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Bioscience, Biotechnology, and Biochemistry Volume 57, 1993 - Issue 11
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Short Communication

Botcinolide: A Biologically Active Natural Product from Botrytis cinerea

Horace G. CutlerUSDA, ARS, Richard B. Russell Resarch Center, P.O. Box 5677, Athens, Georgia30613, U.S.A.
,
John M. JacynoOhio Northern University, College of Pharmacy, Ada, Ohio45810, U.S.A.
,
John S. HarwoodUniversity of Georgia, Department of Chemistry, Athens, Georgia30602, U.S.A.
,
Deanne DulikDepartment of Drug Metabolism, Smith Kline Beecham Pharmaceuticals, King of Prussia, Pennsylvania19406–0930, U.S.A.
,
Patsy D. GoodrichUSDA, ARS, Richard B. Russell Resarch Center, P.O. Box 5677, Athens, Georgia30613, U.S.A.
&
Rodney G. RobertsUSDA, ARS, Tree Fruit Research Laboratory, Wenatchee, Washington98801, U.S.A.
Pages 1980-1982 | Received 21 May 1993, Published online: 12 Jun 2014

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Emi SAKUNO, Hiroko TANI & Hiromitsu NAKAJIMA. (2007) 2-epi-Botcinin A and 3-O-Acetylbotcineric Acid from Botrytis cinerea . Bioscience, Biotechnology, and Biochemistry 71:10, pages 2592-2595.
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Articles from other publishers (33)

Chang Liu, Haiyao Guo, Han Liu, Jiawen Yu, Shuying Li, Tianhui Zhu, Adjei Mark Owusu & Shujiang Li. (2022) Differential Metabolomics Reveals Pathogenesis of Pestalotiopsis kenyana Causing Leaf Spot Disease of Zanthoxylum schinifolium. Journal of Fungi 8:11, pages 1208.
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Mathias Choquer, Christine Rascle, Isabelle R. Gonçalves, Amélie Vallée, Cécile Ribot, Elise Loisel, Pavlé Smilevski, Jordan Ferria, Mahamadi Savadogo, Eytham Souibgui, Marie‐Josèphe Gagey, Jean‐William Dupuy, Jeffrey A. Rollins, Riccardo Marcato, Camille Noûs, Christophe Bruel & Nathalie Poussereau. (2021) The infection cushion of Botrytis cinerea : a fungal ‘weapon’ of plant‐biomass destruction . Environmental Microbiology 23:4, pages 2293-2314.
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Antoine Porquier, Javier Moraga, Guillaume Morgant, Bérengère Dalmais, Adeline Simon, Hind Sghyer, Isidro G. Collado & Muriel Viaud. (2019) Botcinic acid biosynthesis in Botrytis cinerea relies on a subtelomeric gene cluster surrounded by relics of transposons and is regulated by the Zn2Cys6 transcription factor BcBoa13. Current Genetics 65:4, pages 965-980.
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Antoine Porquier, Guillaume Morgant, Javier Moraga, Bérengère Dalmais, Isabelle Luyten, Adeline Simon, Jean-Marc Pradier, Joëlle Amselem, Isidro González Collado & Muriel Viaud. (2016) The botrydial biosynthetic gene cluster of Botrytis cinerea displays a bipartite genomic structure and is positively regulated by the putative Zn(II)2Cys6 transcription factor BcBot6. Fungal Genetics and Biology 96, pages 33-46.
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Isidro G. Collado & Muriel Viaud. 2016. Botrytis – the Fungus, the Pathogen and its Management in Agricultural Systems. Botrytis – the Fungus, the Pathogen and its Management in Agricultural Systems 291 313 .
Steph Heard, Neil A. Brown & Kim Hammond-Kosack. (2015) An Interspecies Comparative Analysis of the Predicted Secretomes of the Necrotrophic Plant Pathogens Sclerotinia sclerotiorum and Botrytis cinerea. PLOS ONE 10:6, pages e0130534.
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M. NAKAJIMA & K. AKUTSU. (2014) Virulence factors of Botrytis cinerea.. Japanese Journal of Phytopathology 80:100th_Anniversary, pages S56-S64.
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Masami Nakajima & Katsumi Akutsu. (2013) Virulence factors of Botrytis cinerea. Journal of General Plant Pathology 80:1, pages 15-23.
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Isamu Shiina & Kenya Nakata. 2013. Natural Lactones and Lactams. Natural Lactones and Lactams 193 227 .
BÉRENGÈRE DALMAIS, JULIA SCHUMACHER, JAVIER MORAGA, PASCAL LE PÊCHEUR, BETTINA TUDZYNSKI, ISIDRO GONZALEZ COLLADO & MURIEL VIAUD. (2011) The Botrytis cinerea phytotoxin botcinic acid requires two polyketide synthases for production and has a redundant role in virulence with botrydial. Molecular Plant Pathology 12:6, pages 564-579.
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Jacinto Ramírez-Fernández, José Manuel Botubol, Antonio J. Bustillo, Josefina Aleu, Isidro G. Collado & Rosario Hernández-Galán. (2019) Botcinolide/Botcinin: Asymmetric Synthesis of the Key Fragments. Natural Product Communications 6:4, pages 1934578X1100600.
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Javier Moraga, Cristina Pinedo, Rosa Durán-Patrón, Isidro G. Collado & Rosario Hernández-Galán. (2011) Botrylactone: new interest in an old molecule—review of its absolute configuration and related compounds. Tetrahedron 67:2, pages 417-420.
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Geum-Jung Kim, Mi-Young Yoon, Heung-Tae Kim, Gyung-Ja Choi, Kyoung-Soo Jang, Yong-Ho Choi, Myung-Soo Park, Byeong-Jin Cha & Jin-Cheol Kim. (2009) Identification and Biological Activity of Two New Phytotoxins Isolated from Botrytis cinerea. Research in Plant Disease 15:2, pages 112-119.
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Hiroki Fukui & Isamu Shiina. (2009) Total Synthesis of Botcinolides and Botcinins; Determination of the Structure of Natural Products Isolated from Botrytis cinerea. Journal of Synthetic Organic Chemistry, Japan 67:6, pages 628-642.
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Isamu Shiina, Hiroki Fukui, Keisuke Tsuji & Yuma Umezaki. (2009) Total Synthesis and the Confirmation of the Revised Structures of Botcinins A and B. HETEROCYCLES 79:1, pages 403.
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Isamu Shiina & Hiroki Fukui. (2009) Chemistry and structural determination of botcinolides, botcinins, and botcinic acids. Chem. Commun.:4, pages 385-400.
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Hiroki Fukui, Seiichi Hitomi, Ryo-suke Suzuki, Tatsuhiko Ikeda, Yuma Umezaki, Keisuke Tsuji & Isamu Shiina. (2008) Asymmetric total synthesis of botcinic acid and its derivatives: synthetic revision of the structure of botcinolides. Tetrahedron Letters 49:46, pages 6514-6517.
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Tushar Kanti Chakraborty & Rajib Kumar Goswami. (2007) Studies directed towards the total synthesis of botcinic acid, the revised structure of botcinolide: synthesis of the highly substituted tetrahydropyran moiety. Tetrahedron Letters 48:37, pages 6463-6465.
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Isidro González Collado, Antonio José Macías Sánchez & James R. Hanson. (2007) Fungal terpene metabolites: biosynthetic relationships and the control of the phytopathogenic fungus Botrytis cinerea. Natural Product Reports 24:4, pages 674.
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Isamu Shiina. (2006) Total Synthesis of Natural 8- and 9-Membered Lactones:  Recent Advancements in Medium-Sized Ring Formation. Chemical Reviews 107:1, pages 239-273.
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Ilona Kars & Jan A. L. van Kan. 2007. Botrytis: Biology, Pathology and Control. Botrytis: Biology, Pathology and Control 99 118 .
Isamu Shiina, Yu-ji Takasuna, Ryo-suke Suzuki, Hiromi Oshiumi, Yuri Komiyama, Seiichi Hitomi & Hiroki Fukui. (2006) Stereoselective Total Synthesis of the Proposed Structure of 2-Epibotcinolide. Organic Letters 8:23, pages 5279-5282.
Crossref
Tushar Kanti Chakraborty & Rajib Kumar Goswami. (2006) Studies directed towards the synthesis of botcinolides: synthesis of the nonalactone ring of 2-epibotcinolide. Tetrahedron Letters 47:28, pages 4917-4919.
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H. Tani, H. Koshino, E. Sakuno, H. G. Cutler & H. Nakajima. (2006) Botcinins E and F and Botcinolide from Botrytis c inerea and Structural Revision of Botcinolides . Journal of Natural Products 69:4, pages 722-725.
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José L. Reino, Rosa M. Durán-Patrón, Mourad Daoubi, Isidro G. Collado & Rosario Hernández-Galán. (2005) Biosynthetic Studies on the Botcinolide Skeleton:  New Hydroxylated Lactones from Botrytis c inerea . The Journal of Organic Chemistry 71:2, pages 562-565.
Crossref
H. Tani, H. Koshino, E. Sakuno & H. Nakajima. (2005) Botcinins A, B, C, and D, Metabolites Produced by Botrytis c inerea , and Their Antifungal Activity against Magnaporthe g risea , a Pathogen of Rice Blast Disease . Journal of Natural Products 68:12, pages 1768-1772.
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Verena Siewers, Muriel Viaud, Daniel Jimenez-Teja, Isidro G. Collado, Christian Schulze Gronover, Jean-Marc Pradier, Bettina Tudzynsk & Paul Tudzynski. (2005) Functional Analysis of the Cytochrome P450 Monooxygenase Gene bcbot1 of Botrytis cinerea Indicates That Botrydial Is a Strain-Specific Virulence Factor . Molecular Plant-Microbe Interactions® 18:6, pages 602-612.
Crossref
Kazuro Shiomi & Satoshi Ōmura. 2003. Macrolide Antibiotics. Macrolide Antibiotics 1 56 .
Theo W. Prins, Paul Tudzynski, Andreas von Tiedemann, Bettina Tudzynski, Arjen Ten Have, Melanie E. Hansen, Klaus Tenberge & Jan A. L. van Kan. 2000. Fungal Pathology. Fungal Pathology 33 64 .
Isidro G. Collado, Josefina Aleu, Rosario Hern?ndez-Gal?n & James R. Hanson. (1996) Some metabolites of Botrytis cinerea related to botcinolide. Phytochemistry 42:6, pages 1621-1624.
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Gérard Rousseau. (1995) Medium ring lactones. Tetrahedron 51:10, pages 2777-2849.
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Isidro G. Collado, Rosario Hern?ndez-Gal?n, Rosa Dur?n-Patr?n & Jes?s M. Cantoral. (1995) Metabolites from a shake culture of Botrytis cinerea. Phytochemistry 38:3, pages 647-650.
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John M. Jacyno, John S. Harwood, Horace G. Cutler & Deanne M. Dulik. (1994) Structure and solution-state conformation of botcinolide, a new biologically active metabolite from the fungus Botrytis cinerea. Tetrahedron 50:40, pages 11585-11592.
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