Terpenoids and steroids from Macaranga tanarius

Phytochemistry
1975.0

Abstract

The light petrol extract of the stems of M. tatarinus has been found to contain diterpenoids: besides macarangonol, 6:10-epoxylathyrol-5,10-diacetate-3-phenylacetate (I) [4], which has previously been isolated only from Euphorbia lathyris (Euphorbiaceae), and triterpenoids: friedel-3-ene, friedelin, friedelan-3β-ol, β-amyrone and β-amyrin. Friedel-3-ene was first prepared in the pure state by Brownlie et al. [15] by dehydration of friedelan-3β-ol, and its natural occurrence has been reported only from Leucopogon membranaceum (Ericaceae) [6]. The steroids, sitosterol, stigmastan-3,6-dione and 6β-hydroxystigmast-4-en-3-one have also been found in the same extract. The former was first reported from Metasequoia glyptostroboides [7] in 1969, though its synthesis from sitosterol [8] had been achieved in 1942. This is its second natural occurrence. 6-β-Hydroxystigmast-4-en-3-one has been isolated twice from plants as inseparable mixtures: one with 6β-hydroxycampest-4-en-3-one from Melia azedarach [9], and the other with 6β-hydroxystigmasta-4,22-dien-3-one from Phaseolus vulgaris [10]. We reported here its first isolation in the pure state as indicated by both its IR and MS being completely identical with those of authentic samples prepared from sitosterol [11]. The EtOH extract of the stems (after extraction with light petroleum) yielded ellagic acid, and the light petroleum extract of the leaves gave friedelin, friedelan-3β-ol, β-amyrin and sitosterol.

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