Elucidation of the Biosynthesis and Degradation of Allantofuranone by Isotopic Labelling and Fermentation of Modified Precursors

被引：21

作者：

Schueffler, Anja ^{[2
]}

Liermann, Johannes C. ^{[1
]}

Opatz, Till ^{[1
]}

Anke, Timm ^{[2
]}

机构：

[1] Johannes Gutenberg Univ Mainz, Inst Organ Chem, D-55128 Mainz, Germany

[2] Inst Biotechnol & Wirkstoff Forsch eV, D-67663 Kaiserslautern, Germany

来源：

CHEMBIOCHEM | 2011年 / 12卷 / 01期

关键词：

allantofuranone; biosynthesis; isotopic labeling; natural products; polyporic acid; ALLANTOPHOMOPSIS-LYCOPODINA; PENIOPHORA-SANGUINEA; ASPERGILLUS-TERREUS; POLYPORIC ACID; DERIVATIVES; INHIBITOR; PIGMENTS; HALIDES; COMPLEX;

D O I：

10.1002/cbic.201000448

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Feeding experiments with the ascomycete Allantophomopsis lycopodina indicated that the potent fungistatic allantofuranone is biosynthesized from phenylalanine. Further experiments with synthetic precursors gave evidence that the naturally occurring polyporic acid serves as a key intermediate in the biosynthesis. In addition to the formation of allantofuranone, its abiotic and metabolic degradation were investigated.

引用

页码：148 / 154

页数：7

共 27 条

[1] Xenofuranones A and B:: Phenylpyruvate dimers from Xenorhabdus szentirmaii [J].

Brachmann, Alexander O. ;

Forst, Steven ;

Furgani, Ghazala M. ;

Fodor, Andras ;

Bode, Helge B. .

JOURNAL OF NATURAL PRODUCTS, 2006, 69 (12) :1830-1832

[2] ANTILEUKAEMIC ACTIVITY OF POLYPORIC ACID [J].

BURTON, JF ;

CAIN, BF .

NATURE, 1959, 184 (4695) :1326-1327

[3] Halorosellins A and B, unique isocoumarin glucosides from the marine fungus Halorosellinia oceanica [J].

Chinworrungsee, M ;

Kittakoop, P ;

Isaka, M ;

Chanphen, R ;

Tanticharoen, M ;

Thebtaranonth, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (22) :2473-2476

[4] THE SYNTHESIS OF VULPINIC ACID FROM POLYPORIC ACID [J].

FRANK, RL ;

CLARK, GR ;

COKER, JN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (04) :1824-1826

[5] The biosynthesis of pigments in Basidiomycetes [J].

Gill, M .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2001, 54 (12) :721-734

[6] NMR chemical shifts of common laboratory solvents as trace impurities [J].

Gottlieb, HE ;

Kotlyar, V ;

Nudelman, A .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7512-7515

[7] FUNGUS PIGMENTS .16. PIGMENTS OF PENIOPHORA SANGUINEA BRES [J].

GRIPENBERG, J .

ACTA CHEMICA SCANDINAVICA, 1965, 19 (09) :2242-+

[8]

Härtl A, 1998, J ANTIBIOT, V51, P528

[9] Synthesis, structure, and properties of benzoquinone dimer and trimers bearing t-Bu substituents [J].

Hayashi, Naoto ;

Yoshikawa, Takahiro ;

Ohnuma, Takahiro ;

Higuchi, Hiroyuki ;

Sako, Katsuya ;

Uekusa, Hidehiro .

ORGANIC LETTERS, 2007, 9 (26) :5417-5420

[10] p-terphenyl- and phenanthraquinone derivatives: An NMR study [J].

Jokela, R ;

Lounasmaa, M .

PLANTA MEDICA, 1997, 63 (04) :381-383

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