Hydroxy juvenile hormones: new putative juvenile hormones biosynthesized by locust corpora allata in vitro.
The in vitro production of sesquiterpenoids was investigated by using corpora allata (CA) of the African locust Locusta migratoria migratorioides. Labeled products from unstimulated biosynthesis were extracted, purified by normal phase HPLC, and derivatized to determine the functional groups present. An extra hydroxyl group was detected in each of two juvenile hormone (JH) biosynthetic products. One compound, NP-8, was found to co-migrate with a chemically-synthesized (Z)-hydroxymethyl isomer, 12'-OH JH-III, but not with the (E)-hydroxymethyl isomer, 12-OH JH III. Mass spectral analyses further supported the identity of the synthetic material with that biosynthesized by the corpora allata. A second compound was identified as the 8'-OH JH-III based on spectroscopic analyses. 12'-OH JH-III exhibited morphogenetic activity when tested on the heterospecific Tenebrio test. These data suggest that 12'-OH JH-III and 8'-OH JH-III are additional biosynthetically-produced and biologically-active juvenile hormones, and constitute the first known members of the class of hydroxy juvenile hormones (HJHs).
Darrouzet
E
E
University of Bordeaux I, Laboratoire de Neuroendocrinologie, ER CNRS 629, Talence, France.
Mauchamp
B
B
Prestwich
G D
GD
Kerhoas
L
L
Ujváry
I
I
Couillaud
F
F
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D003335:Corpora Allata / Q000378:metabolism*; D006110:Grasshoppers / Q000378:metabolism*; D006900:Hydroxylation; D007605:Juvenile Hormones / Q000096:biosynthesis* / Q000737:chemistry / Q000494:pharmacology; D013058:Mass Spectrometry; D015394:Molecular Structure; D009024:Morphogenesis / Q000187:drug effects; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D013057:Spectrum Analysis; D013712:Tenebrio / Q000187:drug effects; D014818:Vitellogenesis / Q000187:drug effects / Q000502:physiology
C109585:12'-hydroxy-juvenile hormone III; C109586:8'-hydroxy-juvenile hormone III; D007605:Juvenile Hormones; D012717:Sesquiterpenes; C036585:juvenile hormone III