Microbial transformation of spirolaxine, a bioactive undecaketide fungal metabolite from the basidiomycete Sporotrichum laxum.
作者： Gianluca Nasini , Adriana Bava , Giovanni Fronza , Giuseppe Giannini
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摘要: b ) Sigma-Tau S.P.A., Research and Development, via Pontina km 30,400, I-00040 Pomezia Incubation of (þ)-spirolaxine ( ¼ (3R)-5-hydroxy-7-methoxy-3-{5-((2R,5R,7R)-2-methyl-1,6-dioxa- spiro(4.5)dec-7-yl)pentyl}-2-benzofuran-1(3H)-one; 1a) with Bacillus megaterium afforded two new mono- one dihydroxylated metabolite(s), all OH groups being introduced on the non-activated six-membered ring. In contrast, exposure 1a to Cunninghamella echinulata gave rise hydroxylation five-membered ring parent structure. The structures absolute configurations products 1b - e were deduced basis MS NMR data. metabolite was investigated, in comparison 1a, for its cytotoxicity (sulforhodamin-B test) antiproliferative activity towards bovine microvascular endothelial cells (BMEC).
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sci-hub.se 参考文章(12)
Ian J. S. Fairlamb, Stephanie Grant, Gideon Grogan, David A. Maddrell, Josephine C. Nichols, A one-pot remote allylic hydroxylation and Baeyer–Villiger oxidation of a bicyclo[3.2.0]hept-2-en-6-one by Cunninghamella echinulata NRRL 3655 Organic and Biomolecular Chemistry. ,vol. 2, pp. 1831- 1833 ,(2004) , 10.1039/B406016D
Alberto Arnone, Gemma Assante, Gianluca Nasini, Orso Vajna De Pava, Spirolaxine and sporotricale: Two long-chain phthalides produced by Sporotrichum laxum Phytochemistry. ,vol. 29, pp. 613- 616 ,(1990) , 10.1016/0031-9422(90)85127-2
Adriana Bava, Marco Clericuzio, Giuseppe Giannini, Luciana Malpezzi, Stefano Valdo Meille, Gianluca Nasini, Absolute Configuration of the Fungal Metabolite Spirolaxine European Journal of Organic Chemistry. ,vol. 2005, pp. 2292- 2296 ,(2005) , 10.1002/EJOC.200400902
Alberto Arnone, Gemma Assante, Gianluca Nasin, Orso Vajna de Pava, Chrysanthones B and C, secondary metabolites produced by the fungus Ascochyta chrysanthemi Phytochemistry. ,vol. 29, pp. 2499- 2502 ,(1990) , 10.1016/0031-9422(90)85174-E
Raffaella Nannei, Sabrina Dallavalle, Lucio Merlini, Adriana Bava, Gianluca Nasini, Synthesis of (+)-spirolaxine methyl ether. Journal of Organic Chemistry. ,vol. 71, pp. 6277- 6280 ,(2006) , 10.1021/JO060839I
KOEN A. DEKKER, TAISUKE INAGAKI, THOMAS D. GOOTZ, KEIJI KANEDA, ETSUKO NOMURA, TATSUO SAKAKIBARA, SHINICHI SAKEMI, YUTAKA SUGIE, YUJI YAMAUCHI, NOBUJI YOSHIKAWA, NAKAO KOJIMA, CJ-12,954 and its congeners, new anti-Helicobacter pylori compounds produced by Phanerochaete velutina: fermentation, isolation, structural elucidation and biological activities. The Journal of Antibiotics. ,vol. 50, pp. 833- 839 ,(1997) , 10.7164/ANTIBIOTICS.50.833
M. J. Blaser, Helicobacter pylori: its role in disease. Clinical Infectious Diseases. ,vol. 15, pp. 386- 393 ,(1992) , 10.1093/CLIND/15.3.386
Ryou OKAZAKI, Takayuki ORITANI, Yoshihiro HARA, Hirotaka YAMAMOTO, Microbial hydroxylation of (+/-)- and (-)-(2Z,4E)-5-(1',2'-epoxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienoic acid into (+/-)- and (-)-xanthoxin acid by Cunninghamella echinulata. Bioscience, Biotechnology, and Biochemistry. ,vol. 65, pp. 943- 946 ,(2001) , 10.1271/BBB.65.943
Adriana Bava, Sabrina Dallavalle, Giovanni Fronza, Gianluca Nasini, Orso Vajna de Pava, Absolute configuration of sporotricale and structure of 6-hydroxysporotricale. Journal of Natural Products. ,vol. 69, pp. 1793- 1795 ,(2006) , 10.1021/NP060212V
Oliver Lentz, Anton Feenstra, Tilo Habicher, Bernhard Hauer, Rolf D. Schmid, Vlada B. Urlacher, Altering the Regioselectivity of Cytochrome P450 CYP102A3 of Bacillus subtilis by Using a New Versatile Assay System ChemBioChem. ,vol. 7, pp. 345- 350 ,(2006) , 10.1002/CBIC.200500266