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

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; in revised form: 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

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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.

AMA 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. Marine Drugs. 2012; 10(6):1266-1287.

Chicago/Turabian Style

Fang, Shi-Ming; Cui, Cheng-Bin; Li, Chang-Wei; Wu, Chang-Jing; Zhang, Zhi-Jun; Li, Li; Huang, Xiao-Jun; Ye, Wen-Cai. 2012. "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 10, no. 6: 1266-1287.

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