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Chemistry of Essential Oils
Published in K. Hüsnü Can Başer, Gerhard Buchbauer, Handbook of Essential Oils, 2020
The santalols (122) and (123) have more complex structures and are the principal components of sandalwood oil. Cedrol (120) is another complex alcohol, but it is more widely occurring in nature than the santalols. It is found in a wide range of species, the most significant being trees of the Juniperus, Cupressus, and Thuja families. Cedrene (146) occurs alongside cedrol in cedarwood oils. Cedrol is dehydrated to cedrene in the presence of acid, and so the latter can be an artifact of the former and the ratio of the two will often depend on the method of isolation. Thujopsene (126) also occurs in cedarwood oils, usually at a similar level to that of cedrol/cedrene, and it is found in various other oils also. Caryophyllene (128) and α-humulene (the all trans-isomer) (133) are widespread in nature, cloves being the best-known source of the former and hops of the latter. The ring systems of these two materials are very strained making them quite reactive chemically, and caryophyllene, extracted from clove oil as a by-product of eugenol production, is used as the starting material in the synthesis of several fragrance ingredients. Longifolene (131) also possesses a strained ring system. It is a component of Indian turpentine and is therefore readily available as a feedstock for fragrance ingredient manufacture.
The traditional herb Polygonum hydropiper from China: a comprehensive review on phytochemistry, pharmacological activities and applications
Published in Pharmaceutical Biology, 2023
Yi-Dan Kong, Ying Qi, Na Cui, Zhi-Hong Zhang, Na Wei, Chang-Fu Wang, Yuan-Ning Zeng, Yan-Ping Sun, Hai-Xue Kuang, Qiu-Hong Wang
The terpenoid compounds of PH are almost all monoterpenes and triterpenes, including α-copaene (219), curcumene (220), neophytadiene (221), 8-(3-methy-2-butanol)-tricyclene (222), cedrene (223), 8-(3-methyl-2-butenyl)-α-pinene (224), β-sesquiphellandrene (225), longifolene aldehyde (226), 7-epi-cis-sesquisabinene hydrate (227), β-caryophyllene (228), selinene (229), aromadendrene (230), eremophilene (231), cubebene (232), α-panasinsene (233), oxide caryophyllene (234), chamigrene (235), widdrene (236), ledene (237), 1,5,5,8a-tetramethyl (238), 8-isopropyl-2,5-dimethyl-1,2,3,4-tetrahydronaphthalene (239), cis-himachalene (240), drimenol (241), naphthol-[1,2-c]-furan-1-(3H)-one-4,5,5a,6,7,8,9,9a-octahydro-6,6,9a-trimethy-(-)-drimenin (242), caryophyllene oxide (243), eudesmol (244), aristolene (245), myrtanal (246), myrtanol (247), trans-α-bergmotene (248), α-muurolene (249), 1-phellandrene (250), camphene (251), α-pinene (252), guaiene (253), α-bisabolol (254), elemol (255), γ-terpinene (256), α-thujene (257), thujopsene (258), humulene epoxide II (259), 1-naphthalenepropanol (260), trans-carene (261), thujopsene-I3 (262), globulol (263), 1,4,4α,5,6,7,8,8a-octahydro-2,5,5,8α-tetramethyl-β-eudesmol (264), 1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1(1-methylethyl) naphthalene (265), 10-epi-γ-eudesmol (266), taraxerone (267), friedelinol (268), ursolic acid (269), oleanolic acid (270), 3β,13β-dihydroxyl-11-ene-28-ursolic acid (271), 3β-angeloyloxy-7-epifutronolide (272), polygonumate (273), dendocarbin L (274), (+) winterin (275), (+) fuegin (276), changweikangic acid A (277), futronolide (278), 7-ketoisodrimenin (279), warburganal (280), polygodial (281), isopolygodial (282), ugandensidal (283), muzigadial (284), polygonal (285), drimenol (286), isodrimeninol (287), octylene (288), monoacetate (289), α,β,β′-disubstituted furano (290), drimanediol (291), isodrimenin (292), and confertifolin (293) (Fukuyama et al. 1980, 1985; Yao et al. 1999; Zhang and Zeng 2005; Li 2007; Wu et al. 2007; Huang et al. 2012; Lin et al. 2012; Goswami et al. 2014; Wang et al. 2017; Xu et al. 2017; Yu et al. 2018). The structures from 219 to 293 are shown in Figure 5.