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Mar. Drugs 2013, 11(4), 1050-1060; doi:10.3390/md11041050
Article

(±)-Pestalachloride D, an Antibacterial Racemate of Chlorinated Benzophenone Derivative from a Soft Coral-Derived Fungus Pestalotiopsis sp.

1,2,†
,
1,†
,
1,* , 3
 and
1,*
1 Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China 2 School of Pharmacy, Guangdong Medical College, Dongguan 523808, China 3 College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, China These authors contributed equally to this work.
* Authors to whom correspondence should be addressed.
Received: 17 February 2013 / Revised: 1 March 2013 / Accepted: 15 March 2013 / Published: 28 March 2013
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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.
Keywords: (±)-pestalachloride D; antibacterial activity; zebrafish embryo teratogenicity assay; marine-derived fungus; Pestalotiopsis sp.; single-crystal X-ray (±)-pestalachloride D; antibacterial activity; zebrafish embryo teratogenicity assay; marine-derived fungus; Pestalotiopsis sp.; single-crystal X-ray
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Wei, M.-Y.; Li, D.; Shao, C.-L.; Deng, D.-S.; Wang, C.-Y. (±)-Pestalachloride D, an Antibacterial Racemate of Chlorinated Benzophenone Derivative from a Soft Coral-Derived Fungus Pestalotiopsis sp.. Mar. Drugs 2013, 11, 1050-1060.

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