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Molecules 2018, 23(2), 348; https://doi.org/10.3390/molecules23020348

Norisoprenoids from the Brown Alga Sargassum naozhouense Tseng et Lu

1
Life Science and Technology School, Lingnan Normal University, Cunjin Road 29, Zhanjiang 524048, China
2
Key Laboratory of Tropical Marine Bio-Resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Xinggang West Road 164, Guangzhou 510301, China
3
Guangdong Provincial Key Laboratory of Food Quality and Safety, College of Food Science, South China Agricultural University, Wushan Road 483, Guangzhou 510642, China
4
University of Chinese Academy of Sciences, Yuquan Road 19(A), Beijing 100049, China
5
South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Xinggang West Road 164, Guangzhou 510301, China
*
Author to whom correspondence should be addressed.
Received: 6 January 2018 / Revised: 31 January 2018 / Accepted: 4 February 2018 / Published: 7 February 2018
(This article belongs to the Section Natural Products Chemistry)
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Abstract

A new C11-norisoprenoid derivative, sargassumone (1), has been isolated from Sargassum naozhouense together with six known norisoprenoids and a highly oxygenated cyclopentene: (2R,6S,8S,9S)-hexahydro-2,9-dihydroxy-4,4,8-trimethyl-6-acetyloxy-3(2H)-benzofuranone (2), (6S,8S,9R)-hexahydro-6,9-dihydroxy-4,4,8-trimethyl-2(2H)-benzofuranone (3), (6S,8S,9R)-hexahydro-6,9-dihydroxy-4,4,8-trimethyl-2(2H)-benzofuranone (4), loliolide (5), (+)-epiloliolide (6), spheciospongones A (7), and (+)-kjellmanianone (8). Compound 1 was identified on the basis of nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis, and the absolute stereochemistry was defined by NOESY spectroscopy, minimizing energy calculation, and circular dichroism (CD) spectra. The known compounds 28, isolated from S. naozhouense for the first time, were identified by comparison of their physical and spectroscopic data with those reported in the literature. Compound 6 was tested for its inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), antioxidant activity with 1,1-diphyl-2-picrylhydrazyl (DPPH) free radicals, and antimicrobial activity against resistant clinical isolates of Candida albicans, methicillin-resistant Staphylococcus aureus (MRSA), and Escherichia coli. View Full-Text
Keywords: brown alga; Sargassum naozhouense; norisoprenoids; cyclopentene brown alga; Sargassum naozhouense; norisoprenoids; cyclopentene
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Peng, Y.; Huang, R.-M.; Lin, X.-P.; Liu, Y.-H. Norisoprenoids from the Brown Alga Sargassum naozhouense Tseng et Lu. Molecules 2018, 23, 348.

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