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Mar. Drugs 2012, 10(6), 1266-1287; doi:10.3390/md10061266

Purpurogemutantin and Purpurogemutantidin, New Drimenyl Cyclohexenone Derivatives Produced by a Mutant Obtained by Diethyl Sulfate Mutagenesis of a Marine-Derived Penicillium purpurogenum G59

1
Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China
2
Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China
3
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
4
Institute of Traditional Chinese Medicine & Natural Products, Jinan University, Guangzhou 510632, China
*
Author to whom correspondence should be addressed.
Received: 9 March 2012 / Revised: 24 May 2012 / Accepted: 24 May 2012 / Published: 4 June 2012
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Abstract

Two new drimenyl cyclohexenone derivatives, named purpurogemutantin (1) and purpurogemutantidin (2), and the known macrophorin A (3) were isolated from a bioactive mutant BD-1-6 obtained by random diethyl sulfate (DES) mutagenesis of a marine-derived Penicillium purpurogenum G59. Structures and absolute configurations of 1 and 2 were determined by extensive spectroscopic methods, especially 2D NMR and electronic circular dichroism (ECD) analysis. Possible biosynthetic pathways for 13 were also proposed and discussed. Compounds 1 and 2 significantly inhibited human cancer K562, HL-60, HeLa, BGC-823 and MCF-7 cells, and compound 3 also inhibited the K562 and HL-60 cells. Both bioassay and chemical analysis (HPLC, LC-ESIMS) demonstrated that the parent strain G59 did not produce 13, and that DES-induced mutation(s) in the mutant BD-1-6 activated some silent biosynthetic pathways in the parent strain G59, including one set for 13 production.
Keywords: purpurogemutantin; purpurogemutantidin; sesquiterpene; meroterpenoid; structure determination; antitumor activity; Penicillium purpurogenum; marine-derived fungus; DES mutagenesis purpurogemutantin; purpurogemutantidin; sesquiterpene; meroterpenoid; structure determination; antitumor activity; Penicillium purpurogenum; marine-derived fungus; DES mutagenesis
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Fang, S.-M.; Cui, C.-B.; Li, C.-W.; Wu, C.-J.; Zhang, Z.-J.; Li, L.; Huang, X.-J.; Ye, W.-C. Purpurogemutantin and Purpurogemutantidin, New Drimenyl Cyclohexenone Derivatives Produced by a Mutant Obtained by Diethyl Sulfate Mutagenesis of a Marine-Derived Penicillium purpurogenum G59. Mar. Drugs 2012, 10, 1266-1287.

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