By Sherif S. Ebada, Neil Lajkiewicz (auth.), A. Douglas Kinghorn, Heinz Falk, Junichi Kobayashi (eds.)
The 3 stories conceal the advances within the chemistry and biology of withanolides during the last sixteen years, assessment the chemistry and biology of the rocaglamide-type derivatives and similar compounds, with emphasis on their structural range, biosynthesis, pharmacological importance and overall synthesis, and summarize the wide chemistry and biology reviews on a traditional product, that have ended in a singular remedy licensed around the world.
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8 ppm) (14, 54, 55). 6 ppm). The same findings were true when the amide group was exchanged to an ester substituent, which likewise had no significant effect on the resultant insecticidal activity of the respective compounds. However, a diminution in insecticidal activity by a factor of 5 or 6 was usually observed for rocaglamide derivatives featuring an unsubstituted C-2 when compared to analogues with an amide or carboxylic acid ester substituent at this particular position (14, 54, 55, 59). In rings A or B, the occurrence of an additional oxygen substituent, when compared to the substitution pattern of the parent compound, rocaglamide (1), revealed only marginal influences on the insecticidal activity of the respective products (54).
Edulis (71). The pannellins 44–46 were isolated from Aglaia elaeagnoidea collected from Thailand (13). For this group of analogues, the amide function at C-2 in aglaroxins A, B, and F was replaced by a methyl ester. Pannellin-1-O-acetate (45) is the acetylated product of 44 while 30 -methoxypannellin (46) is characterized by an additional –OCH3 function in ring B. S. Ebada et al. Proksch et al. described the isolation of a similar group of congeners from the twigs of a Vietnamese collection of A.
Gracilis collected in Fiji (18), is very similar to aglain A (64), except for the hydroxy group at C-10. Recently, ponapensin, the only congener featuring a methoxy group at C-13 instead of the amide side chain in aglain B (67), was isolated from the Micronesian species Aglaia ponapensis (80). In thapsakones A (88) and B (89), obtained from the root bark of Aglaia edulis (southwest Thailand), which lack a proton at C-10, the stereochemistry of H-3 and H-4 was deduced in an elegant manner by observing a shift stronger than a lanthanide-induced shift (LIS) to the respective b-proton (4 in 88, 3 in 89) (15).