Biosynthesis of 2-trans,6-trans- and 2-cis,6-trans-farnesols by soluble enzymes from tissue cultures of Andrographis paniculata

Abstract

A cell-free system obtained from tissue cultures of Andrographis paniculata produces 2-trans,6-trans-farnesol (trans,trans-farnesol) and 2-cis,6-trans-farnesol (cis,transfarnesol) (5:1), incorporating 10% of the radioactivity from 3R-[2-'4C]mevalonate.There is total loss of 3H from 3RS-

Production of essential oils and flavours in plant cell and tissue cultures. A review

“…The stereochemistry of the interconversion of trans, trans-and cis, trans farnesols by a cell-free system of Andrographis paniculata tissue cultures has been studied [105,106,107]. When tt-farnesol was isomerized to ct-farnesol, the 1-pro-R hydrogen of tt-farnesol was retained and the 1-pro-S hydrogen was lost; by contrast, conversion of ct-farnesol proceeded with retention of the 1-pro-S and loss of the l-pro-R hydrogen of ct-farnesol.…”

Biosynthesis of sesquiterpenes

“…More recently there has been considerable widespread interest (ref 108,109,112,117,122,130,132) in another isomer of farnesol, namely c/s,f/-ar?s-farnesol (20). There had been speculation as to both the origin and subsequent utilization of OPP 19 the 2-cis Cío and C15 pyrophosphates.…”

Substrate Requirements for Lepidopteran Farnesol Dehydrogenase

“…Few examples of farnesol metabolism have been seen in other species. Redox-mediated isomerization of farnesol occurs in plants and is believed to be an important terpene biosynthetic pathway for several natural products (Overton and Roberts, 1974;Ikeda et al, 1991). Farnesol was also found to be readily metabolized to famesoic acid in rat liver homogenates by NAD-dependent dehydrogenases; however, the in vivo significance of this chemistry is elusive as this does not represent a normal biosynthetic pathway (Christophe and Popjak, 1961).…”