Re. Krull et al., Iridoid glycoside biosynthesis in Penstemon secundiflorus. Another H-5, H-9 trans-iridoid glycoside, PHYTOCHEM, 49(6), 1998, pp. 1605-1608
Isolation and characterization of the new iridoid 10-hydroxy-(5 alpha H)-6-
epidihydrocornin from Penstemon secundiflorus (Scrophulariaceae) is describ
ed. In biosynthetic experiments, deoxyloganic acid was incorporated into th
e transfused iridoid glycosides (5 alpha H)-6-epidihydrocornin and 10-hydro
xy-(5 alpha H)-6-epidihydrocornin in P. secundiflorus. Formation of the tra
ns-fused compounds is therefore a late event in the biosynthesis and does n
ot occur during iridoid formation by cyclization of the open chain monoterp
ene precursor. In the same plant, 8-epideoxyloganic acid was not incorporat
ed into the trans-iridoids. Deoxyloganic acid was also incorporated into 10
-hydroxyhastatoside (which bears an 8 beta-methyl group), while 8-epideoxyl
oganic acid was incorporated into penstemoside (with an 8 alpha-methyl grou
p). Thus, iridoid biosynthetic pathways leading from both deoxyloganic acid
and 8-epideoxyloganic acid were found in the same plant. (C) 1998 Elsevier
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