Abstract
Hyssop (Hyssopus officinalis) produces an essential oil containing the saturated bicyclic monoterpene ketones pinocamphone and isopinocamphone, with lesser amounts of myrtenol derivatives. A microsomal preparation from leaf epidermis oil glands of this species converts the parent olefin (-)-β -pinene to the allylic alcohol (+)-trans-pinocarveol that presumably gives rise to (-)-pinocamphone and (-)-isopinocamphone by subsequent oxidation and two stereochemical alternatives for reduction of the conjugated double bond. The same preparation catalyzes the hydroxylation of (-)-α-pinene to (-)-myrtenol at a slower rate. The pinene hydroxylase from the oil glands Hyssop has characteristics of a distinct cytochrome P-450 species, yet shares properties with other monoterpene olefin P-450 hydroxylases from the oil glands of several essential oil-producing plants. These results with pinane-type monoterpenes extend the observation that parent cyclic olefins are metabolized by a pathway involving allylic oxidation and conjugate reduction.
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Karp, F., Croteau, R. (1992). Hydroxylation of (-)-β-Pinene and (-)-α-Pinene by a Cytochrome P-450 System from Hyssop (Hyssopus Officinalis). In: Petroski, R.J., McCormick, S.P. (eds) Secondary-Metabolite Biosynthesis and Metabolism. Environmental Science Research, vol 44. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-3012-1_17
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DOI: https://doi.org/10.1007/978-1-4615-3012-1_17
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