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Bioorganic chemistry of microbial secondary metabolites
VOL.
84, 1997
Abstracts of the Articles Printed in Seibutsu-kogaku Kaishi Vol. 75, No. 5 (1997) Inhibition of Melanogenesis in B16 Mouse Melanoma by PolypheoolGlucosides.
Breeding of Zygosaccharomyces rouxiy Producing Enhanced Aroma Components and Its Application to Barley Miso Fermentation. -NoteKAZUHIRO KUSUMEGI,* MASAYUKI BABA, HIDETSUGU YOSHIDA, and MO~UYA.WMNAGI (Yamae Shokuhin Co. Ltd., 3646 Nishimachi, Miyakonojo-shi, Miyazaki 885) Seibutsu-kogaku 75: 343-346. 1997. Flavor improvement of short-period-fermented barley miso (light-colored barley miso) was attempted using mutants of a salttolerant yeast, Zygosaccharomyces rouxii RB-1, that produced sufficient aroma components. Z. rouxii RB-1 was mutated stepwisely by ethidium bromide, and the mutants were isolated using two or three kinds of amino acid analogue (r.-canavanine, 5,5,5trifluoroleutine, or pfluorophenylalanine). The mutants showed higher productivity of several kinds of higher alcohols than that of the parent, RB1. In particular, mutant RBMK-32 exhibited the highest productivity of 2-methyl-1-propanol and 3-methyl-1-butanol among the five mutants in soy sauce medium, produced twice as much 1-butanol and 3-methyl-1-butanol as the parent RB-1 in miso fermentation, and added a highly aromatic character to light-colored barley miso.
MASAT~KAFUNAYIU~A, ‘* HIROICuNl hAIUWA,’ YOSHUCATSUsAL4MA,2 and RYOHEI YAM~MOTO~ (Technical Research Laboratory, Kurabo
Industries Ltd., Shimokida-cho, Neyagawa, Osaka 572’ and Chugai Pharmaceutical Co. Ltd., I-9 Kyobashi 2-chome, Chuo-ku, Tokyo IO&) Seibutsu-kogaku 75: 333-337. 1997. Phenoiic-a-glucosides were synthesized from polyphenols and starch using glucoside synthetase or cyclodextringlucanotransferase. The inhibition of melanogenesis in B16 mouse melanoma by fourteen polyphenol-a-glucosides was investigated, among which hydroquinone, and m- and p-coumaric acid derivatives inhibited melanogenesis (18% at 350 PM. 25% at 5.000 PM. and 70% at 1,000 uM, resoectivelyjwithout mhibition of cell growth. Catecdin-a-glucosidk, which inhibits tyrosinase activity in mushroom, did not inhibit melanogenesis in mouse melanoma. * Corresponding author. Determination of Enantiomers of 1,2-Propanediol in Beer by Gas Chromatography. -NoteNAOKIMOC~JZUKI,~*KAORIKncucrn,* and MITSIJO IKEDA~ (Fukushima Brewery, Asahi Breweries Ltd., I Kami-maehata, Arai, Motomiya-machi, Adachi-gun, Fukushima 969~II1 and Brewing Research and Development Laboratory, Asahi Breweries Ltd., 2-131 Ohmori-kita, Ohta-ku, Tokyo 1439 Seibutsu-kogaku 75: 339-342. 1997. A method for precisely determining the enantiomeric purity of (R)-1,Zpropanediol produced by fermentation in beer was developed. Extraction of 1,2-propanediol was effectively achieved using an Extrelut@ column. The concentrations of (R)-1,2-propanediol and its (S)-isomer in beer were determinated to be in the range 6.413.8 ppm and about 1 ppm, respectively by gas chromatography using a Chirasil-DEX CB column. The optical purity of (R)-1,2propanediol was found to be 78-89% ee.
* Corresponding author. Bioorganic Chemistry of Microbial Secondary Metabolites. -MonographYASURIRO YAMADA(Department of Biotechnology, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565) Seibutsu-kogaku 75: 347-358. 1997. (i) The structures of polyketides isolated from Peniciliium urticae patulin-minus mutants were determined and their versatility is discussed. (ii) The structures, biosynthesis, and activities of chitinase inhibitors, allosamidin congeners, are described and their physiological role is discussed. (iii) The structures, biosynthesis, and modes of action of butyrolactone autoregulators of Streptomyces are described. Finally, the role of microbial secondary metabolites is discussed.
* Corresponding author.
386
84, 1997
Abstracts of the Articles Printed in Seibutsu-kogaku Kaishi Vol. 75, No. 5 (1997) Inhibition of Melanogenesis in B16 Mouse Melanoma by PolypheoolGlucosides.
Breeding of Zygosaccharomyces rouxiy Producing Enhanced Aroma Components and Its Application to Barley Miso Fermentation. -NoteKAZUHIRO KUSUMEGI,* MASAYUKI BABA, HIDETSUGU YOSHIDA, and MO~UYA.WMNAGI (Yamae Shokuhin Co. Ltd., 3646 Nishimachi, Miyakonojo-shi, Miyazaki 885) Seibutsu-kogaku 75: 343-346. 1997. Flavor improvement of short-period-fermented barley miso (light-colored barley miso) was attempted using mutants of a salttolerant yeast, Zygosaccharomyces rouxii RB-1, that produced sufficient aroma components. Z. rouxii RB-1 was mutated stepwisely by ethidium bromide, and the mutants were isolated using two or three kinds of amino acid analogue (r.-canavanine, 5,5,5trifluoroleutine, or pfluorophenylalanine). The mutants showed higher productivity of several kinds of higher alcohols than that of the parent, RB1. In particular, mutant RBMK-32 exhibited the highest productivity of 2-methyl-1-propanol and 3-methyl-1-butanol among the five mutants in soy sauce medium, produced twice as much 1-butanol and 3-methyl-1-butanol as the parent RB-1 in miso fermentation, and added a highly aromatic character to light-colored barley miso.
MASAT~KAFUNAYIU~A, ‘* HIROICuNl hAIUWA,’ YOSHUCATSUsAL4MA,2 and RYOHEI YAM~MOTO~ (Technical Research Laboratory, Kurabo
Industries Ltd., Shimokida-cho, Neyagawa, Osaka 572’ and Chugai Pharmaceutical Co. Ltd., I-9 Kyobashi 2-chome, Chuo-ku, Tokyo IO&) Seibutsu-kogaku 75: 333-337. 1997. Phenoiic-a-glucosides were synthesized from polyphenols and starch using glucoside synthetase or cyclodextringlucanotransferase. The inhibition of melanogenesis in B16 mouse melanoma by fourteen polyphenol-a-glucosides was investigated, among which hydroquinone, and m- and p-coumaric acid derivatives inhibited melanogenesis (18% at 350 PM. 25% at 5.000 PM. and 70% at 1,000 uM, resoectivelyjwithout mhibition of cell growth. Catecdin-a-glucosidk, which inhibits tyrosinase activity in mushroom, did not inhibit melanogenesis in mouse melanoma. * Corresponding author. Determination of Enantiomers of 1,2-Propanediol in Beer by Gas Chromatography. -NoteNAOKIMOC~JZUKI,~*KAORIKncucrn,* and MITSIJO IKEDA~ (Fukushima Brewery, Asahi Breweries Ltd., I Kami-maehata, Arai, Motomiya-machi, Adachi-gun, Fukushima 969~II1 and Brewing Research and Development Laboratory, Asahi Breweries Ltd., 2-131 Ohmori-kita, Ohta-ku, Tokyo 1439 Seibutsu-kogaku 75: 339-342. 1997. A method for precisely determining the enantiomeric purity of (R)-1,Zpropanediol produced by fermentation in beer was developed. Extraction of 1,2-propanediol was effectively achieved using an Extrelut@ column. The concentrations of (R)-1,2-propanediol and its (S)-isomer in beer were determinated to be in the range 6.413.8 ppm and about 1 ppm, respectively by gas chromatography using a Chirasil-DEX CB column. The optical purity of (R)-1,2propanediol was found to be 78-89% ee.
* Corresponding author. Bioorganic Chemistry of Microbial Secondary Metabolites. -MonographYASURIRO YAMADA(Department of Biotechnology, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565) Seibutsu-kogaku 75: 347-358. 1997. (i) The structures of polyketides isolated from Peniciliium urticae patulin-minus mutants were determined and their versatility is discussed. (ii) The structures, biosynthesis, and activities of chitinase inhibitors, allosamidin congeners, are described and their physiological role is discussed. (iii) The structures, biosynthesis, and modes of action of butyrolactone autoregulators of Streptomyces are described. Finally, the role of microbial secondary metabolites is discussed.
* Corresponding author.
386