• Abstract
• Full-Text PDF [962 KB]
• Full-Text XML
• Article Versions Notes
• Supplement File 1

• Article Statistics
• PubMed/Medline
• Google Scholar
• Order Reprints

• Cite this article
• Export to BibTeX
• Export to EndNote

• [+] on DOAJ
• Fang, S
• Cui, C
• Li, C
• Wu, C
• Zhang, Z
• Li, L
• Huang, X
• Ye, W
• [+] on Google Scholar
• Fang, S
• Cui, C
• Li, C
• Wu, C
• Zhang, Z
• Li, L
• Huang, X
• Ye, W
• [+] on PubMed
• Fang, S
• Cui, C
• Li, C
• Wu, C
• Zhang, Z
• Li, L
• Huang, X
• Ye, W

•  CiteULike
•  Facebook
•  Mendeley
•  Twitter

This article is

• freely available
• re-usable

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

Shi-Ming Fang ^1,2 , Cheng-Bin Cui ^1,2,* , Chang-Wei Li ¹ , Chang-Jing Wu ¹ , Zhi-Jun Zhang ¹ , Li Li ³ , Xiao-Jun Huang ⁴  and Wen-Cai Ye ⁴

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

Download PDF Full-Text [962 KB, uploaded 4 June 2012 13:46 CEST]

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 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.

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

Supplementary Files

• Supplementary File 1:

  ZIP-Document (ZIP, 8582 KB)

Article Statistics

Cite This Article