Juvadecene: Discovery of a juvenile hormone mimic in the plant, Macropiper excelsum

Abstract

A compound with significant insect juvenile hormone activity was isolated from the plant, Macropiper excelsurn. The chemical structure was determined by spectral methods to be 1-(3,4methylenedioxyphenyl)-trans-3-decene(l), and confirmed by synthesis. The hormonally active substance applied topically to last (fifth)-instar nymphs of the milkweed bug (Oncopeltus fasciatus) induced a supernumerary metamorphosis at 30 Fg. Higher doses were toxic.

Chemical ecology of insect–plant interactions: ecological significance of plant secondary metabolites

“…Similarly, a compound with a significant JH activity was isolated from the plant, Macropiper excelsum (Piperaceae), and was determined as 1-(3,4-methylenedioxyphenyl)-(E)-3-decene (32) (named juvadecene). 38) It is of great interest if plants have developed specific biosynthetic pathways in response to intensive herbivory by modifying existing molecular units to make a novel arsenal as mentioned above: oviposition deterrent flavonoid triglycosides (26) with rutin (3) + xylose; juvocimenes (31) with monoterpene + phenylpropanoid; juvadecene (32) by extension of side chain of a phenylpropanoid commonly present in Piperaceae.…”

“…They are strongly arrested by root components from the cucurbit plant, Ceratosanthes hilariana (a nonhost for larvae). Although the major phagostimulants were identified as cucurbitacins B and D, the adults selectively accumulated a relatively more stable minor component, 23,24-dihydrocucurbitacin D (38), gaining bitterness effective against a bird predator. 54,57) Similarly, four Asian Cucurbitaceae-feeding specialists in the genus Aulacophora were found to sequester the same compound directly from the larval/adult host cucurbits.…”

Phytochemical defenses targeting the insect endocrine system

“…Macropiper excelsum (Nishida et a/., 1983 ). Combination of elements of the phytochemicals with those of JH resulted in the synthesis of seveJuvabioue = paper factor Ex.…”

Hormonal Interactions Between Plants and Animals

“…Juvadecene, which occurs in the roots of Macropiper excelsum (Piperaceae), is likewise hormonally active. It induces supemumary metamoφhosis, when applied to last-instar nymphs of the milk weed bug, at a concentration of 30 μg and is quite toxic at higher doses (Nishida et al, 1983). …”