Structure and syntheses of texazone. 2-(N-methylamino)-3H-phenoxazin-3-one-8-carboxylic acid, an actinomycete metabolite.

Cultures of actinomycete strain WRAT-210 produced a dark red crystalline metabolite which was named texazone. Spectroscopic evidence suggested that the structure of texazone is 2-(N-methylamino)-3H-phenoxazin-3-one-8-carboxylic acid. The structure was confirmed by chemical synthesis through oxidative dimerization of ethyl 3-amino-4-hydroxybenzoate with 2-(N-methylamino)phenol and subsequent hydrolysis of the resultant phenoxazinone ester.

Transformation of Adenine to 8-Hydroxyadenine by Strains of Oerskovia xanthineolytica.

The 8-hydroxy derivative of adenine (6-amino-1,7-dihydro-8H-purin-8-one) is produced from adenine by two Oerskovia xanthineolytica strains. This transformation by a microorganism has not been reported previously. No novel products of dissimilation of xanthine (3,7-dihydro-1H-purine-2,6-dione) or hypoxanthine (1,7-dihydro-6H-purin-6-one) were found. Xanthine was oxidized to uric acid, but intermediates in the breakdown of hypoxanthine could not be demonstrated.

Structures and antimicrobial activity of peniophorin A and B, two polyacetylenic antibiotics from Peniophora affinis Burt.

Two polyacetylenic antibiotics, peniophorin A and B, have been isolated from a strain of Peniophora affinis. Both have antibacterial and antifungal activity, but B is 3 to 20 times more active than A. Gram-positive cocci and a strain of Proteus vulgaris were especially susceptible to these two antibiotics. Both peniophorins contained an aromatic ring; B was an acid, and A was neutral. Peniophorin B was shown to be 2-(1-oxo-2,4-pentadiynl)phenyl acetic acid. The structure of A was only partially elucidated; it is suspected to be 6-[2-(1-oxo-2,4-pentadiynl)phenyl]5-methoxy-3-oxo-4-hexene-1-ol.

New antibiotic pigments related to fusarubin from Fusarium solani (Mart.) Sacc. I. Fermentation, isolation, and antimicrobial activities.

A cholesterol-decomposing fungus, Fusarium solani (Mart.) SACC. strain PP 96, was found to produce several different naphthaquinone pigments in a glycerol-mineral salts medium. Three novel compounds structurally related to fusarubin were isolated by chloroform extration followed by silicic acid column chromatography and preparative thin-layer chromatography. The purified compounds were found to have relatively low activity against bacteria, yeasts and filamentous fungi.

New antibiotic pigments related to fusarubin from Fusarium solani (Mart.) Sacc. II. Structure elucidations.

Three antibiotic pigments isolated from Fusarium solani and related to fusarubin (4) were shown to be O-ethylfusarubin (2), hydroxidihydrofusarubin (3) and O-ethylhydroxydihydrofusarubin (1).

New prodigiosin-like pigment from Alteromonas rubra.

The red prodigiosin-like pigment from Alteromonas rubra was shown to be a mixture of prodigiosin (pigment 1) and a new cyclic isomer (pigment 2). The new structure was elucidated by mass and nuclear magnetic resonance spectra. Careful examinations of the prodigiosins produced by Serratia marcescens, Vibrio psychoerythrus, and an unidentified red bacterium (LL-100-6) failed to disclose any of the new pigment, pigment 2.

Pattern of phenazine pigment production by a strain of Pseudomonas aeruginosa.

An atypical strain of Pseudomonas aeruginosa capable of synthesizing three phenazine pigments was isolated. Cultural conditions, under which the strain forms either chlororaphin, oxychlororaphin, or pyocyanine, are described. This broad spectrum of pigment production, as well as some other characteristics, sets this strain apart from previously described chlororaphin producers.

Production of geosmin in fermentors and extraction with an ion-exchange resin.

A method for growing Streptomyces griseus LP-16 in fermentors and extracting and purifying geosmin, using an ion-exchange resin, is described.

Prodiginine (prodigiosin-like) pigments from Streptomyces and other aerobic Actinomycetes.

About 95 microorganisms, mainly streptomycetes, were examined for prodiginine pigments. The test methods, including some media for stimulating pigment production, are given. All nine strains which produced prodiginine pigments were characterized and the pigments identified. The results were used to propose structures for five prodigiosin-like pigments from actinomycetes reported in the literature between 1947 and 1964. Streptoverticillium sp. 26-1 furnished good yields of butylcycloheptylprodiginine (I), whose antimicrobial activity is given.

Prodiginine (prodigiosin-like) pigments from Streptoverticillium rubrireticuli, an organism that causes pink staining of polyvinyl chloride.

Red pigments were extracted from Streptoverticillium rubrireticuli strain 100-19, an organism frequently incriminated in pink staining of polyvinyl chloride. These pigments were identified as undecylprodiginine and butylcycloheptylprodiginine.

Prodigiosin-like pigments.

Prodigiosin, the bright red tripyrrole pigment from Serratia marcescens, has also been identified in Pseudomonas magnesiorubra, Vibrio psychroerythrus, and two Gram-negative rod-shaped mesophilic marine bacteria not members of the genus Serratia. Prodigiosin is sometimes bound to proteins; thus, extracts may require acid treatment before isolation of the pigment. Higher homologs of prodigiosin have been detected by mass spectroscopy. A mutant strain of S. marcescens produced nor-prodigiosin, in which the methoxy group of prodigiosin is replaced by a hydroxy group. Another mutant strain produced a blue tetrapyrrole pigment whose structure is a dimer of prodigiosin's rings A and B. Three novel biosynthetic analogs of prodigiosin have been obtained using a colorless mutant which does make rings A and B but not ring C and which can couple rings A and B with some added monopyrroles similar to ring C. The structures of three prodiginine (prodigiosin-like) pigments from streptomyces have been elucidated. All have the methoxytripyrrole aromatic nucleus of prodigiosin and all have an 11 carbon aliphatic side chain attached at carbon 2 of ring C. In two of the pigments the side chain is also linked to another carbon of ring C. The earlier literature about prodiginine pigments from actinomycetes has been interpreted and evaluated in light of the most recent findings. The structure elucidation of six prodiginine pigments from Actinomadurae (Nocardiae) has been completed. Only one, undecylprodiginine, is the same as from a streptomycete. For three of the six pigments, nine carbon side chains are observed and in four of them the side chain is attached to carbon 5 of ring A as well as carbon 2 of ring C so that a large ring is formed which includes the three pyrrole moieties. A section on identification summarized useful methods and presents information with which any known prodiginine pigment can be identified. The final step in the biosynthesis of prodigiosin was known to be the coupling of methoxybipyrrolecarboxaldehyde (rings A and B) with methylpentylpyrrole (ring C). Recent work using 13C-labeled precursors and Fourier transform 13C nuclear magnetic resonance has shown the pattern of incorporation for acetate, proline, glycine, serine alanine, and methionine into prodigiosin. Each pyrrole ring is constructed in a different way. Two of the streptomyces pigments have also been investigated; the pattern of incorporation is similar to that for prodigiosin. The biological activities of some prodiginine pigments are summarized. All show activity against several Gram-positive bacteria; some have anti-malarial activity. Prodigiosin has been tested clinically against coccidioidomycosis.

A new prodiginne (prodigiosin-like) pigment from Streptomyces. Antimalarial activity of several prodiginnes.

Two prodigiosin-like pigments from Streptomyces sp. were shown to be undecylprodiginine (i) and butylcycloheptylprodiginine (v). The antimalarial activity of five prodiginine pigments is given.

Isolation and purification of prodigiosin from Vibrio psychroerythrus.

The red pigment of Vibrio psychroerythrus (formerly marine psychrophile NRC 1004) was identified as prodigiosin by comparison of its mass spectrum, absorption spectrum in the visible range, and chromatographic behavior with prodigiosin isolated from Serratia marcescens. The properties of the V. psychroerythrus pigment were clearly distinguishable from five other prodigiosin-like compounds isolated from three different microorganisms.