Phytochemistry p. 479 - 482 (1990)
Update date:2022-09-26
Topics:
Whitehead, Ian M.
Ewing, David F.
Threlfall, David R.
Cane, David E.
Prabhakaran, P. C.
(+)-5-epi-Aristolochene, a common precursor of the phytoalexins capsidiol and debneyol, was synthesized from capsidiol (ex.Capsicum annum) via (+)-1-deoxycapsidiol.It is identical (TLC, GC, GC-MS, 1H NMR) with the enzymic product from cell-free preparations from elicitor-treated suspension cultures of Nicotiana tabacum incubated with either <1-14C>isopentenyl pyrophosphate or E,E-<1-3H2>farnesyl pyrophosphate.The (+)-1-deoxycapsidiol was identical (GC, MS, 13C and 1H NMR) to a natural sample previously obtained from elicitor-treated fruits of C. annum.An isomer of 1-deoxycapsidiol, formed during the synthesis of this compound, was identified as 4-epi-eremophila-1(10),11-diene.
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