Sulfone sponge

A sulfone (636) is a minor constituent of the Mediterranean sponge Anchinoe tenacior [502]. Sulfolane (637), a familiar industrial chemical, was isolated from a mixture of the sponge Batzella sp. and a Lissoclinum tunicate from Victoria, Australia [503]. It is possibly an absorbed compound rather than a natural product [12]. 

Most of the reported sulfone-containing marine metabolites have been obtained from sponges and bryozoa. The hypotaurocyamine-containing agelasidines, some adociaquinone derivatives, and the euthyroideones constitute small groups of compounds bearing a sulfone group. 

A sulfone group incorporated within a l,l-dioxo-l,4-thiazine ring is also present in 6-(p-hydroxyphenyl)-2i/-3,4-dihydro-l,l-dioxo-l,4-thiazine (286), a compound obtained from the sponge Anchinoe tenacior [211], and in euthyroideones A-C (287-289), which are brominated quinone methides isolated from the New Zealand bryozoan Euthyroides episcopalis (order Cheilostomatida, suborder Ascophotina, family Euthyroididae) [212]. The spectral data of euthyroideone A (287), secured by X-ray analysis, was used for the structural determination of euthyroideones B (288) and C (289). Compound 288 showed a weak cytotoxic activity towards the BSC-1 cell line. 

Very simple sulfones have also been isolated from marine organisms. The isolation of sulfolane (290) from the sponge/tunicate composite Batzella spJLissoclinum sp. was the first report, either terrestrial or marine, of this compound as a natural product [213]. The pyrogallol Phenol B (291), obtained from the red alga Grateloupia filicina, was... 

Ovenden SPB, Capon RJ (1999) Echinosulfonic Acids A-C and Echinosulfone A Novel Bromoindole Sulfonic Acids and a Sulfone from a Southern Australian Marine Sponge, Echinodictyum. J Nat Prod 62 1246... 

Vinyl sulfones were prepared from PhS02Na and vinyl iodinium salts C=C—I Ph BF4 Sulfinate esters (RS(=0)0R were prepared from alcohols and sulfinyl chlorides, in the presence of Proton Sponge . " ... 

The sulfone group is relatively rare in natural products, but a simple example is the l,4-thiazine-l,l-dioxide 10 (Figure 2), isolated from the marine sponge Anchinoe tenacior (94TL2421). The structure was assigned on the basis of NMR spectroscopy, but has yet to be confirmed by S5mthesis. 

Dysinosins are alkaloid tripeptides with very unusual a-substituted acid residues, including 5,6-dyhydroxyoctahydroindole-2-carboxylic acid and 3-sulfonic-2-methoxy propionic acid, as well as the basic moiety 2-aminoethyl-(l-N-amidino-A-3-pyrroline). Among them, dysinosin A (170), isolated from an identified sponge belonging to the family Dysideidae, inhibited factor Vila with a Ki of 108 nM and thrombin with a of 452 nM [159],... 

Ovenden, S.P.B. and Capon, R.J. (1999) Echinosulfonic adds A-C and echinosulfone A novel bromoindole sulfonic adds and a sulfone from a Southern Australian marine sponge Echinodictyum. J. Nat. Prod., 62,1246-1249. 

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