Bhimsen A. Nagasampagi

Terpenoid and other extractives of western white pine bark

Abstract A detailed chemical analysis of the benzene extract of western white pine bark was conducted. The extract consisted of 13% phlobaphenes, 18% strong acids, 21% polar weak acids, 6.5% fatty acids, 9.5% resin acids, and 32% neutrals. The fatty acids consisted mainly of C 20:0 , C 22:0 , and C 24:0 acids. The resin acids were identified as: isopimaric, anticopalic, dehydroabietic, sandaracopimaric, abietic, 6,8,11,13-abietatetraen-18-oic and pimaric acids. The neutrals on saponification gave fatty acids, sterols, wax alcohols, nonsaponifiables, and other components. The esterified fatty acids consisted primarily of the C 16:0 , C 18:0 , C 20:0 and C 24:0 acids. The sterols included major amounts of sitosterol, campesterol, and stigmasterol, and traces of cholesterol. Over 70 individual compounds were isolated and identified from the nonsaponifiables. These included borneol, sesquiterpenes, diterpenes, steroidal ketones, as well as lanostane and serratane triterpenes. The characterization of12 new natural products or natural products isolated for the first time from Pinus species is reported.

Sterols of coffee

Abstract The sterols of the bean of the coffee tree ( Coffea arabica L.) have been identified as cycloartenol, 24-methylenecyloartanol, cycloeucalenol, obtusifoliol, citrostadienol, 24-methylenelophenol, stigmasterol, sitosterol, campesterol, stigmastanol, and campestanol. No trace of the previously reported lanosterol, dihydrolanostero, or coffeasterol could be detected in either the beans or in the commercial coffee oil. Trace amounts of cholesterol and cholestanol were also indicated. Combined gas chromatography-mass spectrometry has tentatively identified 4α,24 R -dimethyl-5α-cholest-8-en-3β-ol, 4α-24 R -dimethyl-5α-cholest-7-en-3β-ol, and 4α-methyl-5α-stigmast-7-en-3β-ol.

Terpenoids of lodgepole pine bark

Abstract Additional extractives of lodgepole pine bark include pimaradiene, γ-cadinene, oplopanone (I), and the new natural products, 21-episerratenediol 21-methyl ether (IIa) and 18-norpimara-8(14),15-dien-4-ol (III). The structure of IIa was proved by converting it to 21β-methoxy-14-serraten-3-one (IIc) and to 21-episerratenediol dimethyl ether (IIb). The structure of III was proved by converting it and dihydropimaric acid (IVa) to 18-norpimar-8(14)-en-4-ol (IVb). The corresponding 19-norpimar-8(14)-en-4-ol (IVc) was also prepared.

Derivatives of nordehydroabietane from pine bark

Abstract 18- And 19-norabieta-8,11,13-trien-4-ol and 18-hydroxy-8,11,13-abietatrien-7-one have been isolated from jack pine ( Pinus banksiana Lamb.) and their constitution confirmed by synthesis. Three 19-norabietatetraenes have been detected in western white pine ( Pinus monticola Dougl.).

Five chromenes from Blepharispermum subsessile

Abstract Four new chromenes along with the known desmethoxyencecalin have been isolated from the acetone extract of B. subsessile . The new chromenes have be

A diterpene from Cipadessa fruticosa and Grangea maderaspatana

Abstract A new diterpenoid has been isolated from the acetone extract of both Cipadessa fruticosa (BI Bijdr) and Grangea maderaspatana (Poir). Its structure has been established by spectral studies and its conversion to the known 8-hydroxy- 13 E -labdane-15yl-acetate.

Eudesmane derivatives from Epaltes divericata

Abstract Five closely related eudesmane derivatives have been isolated from the acetone extract of Epaltes divericata . A new eudesmane natural product has been isolated and its structure established by chemical correlation and spectral data as 3α-angeloyloxy-4α-acetoxy-8-oxoeudesm-7(10)-ene.

A new germacranolide from Artemisia pallens.

A new germacranolide has been isolated from the aerial parts of Artemisia pallens and the structure was established as 4,5 beta-epoxy-10 beta-hydroxy-1-en-3-one-trans-germacran-6 alpha,12-olide (1) by comparison with its 10 alpha-epimer isolated from the same plant.

Tetranortriterpenoids From Azadirachta indica

Abstract Two new tetranortriterpenoids, an aldehyde named nimbanal and the 3-acetyl derivative of salannol, were isolated from the seed extract of neem, Azadirachta indica . The structure of nimbanal was established by spectral data while that of salannol-3-acetate was proved by its correlation with salannin.

7-Hydroxyeudesmanolides from Sphaeranthus indicus

Abstract Two new eudesmanolides, along with one known eudesmanolide and two sesquiterpenoids, cryptomeridiol and 4-epicryptomeridiol, have been isolated from Sphaeranthus indicus. The structures of the new compounds have been established by spectral methods, and in one case by chemical correlation.