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Mar. Drugs 2018, 16(11), 402; https://doi.org/10.3390/md16110402

Cytotoxic Tricycloalternarene Compounds from Endophyte Alternaria sp. W-1 Associated with Laminaria japonica

1
Institute of Translational Medicine, Medical College, Yangzhou University, Yangzhou 225001, China
2
Jiangsu Key Laboratory of Integrated Traditional Chinese and Western Medicine for Prevention and Treatment of Senile Diseases, Yangzhou University, Yangzhou 225001, China
3
Jiangsu Co-Innovation Center for Prevention and Control of Important Animal Infectious Diseases and Zoonoses, Yangzhou 225009, China
4
College of Food Science and Engineering, Qingdao Agricultural University, Qingdao 266109, China
5
Jiangsu Co-Innovation Center for Modern Production Technology of Grain Crops/Jiangsu Key Laboratory of Crop Genetics and Physiology, Yangzhou University, Yangzhou 225009, China
*
Authors to whom correspondence should be addressed.
Received: 29 September 2018 / Revised: 17 October 2018 / Accepted: 18 October 2018 / Published: 23 October 2018
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Abstract

The chemical investigation of the culture filtrate of endophyte Alternaria sp. W-1 associated with Laminaria japonica provided a new tricycloalternarene compound, 2H-(2E)-tricycloalternarene 12a (1), together with five known analogs: (2E)-tricycloalternarene 12a (2), tricycloalternarene 3a (3), tricycloalternarene F (4), 15-hydroxyl tricycloalternarene 5b (5), and ACTG-Toxin D (6). In vitro cytotoxicity against the human hepatocellular carcinoma cell line SMMC-7721 and the human gastric carcinoma cell line SGC-7901 was evaluated by the MTT method. Compounds 1, 3, and 4 inhibited the growth of SMMC-7721 cells with IC50 values of 49.7 ± 1.1, 45.8 ± 4.6, and 80.3 ± 3.8 μg/mL, respectively, while the IC50 value of the positive control cisplatin was 6.5 ± 0.5 μg/mL. Compounds 3 and 6 also showed moderate anti-proliferation activity against SGC-7901 cells with IC50 values of 53.2 ± 2.9 and 35.1 ± 0.8 μg/mL, respectively, while the IC50 value of cisplatin was 4.5 ± 0.6 μg/mL. Further studies revealed that the in vitro anticancer activity of compound 3 to SMMC-7721 cells was related to G1 phase cell cycle arrest and cell apoptosis, and the induced apoptosis was involved in both the mitochondrial pathway and the death receptor pathway. This is the first report on the anticancer mechanism of tricycloalternarene compounds. View Full-Text
Keywords: Laminaria japonica; endophyte; Alternaria sp.; tricycloalternarene compound; cytotoxicity Laminaria japonica; endophyte; Alternaria sp.; tricycloalternarene compound; cytotoxicity
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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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Shen, L.; Tian, S.-J.; Song, H.-L.; Chen, X.; Guo, H.; Wan, D.; Wang, Y.-R.; Wang, F.-W.; Liu, L.-J. Cytotoxic Tricycloalternarene Compounds from Endophyte Alternaria sp. W-1 Associated with Laminaria japonica. Mar. Drugs 2018, 16, 402.

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