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Open AccessArticle

1H NMR-Based Isolation of Anti-Inflammatory 9,11-Secosteroids from the Octocoral Sinularia leptoclados

1
Research Center for Chinese Herbal Medicine, Graduate Institute of Healthy Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 333324, Taiwan
2
Chinese Herbal Medicine Research Team, Healthy Aging Research Center, Chang Gung University, Taoyuan 333323, Taiwan
3
Department of Cosmetic Science, Providence University, Taichung 433303, Taiwan
4
Department of Nursing, Division of Basic Medical Sciences, Chang Gung University of Science and Technology, Taoyuan 333324, Taiwan
5
Department of Neurology, Chang Gung Memorial Hospital, Taoyuan 333423, Taiwan
6
National Museum of Marine Biology and Aquarium, Pingtung 944401, Taiwan
7
Graduate Institute of Marine Biology, National Dong Hwa University, Pingtung 944401, Taiwan
8
Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404394, Taiwan
9
Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333323, Taiwan
10
Department of Anaesthesiology, Chang Gung Memorial Hospital, Taoyuan 333423, Taiwan
11
Department of Chemical Engineering, Ming Chi University of Technology, New Taipei City 243303, Taiwan
*
Authors to whom correspondence should be addressed.
Mar. Drugs 2020, 18(5), 271; https://doi.org/10.3390/md18050271
Received: 2 May 2020 / Revised: 18 May 2020 / Accepted: 19 May 2020 / Published: 21 May 2020
Octocoral Sinularia leptoclados has been identified as a source of bioactive 9,11-secosteroids. This study adopted a targeted isolation approach to the discovery and analysis of five 9,11-secosteroids, including two novel compounds named sinleptosterols A (1) and B (2) as well as five known analogues (8αH-3β,11-dihydroxy-24-methylene-9,11-secocholest-5-en-9-one (3), 8βH-3β,11-dihydroxy-24-methylene-9,11-secocholest-5-en-9-one (4), leptosterol A (5), (24S)-3β,11-dihydroxy-24-methyl-9,11-secocholest-5-en-9-one (6), and 3β,11-dihydroxy-9,11-secogorgost-5-en-9-one (7)) in terms of 1H-NMR patterns and potency against neutrophilic inflammation. The structure of secosteroids 1 and 2 was deduced from general spectroscopic analysis and an examination of NMR spectra. Among the above-mentioned isolates, compound 4 had the most pronounced effect in inhibiting elastase release and superoxide anion generation, with the IC50 values of 2.96 and 1.63 μM, respectively. View Full-Text
Keywords: Sinularia leptoclados; secosteroids; antineutrophilic inflammation; elastase; superoxide anion Sinularia leptoclados; secosteroids; antineutrophilic inflammation; elastase; superoxide anion
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Chang, Y.-C.; Lai, K.-H.; Kumar, S.; Chen, P.-J.; Wu, Y.-H.; Lai, C.-L.; Hsieh, H.-L.; Sung, P.-J.; Hwang, T.-L. 1H NMR-Based Isolation of Anti-Inflammatory 9,11-Secosteroids from the Octocoral Sinularia leptoclados. Mar. Drugs 2020, 18, 271.

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