John W. Rowe

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.

The sterols of pine bark

Abstract The sterols of several pine barks have been shown to consist predominantly of β-sitosterol with about one-tenth as much campesterol. The presence of traces of various dihydrosterols, cholesterol, α 1 -sitosterol, triterpenoids, Δ 3,5 -stigmastadien-7-one, Δ 4 -stigmasten-3-one, and 7-keto-β-sitosterol was indicated. Possible biosynthetic interrelationships are discussed.

Chemotaxonomy of ulmus

Abstract The heartwoods of 10 elm species have been examined for the sesquiterpenes, 7-hydroxycadalenal (I), 7-hydroxy-3-methoxycadalenal (II), 7-hydroxycadalene (III), 7-hydroxycalamenenal (IV), 7-hydroxycalamenene (V), and mansonone C (VI), and for the lignans, thomasic acid (VII), thomasidioic acid (VIII), lyoniresinol (IX), and lyoniresinol 2a- O -rhamnoside (X). Cholesterol, campesterol, stigmasterol, sitosterol, 24-methylenelophenol, and citrostadienol were also found. The Section Madocarpus was distinctly different in its chemistry from the other four sections of this genus.

Neutrals in southern pine tall oil

Black-liquor soap skimmings from commercial pulping of southern pine wood contained 4.8% neutrals by wt. The neutrals were quantitatively analyzed and more than 80 compounds found. All of the compounds that comprised 0.1% or more of the neutrals were identified; these included 0.3% α-terpineol, 2.5% diterpene hydrocarbons, 8.1% resin alcohols, 10.0% resin aldehydes, 0.5% resin acid methyl esters, 1.2% norditerpene alcohols, 16.8% labdane diterpenes, 2.1% other diterpenes, 32.4% steroids, 0.6% triterpenes, 0.7% polyprenols, 6.1% wax alcohols, 5.7% stilbenes, 4.4% lubricating oil, and 8.6% minor (<0.1%) constituents. Sitosterol, campesterol, stigmastanol, pinosylvin dimethyl ether, lignoceryl and ceryl alcohols, agathadiol, isoagatholal, communol, abietal, and diterpenes with the pimarane or isopimarane skeleton were the major components.

Extractives of jack pine bark: Occurrence of cis- and trans-pinosylvin dimethyl ether and ferulic acid esters

Abstract A new natural product, cis -pinosylvin dimethyl ether (3,5-dimethoxy- cis -stilbene) has been isolated from the benzene extract of the bark of jack pine ( Pinus banksiana ). The only other nonpolar benzenoid extractives isolated were trans -pinosylvin dimethyl ether, was alcohol esters of ferulic acid, dehydroabietic acid and related diterpenes, and phlobatannin esters. Data are given also on the wax alcohols, free and esterified wax acids, and n -paraffins.

The structure and the stereochemistry of abieslactone

Abstract Abieslactone, a triterpenoid isolated from several firs ( Abies spp.) has been shown to beα-methoxylanosta-9(11), 24-dien-27, 23R-olide (I).

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.

New neutral diterpenes from southern pine tall oil

Abstract Five new diterpene natural products isolated from southern pine ( Pinus spp.) tall oil were characterized as 8(14),15-pimaradiene-3β,18-diol, 19-hydroxy-15,16-dinorlabd-8(17)-en-13-one, 8,13β-epoxy-14-labden-6α-ol, 8,11, 13-abietatriene-15,18-diol and 9,10-secoabieta-8,11,13-trien-18,10-olide.

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.).