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Mar. Drugs 2015, 13(1), 354-365; doi:10.3390/md13010354

Preparative Separation of Sulfur-Containing Diketopiperazines from Marine Fungus Cladosporium sp. Using High-Speed Counter-Current Chromatography in Stepwise Elution Mode

1
School of Marine Sciences, Laboratory of Marine Natural Products, Ningbo University, Ningbo 315211, China
2
CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China
3
College of Pharmacy, Jinan University, Guangzhou 510632, China
4
Ocean College, Zhejiang University, Hangzhou 310058, China
5
Key Laboratory of Applied Marine Biotechnology of Ministry of Education, Ningbo University, Ningbo 315211, China
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editor: Alejandro M. Mayer
Received: 14 October 2014 / Accepted: 1 January 2015 / Published: 9 January 2015
View Full-Text   |   Download PDF [804 KB, uploaded 24 February 2015]   |  

Abstract

High-speed counter-current chromatography (HSCCC) was successively applied to the separation of three sulfur-containing diketopiperazines (DKPs) (including two new compounds cladosporin A (1) and cladosporin B (3), and a known compound haematocin (2)) from a marine fungus Cladosporium sp. The two-phase solvent system composed of n-hexane-ethyl acetate-methanol-water at (1:1:1:1, v/v) and (2:1:2:1, v/v), in stepwise elution mode, was used for HSCCC. The preparative HSCCC separation was performed on 300 mg of crude sample yielding 26.7 mg of compound 3 at a purity of over 95%, 53.6 mg of a mixture of compounds 1 and 2, which was further separated by preparative-HPLC yielding 14.3 mg of compound 1 and 25.4 mg of compound 2 each at a purity of over 95%. Their structures were established by spectroscopic methods. The sulfur-containing DKPs suppressed the proliferation of hepatocellular carcinoma cell line HepG2. The present work represents the first application of HSCCC in the efficient preparation of marine fungal natural products. View Full-Text
Keywords: Cladosporium; high-speed counter-current chromatography; marine fungus; sulfur-containing diketopiperazines Cladosporium; high-speed counter-current chromatography; marine fungus; sulfur-containing diketopiperazines
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Gu, B.; Zhang, Y.; Ding, L.; He, S.; Wu, B.; Dong, J.; Zhu, P.; Chen, J.; Zhang, J.; Yan, X. Preparative Separation of Sulfur-Containing Diketopiperazines from Marine Fungus Cladosporium sp. Using High-Speed Counter-Current Chromatography in Stepwise Elution Mode. Mar. Drugs 2015, 13, 354-365.

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