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. 2013 Dec 2;11(12):4761-72.
doi: 10.3390/md11124761.

Two novel hepatocellular carcinoma cycle inhibitory cyclodepsipeptides from a hydrothermal vent crab-associated fungus Aspergillus clavatus C2WU

Wei Jiang  1 , Panpan Ye, Chen-Tung Arthur Chen, Kuiwu Wang, Pengyuan Liu, Shan He, Xiaodan Wu, Lishe Gan, Ying Ye, Bin Wu
Affiliations

Two novel hepatocellular carcinoma cycle inhibitory cyclodepsipeptides from a hydrothermal vent crab-associated fungus Aspergillus clavatus C2WU

Wei Jiang et al. Mar Drugs. .

Abstract

Two novel cyclodepsipeptides containing an unusual anthranilic acid dimer and a D-phenyllactic acid residues, clavatustides A and B, were identified from cultured mycelia and broth of Aspergillus clavatus C2WU isolated from Xenograpsus testudinatus, which lives at extreme, toxic habitat around the sulphur-rich hydrothermal vents in Taiwan Kueishantao. This is the first example of cyclopeptides containing an anthranilic acid dimer in natural products, and the first report of microbial secondary metabolites from the hydrothermal vent crab. Clavatustides A and B suppressed the proliferation of hepatocellular carcinoma (HCC) cell lines (HepG2, SMMC-7721 and Bel-7402) in a dose-dependent manner, and induced an accumulation of HepG2 cells in G1 phase and reduction of cells in S phase.

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Figures

Chart 1
Chart 1
Structures of compounds 1 and 2.
Figure 1
Figure 1
Key 1H 1H COSY and HMBC correlations of compound 1.
Figure 2
Figure 2
CID illustration of compound 1.
Figure 3
Figure 3
The suppression of cell proliferation of clavatustide A (A) and clavatustide B (B) in a dose-dependent manner.
Figure 4
Figure 4
The suppression of cell proliferation of clavatustide A and clavatustide B in L02 (A) and HepG2 (B) was in a time dependent manner. * P < 0.05 if treatment group vs. control group. L02, liver cells; HepG2, SMMC-7721 and Bel-7402, human hepatocellular carcinoma (HCC) cell lines.
Figure 5
Figure 5
The comparison of cell cycle (A), cell migration (B) and invasion (C) between HepG2 cells treated with clavatustide A/clavatustide B and the blank control. A: Clavatustide A/clavatustide B treated cells showed significantly accumulation in G1 phase and reduction of cells in S phase, compared with control group (P < 0.05). B and C: The counted migrated/invaded cell numbers did not differ significantly between treated groups and control group.
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