New Terpenoids from Tricholoma saponaceum (original) (raw)

A new triterpenoid from Sapium baccatum (Euphorbiaceae

Natural Product Research,, 2014

A new triterpene, malaytaraxerate (1), and four known compounds, taraxerol (2), taraxerone (3), docosyl isoferulate (4) and docosanoic acid 20,30-dihydroxypropyl ester (5), were isolated from the acetone extract of Sapium baccatum stem bark. The structures of the isolated compounds were determined using several spectroscopic methods, including UV–Vis, FT-IR, 1D and 2D NMR, and mass spectrometry. Major isolated compounds were assayed for cytotoxicity. The chemotaxonomic significance of this plant was also studied.

Triterpenoid saponins from the roots of Gypsophila trichotoma Wender

Phytochemistry, 2013

Eleven triterpenoid saponins were isolated from the roots of Gypsophila trichotoma Wender. (G. trichotoma Wender. var. trichotoma) (Caryophyllaceae), together with one known compound. The structures were established on the basis of extensive NMR analysis ( 1 H, 13 C NMR, COSY, TOCSY, ROESY, HSQC, and HMBC), completed by analysis of HR-ESI-MS and ESI-MS n . The saponins have the commonly found gypsogenin as the aglycone substituted at C-3 with trisaccharide and at C-28 with oligosaccharide through a fucose residue, as saponins isolated from Gypsophila perfoliata L. originated from China. The oligosaccharide attached to C-28 is substituted with acetyl and (or) sulfate groups.

Acylated triterpenoid saponins from roots of Gypsophila trichotoma

Planta Medica, 2012

Eleven triterpenoid saponins were isolated from the roots of Gypsophila trichotoma Wender. (G. trichotoma Wender. var. trichotoma) (Caryophyllaceae), together with one known compound. The structures were established on the basis of extensive NMR analysis ( 1 H, 13 C NMR, COSY, TOCSY, ROESY, HSQC, and HMBC), completed by analysis of HR-ESI-MS and ESI-MS n . The saponins have the commonly found gypsogenin as the aglycone substituted at C-3 with trisaccharide and at C-28 with oligosaccharide through a fucose residue, as saponins isolated from Gypsophila perfoliata L. originated from China. The oligosaccharide attached to C-28 is substituted with acetyl and (or) sulfate groups.

New Triterpenoid Saponins from Glochidion eriocarpum and Their Cytotoxic Activity

CHEMICAL & PHARMACEUTICAL BULLETIN, 2009

is a relatively large genus of the Euphorbiaceae family, comprising approximately 300 species distributed from Madagascar to the Pacific Islands and distributed mainly in tropical Asia. In Vietnam, this genus comprises 22-24 species, whereby G. eriocarpum CHAMP. is a shrub plant and abundantly found throughout. 1) In Vietnamese folk medicine, the roots and leaves are used to treat enteritis, indigestion, asthma, cholera, and rheumatism. The whole plant decoction showed antimicrobial activity against Staphylococcus aureus and Bacillus pyocyaneus. 1) Previous investigation resulted in the isolation of six lupanes from the roots and stem wood: lupenone; 3-epi-lupeol; glochidone; glochidonol; glochidiol; and lup-20(29)-ene-1b,3b-diol. Among them, glochidonol and glochidiol exhibited strong inhibitory effects against three human tumor cell lines, MCF-7, NCI-H-460, and SF-268. In addition, the two compounds exerted their antiproliferative activity through the involvement of apoptosis. 2) In continuation of our focusing investigation on cytotoxic constituents from Vietnamese medicinal plants, we report herein the isolation, structural elucidation, and cytotoxic evaluation of two new triterpenoid saponins, glochieriosides A and B (1, 2), along with three known triterpenes, glochidone (3), lup-20(29)-en-3b,23-diol (4), and lup-20(29)-en-1b,3b-diol (5), from the aerial parts of G. eriocarpum. Results and Discussion From the methanol extract of aerial parts of G. eriocarpum, two new triterpenoid saponins, 1 and 2, were isolated by various chromatographic methods. Compound 1 was obtained as an amorphous white powder. The IR spectrum suggested the presence of hydroxyl groups (br, 3392 cm Ϫ1), carbonyl group (1709 cm Ϫ1), aromatic ring 102 Vol. 57, No. 1 Notes

New triterpenoid saponins from the roots of Saponaria officinalis

Natural product communications, 2013

Three new triterpenoid saponins (1-3), along with nine known saponins, were isolated from the roots of Saponaria officinalis L. Two of them: vaccaroside D (4) and dianchinenoside B (5) are known, but not previously reported for S. officinalis, and seven others: saponarioside C (6), D (7), F (8), G (9), I (10), K (11), and L (12) have been previously isolated from this plant. The structures of the new saponins were established as 3-O-beta-D-xylopyranosyl-16alpha-hydroxygypsogenic acid-28-O-[beta-D-glucopyranosyl-(1 -->6)-beta-D-glucopyranoside (1), 3-O-beta-D-xylopyranosyl-16alpha-hydroxygypsogenic acid-28-O-[beta-D-glucopyranosyl-(1-->3)]-[alpha-D-galactopyranosyl-(1-->6)-alpha-D-galactopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside (2) and 3-O-beta-D-xylopyranosyl-gypsogenic acid-28-O-[beta-D-glucopyranosyl-(1-->3)]-[6-O-(3-hydroxy-3-methylglutaryl)-beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside (3). Their structures were elucida...

Triterpene Saponins from the Aerial Parts of Trifolium medium L. var. sarosiense

Journal of Agricultural and Food Chemistry, 2013

Seven previously unreported triterpene glycosides (1−7) were isolated from methanol extract of the aerial parts of Trifolium medium var. sarosiense (zigzag clover). Their structures were established by the extensive use of 1D and 2D NMR experiments along with ESI-MS and HRMS analyses. Compounds 1−7 are oleanane derivatives characterized by the presence of a keto group at C-22 of an aglycone and a primary alcoholic function at C-24 and differing functions at C-30. Among these, compounds 1−3 and 6 showed a secondary alcoholic function at C-11, which is methoxylated in compounds 4 and 7. Compound 5 was shown to possess a known aglycone, wistariasapogenol A; however, it is described here for the first time as a saponin constituent of the Trifolium genus. Some aspects of taxonomic classification of zigzag clover are also discussed.

Phytochemistry of the Genus Trichocolea

Natural Product Communications, 2018

The genus Trichocolea (Fam. Trichocoleaceae) comprise 31 species of liverworts, most of which are endemic in a wide geographical area of the southern Pacific Ocean including New Zealand, Tasmania, and South Australia. Although few reports have been reported on the phytochemistry and pharmacognosy of these briophytes, data reported so far show a great pharmacological potential for their secondary metabolites. Phytochemicals isolated from Trichocolea spp. include benzoate esters, flavonoids, and diterpenes. The reported biological activities of these natural compounds refer to cancer cells growth inhibitory, antibacterial, anti-fungal, and anti-oxidant effects. The aim of this short review is to examine in detail from a phytochemical and pharmacological point of view what is reported in the current literature about the properties of phytopreparations or individual chemicals obtained from liverworts belonging to the Trichocolea genus.

Antiproliferative Triterpenoid Saponins of Dodonaea viscosa from the Madagascar Dry Forest(1)

Journal of Natural Products, 2009

Bioassay-guided fractionation of an EtOH extract obtained from the roots of the Madagascan plant Dodonaea viscosa led to the isolation of two new antiproliferative oleanane-type triterpenoid saponins, dodoneasides A and B (1 and 2). The structures of these two new compounds were elucidated using 1D and 2D NMR experiments and mass spectrometry. Compounds 1 and 2 showed antiproliferative activity against the A2780 human ovarian cancer cell line with IC 50 values of 0.79 and 0.70 μM, respectively.

Triterpenoids with Cytotoxic Potential from the Leaves of Tridax procumbens L

International Journal of Phytomedicine, 2017

The breast cancer cell lines an attempt was made to identify the anticancer principle. ethanol (TPE) and chloroform (TPC) as solvents were screened f against MCF the three extracts, TPC was effective at an IC and MDA presence of only steroids and terpenoids and their concentration was high (77.4% w/w). MS of the chloroform soluble crude extract revealed a major peak (57.59% concentration) at a retention time of 4.78 min and molecular weight 475.80 and 701.80. The compounds were identified to be 18α respectively, bot Key Tridax procumbens Linn. (T. procumbens L.,) from the family Asteraceae is commonly known as 'Ghamra' in local language and 'coat buttons' in English. The plant is endemic to tropical regions of Asia, America, Africa and Australia. In India, Tridax is a widely distributed weed. It is seen along the roadsides, waste grounds, dikes, railroads, riverbanks, meadows, and dunes [3]. This herb/ weed is known to have a wide range of pharmacological activities which have been used in the traditional Indian systems of medicine like Ayurveda, Sidhha and Unani [4]. In Ayurvedic medicine in particular, Tridax is a component of "Bhringraj", which is a composition used in treatment of various disorders [5]. The wide range of therapeutic applications is attributed to the presence of phytochemicals such as alkaloids, carotenoids, flavonoids, terpenoids, saponins and tannins [4]. Compounds with anticancer property such as β-sitosterol, β-sitosterol-3-O-β glucoluteolin, quercetin, luteolin, and procumbenetin have been isolated / purified from the leaves of T. procumbens