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Synthesis of (+)-5-epi-aristolochene and (+)-1-deoxycapsidiol from capsidiol


, : Synthesis of (+)-5-epi-aristolochene and (+)-1-deoxycapsidiol from capsidiol. Phytochemistry 29(2): 479-482

Capsidiol was obtained from the fruits of Capsicum annum From this compound, (+)-5-epi-aristolochene, a common precursor of the phytoalexins capsidiol and debneyol, was synthesized via (+)-1-deoxycapsidiol.

Accession: 001962514

DOI: 10.1016/0031-9422(90)85100-t

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Related references

Whitehead I.M.; Ewing D.F.; Threlfall D.R.; Cane D.E.; Prabhakaran P.C., 1990: Synthesis of dextro 5 epi aristolochene and dextro 1 deoxycapsidiol from capsidiol. (+)-5-epi-Aristolochene, a common precursor of the phytoalexins capsidiol and debneyol, was synthesized from capsidiol (ex. Capsicum annuum) via (+)-1-deoxycapsidiol. It is identical (TLC, GC, GC-MS, 1H NMR) with the enzymic product from cell-free...

Lee HyeJung; Lee DaEun; H.S.kBong; Jang SooWon; Lee InJung; Ryu, S.B.; Back, K.W., 2004: The characterization of transgenic rice plants expressing a pepper 5-epi aristolochene synthase, the first committed step enzyme for capsidiol synthesis in isoprenoid pathway. 5-Epi-aristolochene synthase (EAS) from Capsicum annuum was introduced into the rice genome under the control of a maize ubiquitin promoter by Agrobacterium-mediated transformation. Fifteen independent transgenic rice plants were isolated and char...

Yoshizawa, Yuko; Yamaura, Takao; Kawaii, Satoru; Hoshino, Tamotsu; Mizutani, Junya, 1994: Incorporation of 13C-labelled 5-epi-aristolochene into capsidiol in green pepper seedlings. As a part of investigations on the biosynthesis and induction mechanisms of capsidiol, a green pepper phytoalexin, we focussed our attention on the enzymatic oxidation of 5-epi-aristolochene, a non-oxidized elemophilane biosynthetic intermediate,...

Whitehead I.M.; Threlfall D.R.; Ewing D.F., 1989: 5 epi aristolochene is a common precursor of the sesquiterpenoid phytoalexins capsidiol and debneyol. 5-epi-Aristolochene (4-epi-eremophila-9,11-diene) has been identified (GC-MS and high-field 1H NMR) as the hydrocarbon (unknown I) which is accumulated when the formation of capsidiol and debneyol from [1-3H2]FPP in cell-free preparations of cells...

Bohlmann, Jörg.; Stauber, E.J.; Krock, B.; Oldham, N.J.; Gershenzon, J.; Baldwin, I.T., 2002: Gene expression of 5-epi-aristolochene synthase and formation of capsidiol in roots of Nicotiana attenuata and N. sylvestris. Three new copies of a sesquiterpenoid synthase gene encoding 5-epi-aristolochene synthase (EAS) were cloned as cDNAs from Nicotiana attenuata and functionally characterized after expression of the recombinant enzymes in E. coli. Differential patte...

Bohlmann, J.; Stauber, E.J.; Krock, B.; Oldham, N.J.; Gershenzon, J.; Baldwin, I.T., 2002: Gene expression of 5-epi-aristolochene synthase and formation of capsidiol in roots of Nicotiana attenuata and N. sylvestris. Three new copies of a sesquiterpenoid synthase gene encoding 5-epi-aristolochene synthase (EAS) were cloned as cDNAs from Nicotiana attenuata and functionally characterized after expression of the recombinant enzymes in E. coli. Differential patte...

Brodelius, M.; Lundgren, A.; Mercke, P.; Brodelius, P.E., 2002: Fusion of farnesyldiphosphate synthase and epi-aristolochene synthase, a sesquiterpene cyclase involved in capsidiol biosynthesis in Nicotiana tabacum. A clone encoding farnesyl diphosphate synthase (FPPS) was obtained by PCR from a cDNA library made from young leaves of Artemisia annua. A cDNA clone encoding the tobacco epi-aristolochene synthase (eAS) was kindly supplied by J. Chappell (Univers...

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Calvert, M.J.; Ashton, P.R.; Allemann, R.K., 2002: Germacrene A is a product of the aristolochene synthase-mediated conversion of farnesylpyrophosphate to aristolochene. The biosynthesis of several sesquiterpenes has been proposed to proceed via germacrene A. However, to date, the production of germacrene A has not been proven directly for any of the sesquiterpene synthases for which it was postulated as an interm...

Calvert, M.J.; Ashton, P.R.; Allemann, R.K., 2002: Germacrene A is a product of the aristolochene synthase-mediated conversion of farnesylpyrophosphate to aristolochene. The biosynthesis of several sesquiterpenes has been proposed to proceed via germacrene A. However, to date, the production of germacrene A has not been proven directly for any of the sesquiterpene synthases for which it was postulated as an interm...