Dysiherbols A-C and Dysideanone E, Cytotoxic and NF-κB Inhibitory Tetracyclic Meroterpenes from a Dysidea sp. Marine Sponge

J Nat Prod. 2016 Feb 26;79(2):406-11. doi: 10.1021/acs.jnatprod.5b01079.

Wei-Hua Jiao ¹, Guo-Hua Shi ¹, Ting-Ting Xu ¹, Guo-Dong Chen ², Bin-Bin Gu ¹, Zhuo Wang ¹, Shuang Peng ¹ ³, Shu-Ping Wang ¹, Jia Li ⁴, Bing-Nan Han ¹, Wei Zhang ³, Hou-Wen Lin ¹

Affiliations

1 Research Center for Marine Drugs, Department of Pharmacy, State Key Laboratory of Oncogenes and Related Genes, Ren Ji Hospital, School of Medicine, Shanghai Jiao Tong University , Shanghai 200127, People's Republic of China.
2 Institute of Traditional Chinese Medicine and Natural Products, Jinan University , Guangzhou 510632, People's Republic of China.
3 Center for Marine Bioproducts Development, Flinders University , Adelaide 5001, Australia.
4 National Center for Drug Screening, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai, 201203, People's Republic of China.

PMID: 26863083 DOI: 10.1021/acs.jnatprod.5b01079

Abstract

Four new tetracyclic meroterpnes, dysiherbols A-C (1-3) and dysideanone E (4), were isolated from a Dysidea sp. marine Sponge collected from the South China Sea. Their complete structures and absolute configurations were unambiguously determined by a combination of NMR spectroscopic data, ECD calculations, and single-crystal X-ray diffraction analysis. Within the sesquiterpene quinol structures, dysiherbols A-C possess an intriguing 6/6/5/6-fused tetracyclic carbon skeleton. The NF-κB inhibitory and cytotoxic activity evaluation disclosed that dysiherbol A (1) showed potent activity with respective IC50 values of 0.49 and 0.58 μM, which were about 10-fold and 20-fold more potent than those of dysiherbols B (2) and C (3), which feature hydroxy and ketone carbonyl groups at the C-3 position.

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