EXTRACTIVE COMPONENTS FROM INCENSE-CEDAR HEART-WOOD (Libocedrus decurrens Torrey) II. OCCURRENCE AND SYNTHESIS OF p-METHOXYTHYMOL AND p-METHOXYCARVACROL, TWO NEW PHENOLIC COMPOUNDS

Abstract

Two new isomeric phenolic compounds, CuHieOi, have been isolated from incense-cedar heartwood. These compounds proved to be p-methoxythymol, 1.00 per cent dry wood basis, and p-methoxycarvacrol, 0.04 per cent dry wood basis, and their structures were established through synthesis. In addition to the interest from the taxonomic standpoint, preliminary bioassays against various wood destroying fungi indicated that each of these new isomeric phenols has fungicidal properties and thus they appear to be responsible, in part, for the decay resistance of incense-cedar heartwood.Berkeley 4, California

Studies on the Constituents of the Leaves of Baccharis dracunculifolia (Asteraceae) and their Cytotoxic Activity

“…1). Therefore, the MeOH fraction was further separated on a silica gel column eluted with stepwise gradients of nhexane-EtOAc and then purified by HPLC to give compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) as shown in Fig. 2 .…”

“…Two new compounds (1, 2) and seventeen known compounds (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) were isolated from the leaves of B. dracunculifolia and the chemical structures were determined by spectroscopic means. Cytotoxicity testing of the compounds isolated in this study revealed the monoterpene phenols like compounds 4, 6, and 17 (dimer) and the sesquiterpene alcohols such as compounds 8, 10, 11, 13, and 16 exhibited strong cytotoxicity.…”

“…Our biological studies of the alcoholic extracts of the leaves found that the extracts exhibited potent cytotoxic activity against leukemia cells (L 1210). In this paper, we describe the isolation and structure elucidation of two new compounds, baccharisketone (1) and p-methoxythymol acetate (2), along with seventeen known compounds; caryophyllene oxide (3), 6) thymol (4), 7) carvacrol (5), 8) p-methoxythymol (6), 8) 4-isopropyl-2-methylphenol (7), 7) spathulenol (8), 9) p-cymene-2,3-diol (9), 10) bisacumol (10), 11) 2-methyl-6-(4Ј-methylphenyl)-3-hepten-2-ol (11), 12) 1b-hydroxyeudesma-4(15),7-diene (12), 13) cadinol (13), 14) an oppositanetype sesquiterpene (14), 15) germacra-1(11),5(12),6(E)-trien-2-ol (15), 16) a tricyclic sesquiterpene (16), 15) 3,4,3Ј,4Ј-tetrahydroxy-5,5Ј-diisopropyl-2,2Ј-dimethylbiphenyl (17), 17) 3-acetoxy-4Ј,5-dihydroxy-7-methoxyflavanone (18), 18) and naringenin (19), 19) and discuss their growth inhibitory activities against L 1210.…”

Two New Diterpene Phenols from Calocedrus decurrans

“…NMR data was also assigned for compounds 3-5 in Tables 1 and 2, since Obviously, the nature of compounds 1-5 suggests their formation through oxidative coupling reactions involving p-methoxycarvacrol, p-methoxythymol and thymoquinone monomers, that have all been isolated earlier by Zavarin et al [1,2]. Verification of these monomeric components can be elucidated by signals of their isopropyl methine protons as shown for compounds 1-5 in Figure 3.…”

“…Florin., is a native tree in Oregon and California which is perhaps best known for its historical role in the manufacture of wooden pencils. Previous studies have identified carvacrol, thymoquinone, various related p-cymene derivatives and tropolones [1][2][3][4][5][6], although structural data in some cases was inconclusive due to the lack of modern NMR and HRMS techniques. Recent studies have shown the extracts and essential oils from its heartwood have significant antimicrobial activity against Phytophthora ramorum (sudden oak death) [7] and biocidal activity against anthropods of public health importance such as fleas, ticks, and mosquitoes [8].…”