Triterpenoids and their glucosides from Terminalia bellerica

Nandy, Abhishek; Podder, G.; Sahu, Niranjan P.; Mahato, Shashi B.

doi:10.1016/s0031-9422(00)98085-3

Cited by 66 publications

(32 citation statements)

References 10 publications

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“…This indicated that 1 is an 12 -oleanene type of triterpene, with two methyl groups oxidized and another methyl group transformed into a carboxylic group. This was also confirmed by HREIMS, which showed the characteristic retro Diels-Alder fragments at m/z 224.1776 (C 14 H 24 O 2 ) and 280.1674 (C 16 H 24 O 4 ), revealing the presence of two hydroxylic moieties in ring A or B and two hydroxyl groups and a carboxylic moiety in ring C, D or E. [9] The ready loss of carboxyl group from the molecular ion gave a peak at m/z 459.3474 [M − COOH] + (C 29 H 47 O 4 ) indicating its presence at the angular C-17 position (Fig. 1).…”

Section: Resultsmentioning

confidence: 53%

Structural determination of salsolins A and B, new antioxidant polyoxygenated triterpenes from Salsola baryosma, by 1D and 2D NMR spectroscopy

Ahmad

Mehmood

Fatima

et al. 2007

Magnetic Reson in Chemistry

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Salsolins A (1) and B (2), the new triterpenes, have been isolated from the chloroform soluble fraction of Salsola baryosma along with 2alpha,3beta,23,24-tetrahydroxyurs-12-en-28-oic acid (3) reported for the first time from this species. Their structures have been assigned from 1H and 13C NMR spectra, DEPT and by 2D COSY, NOESY, HMQC and HMBC experiments. The compounds 1-3 showed significant antioxidant activity.

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Section: Resultsmentioning

confidence: 53%

Structural determination of salsolins A and B, new antioxidant polyoxygenated triterpenes from Salsola baryosma, by 1D and 2D NMR spectroscopy

Ahmad

Mehmood

Fatima

et al. 2007

Magnetic Reson in Chemistry

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“…Compound 6 was identified by means of 1 H and 13 C NMR as arjunglucoside I, a triterpene glucoside previously characterized in several species of Terminalia (e.g., T. arjuna 17 and T. bellerica 18 ). The structure of 7 was shown to be of stigmastane-3β-6α-diol on the basis of its 1 H and 13 C NMR spectral data, which were in accordance with those reported for the same steroid previously isolated from Trichosantes kirilowii (Cucurbitaceae), 19 Spatholobus suberetus (Leguminosae) 20 and Urtica dioica (Urticaceae) 21 and until now, not yet described in Combretaceae.…”

Section: Resultsmentioning

confidence: 99%

“…[1][2][3][4][5][6][7][8] Terminalia glabrescens Mart., which has not previously been chemically investigated, is a medium-sized tree widespread in Mato Grosso do Sul, Brazil. In the present paper, we describe the isolation and structural elucidation of a new oleanane-type triterpene (3β,6β,23,28-tetrahydroxyolean-12-ene) from the leaves of this species.…”

Section: Introductionmentioning

confidence: 99%

Chemical constituents from Terminalia glabrescens

Garcez¹,

Garcez²,

Miguel³

et al. 2003

J. Braz. Chem. Soc.

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Das folhas de Terminalia glabrescens foram obtidos um novo triterpeno pentacíclico (3β,6β,23,28-tetraidroxiolean-12-eno), além dos ácidos ursólico, 2α-hidroxiursólico, oleanólico, maslínico, arjunólico, sumaresinólico e asiático, esqualeno, fitol, sitosterol-3-O-β-D-glucopiranosídeo e nalcanos. Da casca do caule foram obtidos friedelina, taraxerol, lupeol, lupenona, betulina, betulona, ácido betulínico, arjunglucosídeo I, estigmastano-3β,6α-diol, β-sitosterol, (-) catequina, β-Dpiranotagatose, β-D-furanofrutose e α-D-furanofrutose.A new oleanane-type triterpene (3β,6β,23,28-tetrahydroxyolean-12-ene) was isolated from the leaves of Terminalia glabrescens, together with ursolic, 2α-hydroxyursolic, oleanolic, maslinic, arjunolic, sumaresinolic and asiatic acids, squalene, phytol, sitosterol-3-O-β-D-glucopyranoside and n-alkanes. Friedelin, taraxerol, lupeol, lupenone, betulin, betulone, betulinic acid, arjunglucoside I, stigmastane-3β,6α-diol, β-sitosterol, (-) catechin, β-D-pyranotagatose, β-D-furanofructose and α-D-furanofructose were obtained from the trunk bark. Combretaceae, triterpenes, 3β,6β,23, Keywords: Terminalia glabrescens, IntroductionPlants of the genus Terminalia (Combretaceae) are known as a rich source of secondary metabolites, such as pentacyclic triterpenes and their glycoside derivatives, flavonoids, tannins and other aromatic compounds, some of which with antibacterial, antifungal, anticancer and hepatoprotective activities. 1-8Terminalia glabrescens Mart., which has not previously been chemically investigated, is a medium-sized tree widespread in Mato Grosso do Sul, Brazil. In the present paper, we describe the isolation and structural elucidation of a new oleanane-type triterpene (3β,6β,23,28-tetrahydroxyolean-12-ene) from the leaves of this species. The known pentacyclic triterpenes ursolic, 2α-hydroxyursolic, oleanolic, maslinic, arjunolic, sumaresinolic and asiatic acids together with squalene, phytol, sitosterol-3-O-β-Dglucopyranoside and foliar wax hydrocarbons were also obtained from the leaves, while the trunk bark afforded the triterpenes friedelin, taraxerol, lupeol, lupenone, betulin, betulone, betulinic acid and arjunglucoside I in addition to stigmastane-3β,6α-diol, β-sitosterol, (-) catechin, β-D-pyranotagatose, β-D-furanofructose and α-D-furanofructose.The structures of the known and new compounds were established on the basis of spectral data, mainly 1 H and 13 C (1D and 2D) NMR spectra and by comparison with authentic samples. Results and DiscussionThe hexane and CHCl 3 solubles obtained from partition of the ethanol extract of leaves were subjected to a series of normal and reversed phase silica gel column chromatography, gel filtration and preparative TLC on silica gel separations to yield the new pentacyclic triterpene 3β,6β,23,28-tetrahydroxyolean-12-ene (1) in addition to ursolic, 9 oleanolic, 9 2α-hydroxyursolic, 9 maslinic, 9 sumaresinolic (2), 9 asiatic (3) 9 and arjunolic (4) 9 acids, squalene, 10 phytol, sitosterol-3-O-β-D-glucopyranoside and long chain hydrocarbons...

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“…13 C-NMR data for 3 (2α,3β,19α,24-tetrahydroxyolean-12-en-28 oic acid) were not available in the literature, and the signals were attributed by comparison with the respective data for rings A/B of 4 (2α,3β,19,24-tetrahydroxyurs-12-en-28 oic acid) 6 and for rings C/D/E of arjungenin (2α,3β,19α,23-tetrahydroxyolean-12-en-28 oic acid) 7 . Reaction of 3 with diazomethane afforded the respective methyl ester, 1 H-NMR data were in agreement with data previously published 8 .…”

Section: Me-26mentioning

confidence: 99%

Divergioic Acid, a Triterpene from Vochysia divergens

Hess¹,

Monachè²

1999

J. Braz. Chem. Soc.

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Um novo triterpeno lupânico, ácido divergióico, além de β-sitosterol, ácidos betulínico, serícico e 24-hidroxitormêntico, e o éster (28 → 1) β-D-glucopiranosílico do último, foram obtidos a partir da casca do caule de Vochysia divergens. A estrutura do ácido divergióico foi elucidada por meio de técnicas espectroscópicas, e caracterizada como sendo o ácido 2α,3β,6β-trihidroxi-lup-20(29)-en-28-óico.A new lupane triterpene, divergioic acid, has been isolated from the stem bark of Vochysia divergens together with β-sitosterol, betulinic, sericic and 24-hydroxytormentic acids and the (28 → 1) β-D-glucopyranosyl ester of the latter. The structure of divergioic acid was elucidated by spectroscopic techniques and characterized as 2α,3β,6β-trihydroxy-lup-20(29)-en-28-oic acid.

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Triterpenoids and their glucosides from Terminalia bellerica

Cited by 66 publications

References 10 publications

Structural determination of salsolins A and B, new antioxidant polyoxygenated triterpenes from Salsola baryosma, by 1D and 2D NMR spectroscopy

Structural determination of salsolins A and B, new antioxidant polyoxygenated triterpenes from Salsola baryosma, by 1D and 2D NMR spectroscopy

Chemical constituents from Terminalia glabrescens

Divergioic Acid, a Triterpene from Vochysia divergens

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