中国南海豆荚软珊瑚Lobophytum sp. 的化学成分及其抗菌活性研究

doi:10.11978/2023132

热带海洋学报 ›› 2024, Vol. 43 ›› Issue (4): 189-197.doi: 10.11978/2023132CSTR: 32234.14.2023132

• 海洋资源开发 • 上一篇

中国南海豆荚软珊瑚Lobophytum sp. 的化学成分及其抗菌活性研究

孙曼曼¹^,²^,³(), 曾艳波¹^,³(), 许含²^,⁴, 姚励功², 郭跃伟², 苏明智²()

1.河北农业大学海洋学院, 河北秦皇岛 066000
2.烟台新药创制山东省实验室/中科环渤海(烟台)药物高等研究院, 山东烟台 264117
3.海南省海洋生物资源功能性成分研究与利用重点实验室, 热带生物技术研究所, 中国热带农业科学院, 海南海口 571101
4.烟台大学药学院, 山东烟台 264000

收稿日期:2023-09-04 修回日期:2023-10-05 出版日期:2024-07-10 发布日期:2024-07-22
作者简介:
孙曼曼(1998—), 女, 河南省驻马店市人, 硕士研究生, 从事渔业发展研究。email: mmsun@baridd.ac.cn
基金资助:
国家自然科学基金(81991521); 国家重点研发计划(2022YFC2804100)

Chemical composition and antibacterial activities of the soft coral Lobophytum sp. from the South China Sea

SUN Manman¹^,²^,³(), ZENG Yanbo¹^,³(), XU Han²^,⁴, YAO Ligong², GUO Yuewei², SU Mingzhi²()

1. Ocean College of Hebei Agricultural University, Qinhuangdao 066000, China
2. Shandong Laboratory of Yantai Drug Discovery, Bohai Rim Advanced Research Institute for Drug Discovery, Yantai 264117, China
3. Hainan Provincial Key Laboratory for Functional Components Research and Utilization of Marine Bio-resources, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China
4. School of Pharmcy, Yantai University, Yantai 264000, China

Received:2023-09-04 Revised:2023-10-05 Online:2024-07-10 Published:2024-07-22
Supported by:
National Natural Science Foundation of China(81991521); National Key Research and Development Program of China(2022YFC2804100)

摘要/Abstract

摘要：

对采集自中国南海的豆荚软珊瑚Lobophytum sp.的化学成分及生物活性进行研究。采用硅胶柱色谱、凝胶柱色谱、半制备高效液相色谱等分离手段进行分离纯化, 通过对¹H NMR、¹³C NMR等波谱数据分析并对比相关参考文献数据, 确定了化合物的结构。从豆荚软珊瑚Lobophytum sp.中共分离鉴定了12个化合物, 包括9个二萜类化合物: (+)-(7R, 8R)-epoxy-7, 8-dihydrocembrene C(1)、(1R, 2E, 4R, 7E, 11E)-cembra-2, 7, 11-triene-4-ol(2)、(-)-(2R, 7R, 8R)-sarcophytoxide(3)、entsarcophine(4)、sarcotenusene C(5)、(7S, 8S)-epoxy-1, 3, 11-cembratrien-16-oic methyl ester(6)、sarcophytonin B(7)、sarcoconvolutum D(8)、laevigatol A(9); 3个甾体类化合物: 菜油甾醇(10)、(24S)-24-甲基胆甾醇(11)、柳珊瑚甾醇(12)。化合物8为首次从豆荚软珊瑚Lobophytum sp.中分离得到。化合物3、4、5、7、10对鱼类致病菌美人鱼发光杆菌FP2244、耐土霉素的副乳房链球菌SPOF3K, 以及人类致病菌耐万古霉素屎肠球菌均具有显著的抗菌活性。

关键词: 软珊瑚, Lobophytum sp., 二萜, 甾体, 抗菌活性, 耐药菌

Abstract:

To investigate the chemical composition and biological activity of the soft coral Lobophytum sp. collected from South China Sea. A series of methods such as silica gel column chromatography, thin-layer chromatography, Sephadex LH-20 column chromatography, and semi-preparative high performance liquid chromatography were used to separate and purify. The structure of the compounds was characterized by analysis of NMR data and comparison with the data reported in literature. Twelve compounds were identified from the soft coral Lobophytum sp., including nine diterpenoids: (+)-(7R, 8R)-epoxy-7, 8-dihydrocembrene C(1), (1R, 2E, 4R, 7E, 11E)-cembra-2, 7, 11- triene-4-ol(2), (-)-(2R, 7R, 8R)-sarcophytoxide(3), entsarcophine(4), sarcotenusene C(5), (7S, 8S)-epoxy-1, 3, 11-cembratrien-16-oic methyl ester(6), sarcophytonin B(7), sarcoconvolutum D(8), laevigatol A(9); three steroids: campesterol(10), (24S)-24-methylcholesterol(11), gorgonol(12). Compound 8 was isolated from the soft coral Lobophytum sp. for the first time. The bioassay results revealed that compounds 3, 4, 5, 7 and 10 show significant antibacterial activity against fish pathogens Photobacterium damselae FP2244, oxytetracycline-resistant Streptococcus parauberis SPOF3K, and human pathogen vancomycin-resistant Enterococcus faecium.

Key words: soft coral, Lobophytum sp., diterpenoid, steroid, antibacterial activity, drug-resistance bacteria

孙曼曼, 曾艳波, 许含, 姚励功, 郭跃伟, 苏明智. 中国南海豆荚软珊瑚Lobophytum sp. 的化学成分及其抗菌活性研究[J]. 热带海洋学报, 2024, 43(4): 189-197.

SUN Manman, ZENG Yanbo, XU Han, YAO Ligong, GUO Yuewei, SU Mingzhi. Chemical composition and antibacterial activities of the soft coral Lobophytum sp. from the South China Sea[J]. Journal of Tropical Oceanography, 2024, 43(4): 189-197.

图/表 2

参考文献 22

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菌种	化合物MIC
菌种	3	4	5	7	10	Tetr	Oxy	Lev	Amp	Van
vancomycin-resistant E. faecalis G1	-	-	-	-	38.7	0.09	0.19	>39.78	>37.14	>297
vancomycin-resistant E. faecalis G4	-	-	-	-	38.7	0.19	0.19	>39.78	>37.14	>297
vancomycin-resistant E. faecalis G7	30.2	31.6	33.2	1.5	0.48	0.09	0.09	>39.78	>37.14	18.56
vancomycin-resistant E. faecalis G8	-	-	-	-	38.7	0.09	0.05	39.78	>37.14	74.25
A. salraonicida AS42	-	-	-	-	-	6.11	0.39	0.31	>18.57	NT
E. piscicida TH1	-	-	-	-	-	1.5	0.78	0.62	9.28	>148.5
P. damselae FP2244	30.2	31.6	33.2	30	38.7	0.02	0.02	0.02	0.02	NT
oxytetracycline-resistant S. parauberis SPOF3K	30.2	-	-	30	38.7	>24.05	12.42	1.24	0.58	NT
S. agalactiae WR10	-	-	-	-	-	0.75	0.78	2.49	1.16	<0.2
V. algaelyticus RZ53	-	-	-	-	-	1.5	1.55	0.31	>37.14	18.56

中国南海豆荚软珊瑚Lobophytum sp. 的化学成分及其抗菌活性研究

Chemical composition and antibacterial activities of the soft coral Lobophytum sp. from the South China Sea

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