6,10,14-Trimethylpentadecan-2-one and 6,10,14-trimethyl-5-trans, 9-trans, 13-pentadecatrien-2-one from the androgenic glands of the male crab Carcinus maenas

Férézou, Jacqueline; Berreur-Bonnenfant, J.; Meusy, Jean-Jacques; Barbier, Michel; Suchý, M.; Wipf, H.‐K.

doi:10.1007/bf02002784

Cited by 33 publications

(7 citation statements)

References 2 publications

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“…Several authors established the proteinaceous nature of the androgenic hormone in M. rosenbergii [18,31,52]. On the contrary, Veith and Malecha [46] [53] reported the presence of terpenoids in the androgenic gland of C. maenas. The lipoidal substance extracted and purified from the androgenic gland in O. gammarella inhibited vitellogenesis when injected into females [32].…”

Section: Discussionmentioning

confidence: 99%

Seasonal changes in the structure and secretory activity of the androgenic gland of Travancoriana schirnerae

Devi¹,

Smija²

2013

Open Life Sciences

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This study investigated the seasonal variation in the structure and secretory activity of the androgenic gland (AG) in the freshwater crab: Travancoriana schirnerae. The androgenic gland is an elongate structure, attached to one side on the wall of the ejaculatory duct. Histological studies showed the presence of three cell types, which differ in size, shape of nuclei, and presence or absence of secretory vesicles. Type I cells are small with large nuclei whereas type II cells are large with small nuclei. Type III cells are intermediate in size and exhibited streak-like nuclei and transparent cytoplasm. Seasonal changes were discerned in the morphology, histology and secretory activity of the gland. March-June appeared to be the active season with type II cells containing secretory vesicles. The mode of release of secretion found to be holocrine. The secretory activity almost completed by July-August (the mating season) with vacuolization of type II cells. The gland remained inactive from September-December with abundance of vacuoles, scattered pycnotic nuclei, indistinct cell membranes and total cellular degeneration. January-February was the revival period with type I cell proliferation. The present study revealed that the secretory activity of the gland is in tune with the male reproductive cycle.

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Section: Discussionmentioning

confidence: 99%

Seasonal changes in the structure and secretory activity of the androgenic gland of Travancoriana schirnerae

Devi¹,

Smija²

2013

Open Life Sciences

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“…Furthermore, non‐C 5 ‐unit terpenoids (norisoprenoids) have also been reported. Norisoprenoids having an acetonyl group (C 5 × n +C 3 ) are widely distributed in nature, especially in crustacean hormones, insect pheromones, plant odorants, and microbial volatiles (Figure ) . Geranylgeranylacetone (a non‐natural product) is used to treat gastric ulcers and is known to induce heat shock proteins (Figure ) .…”

Section: Figurementioning

confidence: 99%

A Non‐Enzymatic Pathway with Superoxide in Intracellular Terpenoid Synthesis

et al. 2018

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Non-C 5 -units terpenoids (norisoprenoids) with an acetonyl group are widely distributed in nature.H owever, studies on the biosynthesis of norisoprenoids are scarce.Now, the C 33 norisoprenoid, (all-E)-farnesylfarnesylacetone,w as identified from Bacillus spp.and it was elucidated for the first time that superoxidem ediates the cleavage of menaquinones (vitamin K) to form norisoprenoids in saponification treatment. From in vivo experiments using gene-disrupted Bacillus subtilis strains targeted for enzymes responsible for menaquinone biosynthesis and for superoxided ismutase,i tw as suggested that the non-enzymatic cleavage (autoxidation) of menaquinone with superoxide resulted in norisoprenoid synthesis in Bacillus cells.F urthermore,t he bioactive norisoprenoids,farnesylacetone and phytone,were produced in Bacillus cells by this novel synthesis system.

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“…Dedicated to Professor Pierre Favard, who introduced so many students to the analysis of mitochondrial structure and function. F~r~zou et al [16]. The synthetic FA was kindly given by Hoffmann La Roche, France.…”

Section: Chemicalsmentioning

confidence: 99%

“…Succinate potassium ferricyanide reductase activity was carried out either on osmotically-swollen mitochondria or on intact mitochondria. The activities were followed using the wavelength pair 422-470 nm [16]. When assayed on swollen mitochondria, ferricyanlde was used for the assay of succinate dehydrogenase [9].…”

Section: Reducing Activitiesmentioning

confidence: 99%

Farnesylacetone, a sesquiterpenic hormone of crustacea, inhibits electron transport in isolated rat liver mitochondria

Dupont¹

1989

Biology of the Cell

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Farnesylacetone (C18 H30 0) is a male hormone extracted from the androgenic gland of crab, Carcinus maenas. Appropriate enzymatic assays, as well as spectrophotometric studies, indicate that micromolar concentrations of farnesylacetone interact with the electron transport pathway of rat liver mitochondria. By the use of artificial electron donors and electron acceptors, it is shown that farnesylacetone immediately inhibits the electron transfer within complex I (NADH ubiquinone reductase activity) and complex II (succinate ubiquinone reductase activity). It is proposed that farneylacetone could interact with these two complexes of the respiratory chain at the level of the iron-sulfur centers implicated in the dehydrogenase activities. These observations are compared with the results obtained with terpenic molecules which interact with mitochondrial respiration.

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6,10,14-Trimethylpentadecan-2-one and 6,10,14-trimethyl-5-trans, 9-trans, 13-pentadecatrien-2-one from the androgenic glands of the male crab Carcinus maenas

Cited by 33 publications

References 2 publications

Seasonal changes in the structure and secretory activity of the androgenic gland of Travancoriana schirnerae

Seasonal changes in the structure and secretory activity of the androgenic gland of Travancoriana schirnerae

A Non‐Enzymatic Pathway with Superoxide in Intracellular Terpenoid Synthesis

Farnesylacetone, a sesquiterpenic hormone of crustacea, inhibits electron transport in isolated rat liver mitochondria

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