Two new p-cymene based diphenols (1-2) were isolated from the heartwood of Calocedrus decurrans. Structures were elucidated by 1D and 2D NMR techniques and HRMS. Libocedroquinone (3) was also isolated as a natural product for the first time. A new system of nomenclature is proposed for description of such oligomeric p-cymene derivatives.
ZavarinE, AndersonAB. (1955) Extractive components from incense-cedar heartwood (Libocedrus decurrens Torrey). I. Occurrence of carvacrol, hydrothymoquinone, and thymoquinone. Journal of Organic Chemistry, 20, 82–88.
2.
ZavarinE, AndersonAB. (1955) Extractive components from incense-cedar heartwood (Libocedrus decurrens Torrey). II. Occurrence and synthesis of p-methoxythymol and p-methoxycarvacrol, two new phenolic compounds. Journal of Organic Chemistry, 20, 443–447.
3.
ZavarinE, AndersonAB. (1955) Extractive components from incense-cedar heartwood (Libocedrus decurrens Torrey). III. Occurrence of libocedrol, a new phenol ether, and its p-methoxythymol addition complex. Journal of Organic Chemistry, 20, 788–796.
4.
ZavarinE. (1958) Extractive components from incense cedar heartwood (Heyderia decurrens Torrey). VII. On the occurrence of heyderiol. Journal of Organic Chemistry, 23, 1264–1268.
5.
AndersonAB, ZavarinE, SchefferTC. (1958) Nature of some decay-retardant extractive components in incense cedar heartwood (Libocedrus decurrens Torrey). Nature, 181, 1275–1276.
6.
ZavarinE, AndersonAB. (1956) Paper chromatography of the tropolones of Cupressaceae. Journal of Organic Chemistry, 21, 332–335.
7.
ManterDK, KelseyRG, KarchesyJJ. (2007) Antimicrobial activity of extractable conifer heartwood compounds toward Phytophthora ramorum. Journal of Chemical Ecology, 33, 2133–2147.
8.
DolanMC, DietrichG, PanellaNA, MontenieriJA, KarchesyJJ. (2007) Biocidal activity of three wood essential oils against Ixodes scapularis (Acari: Ixodidae), Xenopsylla cheopis (Siphonaptera: Pulicidae), and Aedes aegypti (Diptera: Culicidae). Journal of Economic Entomology, 100, 622–625.
9.
KolodziejH, FerreiraD, LemiereG, De BruyneT, PietersL, VlietinckA. (1993) On the nomenclature of oligoflavanoids with an A-type unit. Journal of Natural Products, 56, 1199–1200
10.
HemingwayRW, FooLY, PorterLJ. (1982) Linkage isomerism in trimeric and polymeric 2,3-cis-procyanidins. Journal of Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry, 1209–1216.
