Bioactive Steroids with Structural Diversity from the South China Sea Soft Coral Lobophytum sp. and Sponge Xestospongia sp.

被引:1
作者
Ke, Lin-Mao [1 ]
Zhang, Zi-Ru [1 ,2 ,3 ]
Li, Song-Wei [4 ]
Zeng, Yan-Bo [2 ]
Su, Ming-Zhi [1 ]
Guo, Yue-Wei [1 ,4 ]
机构
[1] Bohai Rim Adv Res Inst Drug Discovery, Shandong Lab Yantai Drug Discovery, Yantai 264117, Peoples R China
[2] Chinese Acad Trop Agr Sci, Inst Trop Biosci & Biotechnol, Hainan Prov Key Lab Funct Components Res & Utiliza, Haikou 571101, Peoples R China
[3] Hebei Agr Univ, Ocean Coll, Qinhuangdao 066000, Peoples R China
[4] Shanghai Univ, Sch Med, Shanghai 200444, Peoples R China
基金
中国国家自然科学基金;
关键词
soft coral; sponge; oxygenated steroids; antibacterial activity; anti-inflammatory activity; DERIVATIVES;
D O I
10.3390/md23010036
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A chemical investigation of the soft coral Lobophytum sp. and the sponge Xestospongia sp. from the South China Sea led to the isolation of five steroids, including two new compounds (1 and 4) and one known natural product (3). Compounds 1-3 were derived from the soft coral Lobophytum sp., while 4 and 5 were obtained from the sponge Xestospongia sp. The structures of these compounds were determined by extensive spectroscopic analysis, the time-dependent density functional theory-electronic circular dichroism (TDDFT-ECD) calculation method, and comparison with the spectral data previously reported in the literature. The antibacterial and anti-inflammatory activities of isolated compounds were evaluated in vitro. Compounds 1-3, 4, and 5 exhibited weak antibacterial activity against vancomycin-resistant Enterococcus faecium G1, Streptococcus parauberis KSP28, Photobacterium damselae FP2244, Lactococcus garvieae FP5245, and Pseudomonas aeruginosa ZJ028. Moreover, compound 3 showed significant anti-inflammatory activity by inhibiting lipopolysaccharide (LPS)-induced NO production in RAW 264.7 cells, with an IC50 value of 13.48 mu M.
引用
收藏
页数:12
相关论文
共 22 条
[1]   Tandem beta-fragmentation hydrogen abstraction reaction of alkoxy radicals in steroidal systems [J].
Boto, A ;
Freire, R ;
Hernandez, R ;
Suarez, E ;
Rodriguez, MS .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (09) :2975-2981
[2]   Cytotoxic steroid derivatives from the Vietnamese soft coral Sinularia brassica [J].
Hong Hanh Thi Tran ;
Phong Nguyen Viet ;
Thanh Nguyen Van ;
Huong Thu Tran ;
Cuong Nguyen Xuan ;
Nam Nguyen Hoai ;
Thung Do Cong ;
Kiem Phan Van ;
Minh Chau Van .
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2017, 19 (12) :1183-1190
[3]   Anti-Inflammatory Polyoxygenated Steroids from the Soft Coral Lobophytum michaelae [J].
Huang, Chiung-Yao ;
Tseng, Wan-Ru ;
Ahmed, Atallah E. ;
Chiang, Pei-Lun ;
Tai, Chi-Jen ;
Hwang, Tsong-Long ;
Dai, Chang-Feng ;
Sheu, Jyh-Horng .
MARINE DRUGS, 2018, 16 (03)
[4]   Recent Progress of Novel Steroid Derivatives and Their Potential Biological Properties [J].
Ke, Shaoyong .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2018, 18 (09) :745-775
[5]   MINOR AND TRACE STEROLS OF MARINE-INVERTEBRATES .25. NOVEL DINOFLAGELLATE 4-ALPHA-METHYLATED STEROLS FROM 4 CARIBBEAN GORGONIANS [J].
KOKKE, WCM ;
BOHLIN, L ;
FENICAL, W ;
DJERASSI, C .
PHYTOCHEMISTRY, 1982, 21 (04) :881-887
[6]   Erectsterates A and B, a pair of novel highly degraded steroid derivatives from the South China Sea soft coral Sinularia erecta [J].
Liu, Jiao ;
Wu, Xin ;
Yang, Min ;
Gu, Yu-Cheng ;
Yao, Li-Gong ;
Huan, Xia-Juan ;
Miao, Ze-Hong ;
Luo, Hui ;
Guo, Yue-Wei .
STEROIDS, 2020, 161
[7]   Steroid and cembranoids from the Dongsha atoll soft coral Lobophytum sarcophytoides [J].
Lu, Yi ;
Lin, You-Cheng ;
Wen, Zhi-Hong ;
Su, Jui-Hsin ;
Sung, Ping-Jyun ;
Hsu, Chi-Hsin ;
Kuo, Yao-Haur ;
Chiang, Michael Y. ;
Dai, Chang-Feng ;
Sheu, Jyh-Horng .
TETRAHEDRON, 2010, 66 (35) :7129-7135
[8]   Good Computational Practice in the Assignment of Absolute Configurations by TDDFT Calculations of ECD Spectra [J].
Pescitelli, Gennaro ;
Bruhn, Torsten .
CHIRALITY, 2016, 28 (06) :466-474
[9]   Antibacterial Activity of Steroids Isolated from the Madagascar Marine Sponge Biemna laboutei: Δ7 Steroids as New Potential Agents Against Pathogenic Bacteria [J].
Ralambondrahety, Rahanira ;
Couzinet-Mossion, Aurelie ;
Rabesaotra, Vony ;
Andriambeloson, Onja ;
Barnathan, Gilles ;
Rakotovao, Marcelle ;
Wielgosz-Collin, Gaetane .
NATURAL PRODUCTS JOURNAL, 2021, 11 (01) :57-62
[10]   A Brief Review on New Naturally Occurring Cembranoid Diterpene Derivatives from the Soft Corals of the Genera Sarcophyton, Sinularia, and Lobophytum Since 2016 [J].
Rodrigues, Inna Glibka ;
Miguel, Maria Graca ;
Mnif, Wissem .
MOLECULES, 2019, 24 (04)