STIGMASTEROL GLUCOSIDE A CONSTITUENT OFADENANTHERA PAVONINASEED AND LEAF

Abstract

Adenanthera pavonina Li n n. (Mimosaceae) [I], a large deciduous tree, commonly known as 'red wood,' is found in the Eastern Sub-Himalayan tract, the Western Ghats and the Andamans. It is an avenue tree [2] especially in southern part of the country and its wood is used as a dye and as a substitute for the true red sandal wood (Pterocarptls santalintts). The tree yields a gum called m a d at i a [I]; and the seed besides yielding the fixed fat [2], is reported to have medicinal properties [I, 21. While pursuing the investigation with the different plants of Legtrminosae, a systematic chemical examination of the seed kernel, seed coat and the leaves of A. pavonina was also carried out. The dark red seed (3.2 kg) yielded 53% kernel and 47% seed coat. T h e alcoholic extractive of the powdered kernel taken up in excess of n-hexane and left over night, deposited white precipitate (177 g). The precipitate crystallised from alcohol furnished cubical crystals (23 g; 0.8%), identified as dulcitol through m. p. 184-186" (dec.), mixed m. p. and co-TLC(CHC13-CH30H, 5:20). The filtrate freed of the sugar alcohol on removal of the solvent gave a polysaccharide as a foam (150 g) which on acid (alc. HC15%) hydrolysis yielded a sugar mixture consisting of glucose, xylose, arabinose, rhamnose and two unidentified spots (paper co-chromatography). The hexane soluble portion of the alcoholic extractive on chromatography over neutral alumina yielded from the hexane eluents, stigmasterol, m.p. 163-165", m/e 410 Mf, identity established through mixed m. p., superposable IR-spectrum [3], mass fragmentation and acetate, m. p. 140-141'; and from the methanol eluents, a microcrystalline substance, m. p. 290-291°, single spot o n thin layer (silica gel G, Bz-MeOH, 98:2) plates, mol. wt. 574 (Mf). Found [3]: C, 73.10; H, 10.72. C35H580s requires: C, 73.13; H, 10.28%. The compound was Lieberman-Burchard (pink-violet-blue-green) positive and showed in its IR-spectrum [3], broad absorption [4] due to bonded hydroxyl similar to that of a sterol glucoside. Bands [4] at 1250 and 1226 cm-I for the CC stretching frequencies associated with the glucosidic linkage were also prominent. It formed a tetraacetate, C4,Hao Ole, m. p. 144-145", finally indicating the compound to be a sterol glucoside. The conventional dilute acid hydrolysis of the glucoside failed to give either the aglycone o r the sugar moiety in contradistinction to the character of the common phytosterol glucosides [S-71. T o explain the difficulty in hydrolysing the compound, its physico-chemical properties were thoroughly studied. With con

1 ß-Hydroxyfriedel-6(7)-ene-3-one from Momordica foetida

“…was identified as stigrnastero1-ß-Dglucoside through rn.p. and IR properties of the glycoside and its pentaacetate, as well as the rnp., IR and MS properties of the aglycone which accorded well with published data [8].…”

Isolation and Characterization of a New Allelochemical from Seeds of Adenanthera pavonina Linn.

“…This decoction is said to be useful in haemorrhage from the bowels and haematuria 1,2 . Earlier workers [3][4][5][6][7] have reported various chemical constituents from this plant. In the present paper we report the isolation and structural elucidation of a new allelochemical 3,5,7,3',4'-pentahydroxy flavone-3'-O-α-Lrhamnopyranosyl-(1→4)-O-α-L-arabinopyranosyl-(1→3)-Oβ-D-xylopyranoside (1) alongwith two known compounds 2,4,7-trihydroxyisoflavone (2) and isovitexin (3) from methanolic extract of the seeds of this plant.…”

A selection of eleven plants used as traditional Polynesian cosmetics and their development potential as anti-aging ingredients, hair growth promoters and whitening products

“…β-glucopyranoside and quercetin-3-O-rhamnopyranosyl (1''' -> 2'')-βglucopyranoside (Mohammed et al, 2014) stigmasterol glucoside, dulcitol, stigmasterol, octacosanol and glucosides of β-sitosterol (Nigam et al, 1973) Anti-inflammatory (Ara et al, 2010) Antioxidant (Mohammed et al, 2014;Wickramaratne et al, 2016) Anti-quorum sensing (Vasavi et al, 2015) Aleurites , 1998). Also, moluccanic acid, methyl ester moluccanic acid, 6,7-dehydromoluccanic acid (Liu et al, 2008) Stem: Coumarinolignoids extract such as moluccanin (Shamsuddin et al, 1988) Twigs: Moluccanic acid, methyl ester moluccanic acid and 6,7dehydromoluccanic acid (Liu et al, 2008) Cutaneous anti-inflammatory activity (Cesca et al, 2012;Hoepers et al, 2015), antinociceptive (Cesca et al, 2012;Quintao et al, 2011 and2012), bacopaside X, bacoside A3 (Sivaramakrishna et al, 2005) bacopasaponins A-C (Garai et al, 1996) Bidens pilosa L Sesquiterpenes and polyacetylenes E-caryophyllene, β-gurjunene, αhumulene, germacrene-D, biciclogermacrene, α-muurolene, Z-γbisabolene, selina-3,7(11)-diene (Grombone-Guaratini et al, 2005) Stigmasterol, squalene, elaidic and behenic acids, and phytyl heptanoate (Zulueta et al, 1995) Several volatile compounds were found in the hydrodistillate, some Cyclooxygenase and PGE2 inhbitor (Yoshida, 2006) Antioxidant: ROS inhibition and NO activation in dermal endothelial cells (Kohda et al, 2013) antimicrobial (Geissberger & Séquin, 1991) Antioxidant: DPPH, anti-radical and NO inhibitor (Chiang et al, 2004;Cortés-Rojas et al, 2013) immunomodulatory (Chang et al, 2007) anti-aging activity of phytol (Dieamant et al, 2015).…”