Triterpenoids from two Mallotus species: a nor-triterpene and two new acids

The carbonyl compound, previously isolated from the stems of Mallotus paniculatus, has been proved to be 29-nor-21αH-hopane-3,22-dione. The light petrol extracts of both the leaves and stems of M. hookerianus have been found to contain friedelin, friedelan- 3β-ol and sitosterol, and the ethanol extract of the former two new triterpene acids, 3-oxours-12-ene-27,28-dioic and 3β,28-dihydroxyurs-12-en-27-oic acids.     

Lanostane triterpenes of Canscora decussata

From the aerial parts of Canscora decussata Schult (Gentianaceae), five triterpenes, viz. gluanone, canscoradione, friedelin, fridelan-3-β-ol, and β-amyrin, three sterols, viz. sitosterol, stigmasterol, and campesterol, besides liberal amount of a mixtures of n-alkanes (C₂₇-C₃₁) and n-alkanols (C₂₆-C₃₂) have been isolated. The identity of the compounds has been established by chemical transformations, spectral evidence, and by direct comparison, where possible, with authentic reference materials. Gluanone and canscoradione have not been encountered before in nature.     

Epoxyparvinolide,a secocaryophyllanolide from Pogostemon parviflorus

Epoxyparvinolide which belongs to a new class of sesquiterpenoid lactones, the secocaryophyllanolides, was isolated from Pogostemon parviflorus along with friedelin, friedelan-3-ol, phytol and sitosterol. Epoxyparvinolide was characterized as 4,5-epoxy-9,10-secocaryophyllen-9β,10-olide.     

A new compound, 21α-hydroxyfriedel-4(23)-en-3-one and other triterpenoids from Phyllanthus reticulatus

The petrol extracts of the stems and leaves of Phyllanthus reticulatus both gave friedelin and sitosterol, and that of the former also friedelan-3β-ol, glochidonol, 21α-hydroxyfriedelan-3-one and a new compound, which was proved to be 21α-hydroxyfriedel-4(23)-en-3-one. The ethanol extract of the stems yielded betulinic acid.     

Triterpenes of five euphorbiaceae species of Sri Lanka

Five endemic species of Euphorbiaceae have been investigated. Aleuritolic acid and its derivatives were isolated from P. thwaitesii. A. cardiosperma had friedelan derivatives. The Glochidion species contained the same triterpenes, viz. glochidonol, lup-20(29)-ene-3α,23-diol and glochidiol. The bark extractives of a new Glochidion species had, in addition, glochidone and probably lup-20(29)-ene-1α,3α,23-triol. The latter is a new natural product. Glochidone was isolated for the first time outside the genus Glochidion from Bridelia moonii.     

Triterpenes and neoflavonoids of Calophyllum lankaensis and Calophyllum thwaitesii

The petrol extracts of the leaves of Calophyllum lankaensis and C. thwaitesii yielded D:A-friedo-oleanan-3-one, 28-hydroxy-D:A-friedo-oleanan-3-one (canophyllol), 28-oxo-D:A-friedo-oleanan-3-one (canophyllal calozeylanic acid, thwaitesic acid, isothwaitesic acid and apetalactone. Thwaitesic acid and iso-thwaitesic acid are two novel neoflavonoids.     

Three triterpenes and other terpenoids from Catha cassinoides

The investigation of stems and leaves of Catha cassinoides afforded, in addition to sitosterol, β-amyrin, ursolic acid, lup-20(29)-en-3β,30-diol and friedelin, three new pentacyclic triterpenes: 30-hydroxyfriedelan-3-one, 29-hydroxyfriedelan-3-one and 3-oxo-friedelan-29-oic acid. The structures ofthese were determined by spectral studies and correlations, and were confirmed by X-ray analysis of 29-hydroxyfriedelan-3-one acetate.     

Triterpenoids and coumarins from the leaves of calophyllum cordato-oblongum

The hot light petrol extractives of the leaves of Calophyllum cordato-oblongum gave D:A-friedo-oleanan-3-one, 28-hydroxy-D:A-friedo-oleanan-3-one (canophyllol) and three new coumarins: cordatolides A and B and oblongulide.     

Triterpene constituents of Caltha palustris

The structure of a new triterpene lactone, palustrolide, has been elucidated as 3β,23-dihydroxylupan-13β→28 lactone on the basis of physico-chemical studies. In addition, sitosterol, its glucoside, hederagenin, 16,17-dihydroxykauran-19-oic acid and hederagenic acid have been characterized.     

Triterpenoid acids from Sapium sebiferum

Sebiferenic acid, isolated from the bark of Sapium sebiferum, has been characterized as 2α,3β-dihydroxytaraxer-14-en-28-oic acid on the basis of ¹H NMR, ¹³C NMR and mass spectral evidence and chemical transformations. The structure of sebiferic acid has been revised.     

Isolation of a natural sterol and an aliphatic acid from Vernonia cinerea

From the roots of Vernonia cinerea a new natural sterol and a new aliphatic acid characterized as stigmast-5,17(20)-dien-3β-ol and 26-methylheptacosanoic acid, respectively, have been isolated together with stigmasterol and sitosterol.     

Triterpenoids and sterols from seeds of Phytolacca esculenta

Chromatographic separation of the chloroform-soluble part of the methanol extract from Phytolacca esculenta seeds resulted in the isolation of acetylaleuritolic acid, 3-acetylmyricadiol, α-spinasterol and stigmast-7-en-3β-ol.     

Chemical constituents of leaves and stem bark of Plumeria obtusa

The continued studies on the constituents of the fresh leaves and stem bark of Plumeria obtusa Linn. have led to the isolation and characterization of four new triterpenoids, dammara-12,20(22)Z-dien-3-one (1), dammara-12,20(22)Z-dien-3beta-ol (2), olean-12-en-3beta,27-diol (3), and 27-hydroxyolean-12-en-3-one (4) and 12 known compounds, which included eight triterpenoids; dammara-3beta,20(S),25-triol (5), urs-12-en-3beta-hydroxy-27-Z-feruloyloxy-28-oic acid (6), 3beta-hydroxyolean-12-en-28-oic acid (7), 3beta,27-dihydroxylupan-29-ene (8), 3beta-hydroxylupan-29-en-28-oic acid (9), 3beta-hydroxyursan-12-en-28-oic acid (11), 3beta-hydroxy-27-p-coumaroyloxy-olea-12-en-28-oic acid (12) and urs-12-en-3-one (15); an iridoid 1alpha-plumieride (10); a cardenolide 3alpha,14beta-dihydroxy-17beta-card-20(22)-enolide (13); a fatty acid ester methyl n-octadecanoate (14) and a steroid 3beta-hydroxy-delta5-stigmastane (16). The new constituents were characterized through spectroscopic studies including 1D (1H and 31C NMR) and 2D (COSY-45, NOESY, J-resolved, HMQC and HMBC) NMR and chemical transformations. This is the first report on the isolation of dammarane triterpenoids from P. obtusa. Compounds 5 and 6 are hitherto unreported from P. obtusa. The known compounds were identified by comparison of their spectral data with those reported in the literature.     

Triterpenes of Prunus serotina and P. lusitanica

The leaves of Prunus serotina and P. lusitanica contain a new triterpene, 2α,3α-dihydroxyurs-12-en-28-oic acid, isolated in form of its methyl ester. Other triterpenes present in these species are ursolic acid and ursol aldehyde. P. lusitanica also yields friedeline.