Production and Isolation of a New Antifungal Antibiotic,Prumycin and Taxonomic Studies of Streptomyces sp., Strain No. F-1028

A newly described species of Streptomyces (named Sm. kagawaensis ATCC No. 21811) isolated from soil was found to produce a new antifungal antibiotic, prumycin, which belongs to amino sugar group. Prumycin was isolated from the fermentation broth by ion-exchange adsorption and gel-filtration methods. This antibiotic inhibited specifically the growth of Sclerotinia sp. and Botrytis sp. on flower pot test with kidney bean leaves and also was effective on the field test with various plants.     

Isolation,Structure and Physiological Activities of Piericidin B,Natural Insecticide Produced by a Streptomyces

Piericidin B was isolated from mycellia of Streptomyces mobaraensis besides piericidin A. On the basis of IR, NMR and mass spectral studies together with chemical evidences, its structure was assigned as Id. Its physiological activities are also deescribd.     

Evaluation of O,O-Dialkyl O-Cyanophenyl Phosphates and Phosphorothioates as Insecticides

Various O,O-dialkyl O-cyanophenyl phosphates and phosphorothioates were prepared and their biological activities were examined. Among them, O,O-dimethyl O- (4-chloro-2-cyanophenyl) phosphorothioate was found to have selective and high toxicity to houseflies. O,O-Dimethyl O- (4-cyanophenyl) phosphorothioate, O,O-diethyl O- (4-cyanophenyl) phosphorothioate and O,O-diethyl O- (2-chloro-4-cyanophenyl) phosphorothioate showed high insecticidal activty to American cockroaches, though the former two were not so effective to houseflies. The dimethyl esters of these series exhibited markedly lowered mammalian toxicity. Among the O-ethyl O-cyanophenyl phenylphosphonothioates, O-ethyl O- (2-chloro-4-cyanophenyl) phenylphosphonothioate was highly effective to mites, while less effective to insects.     

New Coumaronochromones from White Lupin,Lupinus albus L. (Leguminosae)

A further investigation of the isoflavonoid constituents occurring in roots of the white lupin (Lupinus albus L. cv. Kievskij Mutant) has yielded five new coumaronochromones named lupinalbin A (la), B (2a), C (3), D (4) and E (5). These isoflavonoids were identified by physicochemical methods involving the use of biogenetically related 2′-hydroxyisoflavones as reference compounds. The presence of the rare dihydrofurano-isoflavone, erythrinin C (16), in white lupin roots has also been established.     

Isolation of Extracellular Cobalt-free Corrinoid from Methanosarcina barkeri

Cobalt-free corrinoids (CFCs) were isolated from Methanosarcina barkeri Fusaro cells growing on a methanol minimum medium. The methanogen cells excreted a trace of CFCs (9.1 μg/I) into the culture medium when cobalt-deficient methanol medium was used. Several CFCs were separated by column chromatographies on ion exchangers and paper electrophoresis, where a major CFC showed a similar characteristic to that of nucleotide-free corrinoid, Factor B (cobinamide), suggesting to be hydrogenobinamide. By chemical insertion of Co^{2 +}, Cu^{2 +}, and Zn²⁺ into CFCs, the corresponding corrinoid and its metal analogues were observed. Bioassay using Escherichia coli 215 revealed that the major CFC (a yellow product obtained after alkaline treatment) and its copper and zinc analogues were inactive as cobalamin but were active as antimetabolites of cobalamin. However, the CFC greatly stimulated the cell growth of M. barkeri grown under cobalt-deficient conditions.     

Carboxylic Acids in Cultured Broth of Sporobolomyces odorus

Carboxylic acids found in the cultured broth of Sporobolomyces odorus AHU 3246 which produces γ-lactones as principles of the aromatic flavor, were analyzed. The concentrate of methylated acids was steam-distilled and in the residue, succinic acid, nonanedioic acid (azelaic acid), undecanedioic acid and 2-hydroxy-3-phenylpropionic acid (β-phenyllactic acid) were identified as their methyl esters by GLC and spectroscopic methods. Phthalic acid and its mono-n-butyl ester were also found, but these compounds were thought to arise from di-n-butyl phthalate, one of impurities of deionized water.     

Chemical Structure of Piericidin A

Molecular formula C₂₅H_37–39NO₄ was assigned to Piericidin A. Through the examination of the ultraviolet, infrared and n.m.r. spectra and of chemical evidences, it was shown that Piericidin A contains one secondary alcohol, one acidic hydroxyl group, two methoxyl groups, tri- and tetra-substituted conjugated dienes and one polysubstituted heteroaromatic ring.     

Structures of Novel Sesquiterpene Alcohols from Chloranthus japonicus (Chloranthaceae)

Three novel sesquiterpene alcohols, shizuka-acoradienol (2), shizukafuranol (3) and shizukol-idol (4), were isolated from Chloranthus japonicus Sieb. (Japanese name: Hitori-shizuka, Chloranthaceae). Their structures were elucidated on the basis of their physicochemical properties and some chemical reactions. Furanodienone (5), scopoletin (6a) and isoscopoletin (6b) were also isolated from this plant.