Triterpenoid sapogenols from Androsace saxifragifolia: The structure of androsacenol

Pal, Buddhadev; Roy, Gita; Mahato, Shashi B.

doi:10.1016/s0031-9422(00)80489-6

Cited by 14 publications

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“…(Primulaceae) is a perennial plant distributed in China, which is being used as ananticancer and antiphlogistic herb and in the treatment of sore throat in traditional Chinese medicine [1]. Several members of this genus have been reported to be useful as contraceptive and abortifacient agents in India [2], [3], [4]. Previous phytochemical investigations had demonstrated that triterpenoid saponins are the main chemical components of this genus [2], [3], [4].…”

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Triterpenoid Saponins fromAndrosace umbellataand their Anti-proliferative Activities in Human Hepatoma Cells

Wang¹,

Zhang²,

Ye³

et al. 2008

Planta Med

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Two new triterpenoid saponins, along with five known ones, were isolated from the EtOH extract of the whole plants of Androsace umbellata. The structures of the new triterpenoid saponins were identified as 3- O-[ beta- D-xylopyranosyl-(1-->2)- beta- D-glucopyranosyl-(1-->4)-[ beta- D-glucopyranosyl-(1-->2)]- alpha- L-arabinopyranosyl]-3 beta-hydroxy-13 beta,28-epoxy-16-oxo-oleanan-30-al ( 1) and 3- O- beta- D-xylopyranosyl-(1-->2)- beta- D-glucopyranosyl-(1-->4)- alpha- L-arabinopyranosyl-3 beta-hydroxy-13 beta,28-epoxy-16-oxo-oleanan-30-al ( 2) on the basis of their spectral and chemical properties. All these compounds showed significant cytotoxic activities in human hepatoma cells.

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“…Several members of this genus have been reported to be useful as contraceptive and abortifacient agents in India [2], [3], [4]. Previous phytochemical investigations had demonstrated that triterpenoid saponins are the main chemical components of this genus [2], [3], [4]. Hepatocellular carcinoma (HCC) is the fifth most common type of cancer worldwide.…”

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confidence: 99%

Triterpenoid Saponins fromAndrosace umbellataand their Anti-proliferative Activities in Human Hepatoma Cells

Wang¹,

Zhang²,

Ye³

et al. 2008

Planta Med

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“…ODS column as stationary phase and MeOH-water (70: 30) as mobile phase. Acid hydrolysis of compound (6) led to the formation of an aglycone characterized as androsacenol (1) and to monosaccharide constituents identified as D-glucose, Dxylose, and L-arabinose by comparison with authentic samples; the absolute configuration is assumed for glucose and xylose constituents and that of arabinose was determined by its isolation and by a study of its properties (see Experimental section).…”

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New triterpenoid pentasaccharides from Androsace saxifragifolia

Pal¹,

Mahato²

1987

J. Chem. Soc., Perkin Trans. 1

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T w o n e w triterpenoid pentasaccharides, saxifragifolins C and D, isolated from the aerial part of Androsace saxifragifolia were characterized as androsacenol 3-0-{j3-~-xylopyranosyl-(1 --+ 2 ) -P-Dglucopyranosyl-(I ---4)-[p-~-glucopyranosyl-(l ---4)-~-~-glucopyranosyl-(l ---2 ) ] -a-L-arabinopyranoside} (6) and cyclamiretin A 3-0-{~-~-xylopyranosyl-(l -+ 2) -p-o-glucopyranosyl-(1 --+ 4)-[~-~-glucopyranosyl-(I --+ 4)-j3-~-glucopyranosyl-(l ---2)]-a-~-arabinoside} (7). The structures were elucidated b y a combination of field desorption mass spectrometry, chemical degradation, and 'H and 13C n.m.r. spectroscopy.In previous communications the isolation and characterization of the sapogenols androsacenol (l), cyclamiretin A (2), and cyclamiretin D (3) and the saponins saxifragifolin A (4) and saxifragifolin B (5) from A . saxfragifolia have been reported. Further work on the saponin mixture of the plant led to the isolation of two new triterpenoid pentasaccharides, saxifragifolin C and saxifragifolin D. This paper reports the isolation and structure elucidation of these two glycosides. Results and DiscussionThe ethanolic extract of the aerial part of A . saxfragifolicr on repeated chromatographic purification on silica gel column afforded, besides fractions A and B whose characterization has already been reported,2 a third fraction, C, which gave positive colour tests for triterpenoid glycosides. This fraction, although apparently homogeneous by t.l.c., was found to be a mixture of two compounds by h.p.l.c., and could successfully be separated by preparative h.p.1.c. to afford saxifragifolin C (6) and saxifragifolin D (7) using a reversed-phase Spherisorb S-10-

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Triterpenoids

Connolly¹,

Hill²

1991

Dictionary of Terpenoids

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Triterpenoid sapogenols from Androsace saxifragifolia: The structure of androsacenol

Cited by 14 publications

References 6 publications

Triterpenoid Saponins fromAndrosace umbellataand their Anti-proliferative Activities in Human Hepatoma Cells

Triterpenoid Saponins fromAndrosace umbellataand their Anti-proliferative Activities in Human Hepatoma Cells

New triterpenoid pentasaccharides from Androsace saxifragifolia

Triterpenoids

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