Michel Barbier

Isolation of the two paragonial substances deposited into the spermatophores ofAcanthoscelides obtectus (Coleoptera, Bruchidae)

Aqueous extracts from spermatophores ofAcanthoscelides obtectus (Coleoptera, Bruchidae) have been chromatographed on Sephadex G 25 and G 15 columns, the active fractions being further purified by preparative SiO2 TLC. The isolation and properties of 2 biologically active compounds are reported. The paragonial substance A has a favourable action upon oogenesis, is a low molecular weight molecule (500–1000) and gives 1 single amino acid on hydrolysis, corresponding to glycin on TLC. The paragonial substance B is toxic, or an inhibitor of oogenesis at lower concentration, thus showing an antagonistic effect.

Brassilexin, a novel sulphur-containing phytoalexin from Brassica juncea L., (Cruciferae)

Structure 1 is established for brassilexin, a new sulphur-containing phytoalexin isolated from the leaves of Brassica juncea (Cruciferae), on the basis of spectrographical data (UV, IR, high resolution MS, 13C and 1H NMR).

Sur la biosynthèse des stérols de l'huître (Ostrea gryphea) et de l'oursin (Paracentrotus lividus)☆

Abstract 1. 1. The sterols of the oyster Ostrea grypthea and of the sea urchin Paracentrotus lividus have been studied by mass spectrometry of their acetates. One of the main sterols of the oyster is 24-methylene cholesterol, confirming the previous work of Idler & Fagerlund (1955); the main sterol of the sea urchin is cholesterol. 2. 2. Under the experimental conditions described in this paper, the oyster Ostrea gryphea does not incorporate any radioactivity from 2-C 14 -mevalonate or C 14 -CH 3 l -methionine into squalene or sterols. 3. 3. Under the experimental conditions described, the urchin Paracentrotus lividus does not incorporate any radioactivity from 1,2-C 14 -acetate into squalene nor into sterols.

Pigments from Nectria haematococca: Anhydrofusarubin lactone and nectriafurone

Abstract The structures of anhydrofusarubin lactone and of nectriafurone, two new naphthoquinone pigments isolated from the fungus Nectria haematococca , are

The status of blue-green bile pigments of butterflies, and their phototransformations

Blue-green bile pigments are found in adults or larvae of many species of butterfly. They are reviewed here. In contrast to the presence of biliverdin IX α1 in some insect species, many Lepidoptera contain pterobilin2 (biliverdin IX γ), phorcabilin3, and sarpedobilin4, derived from2 by cyclization. Pigments3 and4 are members of a new natural family of heterocyclic systems which can also be obtainedin vitro from2, by irradiation under visible light. This review presents the information so far available about the chemistry and biochemistry of these pigments, together with a discussion about the possible biological significance of their photosensitivity.

Pollen sterols—a mass spectrographic survey

Abstract The fractions of sterol in pollens from fifteen species of plants in eleven families were analyzed by mass spectrometry. 24-Methylene-cholesterol was the principal sterol of red clover (Trifolium pratense L.), saguaro cactus (Carnegiea gigantea (Engelm.) Britt. & Rose), mustard (Brassica nigra (L.) Koch), London-rocket (Sisymbrium irio L.), rye (Secale cereale L.), timothy (Phleum pratense L.), and sweet corn (Zea mays var. saccharata (Sturtev.) Bailey). β-Sitosterol was the principal sterol of mule fat (Baccharis viminea DC.), juniper (Juniperus utahensis (Engelm.) Lemm.), heartsease (Polygonum sp.), waterleaf (Hydrophyllum capitatum Dougl.), Scotch pine (Pinus sylvertris L.), European alder (Alnus glutinosa (L.) Gaertner), and Lombardy poplar (Populus nigra var. italica Muenchh.). Cholesterol was the principal sterol of cottonwood (Populus fremontii S. Wats.). The presence of cholesterol in the pollen from cottonwood has been confirmed by gas-liquid chromatography. 24-Methylene-cholesterol in saguaro cactus was further verified by the preparation of 24-ketocholesterol by ozonolysis, saponification of the acetate, and then a direct comparison of the thin-layer chromatograph of the free sterol with an authentic sample of 24-ketocholesterol.

La diatomee marine chaetoceros simplex calcitrans paulsen et son environnement, I. Relations avec le milieu de culture; étude de la fraction insaponifiable, des stérols et des acides gras☆

Abstract Detailed analysis of the lipids present in seawater medium before and after growing cultures of the diatom Chaetoceros simplex calcitrans Paulsen in them has been carried out and compared with the lipids found in the diatom itself. Fatty Acids . The seawater contained 1.0 μg fatty acids/ml, C 16:0, C 18:0 and C 18:1 being the predominant components. After removal of 12-day cultures of the diatom, the medium contained 1.1 μg fatty acids/ml and showed 47% decrease of the C 18:0 acid, and decreases of 37% in the C 13:0 and 56% in the C 15:1 contents. The diatom itself contained 10.7% fatty acids of the dry weight, among which C 16:1, C 16:0 and C 14:0 predominated. Sterols . Cholesterol dominated the sterol composition of seawater, which was found to contain 0.15 μg total sterols/ml. The filtered culture medium contained 0.18 μg total sterols/ml, had lost some of its cholesterol content, but contained a significant amount of 24-methylene-cholesterol. Other minor sterols in seawater both prior to and after growing diatoms cultures in it were β-sitosterol, stigmasterol and campesterol. The diatom itself contained 0.47% total sterols of the dry weight with cholesterol and 24-methylene-cholesterol making up ca. 40% of the total each. Minor sterols found were stigmasterol (or fucosterol), campesterol and β-sitosterol.

Chemistry and biological activity of the secretions of queen and worker honeybees (Apis mellifica L.)

Abstract 1. 1. Analysis of the lipids of queen bee larvae showed that on hydrolysis the following acids were present; myristic, palmitic, sebacic, dec-2-endioic, suberic, aand trans-10-hydroxy-dec-2-enoic. The latter accounts for 20 per cent of the fatty acids. 2. 2. The queen larva extracts also contain 24 methylene cholesterol. 3. 3. Royal jelly contains adipic, pimelic, suberic and sebacic acids. 4. 4. The relationship of trans-9-oxo-dec-2-enoic acid and various volatile compounds to the substances responsible for inhibition of ovarian development, inhibition of queen rearing and attractivity to workers is discussed.

Cyclobrassinin sulphoxide, a sulphur-containing phytoalexin from Brassica juncea

Abstract Cyclobrassinin sulphoxide, a new sulphur-containing phytoalexin, was isolated from elicited leaves of Brassica juncea , and identified on the basis of physico-chemical data (IR, high resolution MS and 1 H NMR). The results so far obtained within this series of natural compounds are discussed in relationship with their possible biosynthesis.

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

2 C18 isoprenoid ketones, hexahydrofarnesylacetone (1) and farnesylacetone (2) have been identified for the first time in lipid extracts from the androgenic glands of the male crab Carcinus maenas, using coupled gas chromatography-mass spectrometry. The 2 compounds prepared by synthesis, are biologically active, inhibiting the incorporation of3H-leucine in Crustaceans ovaries subcultures.