Chondria californica

The structures of nine of these compounds were determined by spectroscopic methods, while those of the 14 remaining materials were established by GC-MS only. The compounds can be classified into four types (A to D) the 1,2,4-trithiolanes (145-154), 1,2,4,5-tetrathianes (155-157), 1,2,3,5,6-pentathiepanes (158-163), which are all generally quite stable compounds, and the monoalkyl-substituted polysulfides (164-167), which tend to disproportionate into sulfur and disubstituted cyclic polysulfides. These compounds are structurally related to the cyclic polysulfide compounds reported from red alga Chondria californica in 1976 [136] and to compound 168 (3-hexyl-4,5-dithiacycloheptanone) reported from the brown algae of the Dictyopteris genus in 1971 [137]. The latter compound has more recently been found to be a potent inhibitor of bee venom-derived phospholipase A2 (PLA2) [138]. 

Lenthionine and related cyclic methylene disnlfanes of ring sizes 6-12 have also been obtained from the alga Chondria californica and from the seed of the mimosacea Parkia speciosa ... 

Besides 1,2,4-trithiolane, the 1- and 4-oxides were also isolated from Chondria californica. b Mixture of cis and trans isomers. 

Wratten S.J. and Faulkner D.J. (1976) Cyclic polysulfides from the red alga Chondria californica. J. Org. Chem. 41, 2465-7. 

Fig. 2. Electron capture—gas chromatographic analyses of standard pollutants and extracts of several marine organisms A, DDT B, DDE (first peak), DDD C, Laurencia pacifica-, D, Laurencia subopposita E, Chromobacterium sp. F, Arochlor 1242 G, Arochlor 1254 H, Plocamium cartilagineum I, Verongia sp. J, Chondria californica. The GC conditions are identical to those used to produce Fig, 1.

DDT (trace A) and its metabolites DDE and DDD (trace B), and traces F and G are the commercial polychlorinated biphenyl (PCB) mixtures Arochlor 1242 (trace F) and Arochlor 1254 (trace G). As is illustrated, extracts of local Laurencia species (traces C and D), and the extract of a halogenating bacterium Chromobacterium sp. (trace E), contain compounds of similar retention time to DDT and its metabolites. Traces H and J were produced from extracts of Plocamium cartilagineum and Chondria californica, two locally abundant red algae, and trace I was produced from a species unidentified sponge of the genus Verongia. In this case mixtures of halogenated natural compounds fall within the limits of detectability of the PCBs. 

C2H4S5, Mr 188.35, cryst., mp. 60-61 °C. L. is a component of the East Asian edible mushroom shiitake (Lentinus edodes, Basidiomycetes) and, together with the polythiepanes and 1,2,4-trithioIane shown in the formula scheme, is responsible for the characteristic odor of the mushroomPrecursors of this flavor substance are 2,4,5,7-tetrathiaoctane 2,2,7,7-tetraoxide and 2,3,5,7,9-pentathiadecane 9,9-dioxide (SE-3), the structures of which were confirmed by synthesis (see also dysoxysulfone). The cyclic flavor substances can be prepared simply by reaction of dichloromethane with NajSj.s (from NajS and sulfur)Shiitake mushrooms - cultivated on dead wood - are becoming increasingly popular in Europe and North America on account of their excellent flavor. L. is also found as a volatile component of cooked mutton and in the alga Chondria californica. ... 

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