Showing papers on "Triterpene published in 2005"

Genomics‐based selection and functional characterization of triterpene glycosyltransferases from the model legume Medicago truncatula

Abstract: The biosynthesis of triterpene saponins is poorly characterized in spite of the importance of these glycosylated secondary metabolites for plant defense and animal health. The model legume Medicago truncatula synthesizes more than 30 different saponins based on at least five triterpene aglycones; soyasapogenols B and E, medicagenic acid, hederagenin and bayogenin. We have employed an inducible cell culture system, DNA array-based and in silico transcript profiling, and targeted metabolite profiling, to identify triterpene glycosyltransferases (GTs) from among the more than 300 GTs expressed in M. truncatula. Two uridine diphosphate glucosyltransferases were functionally characterized; UGT73K1 with specificity for hederagenin and soyasapogenols B and E, and UGT71G1 with specificity for medicagenic acid. The latter enzyme also glycosylated certain isoflavones and the flavonol quercetin with higher efficiency than triterpenes; however, integrated transcript and metabolite profiling supported a function for UGT71G1 in terpenoid but not (iso)flavonoid biosynthesis in the elicited cell cultures.

Three new triterpenes from Nerium oleander and biological activity of the isolated compounds

Abstract: New ursane-type triterpene 1, oleanane-type triterpene 2, and dammarane-type triterpene 15 were isolated from the leaves of Nerium oleander together with 12 known triterpenes, 3beta-hydroxy-12-ursen-28-oic acid (ursolic acid, 3), 3beta,27-dihydroxy-12-ursen-28-oic acid (4), 3beta,13beta-dihydroxyurs-11-en-28-oic acid (5), 3beta-hydroxyurs-12-en-28-aldehyde (6), 28-norurs-12-en-3beta-ol (7), urs-12-en-3beta-ol (8), urs-12-ene-3beta,28-diol (9), 3beta-hydroxy-12-oleanen-28-oic acid (oleanolic acid, 10), 3beta,27-dihydroxy-12-oleanen-28-oic acid (11), 3beta-hydroxy-20(29)-lupen-28-oic acid (betulinic acid, 12), 20(29)-lupene-3beta,28-diol (betulin, 13), and (20S,24R)-epoxydammarane-3beta,25-diol (14). On the basis of their spectroscopic data, the structures of the new compounds 1, 2, and 15 were established as 3beta,20alpha-dihydroxyurs-21-en-28-oic acid, 3beta,12alpha-dihydroxyoleanan-28,13beta-olide, and (20S,24S)-epoxydammarane-3beta,25-diol, respectively. The anti-inflammatory activity of the seven isolated compounds and methyl esters of ursolic acid and oleanoic acid in vitro was examined on the basis of inhibitory activity against the induction of the intercellular adhesion molecule-1 (ICAM-1). The anticancer activity of the 14 isolated compounds, including 1, 2, 15, and methyl esters of ursolic acid and oleanolic acid in vitro was examined on the basis of the cell growth inhibitory activities toward three kinds of human cell lines.

Antiviral Terpenoid Constituents of Ganoderma pfeifferi.

Abstract: Four sterols and 10 triterpenes were isolated from the fruiting bodies of Ganoderma pfeifferi, including the three new triterpenes 3,7,11-trioxo-5alpha-lanosta-8,24-diene-26-al (lucialdehyde D, 1), 5alpha-lanosta-8,24-diene-26-hydroxy-3,7-dione (ganoderone A, 2), and 5alpha-lanosta-8-ene-24,25-epoxy-26-hydroxy-3,7-dione (ganoderone C, 3). The structures of 1-3 were determined on the basis of spectroscopic evidence. Antibacterial, antifungal, and antiviral activity were studied for some of the isolated compounds. Ganoderone A (2), lucialdehyde B (4), and ergosta-7,22-dien-3beta-ol (7) were found to exhibit potent inhibitory activity against herpes simplex virus.

Quantification of saponins in aerial and subterranean tissues of Medicago truncatula.

Abstract: Triterpene saponins from aerial and subterranean organs of Medicago truncatula cv. Jemalong A-17 were qualitatively profiled and quantified using reverse-phase HPLC with on-line photodiode array detection and electrospray-ionization mass spectrometry (HPLC/PDA/ESI/MS). Absolute quantifications were performed for 3-O-beta-D-glucopyranosyl-medicagenic acid and soyasaponin 1 (3-O-[alpha-L-rhamnopyranosyl(1-->2)-beta-D-galactopyranosyl(1-->2)-beta-D-glucuronopyranoside] soyasapogenol B), whereas relative quantifications were determined for 29 other saponins in root, stem, leaf, seedpod, and seed. Roots contained the greatest total amount of saponins followed by leaf and seed, respectively. The quantitative data also reveal the differential accumulation of triterpene saponins in the various organs of M. truncatula. Specifically, relatively higher quantities of medicagenic acid conjugates accumulated in leaf and seed, whereas relatively higher levels of soysapogenol conjugates were observed in root. The differential accumulation of specific triterpene saponins is suggestive of spatially differentiated biosynthesis and/or biological function.

Floratheasaponins A-C, acylated oleanane-type triterpene oligoglycosides with anti-hyperlipidemic activities from flowers of the tea plant (Camellia sinensis).

Abstract: The methanolic extract and its n-butanol-soluble fraction from the flowers of the tea plant (Camellia sinensis) were found to suppress serum triglyceride elevation in olive oil-treated mice. From the n-butanol-soluble fraction, three new acylated oleanane-type triterpene oligoglycosides, floratheasaponins A−C (1−3), were isolated together with several flavonol glycosides and catechins. The structures of 1−3 were elucidated on the basis of chemical and physicochemical evidence as 21-O-angeloyl-22-O-acetyltheasapogenol B 3-O-[β-d-galactopyranosyl(1→2)][β-d-xylopyranosyl(1→2)-α-l-arabinopyranosyl(1→3)]-β-d-glucopyranosiduronic acid, 21,22-di-O-angeloyl-R1-barrigenol 3-O-[β-d-galactopyranosyl(1→2)][β-d-xylopyranosyl(1→2)-α-l-arabinopyranosyl(1→3)]-β-d-glucopyranosiduronic acid, and 21-O-angeloyl-22-O-2-methylbutyryl-R1-barrigenol 3-O-[β-d-galactopyranosyl(1→2)][β-d-xylopyranosyl(1→2)-α-l-arabinopyranosyl(1→3)]-β-d-glucopyranosiduronic acid, respectively. Floratheasaponins (1−3) showed inhibitory effects on se...

Bioactive Saponins and Glycosides. XXIII. Triterpene Saponins with Gastroprotective Effect from the Seeds of Camellia sinensis—Theasaponins E3, E4, E5, E6, and E7—

Abstract: The saponin fraction from the seeds of the tea plant [Camellia sinensis (L.) O. KUNTZE (Theaceae)] was found to exhibit potent protective effects on ethanol- and indomethacin-induced gastric mucosal lesions in rats. Five new triterpene saponins, theasaponins E3 (1), E4 (2), E5 (3), E6 (4), and E7 (5), were isolated together with 11 known saponins from the saponin fraction. The chemical structures of 1-5 were elucidated on the basis of chemical and physicochemical evidence. Among the isolated saponins, theasaponins E1 (6), E2 (7), and E5 (3) and assamsaponin C (10) showed an inhibitory effect on ethanol-induced gastric mucosal lesions at a dose of 5.0 mg/kg, p.o. and their activities were stronger than that of omeplazole. With regard to the structure-activity relationships of theasaponins, the following structural requirements for a protective effect on ethanol-induced gastric lesions were suggested; 1) the 21- and/or 22-acyl groups are essential for the activity, 2) acetylation of the 16-hydroxyl group reduce the activity.

Triterpenoid saponin anthranilates from Albizia grandibracteata leaves ingested by primates in Uganda.

Abstract: Three new oleanane-type triterpene saponins (1−3), named grandibracteosides A−C, were isolated from the methanolic extract of leaves of Albizia grandibracteata, a species consumed by primates in the Kibale National Park, Uganda. The structures of the saponins were established using 1D and 2D NMR experiments and mass spectrometry and confirmed by acid and alkaline hydrolysis. The crude extract and the pure compounds showed significant inhibitory activity against KB and MCF7 tumoral cell lines in vitro. The compounds are glycosides of acacic acid acylated by an o-aminobenzoyl unit. This is the first report of such ester saponins in dicotyledonous plants. Studies of the primate diet may provide a useful method for finding naturally occurring compounds of medicinal significance.

Cucurbitane-Type Triterpenoids from the Fruit of Momordica charantia

Abstract: The structures of three new cucurbitane-type triterpenoids isolated from the methanol extract of the fruit of Japanese Momordica charantia were established as (19R,23E)-5β,19-epoxy-19-methoxycucurbita-6,23,25-trien-3β-ol (1), (23E)-3β-hydroxy-7β-methoxycucurbita-5,23,25-trien-19-al (2), and (23E)-3β-hydroxy-7β,25-dimethoxycucurbita-5,23-dien-19-al (3) on the basis of spectroscopic methods. These compounds were accompanied by the known (19R,23E)-5β,19-epoxy-19,25-dimethoxycucurbita-6,23-dien-3β-ol (4) and (19R,23E)-5β,19-epoxy-19-methoxycucurbita-6,23-diene-3β,25-diol (5). This is the first report of the isolation of tetracyclic triterpenoids possessing a Δ23,25-conjugated diene system, viz., 1 and 2, from a natural source.

Cytotoxic activity of lupane-type triterpenes from Glochidion sphaerogynum and Glochidion eriocarpum two of which induce apoptosis.

Abstract: Six known lupanes lupenone ( 1), 3- epi-lupeol ( 2), glochidone ( 4), glochidonol ( 5), glochidiol ( 6) and lup-20(29)-ene-1beta,3beta-diol ( 7) were isolated from the roots and stem wood of Glochidion eriocarpum and three, 5, 6 and lup-20(29)ene-3alpha,23-diol ( 3), were isolated from the roots and stem wood of Glochidion sphaerogynum. Compounds were identified by (1)H- and (13)C-NMR techniques. Triterpenes 2 - 7 were tested against the growth of three human tumor cell lines, MCF-7, NCI-H-460 and SF-268. Lupanes 3, 5, and 6 exhibited strong inhibitory effects against all three; thus GI (50) values for 3 were 12.7 +/- 3.7, 17.9 +/- 1.1 and 17.9 +/- 0.5, for 5 9.0 +/- 3.7, 4.9 +/- 0.2 and 9.8 +/- 0.5, and for 6 6.63 +/- 0.7, 7.5 +/- 0.5 and 9.7 +/- 0.3.3. Epilupeol was less active, with GI (50) values of 75.6 +/- 11.7, 86.1 +/- 12.4 and 80.9 +/- 2.6 while 7 was moderately active only against MCF-7 (GI (50) = 79.2 +/- 2.4). Additional studies indicated that triterpenes 5 and 6 exerted their antiproliferative activity through the involvement of apoptosis while triterpene 3 did not.

Triterpene Acids from the Leaves of Planchonella duclitan (Blanco) Bakhuizan

Abstract: From the methanolic extract of the leaves of Planchonella duclitan, 2α,3α,19α,23-tetrahydroxy-13,27-cyclours-11-en-28-oic acid (1), myrianthic acid (2), 2-hydroxyursolic acid (3), ursolic acid (4), pomolic acid (5), rotundic acid (6), andjacoumaric acid (7) were isolated, and their structures were elucidated on the basis of their spectroscopic analysis. Among them, compound 1 was a new cyclopropyl ursane-type triterpene acid. Additionally, compounds 4 and 7 showed significant cytotoxicity toward human colorectal carcinoma cell line HT29 and human breast carcinoma cell line MCF-7 with IC 50 values ranging from 5.8 ± 1.4 to 6.5 ± 1.9 μM.

Intercedensides D-I, cytotoxic triterpene glycosides from the sea cucumber Mensamaria intercedens Lampert.

Abstract: Six new triterpene glycosides, intercedensides D-I (1-6), were isolated from the whole bodies of the sea cucumber Mensamria intercedens Lampert, which is found in the South China Sea. Their structures were elucidated by extensive spectroscopic analysis (NMR and ESIMS) and chemical methods. lntercedensides D (1), E (2), G (4), and H (5) have a conjugated double bond system (22Z,24-diene) in the aglycon side chain, while intercedensides F (3) and I (6) have only a single double bond (24, 25) in this same chain. lntercedensides D-H (1-5) showed significant cytotoxicity (ED(50) 0.96-5.0 mug/mL) against 10 human tumor cell lines.

Bioactive constituents from Boswellia papyrifera

Abstract: Phytochemical investigation of the stem bark extract of Boswellia papyrifera afforded two new stilbene glycosides, trans-4',5-dihydroxy-3-methoxystilbene-5-O-{alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranoside (1), trans-4',5-dihydroxy-3-methoxystilbene-5-O-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranoside (2), and a new triterpene, 3alpha-acetoxy-27-hydroxylup-20(29)-en-24-oic acid (3), along with five known compounds, 11-keto-beta-boswellic acid (4), beta-elemonic acid (7), 3alpha-acetoxy-11-keto-beta-boswellic acid (8), beta-boswellic acid (9), and beta-sitosterol (10). The stilbene glycosides exhibited significant inhibition of phosphodiesterase I and xanthine oxidase. The triterpenes (3-9) exhibited prolyl endopeptidase inhibitory activities.

Lanostane Triterpenoids and Triterpene Glycosides from the Fruit Body of Fomitopsis pinicola and Their Inhibitory Activity against COX-1 and COX-2

Abstract: Two new lanostane triterpenoids (1, 2) and 10 new lanostane triterpene glycosides (3-12) have been isolated from the fruit bodies of Fomitopsis pinicola. Their structures were established primarily by NMR experiments and chemical methods, and their biological activity against COX-1 and COX-2 was investigated.

Lupane triterpenoids from Maytenus species.

Abstract: Five new lupane triterpenes (1-5), in addition to 24 known ones, were isolated from Maytenus cuzcoina and M. chiapensis. Their structures were elucidated on the basis of spectroscopic analysis, including homonuclear and heteronuclear correlation NMR (COSY, ROESY, HSQC, and HMBC) experiments. The compounds were assayed for antimicrobial and cytotoxic activities, with 3-epi-betulinic acid and 28,30-dihydroxy-3-oxolup-20(29)-ene showing moderate cytotoxicity.

Triterpene saponins from barrel medic (Medicago truncatula) aerial parts

Abstract: Triterpene saponins from Medicago truncatula aerial parts have been separated and their structures determined by the extensive use of 1D- and 2D-NMR experiments including 1H−1H (DQF-COSY, 1D-TOCSY) and 1H−13C (HSQC, HMBC) spectroscopy along with ESIMS. Fifteen individual compounds were isolated that included seven medicagenic acid and eight zanhic acid glycosides. Additionally, two soyasapogenol B and soyasapogenol E glycosides were identified by MS/MS and TLC. Four medicagenic acid glycosides (5, 11, 12, 14) and eight zanhic acid glycosides (1−4, 6−9) are reported here for the first time. The common feature of M. truncatula aerial part saponins is the (1→3) linkage between the two glucose units at C-3 of medicagenic and zanhic acids, which is different from that found in alfalfa (Medicago sativa), where this linkage was always (1→2). This may suggest differences in glucosyltransferases between these two Medicago species. Keywords: Barrel medic; Medicago truncatula; triterpene saponins

Triterpene saponins from the leaves of Ilex kudingcha.

Abstract: Nine new triterpene saponins, ilekudinosides K-S (1-9), and eight known triterpene saponins were isolated from the 70% ethanol extract of the leaves of Ilex kudingcha. The new saponins were characterized as 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-alpha-kudinlactone (1), 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranosyl-beta-kudinlactone (2), 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl-gamma-kudinlactone (3), 3-O-beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl-alpha-kudinlactone (4), 3-O-beta-D-glucopyranosyl(1-->2)-alpha-L-arabinopyranosyl-alpha-kudinlactone (5), 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranosyl-alpha-kudinlactone (6), 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-beta-kudinlactone (7), 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl-beta-kudinlactone (8), and 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-gamma-kudinlactone (9), respectively. The structures and stereochemistry of compounds 1-9 were elucidated by spectroscopic data interpretation and chemical degradation.

Triterpenoid glycosides from leaves of Medicago arborea L.

Abstract: Eighteen triterpene saponins (1−18) from Medicago arborea leaves have been isolated and their structures elucidated by spectroscopic, spectrometric (1D and 2D NMR, FAB-MS, ESI-MS/MS), and chemical methods. They have been identified as glycosides of medicagenic, zanhic, and 2β-hydroxyoleanolic acids, soyasapogenol B, bayogenin, and 2β,3β-dihydroxyolean-12-en-23-al-28-oic acid. Twelve of them, identified as 3-O-β-d-glucopyranosyl-28-O-[α-l-arabinopyranosyl(1→3)-α-l-rhamnopyranosyl(1→2)-α-l-arabinopyranoside] zanhic acid (3), 3-O-β-d-glucopyranosyl-28-O-{β-d-xylopyranosyl(1→4)-[α-l-arabinopyranosyl-(1→3)]-α-l-rhamnopyranosyl(1→2)-α-l-arabinopyranoside} zanhic acid (4), 3-O-[α-l-rhamnopyranosyl(1→2)-α-l-arabinopyranosyl(1→2)-β-d-glucopyranosyl]-2β-hydroxyoleanolic acid (5), 3-O-β-d-glucuronopyranosyl-28-O-[α-l-rhamnopyranosyl(1→2)-α-l-arabinopyranoside]medicagenic acid (6), 3-O-β-d-glucuronopyranosyl-28-O-[β-d-xylopyranosyl(1→4)-α-l-rhamnopyranosyl(1→2)-α-l-arabinopyranoside]bayogenin (9), 3-O-β-d-glucuronopy...

Dammarane triterpenes from the hypocotyls and fruits of Ceriops tagal.

Abstract: Three new dammarane triterpenes, cereotagaloperoxide (1), cereotagalol A (2), and cereotagalol B (3), together with four known dammarane triterpenes, an oleanane triterpene, and 13 known lupane triterpenes were isolated from the hypocotyls and fruits of Ceriops tagal. The structures of 1−3 were characterized on the basis of their spectroscopic data.

Cytotoxic hydroxylated triterpene alcohol ferulates from rice bran.

Abstract: Three hydroxylated triterpene alcohol ferulates, (24S)-cycloart-25-ene-3 beta,24-diol-3 beta-trans-ferulate (1), (24R)-cycloart-25-ene-3 beta,24-diol-3 beta-trans-ferulate (2), and cycloart-23Z-ene-3 beta,25-diol-3 beta-trans-ferulate (3), along with known compounds cycloartenol trans-ferulate (4) and 24-methylenecycloartanol trans-ferulate (5) were isolated from rice bran. Their structures were elucidated by means of chemical and spectroscopic analysis. Compounds 2-5 showed moderate cytotoxicity against MCF-7 cells.

Two new cycloartane triterpene glycosides and a new alkaloid from Souliea vaginata

Abstract: Chemical investigation on the rhizome of Souliea vaginata resulted in the isolation of two new cycloartane triterpene glycosides and a new alkaloid, soulieosides D and E, and soulieotine (1-3), and their structures were elucidated on the basis of extensive NMR spectral experiments and chemical methods as (20S*,22R*,23S*,24R*)-16β:23;22:25-diepoxy-3β,24-dihydroxy-23-methoxy-9,19-cyclolanostane-3-O-β-D-(4-acetyl)xylopyranoside (1), (20S*,22R*,23S*,24R*)-16β:23;22:25-diepoxy-3β,23,24-trihydroxy-9,19-cyclolanostane-3-O-β-D-(3-acet yl)xylopyranoside (2), E-3-(3'-methyl-2'-butenylidene)-6-methoxy-2-indolinone (3).

Two new triterpene saponins from Eryngium campestre.

Abstract: Two new triterpene saponins, 3-O-beta-D-glucopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucuronopyranosyl-22-O-angeloyl-R1-barrigenol (1) and 3-O-beta-D-glucopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucuronopyranosyl-22-O-beta,beta-dimethylacryloyl-A1-barrigenol (2), were isolated from the roots of Eryngium campestre (Apiaceae). Their structures were established mainly by 2D NMR techniques and mass spectrometry.