated from the aerial parts of Baccharis gaudichaudiana, together with the known compounds, apigenin, hispidulin, spathulenol, and ursolic acid. Through the application of 1D- and 2D nmr spectroscopy, the structures of the new diterpenoids [1-4] were, in turn; elucidated as 15,16,18,19-tetrahydroxylabd-5-ene, 15-O-acetyl-16,18,19-trihydroxylabd-5-ene, 16-O-p-trans-coumaroyl-15,18,19-trihydroxylabd-5-ene, and 2 beta-hydroxy-15,16-epoxycleroda-1(10),15,16-trien-18,19-olide++ +. The isolated compounds were evaluated in P-388 lymphocytic leukemia cells as well as a battery of human cancer cell lines. Among the diterpenoids, gaudichaudol C [3], gaudichaudone [4], and articulin acetate [5] exhibited significant cytotoxic activity against certain cancer cells.

Animals↗
PubMed1989

Current aspects of practical two-dimensional (2D) nuclear magnetic resonance (NMR) spectroscopy: applications to structure elucidation.

The intense effort in developing new 2D NMR methodology over the past decade has been driven by the desire to study molecules of progressively greater complexity. The need for refined structural detail has produced new types of experiments that require more involvement on the part of the practicing spectroscopist in understanding the theoretical bases leading to their experimental realization. In this Review we discuss several concepts that are important in the successful application of current versions of the most useful 2D NMR experiments, such as coherence transfer, phase cycling, apodization functions, and obtaining pure-phase 2D NMR spectra. The intimate interconnections among these concepts are emphasized. The principles underlying the 2D NMR experiments are described and then the experiments are illustrated in assigning the 1H and 13C NMR spectra of the triterpene, ursolic acid.

Magnetic Resonance Spectroscopy↗
PubMed2002

Cytotoxic ent-kaurane diterpenoids from Isodon sculponeata.

Four new ent-kaurane diterpenoids, sculponeatins F-I (1-4), together with six known compounds, sculponeatin E (5), epi-nodosin (6), epi-nodosinol (7), enmein (8), and macrocalyxoformins A and B (9 and 10), were isolated from the leaves of Isodon sculponeata. Also obtained were ursolic acid, 2alpha,3beta-dihydroxy-urs-12-en-28-oic acid, 2alpha,3beta,19alpha-trihydroxy-urs-12-en-28-oic acid, beta-sitosterol, daucosterol, quercetin, pedalitin, rosmarinic acid, caffeic acid and ethyl caffeic acid. Their structures were determined by spectral methods (1D-, 2D-NMR and MS). Some diterpenoids were tested for their cytotoxicity to inhibit three kinds of human tumor cells K562, A549 and T24. Compounds 3, 4, 6, 8, and 10 showed significant inhibitory effect toward K562 with IC(50) values ranging from 3.2 microg/ml to 8.2 microg/ml, while 3 and 6 exhibited potent antitumor activity against T24, but none exhibited cytotoxicity toward the cells of A549.

Antineoplastic Agents, Phytogenic↗
PubMed2003

Eremophilenolides and other constituents from the roots of Ligularia sagitta.

Chemical investigation of the roots of Ligularia sagitta has resulted in the characterization of six eremophilenolides 6beta,8beta-dimethoxy-10beta-hydroxyeremophil-7(11)-en-12,8alpha-olide (1), 6beta-angeloyloxy-10beta-hydroxy-8beta-methoxyeremophil-7(11)-en-12,8alpha-olide (2), 6beta-(2'-methylbutanoyloxy)-10beta-hydroxy-8beta-methoxyeremophil-7(11)-en-12,8alpha-olide (3), 6beta-angeloyloxy-10beta-hydroxy-8alpha-methoxyeremophil-7(11)-en-12,8beta-olide (4), 6beta-(2'-methylbutanoyloxy)-10beta-hydroxy-8alpha-methoxyeremophil-7(11)-en-12,8beta-olide (5) and 8beta,10beta-dihydroxy-6beta-methoxyeremophil-7(11)-en-12,8alpha-olide (6), together with one monoterpene (3 R,4 R,6 S)-3,6-dihydroxy-1-menthene (7), two triterpenes lupeol (8) and ursolic acid (9), and beta-sitosterol (10). The structures of five new constituents (1-5) were elucidated by spectroscopic methods including 2D-NMR experiments. The compounds 1, 5 and 7 showed antibacterial activity by being assayed against Staphylococcus aureus, Bacillus subtilis and Escherichia coli.

Anti-Bacterial Agents↗
PubMed2003

Inhibitory effect of sterols from Ruprechtia triflora and diterpenes from Calceolaria pinnifolia on the growth of Mycobacterium tuberculosis.

Bioactivity-guided fractionation of the CH 2 Cl 2 /MeOH extract of the aerial part of Ruprechtia triflora Griseb. led to the identification of several sterols and a triterpene as the active components against Mycobacterium tuberculosis. This is the first report of a chemical investigation of a member of the genus Ruprechtia. The novel acylated sterol, 5alpha,8alpha-epidioxyergosta-6,22-dien-3beta-yl stearate, was isolated and its structure determined on the basis of spectral evidence including NMR (especially selective 1D NOE, selective 1D TOCSY, HSQC, HMBC) and MS (HR-FAB). In addition, several terpenes obtained from Calceolaria pinnifolia Cav. were also evaluated for their antimycobacterial activity. In a microplate alamar blue assay, sterols from R. triflora were found to be active with MIC values ranging from 2 - 128 microg/mL, with 5alpha,8alpha-epidioxyergost-6,22-dien-3beta-ol, 5alpha,8alpha-epidioxystigmasta-6,22-dien-3beta-ol and stigmast-4-en-6beta-ol-3-one being the most active, each with an MIC value of 2 microg/mL. Among the diterpenes from C. pinnifolia, 19-malonyloxydehydroabietinol and 19-methylmalonyloxy- ent-isopimara-8(9),15-diene were most active each with an MIC value of 4 microg/mL. MIC values for the triterpenes 3-epi-ursolic acid and 3-epi-oleanolic acid from C. pinnifolia were determined to be 8 and 16 microg/mL, respectively.

Antitubercular Agents↗
PubMed2004

Platelet anti-aggregating triterpenoids from the leaves of Acanthopanax senticosus and the fruits of A. sessiliflorus.

Six triterpenoids, chiisanogenin, chiisanoside, ursolic acid, oleanolic acid, beta-sitosterol and daucosterol, were isolated as the platelet anti-aggregating components from the leaves of Acanthopanax senticosus and the fruits of A. sessiliflorus. Chiisanogenin showed about 50-fold higher potency than acetylsalicylic acid (ASA) on U46619-induced platelet aggregation (IC50o:6.21 microM) and 10-20-fold higher effects than ASA on epinephrine- and arachidonic acid (AA)-induced aggregation (IC50:2.50 and 4.81 microM, respectively).

Animals↗
PubMed2006

Inhibition of protein tyrosine phosphatase 1B by ursane-type triterpenes isolated from Symplocos paniculata.

Inhibition of protein tyrosine phosphatase 1B (PTP1B) has been proposed as a therapy for treatment of type 2 diabetes and obesity. Bioassay-guided fractionation of the MeOH extract of the leaves and stems of Symplocos paniculata (Thunb.) Miq. (Symplocaceae), using an in vitro PTP1B inhibitory assay, resulted in the isolation of three ursane-type triterpenes, ursolic acid (1), corosolic acid (2) and 2alpha,3alpha,19alpha,23-tetrahydroxyurs-12-en-28-oic acid (3). Compounds 1-3 inhibited PTP1B with IC (50) values of 3.8 +/- 0.5, 7.2 +/- 0.8 and 42.1 +/- 1.5 microM, respectively. Kinetic studies suggest that 1 is a competitive inhibitor with a K(i) value of 2.0 microM, whereas 2 is a mixed-type inhibitor of PTP1B. Our results indicate that the substitution of hydroxy groups on the ursane-type triterpenes is responsible for the loss of activity, and thus 1 and 2 possessing only one or two hydroxy groups can be potential PTP1B inhibitors.

Acanthaceae↗
PubMed1998

Angiotensin converting enzyme (ACE) inhibitors from Jasminum azoricum and Jasminum grandiflorum.

Bioactivity-guided fractionation of extracts of the aerial parts of Jasminum azoricum var. travancorense, using an in vitro ACE inhibition assay, led to isolation of three oligomeric, iridoid-type compounds, which were named sambacein I-III. Their structures are based on spectroscopic and chemical evidence. Similarly, fractionation of extracts of aerial parts of J. grandiflorum resulted in the isolation of the previously reported ACE inhibitor, oleacein. The IC50 values of purified ACE inhibitors were 26-36 microM. Moreover, 2-(3,4-dihydroxyphenyl)-ethanol, isoquercitrin and ursolic acid were isolated from J. grandiflorum. Sambaceins and oleacein are formed from genuine iridoid glucosides during processing of the plant material. NMR spectroscopy was used to measure the level of the ACE inhibitors in the traditional medicines prepared in Kerala from these Jasminum species.

Angiotensin-Converting Enzyme Inhibitors↗