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Preparative separation of sulfur-containing diketopiperazines from marine fungus Cladosporium sp. using high-speed counter-current chromatography in stepwise elution mode.

Gu B, Zhang Y, Ding L, He S, Wu B, Dong J, Zhu P, Chen J, Zhang J, Yan X - Mar Drugs (2015)

Bottom Line: 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 Article: PubMed Central - PubMed

Affiliation: School of Marine Sciences, Laboratory of Marine Natural Products, Ningbo University, Ningbo 315211, China. gubin21314@gmail.com.

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.

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HPLC chromatogram of the crude extract from marine fungus Cladosporium sp. HPLC Conditions: column, Waters XBridge C18, 150 mm × 4.6 mm ID, 5 μm; column temperature, 25 °C; mobile phase, methanol and water at the gradient (methanol: 0–60 min, 10%–90%); flow rate, 0.8 mL/min; detection, 254 nm.
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marinedrugs-13-00354-f002: HPLC chromatogram of the crude extract from marine fungus Cladosporium sp. HPLC Conditions: column, Waters XBridge C18, 150 mm × 4.6 mm ID, 5 μm; column temperature, 25 °C; mobile phase, methanol and water at the gradient (methanol: 0–60 min, 10%–90%); flow rate, 0.8 mL/min; detection, 254 nm.

Mentions: As shown in Figure 2, the HPLC chromatogram of the crude sample of Cladosporium sp. showed several compounds where the purities of target compounds 1, 2, and 3 were 12.6%, 20.6%, and 13.3%, respectively, based on HPLC peak area percentage.


Preparative separation of sulfur-containing diketopiperazines from marine fungus Cladosporium sp. using high-speed counter-current chromatography in stepwise elution mode.

Gu B, Zhang Y, Ding L, He S, Wu B, Dong J, Zhu P, Chen J, Zhang J, Yan X - Mar Drugs (2015)

HPLC chromatogram of the crude extract from marine fungus Cladosporium sp. HPLC Conditions: column, Waters XBridge C18, 150 mm × 4.6 mm ID, 5 μm; column temperature, 25 °C; mobile phase, methanol and water at the gradient (methanol: 0–60 min, 10%–90%); flow rate, 0.8 mL/min; detection, 254 nm.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4306941&req=5

marinedrugs-13-00354-f002: HPLC chromatogram of the crude extract from marine fungus Cladosporium sp. HPLC Conditions: column, Waters XBridge C18, 150 mm × 4.6 mm ID, 5 μm; column temperature, 25 °C; mobile phase, methanol and water at the gradient (methanol: 0–60 min, 10%–90%); flow rate, 0.8 mL/min; detection, 254 nm.
Mentions: As shown in Figure 2, the HPLC chromatogram of the crude sample of Cladosporium sp. showed several compounds where the purities of target compounds 1, 2, and 3 were 12.6%, 20.6%, and 13.3%, respectively, based on HPLC peak area percentage.

Bottom Line: 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 Article: PubMed Central - PubMed

Affiliation: School of Marine Sciences, Laboratory of Marine Natural Products, Ningbo University, Ningbo 315211, China. gubin21314@gmail.com.

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.

Show MeSH
Related in: MedlinePlus