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Lipophilic extractive metabolites in different parts of the shoot system (needles and defoliated twigs) of Korean pine, Pinus koraiensis, and Siberian pine, Pinus sibirica, were studied by GC/MS. Korean pine needles comprised mainly bornyl p-coumarate, heterocyclic 15-O-functionalized labdane type acids (lambertianic acid), 10-nonacosanol, sterols and their esters. While Siberian pine needles contained less bornyl p-coumarate, lambertianic acid, sterols and their esters, but were richer in other 15-O-functionalized labdane type acids. The major components of the twig extract of P. koraiensis were lambertianic acid, abietane and isopimarane type acids, cembrane type alcohols, 8-O-functionalized labdanoids, sterols, sterol esters, and acylglycerols. The same extract of P. sibirica differed in larger amounts of other 15-O-functionalized labdane type acids and pinolenic acid glycerides, but in less quantities of cembranoids and 8-O-functionalized labdanoids. The labdane type pinusolic acid was detected for the first time in Korean pine. P. koraiensis was found to be unique in the genus for an ability to synthesize phyllocladane diterpenoids. The content of bound Δ -unsaturated polymethylene-interrupted fatty acids in the twig extracts of the both pines was similar or superior to that in their seed oil. Among the pines' metabolites tested isocembrol was strongest in inhibition of both α-glucosidase (IC 2.9 μg/ml) and NO production in activated macrophages (IC 3.6 μg/ml).

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Hexane extracts of needles and defoliated twigs of Pinus pumila (Pall.) Regel from two distant populations, located in the southwest and the east (i.e., Lake Baikal region and Sakhalin Island) of the species distribution range were studied by GC/MS analysis. Composition and retention indices of major components were determined. A drastic composition divergence for the extracts of P. pumila needles and defoliated twigs, depending on growth location, was established. Needle extracts from the eastern population sample contained mainly labdane-type acids (anticopalic acid derivatives), whereas the predominant components of needle extracts from the other population sample were abietane-type acids (abietic, neoabietic acids) and isopimarane-type diterpenoids (sandaracopimaric acid, sandaracopimaradien-3β-ol). The main components of defoliated twig extracts from Sakhalin Island population sample were abietane-type acids and cembrane-type diterpenoids, while content of these compounds in the extracts of the southwestern marginal population sample was remarkably lower.

Despite a long history of the use of Pinus thunbergii for technical, medicinal, agricultural, and other purposes, the composition of low-volatile metabolites in the used parts of the plant has been poorly investigated. We report here on the distribution of lipophilic extractive compounds in different parts of the shoot system (needles, defoliated twigs, outer bark) of P. thunbergii studied by GC/MS. The highest and lowest contents of lipophilic substances were found in defoliated twigs and in outer bark correspondingly. Acid compounds in the extract of needles comprised mainly labdane type diterpenoids (trans-communic acid), while in the extracts of defoliated twigs and outer bark the acids were represented predominantly by abietane type compounds (neoabietic, dehydroabietic, abietic, levopimaric and palustric acids). The major neutral components of the extract of needles were 10-nonacosanol, labdanoids (18hydroxy-13-epi-manoyl oxide, trans-communol), and β-sitosterol. In the case of the extract of defoliated twigs, labdanoids (18-hydroxy-13-epi-manoyl oxide, trans-communol, 13-epi-torulosol), serratane triterpenoids (3β-methoxyserrat-14-en-21-one), and β-sitosterol were the main neutral constituents, whereas serratanoids (3β-methoxyserrat-14-en-21-one) alone dominated among the neutral compounds of the outer bark extract. Most of the neutral components and the labdane type acids were detected for the first time in organs and tissues of P. thunbergii. The distribution of lipophilic metabolites in the studied parts of P. thunbergii shoot system may be applied for chemotaxonomy purposes. Diversified accumulation of extractive substances in different organs of the plant should be taken into account for isolation of specific components from the pine raw material.