~ ~~From the intact cells of the sulfur-metabolizing hyperthermophilic archea Thermococcus tadjuricus (strain Ob9) and Thermococcus acidaminovorans (strain Vc6bk) 23 predominantly new cyclic polysulfides could be isolated by using chemical screening methods. The structures of nine preparatively separated compounds were determined by spectroscopic methods, whereas those of 14 compounds were established by GC-MS only. Most of the polysulfides are derivatives of 1,2,4-trithiolane, 1,2,4,5-tetrathiane and 1,2,3,5,6-pentathiepane. They differ from each other by aliphatic or aromatic side chains, derived from predominantly metabolized proteinogenic amino acids. The building mechanism and the relevance of the polysulfides are discussed.In 1977 the prokaryotic archaea were established as the "third domain of life" besides eukaryotes and bacteria by WoeseL21. They grow under extreme conditions like absence of oxygen, temperatures of 100°C and saturated salt solutions reminding of the primitive earth. Therefore, the name "archaea" was chosen. Due to their outstanding phylogenetic position and the resistance of their cell components to heat or salt, they are of special interest in science and technol~gy[~I. So far, very few investigations have been made. In this paper the characteristics of various hyperthermophilic archaea in our chemical screening are rep~rted[~.~]. We found several lipophilic compounds in sulfur-metabolizing strains of the genus Thermococcus. From the culture broth of 7: celer (strain Mb2) the known antifungal cyclic polysulfide lenthionin (1,2,3,5,6-~entathiepane, 14)[6,71 could be isolated besides the amino acid catabolites phenylacetic acid, p-hydroxyphenylacetic acid and indoleacetic acid [*]. From the intact cells of 7: tadjuricus (strain Ob9) and 7: uciduminovorans (strain Vc6bk) a large number of related cyclic polysulfides were obtained. The isolation and structure elucidation of most of these components as well as the synthesis and the biological activity of some of them are described in this paper. Isolation and Structure ElucidationThe strains Ob9 and Vc6bk were isolated from marine hydrothermal systems near Obock (Djibouti) of both strains on silica gel TLC plates attracted our attention due to a great number of spots, which were detectable after staining with palladium(I1) chloride. Cultivation of the strains was carried out under nitrogen in 300-1 fermenters at 85°C in a medium containing yeast extract (0.2%), peptone (0.2%) and sulfur (0.2%). After 17 hours the culture broth was cooled to 4°C and centrifuged; the cells were homogenized in acetone to yield 4 g of a malodorous crude extract after evaporation of the solvent. The main compounds 3,5-diisobutyl-l,2,4-trithiolane (7) and 4,7-diisobutyl-l,2,3,5,6-pentathiepane (18) as well as seven minor compounds were isolated after column chromatography on silica gel. The compounds 7 and 12 were additionally purified by gas chromatography. The yields of 7 and 18 in the strain Vc6bk reached nearly 1 mg/l. The remaining compounds were identified...

In the course of our chemical screening program we detected a new naphthoquinone complex containing the naphthgeranines and the naphtherythrines2) produced by Streptomyces sp. (strain Tu 3556). This paper deals with the purification, structural elucidation and biological properties of the naphthgeranines A to E, which are similar to the recently described naphterpin3).After isolation from a soil sample collected in Nepal, the strain Tii 3556 was cultivated in 500ml flasks of 10liter fermenters at 27°C for 96hours or 120 hours using mannitol 2% and soybean meal 2% as a culture medium.Metabolites from the culture filtrate were adsorbed on Amberlite XAD-16 before being eluted with methanol from the resin. The mycelium was extracted with methanol. The combined solutions were concentrated under reduced pressure and the aqueous residues extracted with ethyl acetate. The isolation of the naphthgeranines from the resulting raw product was successful by using a silica gel column (flash chromatography) developed with a chloroform-methanol gradient of increasing polarity: Naphthgeranines A (95 : 5), B (9: 1), E (8 :2), C and D (7: 3). Further purification steps were carried out using silica gel (naphthgeranines A and B: chloroform-methanol (95 : 5 and 9 : 1, respectively), naphthgeranine C: chloroform -

A lactose-containing fermentation medium initiated the formation of 7-O-beta-D-galactosyl-brefeldin A [1] in the brefeldin A-producing organism, Penicillium brefeldianum. The detection, isolation, and physicochemical properties of 1, which has been produced by biological derivatization via transglycosylation, are described. Compound 1 is the first glycosylated brefeldin A derivative to have been prepared.