Cycloartane glycosides from leaves of Oxyanthus pallidus.

From the MeOH extract of leaves of Oxyanthus pallidus, three cycloartane glycosides, named pallidiosides A-C, were isolated together with two known compounds, oleanolic acid and 3-O-β-D-glucopyranosyl-β-sitosterol. The structures of pallidiosides A-C were assigned on the basis of spectral studies and comparison with published literature data. The known compounds were identified by means of Co TLC and confirmed by their physical constants.

Triterpenoid saponins from the fruits of Caryocar villosum.

Fourteen new triterpenoid saponins (1-14) were isolated from the methanol extract of the fruits of Caryocar villosum along with 10 known saponins. Their structures were established on the basis of extensive NMR (1H, 13C, COSY, TOCSY, ROESY, HSQC, and HMBC) and ESIMS studies. The toxicity of the methanolic extracts of the peel and the pulp of fruits and the crude saponin fraction of the peel was assessed using the Artemia salina test.

Triterpenoid saponins from the fruits of Caryocar glabrum.

Twenty-one new triterpenoid saponins, named caryocarosides (1-21), glycosides of 2beta-hydroxyoleanolic acid, hederagenin, bayogenin, and gypsogenic acid, have been isolated from the fruits of Caryocar glabrum along with nine known triterpenoid saponins (22-30) that are described for the first time from a plant in the Caryocaraceae. Their structures were established by 1D and 2D NMR techniques ((13)C, COSY, TOCSY, HSQC, HMBC, and ROESY experiments), ESIMS, and acid hydrolysis. The isolated compounds could be classified into two series: glucosides (1-8, 22, 27, and 30) derived from the 3-O-monoglucoside and glucuronides (9-21, 23-26, 28, and 29) derived from the 3-O-monoglucuronide.

Haemolytic acylated triterpenoid saponins from Harpullia austro-caledonica.

Eight new acylated triterpenoid saponins were isolated from the stem bark of Harpullia austro-caledonica along with the known harpuloside (9). Their structures were established using 1D and 2D NMR and mass spectrometry as 3-O-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylbarringtogenol C (1), 3-O-alpha-L-rhamnopyranosyl-(1-->3)-[beta-D-galactopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloyl barringtogenol C (2), 3-O-alpha-L-arabinofuranosyl-(1-->3)-[beta-D-galactopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylbarringtogenol C (3), 3-O-alpha-L-arabinofuranosyl-(1-->2)-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylprotoaescigenin (4), 3-O-alpha-L-arabinofuranosyl-(1-->3)-[alpha-L-arabinofuranosyl-(1-->2)]-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloyl protoaescigenin (5), 3-O-alpha-L-arabinofuranosyl-(1-->3)-[beta-D-xylopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylprotoaescigenin (6), 3-O-alpha-L-arabinofuranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylprotoaescigenin (7), 3-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylprotoaescigenin (8). The EtOH extract of the stem bark showed in vitro cytotoxic activity against KB cells (90% at 10 microg/ml).

Acetylated glucuronide triterpene bidesmosidic saponins from Symplocos glomerata.

Nine new bidesmosidic 3-O-glucuronide oleanane triterpenoid saponins were isolated from the stem bark of Symplocos glomerata King along with two known saponins, salsoloside C and copteroside E, and two major lignans, (-)-pinoresinol and (-)-pinoresinol-4'-O-beta-D-glucopyranoside. The structures of the new saponins were established using one- and two-dimensional NMR spectroscopy and mass spectrometry as, 3-O-[beta-D-xylopyranosyl(1-->4)-[2-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[beta-D-xylopyranosyl(1-->4)-[3-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[beta-D-xylopyranosyl (1-->4)-[2,3-O-diacetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[alpha-L-arabinopyranosyl(1-->4)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[alpha-L-arabinopyranosyl (1-->4)-[2-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[[beta-D-xylopyranosyl (1-->2)]-[beta-D-xylopyranosyl (1-->4)]-[3-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[[beta-D-glucopyranosyl (1-->2)]-[beta-D-xylopyranosyl (1-->4)]-[3-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[[beta-D-glucopyranosyl (1-->2)]-[alpha-L-arabinofuranosyl (1-->4)]-[3-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, and 3beta-O-[beta-D-xylopyranosyl(1-->4)-[2-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-morolic acid. The EtOH and EtOAc extracts of the stem bark showed no cytotoxic activity.

Oleanolic glycosides from Pometia ridleyi.

Six triterpenoid saponins were isolated from the stem bark of Pometia ridleyi along with two known saponins, acutoside A and calenduloside C. Their structures were established using one- and two-dimensional NMR and mass spectrometry as 3-O-beta-D-apiofuranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranosyl-, 3-O-beta-D-apiofuranosyl-(1-->3)-alpha-L-arabinopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranosyl-, 3-O-beta-D-apiofuranosyl-(1-->3)-beta-D-galactopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranosyl-, 3-O-alpha-L-arabinopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl-, 3-O-beta-D-galactopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl-, 3-O-beta-D-apiofuranosyl-(1-->3)-beta-D-galactopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl-oleanolic acid. The EtOH and EtOAc extracts of the stem bark showed no cytotoxic activity.

Triterpenoid saponins and acylated prosapogenins from Harpullia austro-caledonica.

Three new triterpenoid saponins have been isolated from the stem bark of Harpullia austro-caledonica and identified as 24-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]-28-O-[beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranosyl]-protoaescigenin, 24-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]-28-O-[beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranosyl]-16-desoxyprotoaescigenin, 24-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]-28-O-[beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranosyl]-24-oxo-camelliagenin D. The 21,22-di-O-angeloate esters of protoaescigenin and barringtogenol C were isolated in the acid hydrolysate of the saponin extract together with a new prosapogenin identified as 21beta,22alpha-di-O-angeloyl camelliagenin D. The structures were established using one- and two- dimensional NMR and mass spectrometry.

[Saponins and hemolytic activity. Saponins and glycosides from five species of Sapindaceae].

The haemolytic activity of saponins has been a known phenomenon for many years. In this work, structure-activity relationships were established from various triterpene saponins distinguishing hemolytic activity between mono- and bidesmosidic saponins. Saponins structure in Sapindaceae serve as a chimiotaxonomic criteria for dividing the species into two sub-families.

Saponins from Chenopodium album.

The isolation and spectral data of three saponins from the roots of Chenopodium album L. are reported. One of them is a seco-glycoside analogous to compounds that were previously found in species belonging to Caryophyllales.

Cytotoxic polyisoprenes and glycosides of long-chain fatty alcohols from Dimocarpus fumatus.

The ethanolic extract from the stem bark of Dimocarpus fumatus, showed in vitro cytotoxic activity against KB cells. Fractionation of the extract gave compounds belonging to different classes. The two major components have been identified as a benzoquinone, sargaquinone, and a chromene, sargaol.

Saponins from Harpullia cupanioides.

Five new saponins have been isolated from the stem bark of Harpullia cupanioides and identified as 3-O-beta-D-glucopyranosyl(1-->2)[alpha-L-rhamnopyranosyl(1-->3)] beta-D-glucuronopyranosyl 22-O-angeloyl-A1-barrigenol, 3-O-beta-D-glucopyranosyl(1-->2)[alpha-L-rhamnopyranosyl(1-->3)] beta-D-glucuronopyranosyl 28-O-angeloyl-A1-barrigenol, 3-O-beta-D-galactopyranosyl(1-->2)[alpha-L-rhamnopyranosyl(1-->3)] beta-D-glucuronopyranosyl 28-O-angeloyl-A1-barrigenol. 3-O-beta-D-galactopyranosyl(1-->2)[alpha-L-rhamnopyranosyl(1-->3)] beta-D-glucuronopyranosyl 16-O-beta, beta-dimethylacryloyl-camelliagenin A and 3-O-beta-D-glucopyranosyl(1-->2)[alpha-L-rhamnopyranosyl(1-->3)] beta-D-glucuronopyranosyl 28-O-angeloyl-camelliagenin A. The structures were elucidated by analysis of 2D-NMR spectra and mass spectra.

Saponins from the stem bark of Filicium decipiens.

Four new saponins have been isolated from the stem bark of Filicium decipiens and identified as 3-O-{beta-D-glucopyranosyl(1-->2)-beta- D-glucopyranosyl}-28-O-{[alpha-L-arabinopyranosyl(1-->2)-beta- D-xylopyranosyl (1-->6)]. [4-O-angeloyloxy-alpha-L-arabinopyranosyl(1-->2)-alpha-L- rhamnopyranosyl(1-->2)]}-beta-D-glucopyranosyl gypsogenic acid, 3-O-{beta-D-glucopyranosyl(1-->2)-beta-D- glucopyranosyl}-28-O-{[alpha-L-arabinopyranosyl(1-->2)- beta-D-xylopyranosyl(1-->6)] [4-O-angeloyloxy-alpha-L- arabinopyranosyl(1-->2)-alpha-L-rhamnopyranosyl(1-->2)]}-beta-D- glucopyranosyl medicagenic acid, 3-O-{beta-D-glucopyranosyl(1-->2)-beta-D- glucopyranosyl}-28-O-{[alpha-L-arabinopyranosyl(1-->2)] [beta-D-xylopyranosyl(1-->4)]alpha-L-rhamnopyranosyl(1-->2)-4-O-[3'- hydroxy-2'-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy++ +]-beta-D- fucopyranosyl} medicagenic acid and 3-O-beta-D-glucopyranosyl-28-O- {[alpha-L-arabinopyranosyl(1-->2)] [beta-D-xylopyranosyl(1-->4)] alpha-L-rhamnopyranosyl(1-->2)-4- O-[(3'-hydroxy-2'-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyro yloxy]-beta- D-fucopyranosyl} zanhic acid. These structures were elucidated by analysis of 2D-NMR spectra and of electrospray ionization mass spectra.