title: Preparative separation of sulfur-containing diketopiperazines from marine fungus Cladosporium sp. using high-speed counter-current chromatography in stepwise elution mode.
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.
authors.affiliation: School of Marine Sciences, Laboratory of Marine Natural Products, Ningbo University, Ningbo 315211, China. gubin21314@gmail.com.
authors.forename: Binbin
authors.initials: B
authors.lastname: Gu
authors.affiliation: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China. zyy@scsio.ac.cn.
authors.forename: Yanying
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: College of Pharmacy, Jinan University, Guangzhou 510632, China. huahua20062008@126.com.
authors.forename: Lijian
authors.initials: L
authors.lastname: Ding
authors.affiliation: School of Marine Sciences, Laboratory of Marine Natural Products, Ningbo University, Ningbo 315211, China. heshan@nbu.edu.cn.
authors.forename: Shan
authors.initials: S
authors.lastname: He
authors.affiliation: Ocean College, Zhejiang University, Hangzhou 310058, China. wubin@zju.edu.cn.
authors.forename: Bin
authors.initials: B
authors.lastname: Wu
authors.affiliation: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China. dongjunde@vip.163.com.
authors.forename: Junde
authors.initials: J
authors.lastname: Dong
authors.affiliation: Key Laboratory of Applied Marine Biotechnology of Ministry of Education, Ningbo University, Ningbo 315211, China. zhupeng@nbu.edu.cn.
authors.forename: Peng
authors.initials: P
authors.lastname: Zhu
authors.affiliation: School of Marine Sciences, Laboratory of Marine Natural Products, Ningbo University, Ningbo 315211, China. chenjuanjuan@nbu.edu.cn.
authors.forename: Juanjuan
authors.initials: J
authors.lastname: Chen
authors.affiliation: School of Marine Sciences, Laboratory of Marine Natural Products, Ningbo University, Ningbo 315211, China. zhangjinrong@nbu.edu.cn.
authors.forename: Jinrong
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Applied Marine Biotechnology of Ministry of Education, Ningbo University, Ningbo 315211, China. yanxiaojun@nbu.edu.cn.
authors.forename: Xiaojun
authors.initials: X
authors.lastname: Yan
mesh_terms: D002851:Chromatography, High Pressure Liquid; D002963:Cladosporium / Q000737:chemistry*; D003377:Countercurrent Distribution / Q000379:methods; D054659:Diketopiperazines / Q000737:chemistry / Q000302:isolation & purification*; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification; D049934:Isocoumarins / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure; D010879:Piperazines / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D054659:Diketopiperazines; D007211:Indoles; D049934:Isocoumarins; D010879:Piperazines; C406046:haematocin; C000488:cladosporin