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Biosynthesis of the Monoterpenes Limonene and Carvone in the Fruit of Caraway1
Abstract
The biosynthesis of the monoterpenes limonene and carvone in the fruit of caraway (Carum carvi L.) proceeds from geranyl diphosphate via a three-step pathway. First, geranyl diphosphate is cyclized to (+)-limonene by a monoterpene synthase. Second, this intermediate is stored in the essential oil ducts without further metabolism or is converted by limonene-6-hydroxylase to (+)-trans-carveol. Third, (+)-trans-carveol is oxidized by a dehydrogenase to (+)-carvone. To investigate the regulation of monoterpene formation in caraway, we measured the time course of limonene and carvone accumulation during fruit development and compared it with monoterpene biosynthesis from [U-14C]Suc and the changes in the activities of the three enzymes. The activities of the enzymes explain the profiles of monoterpene accumulation quite well, with limonene-6-hydroxylase playing a pivotal role in controlling the nature of the end product. In the youngest stages, when limonene-6-hydroxylase is undetectable, only limonene was accumulating in appreciable levels. The appearance of limonene-6-hydroxylase correlates closely with the onset of carvone accumulation. At later stages of fruit development, the activities of all three enzymes declined to low levels. Although this correlates closely with a decrease in monoterpene accumulation, the latter may also be the result of competition with other pathways for substrate.
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“These substances are believed to function principally in ecological roles, serving as herbivore-feeding deterrents, antifungal defenses and attractants for pollinators.[33]”
From Anethum graveolens: An Indian traditional medicinal herb and spice (2010) · cites this paper as [33]
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“The biosynthesis of the monoterpenes limonene and carvone proceeds from geranyl diphosphate via a three-step pathway. First, geranyl diphosphate is cyclized to d-limonene by limonene synthase. Secondly, this intermediate is stored in essential oil ducts without further metabolism or is converted by limonene 6-hydroxylase to trans-carveol. Finally trans-carveol is oxidized by a dehydrogenase to d-c”
From Anethum graveolens: An Indian traditional medicinal herb and spice (2010) · cites this paper as [33]
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Citations
Cites
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Amorpha-4,11-diene synthase catalyses the first probable step in artemisinin biosynthesis
Bouwmeester, H. J., Wallaart, T. E., Janssen, M. H. A., van Loo, B., Jansen, B. J. M., Posthumus, M. A., Schmidt, C. O., De Kraker, J.-W., König, W. A., & Franssen, M. C. R. (1999) · Phytochemistry · doi:10.1016/s0031-9422(99)00206-x · Cited by 266
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Metadata
- Authors
- Bouwmeester, H. J., Gershenzon, J., Konings, M. C. J. M., & Croteau, R.
- Venue
- Plant Physiology
- Publisher
- Oxford University Press (OUP)
- Published
- 1998-07-01
- Volume
- 117
- Issue
- 3
- Pages
- 901-912
- ISSN
- 1532-2548
- 0032-0889
- Cited by
- 149
- References
- 2
- Language
- en
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