Molecular Basis for Stellatic Acid Biosynthesis: A Genome Mining Approach for Discovery of Sesterterpene Synthases

被引:69
作者
Matsuda, Yudai [1 ]
Mitsuhashi, Takaaki [1 ]
Quan, Zhiyang [1 ]
Abe, Ikuro [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
RAY CRYSTAL-STRUCTURE; ASPERGILLUS-VARIECOLOR; EMERICELLA-VARIECOLOR; BACILLUS-CLAUSII; IDENTIFICATION; STEREOCHEMISTRY; METABOLITES; CYCLASES; FUNGUS;
D O I
10.1021/acs.orglett.5b02404
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The search for a new sesterterpene synthase in the genome of Emericella variecolor, which reportedly produces diverse sesterterpenoids, is described. One gene product (a chimeric protein with prenyltransferase and terpene cyclase domains) led to the synthesis of a novel tricyclic sesterterpene, stellata-2,6,19-triene (1), from DMAPP and IPP, and the hydrocarbon was further transformed into stellatic acid (2) by cytochrome P450 monooxygenase encoded by the gene adjacent to the sesterterpene synthase gene.
引用
收藏
页码:4644 / 4647
页数:4
相关论文
共 24 条
[1]   Induced-Fit Mechanism in Class I Terpene Cyclases [J].
Baer, Philipp ;
Rabe, Patrick ;
Fischer, Katrin ;
Citron, Christian A. ;
Klapschinski, Tim A. ;
Groll, Michael ;
Dickschat, Jeroen S. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (29) :7652-7656
[2]   Discovery and functional characterization of two diterpene synthases for sclareol biosynthesis in Salvia sclarea (L.) and their relevance for perfume manufacture [J].
Caniard, Anne ;
Zerbe, Philipp ;
Legrand, Sylvain ;
Cohade, Allison ;
Valot, Nadine ;
Magnard, Jean-Louis ;
Bohlmann, Joerg ;
Legendre, Laurent .
BMC PLANT BIOLOGY, 2012, 12
[3]   Identification of Ophiobolin F Synthase by a Genome Mining Approach: A Sesterterpene Synthase from Aspergillus clavatus [J].
Chiba, Ryota ;
Minami, Atsushi ;
Gomi, Katsuya ;
Oikawa, Hideaki .
ORGANIC LETTERS, 2013, 15 (03) :594-597
[4]   Structural biology and chemistry of the terpenoid cyclases [J].
Christianson, David W. .
CHEMICAL REVIEWS, 2006, 106 (08) :3412-3442
[5]   Terpenoid synthase structures: a so far incomplete view of complex catalysis [J].
Gao, Yang ;
Honzatko, Richard B. ;
Peters, Reuben J. .
NATURAL PRODUCT REPORTS, 2012, 29 (10) :1153-1175
[6]   VARIECOLIN, A SESTERTERPENOID OF NOVEL SKELETON FROM ASPERGILLUS-VARIECOLOR MF138 [J].
HENSENS, OD ;
ZINK, D ;
WILLIAMSON, JM ;
LOTTI, VJ ;
CHANG, RSL ;
GOETZ, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10) :3399-3403
[7]   Development of a novel quadruple auxotrophic host transformation system by argB gene disruption using adeA gene and exploiting adenine auxotrophy in Aspergillus oryzae [J].
Jin, FH ;
Maruyama, J ;
Juvvadi, PR ;
Arioka, M ;
Kitamoto, K .
FEMS MICROBIOLOGY LETTERS, 2004, 239 (01) :79-85
[8]   Emervaridione and varioxiranediol, two new metabolites from the endophytic fungus, Emericella variecolor [J].
Liangsakul, Jatupol ;
Pornpakakul, Surachai ;
Sangvichien, Ek ;
Muangsin, Nongnuj ;
Sihanonth, Prakitsin .
TETRAHEDRON LETTERS, 2011, 52 (48) :6427-6430
[9]   Reconstitution of Biosynthetic Machinery for the Synthesis of the Highly Elaborated Indole Diterpene Penitrem [J].
Liu, Chengwei ;
Tagami, Koichi ;
Minami, Atsushi ;
Matsumoto, Tomoyuki ;
Frisvad, Jens Christian ;
Suzuki, Hideyuki ;
Ishikawa, Jun ;
Gomi, Katsuya ;
Oikawa, Hideaki .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (19) :5748-5752
[10]   Uncovering the Unusual D-Ring Construction in Terretonin Biosynthesis by Collaboration of a Multifunctional Cytochrome P450 and a Unique Isomerase [J].
Matsuda, Yudai ;
Iwabuchi, Taiki ;
Wakimoto, Toshiyuki ;
Awakawa, Takayoshi ;
Abe, Ikuro .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (09) :3393-3401