title: (±)-Pestalachloride D, an antibacterial racemate of chlorinated benzophenone derivative from a soft coral-derived fungus Pestalotiopsis sp.
abstract: A new antibacterial chlorinated benzophenone derivative, (±)-pestalachloride D (1), along with a related analog, (±)-pestalachloride C (2), was recently isolated from the marine-derived fungus Pestalotiopsis sp. isolated from a soft coral Sarcophyton sp. collected from Yongxing Island in the South China Sea. Both chiral HPLC analysis and single-crystal X-ray data indicated that 1 is a racemic mixture. Interestingly, 1 did not exhibit any effect in the zebrafish embryo teratogenicity assay, while 2 led to abnormal growth. The potential impact on zebrafish embryo growth is discussed based on their crystal structures. The main difference of crystal structures between 1 and 2 is that the six-member non-aromatic ring (O4, C10, C9, C8, C2', and C3') in 1 exhibits a distorted chair conformation, while 2 shows a distorted boat conformation. Moreover, compounds 1 and 2 both exhibited moderate antibacterial activity.
authors.affiliation: Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. mywei95@126.com
authors.forename: Mei-Yan
authors.initials: MY
authors.lastname: Wei
authors.forename: Dan
authors.initials: D
authors.lastname: Li
authors.forename: Chang-Lun
authors.initials: CL
authors.lastname: Shao
authors.forename: Dong-Sheng
authors.initials: DS
authors.lastname: Deng
authors.forename: Chang-Yun
authors.initials: CY
authors.lastname: Wang
mesh_terms: D000818:Animals; D037421:Anthozoa / Q000382:microbiology; D000900:Anti-Bacterial Agents / Q000302:isolation & purification / Q000494:pharmacology* / Q000633:toxicity; D001572:Benzofurans / Q000302:isolation & purification / Q000494:pharmacology* / Q000633:toxicity; D001577:Benzophenones / Q000302:isolation & purification / Q000494:pharmacology* / Q000633:toxicity; D002681:China; D002851:Chromatography, High Pressure Liquid; D003460:Crystallization; D018360:Crystallography, X-Ray; D007189:Indans / Q000302:isolation & purification / Q000494:pharmacology* / Q000633:toxicity; D018675:Toxicity Tests; D013098:Xylariales / Q000302:isolation & purification / Q000378:metabolism*; D015027:Zebrafish
chemical_list: D000900:Anti-Bacterial Agents; D001572:Benzofurans; D001577:Benzophenones; D007189:Indans; C532660:pestalachloride C; C585602:pestalachloride D
references.citation: J Nat Prod. 2012 Feb 24;75(2):189-97
references.pmid: 22276679
references.citation: Birth Defects Res B Dev Reprod Toxicol. 2010 Feb;89(1):66-77
references.pmid: 20166227
references.citation: J Nat Prod. 2012 Mar 23;75(3):311-35
references.pmid: 22316239
references.citation: J Org Chem. 2009 Feb 6;74(3):1093-8
references.pmid: 19118474
references.citation: J Nat Prod. 1998 Nov;61(11):1433-4
references.pmid: 9834174
references.citation: Bioorg Med Chem. 2008 Sep 1;16(17):7894-9
references.pmid: 18694644
references.citation: Nat Prod Rep. 2012 Jun;29(6):622-41
references.pmid: 22249927
references.citation: J Nat Prod. 2009 May 22;72(5):921-4
references.pmid: 19371069
references.citation: J Nat Prod. 2011 Apr 25;74(4):629-33
references.pmid: 21348465
references.citation: Bioorg Med Chem Lett. 2011 Jan 15;21(2):690-3
references.pmid: 21194945
references.citation: J Nat Prod. 2012 May 25;75(5):935-41
references.pmid: 22545792
references.citation: Nat Prod Rep. 2012 Feb;29(2):144-222
references.pmid: 22193773
references.citation: Nat Protoc. 2008;3(9):1494-500
references.pmid: 18772877
references.citation: Assay Drug Dev Technol. 2002 Nov;1(1 Pt 1):41-8
references.pmid: 15090155
references.citation: Org Lett. 2012 Dec 7;14(23):5936-9
references.pmid: 23163238