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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 Jun; 10(6):1266-1287.MD

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.

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Authors+Show Affiliations

Fang SM
Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China. Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China.
Cui CB
Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China. Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China.
Li CW
Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China.
Wu CJ
Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China.
Zhang ZJ
Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China.
Li L
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.
Huang XJ
Institute of Traditional Chinese Medicine & Natural Products, Jinan University, Guangzhou 510632, China.
Ye WC
Institute of Traditional Chinese Medicine & Natural Products, Jinan University, Guangzhou 510632, China.

MeSH

Antineoplastic AgentsAquatic OrganismsBiological ProductsCell Line, TumorCircular DichroismDrug Screening Assays, AntitumorHL-60 CellsHeLa CellsHumansK562 CellsMCF-7 CellsMagnetic Resonance SpectroscopyMutagenesisMutationPenicilliumSulfuric Acid Esters

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22822371

Citation

Fang, Shi-Ming, et al. "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, vol. 10, no. 6, 2012, pp. 1266-1287.
Fang SM, Cui CB, Li CW, et al. 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(6):1266-1287.
Fang, S. M., Cui, C. B., Li, C. W., Wu, C. J., Zhang, Z. J., Li, L., Huang, X. J., & Ye, W. C. (2012). 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, 10(6), 1266-1287. https://doi.org/10.3390/md10061266
Fang SM, et al. 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(6):1266-1287. PubMed PMID: 22822371.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Purpurogemutantin and purpurogemutantidin, new drimenyl cyclohexenone derivatives produced by a mutant obtained by diethyl sulfate mutagenesis of a marine-derived Penicillium purpurogenum G59. AU - Fang,Shi-Ming, AU - Cui,Cheng-Bin, AU - Li,Chang-Wei, AU - Wu,Chang-Jing, AU - Zhang,Zhi-Jun, AU - Li,Li, AU - Huang,Xiao-Jun, AU - Ye,Wen-Cai, Y1 - 2012/06/04/ PY - 2012/03/09/received PY - 2012/05/24/revised PY - 2012/05/24/accepted PY - 2012/7/24/entrez PY - 2012/7/24/pubmed PY - 2012/12/21/medline KW - DES mutagenesis KW - Penicillium purpurogenum KW - antitumor activity KW - marine-derived fungus KW - meroterpenoid KW - purpurogemutantidin KW - purpurogemutantin KW - sesquiterpene KW - structure determination SP - 1266 EP - 1287 JF - Marine drugs JO - Mar Drugs VL - 10 IS - 6 N2 - 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. SN - 1660-3397 UR - https://www.unboundmedicine.com/medline/citation/22822371/Purpurogemutantin_and_purpurogemutantidin_new_drimenyl_cyclohexenone_derivatives_produced_by_a_mutant_obtained_by_diethyl_sulfate_mutagenesis_of_a_marine_derived_Penicillium_purpurogenum_G59_ L2 - https://www.mdpi.com/resolver?pii=md10061266 DB - PRIME DP - Unbound Medicine ER -