2α, 3α–DIHYDROXYOLEAN–12–EN–28–OIC ACID FROMHOLOPTELEA INTEGRIEOLIAHEARTWOOD

Abstract

2a, 3a-Dihydroxyolean-12-en-28-oic acid has been isolated from Holoptelea integrifolia heartwood and its structure elt~cidated by physico-chemical methods and comparison with synthetic sample. Holoptelea integrifolia PLANCH. syn. Ulmzrs integrifolia ROXB. (Lllmaceae) locally known as Chilbil, is a roadside tree distributed throughout the greater part of India [I]. T h e bark yields friedelin and friedelin-3fi-01 and the leaves yield hexacosanol, octacosanol, fi-sitosterol and fi-amyrin [2]. In pursuance of the investigations on different parts of H. integrifolia, a systematic chemical examination of its heartwood has been taken up and a rare triterpene acid (Fig. 1 a), 2a, 3a-dihydroxyolean-12-en-28-oic acid has been isolated and its structure elucidated. T h e hexane and ether soluble sticky semi-solid fractions of the alcohblic extractive of the heartwood on chromatography (silica gel) yielded an LB and T N M positive product, m. p. 150-200' which was acidic in nature and showed 5 spots on TLC (silica geI G plates; Bz-MeOH, 9 5 5). Repeated column chromatography (silica gel and alumina) could not furnish any pure product. The mixture was, therefore, methylated with diazomethane and the resultant methylester mixture o n chromatography (alumina) resolved into 3 .different fractions having melting ranges 170-190°, 280-290' and 225-230" respectively. The major and the highest melting methylester was purified by rechromatography and crystallisations from alcohol as needles when it melted a t 294-296'; (a):;, + 62.7O! mol. wt. 486 (M'). The elemental analysis answered the molecular formula, CSIHj004 for the compound (Fig. l b) which formed a crystalline dibenzoate, C45H5S06 and an amorphous acetate found mixture of a monoacetate and a diacetate (M* = 570; Fig. lc).

Chemical Investigation and Anti-Inflammatory Activity of Vitex negundo Seeds

“…2 R'=R2=ot-OH, R3=H 3 R1=3-OAc, R2=ot-OAc, R3=H 4 R1 = ß-OH, R2=ct-OH, R3=H 5 R1=a-OAc, R^-OAc, R3=OH Compound 2 formed an acetonide (7), and its eims gave peaks at mlz 510 [M]+ (1%), 464 [ -H -COOH]+ (1%), 452 [M-MeCOMe}+ (1%), 406 (5%), 248 (100%), and 203 (48%). Formation of an acetonide supported the cis configuration or the diequatorial conformation of the hydroxyl groups (8). Acetylation of compound 2 yielded the product as a gum.…”

“…The similarity in chemical shifts of the seven methyl groups in the 'H-nmr spectrum of 2 and its diacetate suggested that the two oxygen functionalities in the molecule were both a. If the hydroxyl groups were ß, the chemical shifts of the C-24 and C-25 methyls of 2 would appear downfield in comparison to those of the diacetate (5,8).…”

CONSTITUENTS OFHOLOPTELEA INTEGRIFOLIAHEARTWOOD

“…The major (10 g) and highest melting methylester was, of course, the rare triterpene acid already reported [3]. The location of the two hydroxyl groups in rings A and/or B is indicated by the peaks at m/e 262 and rnle 223 corresponding to fragments 'a' and 'g' [6].…”

“…While continuing the investigations on different parts of H. integrifolia, a systematic chemical examination of its heartwood was undertaken. Along with the report [3] of isolation and structure elucidation of a rare triterpenoid, 2a, 3a-dihydroxyolean-12-en-28-oic acid, the presence of some other constituents in the heartwood had been indicated. The isolation and characterisation of these constituents is described here.…”

A preliminary study of Cedronella canariensis (L.) var. Canariensis extracts for antiinflammatory and analgesic activity in rats and mice

“…6 g of E was treated with CHzNz, after purification the yields of esters were methyl ursolate (3.5 g), 2a,3a dihydroxy-urs-12-en-28-methyl ester (50 mg) (Misra et al, 1975), 2a,3a dihydroxy-olean-12-en-28 methyl ester (10 mg) (Misra et al, 1975). 2a,3P dihydroxy-urs-12-en-28-methyl ester (100 mg) (Caputo et al, 1974), 2a,3~dihydroxy-olean-l2-en-28-methyl ester (50mg) (Tandon et al, 1980) and 2a,3a, 23 trihydroxy-urs-12-en-28-methyl ester (8 mg) (Tandon et al, 1980 D was washed with pyridine and the solution filtered and analysed by HPLC: five sugars were identified raffinose (lo%), saccharose (5.2%), glucose (l8%), galactose (2%) and fructose (18%).…”