Metabolism Of Sesquiterpenes

8.3.1 Caryophyllene

(-)-b-Caryophyllene is the main sesquiterpene of hops and is being used as a cosmetic additive in soaps and fragrances (Wichtel, 2002). Storage of fresh hops under aerobic conditions leads to rapid oxidation. The main product of this reaction (-)-caryophyllene-5,6-oxide markedly affects the quality of beer. In herbal medicine, (-)-b-caryophyllene is also responsible for the mild sedative properties of hops. Furthermore, it also demonstrates cytotoxicity against breast cancer cells in vitro (Asakawa et al., 1986; DeBarber et al., 2004). The biotransformation of (-)-b-caryophyllene in rabbits yielded the main metabolite [10S-(-)-14-hydroxycaryophyllene-5,6-oxide] and the minor biotransformation product cayrophyllene-5,6-oxide-2,12-diol. The formation of the minor metabolites is easily explained via the diepoxide intermediate. Thus, it is suggested that regioselective hydroxylation of the epoxide occurred (Asakawa et al., 1981, 1986). Whether (-)-b-caryophyllene also shows the same metabolic pathway in human is not known yet. However, based on in vivo data from rabbits, extensive biotransformation in humans is highly suggested after oral administration (Figure 8.22).

8.3.2 Farnesol

Farnesol is a natural organic compound, which is a sesquiterpene alcohol present in many essential oil such as citronella, neroli, cyclamen, lemon grass, rose, and musk. Interestingly, it is also produced in humans where it acts on numerous nuclear receptors and has received considerable attention due to its apparent anticancer properties. It is used in perfumery to emphasize the odors of sweet floral perfumes (DeBarber et al., 2004). In vitro studies using recombinant drug metabolizing

Glucuronide

Glucuronide

Glucuronide

Glucuronide

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