海洋来源真菌Phellinus sp. HN-22倍半萜类化合物及其抗炎活性研究

doi:10.6023/cjoc202412029

有机化学 ›› 2025, Vol. 45 ›› Issue (8): 3033-3038.DOI: 10.6023/cjoc202412029 上一篇下一篇

研究简报

海洋来源真菌Phellinus sp. HN-22倍半萜类化合物及其抗炎活性研究

小红^a^,^b^,^†, 覃玉月^a^,^b^,^c^,^†, 陈烁^a^,^b, 岑福凌^a^,^b^,^d, 高转生^a^,^b, 黎婉珊^a^,^b^,^*(), 陈光英^a^,^b^,^*()

^a 海南师范大学热带药用资源化学教育部重点实验室海口 571158
^b 海南师范大学化学与化工学院热带药用植物化学海南省重点实验室海口 571158
^c 北部湾大学海洋学院广西北部湾海洋生物多样性养护重点实验室广西钦州 535011
^d 福建中医药大学药学院福州 350122

收稿日期:2024-12-27 修回日期:2025-02-19 发布日期:2025-03-13
作者简介:
†共同第一作者.
基金资助:
国家自然科学基金(22177023); 国家自然科学基金(22477021); 海南省自然科学基金(222QN303); 及海南省研究生创新科研(Qhys2023-332); 及海南省研究生创新科研(202411658005); 及海南省研究生创新科研(202411658013)

Research on Sesquiterpenoids from a Marine-Derived Fungus Phellinus sp. HN-22 and Their Anti-inflammatory Activities

Hong Xiao^a^,^b, Yuyue Qin^a^,^b^,^c, Shuo Chen^a^,^b, Fuling Cen^a^,^b^,^d, Zhuansheng Gao^a^,^b, Wanshan Li^a^,^b^,^*(), Guangying Chen^a^,^b^,^*()

^a Key Laboratory of Tropical Medicinal Resources Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158
^b Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158
^c Guangxi Key Laboratory of Beibu Gulf Marine Biodiversity Conservation, Ocean College, Beibu Gulf University, Qinzhou, Guangxi 535011
^d College of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350122

Received:2024-12-27 Revised:2025-02-19 Published:2025-03-13
Contact: *E-mail:mimowanshan@163.com;chgying123@163.com
About author:
†The authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22177023); National Natural Science Foundation of China(22477021); Hainan Provincial Natural Science Foundation(222QN303); Hainan Provincial Postgraduate Innovation Research Project(Qhys2023-332); Hainan Provincial Postgraduate Innovation Research Project(202411658005); Hainan Provincial Postgraduate Innovation Research Project(202411658013)

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摘要/Abstract

运用硅胶柱色谱、凝胶柱色谱和高效液相色谱等分离技术对一株海洋沉积物来源真菌Phellinus sp. HN-22大米发酵提取物的倍半萜类成分进行研究, 从中发现1个新的倍半萜类化合物(3S,6S,7S,10S)-tremulene-10,12-dihydroxy- 11-ylacetate (1)和7个已知的倍半萜类衍生物[6α-hydroxycinnamolide (2), 6β-hydroxycinnamolide (3), 3β-acetoxycinna- molide (4), Ceriponol D (5), 3β-hydroxycinnamolide (6), 2α,3β-dihydroxycinnamolide (7), 3β,6β-dihydroxycinnamolide (8)]. 新化合物1的结构通过高分辨电喷雾电离质谱(HR-ESI-MS)、核磁共振波谱法(NMR)和量子化学计算方法进行确定. 通过抑制炎症因子(NO)生成的活性测试显示, 化合物3能较好地抑制NO的生成, 其半抑制浓度(IC₅₀)值为(27.78±0.04) μmol/L, 与阳性药物地塞米松(IC₅₀值32.56±0.34 μmol/L)活性相当, 表现出较好的抗炎活性.

关键词: 海洋来源真菌, Tremulane型倍半萜, Drimane型倍半萜, 分离与鉴定, 抗炎活性

The study on sesquiterpenoids from a marine-derived fungus Phellinus sp. HN-22 led to the isolation and purifi- cation of a new sesquiterpene compound, (3S,6S,7S,10S)-tremulene-10,12-dihydroxy-11-ylacetate (1), and seven known sesquiterpenes derivatives, 6α-hydroxycinnamolide (2), 6β-hydroxycinnamolide (3), 3β-acetoxycinnamolide (4), Ceriponol D (5), 3β-hydroxycinnamolide (6), 2α,3β-dihydroxycinnamolide (7), and 3β,6β-dihydroxycinnamolide (8). The structure absolute configuration of the new compound was determined by high resolution electrospray ionization mass spectroscopy (HRESIMS), nuclear magnetic resonance (NMR) and electronic circular dichroism calculations (ECD) methods. Based on inhibiting effects of the production of inflammatory factor NO, compound 3 exhibited similar anti-inflammatory activity with a half maximal inhibitory concentration (IC₅₀) value of (27.78±0.04) μmol/L as that of the positive control, dexamethasone (IC₅₀=(32.56±0.34 μmol/L)).

Key words: marine-derived fungi, tremulane-type sesquiterpenes, drimane-type sesquiterpenes, separation and identification, anti-inflammatory activities

引用此文

小红, 覃玉月, 陈烁, 岑福凌, 高转生, 黎婉珊, 陈光英. 海洋来源真菌Phellinus sp. HN-22倍半萜类化合物及其抗炎活性研究[J]. 有机化学, 2025, 45(8): 3033-3038.

Hong Xiao, Yuyue Qin, Shuo Chen, Fuling Cen, Zhuansheng Gao, Wanshan Li, Guangying Chen. Research on Sesquiterpenoids from a Marine-Derived Fungus Phellinus sp. HN-22 and Their Anti-inflammatory Activities[J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 3033-3038.

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Position	δ_H	δ_C	Position	δ_H	δ_C
1		149.8	10	4.10 (1H, br s)	81.1
2		134.9	11α	4.58 (dd, J=11.6, 1.0 Hz, 1H)	60.6
2		134.9	11β	4.80 (dd, J=11.6, 1.0 Hz, 1H)	60.6
3	2.49~2.55 (m, 1H)	45.1	12α	3.58 (dd, J=10.8, 6.0 Hz, 1H)	69.1
3	2.49~2.55 (m, 1H)	45.1	12β	3.79 (dd, J=10.8, 6.0 Hz, 1H)	69.1
4α	1.66~1.71 (m, 1H)	21.0	13	0.86 (d, J=7.0 Hz, 3H)	13.0
4β	1.76~1.81 (overlapped, 1H)	21.0	13	0.86 (d, J=7.0 Hz, 3H)	13.0
5α	1.58~1.63 (m, 1H)	32.6	14	0.79 (s, 3H)	26.2
5β	1.92~2.01 (m, 1H)	32.6	14	0.79 (s, 3H)	26.2
6	1.76~1.81 (overlapped, 1H)	32.3	15	1.03 (s, 3H)	22.6
7	3.02 (dd, J=11.6, 8.2 Hz, 1H)	47.1	16		173.6
8α	1.72 (dd, J=11.6, 11.6 Hz, 1H)	42.6	17	2.07 (s, 3H)	21.0
8β	1.38 (dd, J=11.6, 8.2 Hz, 1H)
9		41.9

Position	δ_H	δ_C	Position	δ_H	δ_C
1		149.8	10	4.10 (1H, br s)	81.1
2		134.9	11α	4.58 (dd, J=11.6, 1.0 Hz, 1H)	60.6
2		134.9	11β	4.80 (dd, J=11.6, 1.0 Hz, 1H)	60.6
3	2.49~2.55 (m, 1H)	45.1	12α	3.58 (dd, J=10.8, 6.0 Hz, 1H)	69.1
3	2.49~2.55 (m, 1H)	45.1	12β	3.79 (dd, J=10.8, 6.0 Hz, 1H)	69.1
4α	1.66~1.71 (m, 1H)	21.0	13	0.86 (d, J=7.0 Hz, 3H)	13.0
4β	1.76~1.81 (overlapped, 1H)	21.0	13	0.86 (d, J=7.0 Hz, 3H)	13.0
5α	1.58~1.63 (m, 1H)	32.6	14	0.79 (s, 3H)	26.2
5β	1.92~2.01 (m, 1H)	32.6	14	0.79 (s, 3H)	26.2
6	1.76~1.81 (overlapped, 1H)	32.3	15	1.03 (s, 3H)	22.6
7	3.02 (dd, J=11.6, 8.2 Hz, 1H)	47.1	16		173.6
8α	1.72 (dd, J=11.6, 11.6 Hz, 1H)	42.6	17	2.07 (s, 3H)	21.0
8β	1.38 (dd, J=11.6, 8.2 Hz, 1H)
9		41.9

海洋来源真菌Phellinus sp. HN-22倍半萜类化合物及其抗炎活性研究

Research on Sesquiterpenoids from a Marine-Derived Fungus Phellinus sp. HN-22 and Their Anti-inflammatory Activities

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