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

Shi-Ming Fang³  Cheng-Bin Cui³  Chang-Wei Li³  Chang-Jing Wu³  Zhi-Jun Zhang³  Li Li²  Xiao-Jun Huang¹ 

[1] Institute of Traditional Chinese Medicine & Natural Products, Jinan University, Guangzhou 510632, China;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;Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China;

关键词: purpurogemutantin;    purpurogemutantidin;    sesquiterpene;    meroterpenoid;    structure determination;    antitumor activity;    Penicillium purpurogenum;    marine-derived fungus;    DES mutagenesis;   

DOI  :  10.3390/md10061266

来源: mdpi

【 摘 要 】

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 1–3 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 1–3, 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 1–3 production.

【 授权许可】

CC BY   
© 2012 by the authors; licensee MDPI, Basel, Switzerland.