Famesoate

Natural products containing the isoprene unit can be prepared in this way. Methyl famesoates have been synthesized from geranyl halides and 1-carbomethoxyallylnickel halides (example 4, Table III). 

The tritium-labelled famesoic acid [3H]-MF, 111, and its diazomethyl ketone analogue, [3H]-FDK, 112, which can be used for the photoaffinity labelling of MF binding... 

The mandibular organ-inhibiting hormone of the crab Cancer pagurus produces two neurohormones that inhibit the secretion of methyl famesoate, which is thought to function as the juvenile hormone in crustaceans 357... 

Juvenile hormones are insect hormones that keep the insect in the juvenile, (larval) stage. They are famesoic acids, acids of the sesquiterpene alcohol farnesol. 

From FDP, a phosphatase or pyrophosphatase catalyzes the removal of the pyrophosphate group, generating famesol (Fig. (5)). The next two steps, oxidation of this alcohol to an aldehyde (famesal), then a carboxylic acid (famesoic acid), are catalyzed by one or two NAD+-dependent dehydrogenase(s) [63]. In the cockroach, D. punctata, methylation of... 

This pathway or variations of it occur in other insect species. The ethyl branches of the higher JH homologs found in the Lepidoptera (Fig. (1)) are derived from isoleucine and valine which are first metabolized to propionate and then incorporated, instead of acetate, in the early steps of biosynthesis [72, 73], The sequence of the final steps of JH biosynthesis may also be different in these insect species. In the adult female CA of some Lepidoptera, epoxidation of famesoic acid to the JH acid occurs before the final methylation step [64,65, 71]. Interestingly, in larval stages of the tobacco homworm, M. sexta, and adult males of the silkworm, Hyalophora cecropia, the CA synthesize and release JH acids into the... 

Essential oil from the seeds of A. katsumadai, a Chinese drug "caodoukou", was analyzed by GLC and 22 components were detected [35]. Three main constituents were isolated and identified as 1,8-cineol, a-humulene and trans,trans- ameso. From the seed residue, after removal of the essential oil by steam, alpinetin and cardamonin were isolated [36]. Together with trans,trans-fameso, rrawj-cinnamaldehyde and three flavonoids, alpinetin, cardamonin and pinocembrin, six diarylheptanoids 34-39 were isolated from the seeds of A. katsumadai and identified on the basis of chemical and spectral evidence [37]. 

Homola E, Chang ES (1997) Methyl famesoate crustacean juvenile hormone in search of functions. Comp Biochem Physiol B 117 347-356... 

Laufer H, Biggers WJ (2001) Unifying concepts learned from methyl famesoate for invertebrate reproduction and post-embryonic development. Am Zool 41 442 -57... 

C7 Diploptera punctata Farnesol, farnesal, famesoic acid, methyl farneso- [251] ... 

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