鲸鱼骨来源真菌Penicillium sp. S2014503化学成分及其生物活性研究

doi:10.11978/2022074

热带海洋学报 ›› 2023, Vol. 42 ›› Issue (2): 132-140.doi: 10.11978/2022074CSTR: 32234.14.2022074

鲸鱼骨来源真菌Penicillium sp. S2014503化学成分及其生物活性研究

张海波¹^,²^,³(), IMRAN Khan¹^,², KUMAR Saurav⁴, 张丽萍¹^,³, 方壮杰¹^,², 张鑫雅¹^,², 彭方⁵, 张长生¹^,²^,³

1.热带海洋生物资源与生态重点实验室, 广东省海洋药物重点实验室, 中国科学院南海海洋研究所海洋微生物研究中心, 广东广州 510301
2.中国科学院大学, 北京 100049
3.南方海洋科学与工程广东省实验室(广州), 广东广州 511458
4.海藻生物技术实验室-海藻技术中心, 捷克科学院微生物研究所, 捷克共和国特热邦 37981
5.武汉大学, 中国典型培养物保藏中心, 湖北武汉 430072

收稿日期:2022-04-11 修回日期:2022-05-10 出版日期:2023-03-10 发布日期:2022-05-16
通讯作者: 张海波。email: zhanghb@scsio.ac.cn
作者简介:
张海波(1980—), 男, 研究员, 硕士生导师, 研究方向为海洋微生物天然产物研究。email: zhanghb@scsio.ac.cn
基金资助:
南方海洋科学与工程广东省实验室(广州)重大专项团队项目(GML2019ZD0406); 国家自然科学基金项目(81872778); 国家自然科学基金项目(41911530078); 国家重点研发计划项目(2018YFC1406705); 国家重点研发计划项目(2018YFC1406704)

Bioactive natural compounds from a whale bone-derived fungus Penicillium sp. S2014503

ZHANG Haibo¹^,²^,³(), IMRAN Khan¹^,², KUMAR Saurav⁴, ZHANG Liping¹^,³, FANG Zhuangjie¹^,², ZHANG Xinya¹^,², PENG Fang⁵, ZHANG Changsheng¹^,²^,³

1. 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, Guangzhou 510301, China
2. University of Chinese Academy of Sciences, Beijing 100049, China
3. Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), Guangzhou 511458, China
4. Laboratory of Algal Biotechnology-Centre-Algatech, Institute of Microbiology of the Czech Academy of Sciences, Trebon 37981, Czech Republic
5. Wuhan University, China Center for Type Culture Collection, Wuhan 430072, China

Received:2022-04-11 Revised:2022-05-10 Online:2023-03-10 Published:2022-05-16
Contact: ZHANG Haibo. email: zhanghb@scsio.ac.cn
Supported by:
Key Special Project for Introduced Talents Team of Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou)(GML2019ZD0406); National Natural Science Foundation of China(81872778); National Natural Science Foundation of China(41911530078); National Key R&D Program of China(2018YFC1406705); National Key R&D Program of China(2018YFC1406704)

摘要/Abstract

摘要：

从一块腐烂的鲸鱼骨头分离鉴定了一株真菌Penicillium sp. S2014503。利用大米固体发酵培养技术从该菌产物中获得10个化合物, 通过核磁共振波谱数据比对分析结合质谱数据分析, 手性化合物测定旋光值或者进行X-射线单晶衍射分析后将这10个化合物分别鉴定为emodin (1)、citreorosein (2)、tetrahydro altersolanol B (3)、conioxanthone A (4)、chrysogine (5)、pyramidamycin B (6)、germicidin O (7)、2-(6-hydroxy-5,7-dimethylbenzefuranone-4-yl) acetaldehyde (8)、astrophenone (9)和chenopodolans A (10)。经生物活性测试发现, 化合物1和2对藤黄微球菌具有弱的抑制活性, 化合物1、2和4对卤虫幼虫具有显著的致死毒性。此外, 化合物1是中药大黄和虎杖的主要致泻成分。文章首次报道了来源于海洋动物样品鲸鱼骨的真菌Penicillium sp.能够生产大黄素类等活性天然产物。

关键词: 鲸鱼骨, 青霉菌, 大黄素

Abstract:

Penicillium sp. S2014503 was isolated from a rotten whale bone sample. Constituent analysis and bioactivity evaluation of S2014503 were carried out to find more bioactive compounds from this fungus. Chemical structures of the purified compounds produced by S2014503 were determined by comprehensive analysis of NMR (nuclear magnetic resonance), MS (Mass spectrum) data of each compound. Stereochemistry of chiral compounds were elucidated by comparison of specific rotation value with the reported ones or determined by X-ray diffraction analysis. Ten compounds emodin (1), citreorosein (2), tetrahydro altersolanol B (3), conioxanthone A (4), chrysogine (5), pyramidamycin B (6), germicidin O (7), 2-(6-hydroxy-5,7-dimethylbenzefuranone-4-yl) acetaldehyde (8), astrophenone (9), and chenopodolans A (10) were found in the fermentation product of S2014503 which was cultured on a solid state rice medium. Bioactivities of all the isolated compounds were evaluated for the antibacterial activities and cytotoxicity against brine-shrimp larvae. Compounds 1 and 2 showed weak activity against Gram positive bacteria Micrococcus luteus. Compounds 1, 2 and 4 were significantly cytotoxic against brine-shrimp larvae (Artemia salina) after 6 hours of incubation at room temperature. Interestingly, compound 1 was a well-known laxative ingredient of Traditional Chinese Medicine Rheum officinale and Polygonam cuspidatum. This work is the first report on the emodin analogs from a whale bone derived fungus Penicillium sp.

Key words: Whale bone, Penicillium sp., emodin

张海波, IMRAN Khan, KUMAR Saurav, 张丽萍, 方壮杰, 张鑫雅, 彭方, 张长生. 鲸鱼骨来源真菌Penicillium sp. S2014503化学成分及其生物活性研究[J]. 热带海洋学报, 2023, 42(2): 132-140.

ZHANG Haibo, IMRAN Khan, KUMAR Saurav, ZHANG Liping, FANG Zhuangjie, ZHANG Xinya, PENG Fang, ZHANG Changsheng. Bioactive natural compounds from a whale bone-derived fungus Penicillium sp. S2014503[J]. Journal of Tropical Oceanography, 2023, 42(2): 132-140.

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参考文献 28

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Identification code	Tetrahydroaltersolanol B	Identification code	Tetrahydroaltersolanol B
Empirical formula	C₁₆H₂₀O₆	μ/mm-1	0.971
Formula weight	308.3g·mol^-1	F(000)	756.0
Temperature/K	100.00 (10)	Crystal size/mm³	0.02 × 0.01 × 0.01
Crystal system	monoclinic	Radiation/Å	Cu Kα (λ=1.54184)
Space group	I2	2Θ range for data collection/(°)	4.864 to 148.83
a/Å	7.88690 (10)	Index ranges	-9 ≤ h ≤ 9, -7 ≤ k ≤ 7, -45 ≤ l ≤ 45
b/Å	5.80710 (10)	Reflections collected	16092
c/Å	36.3377 (4)	Independent reflections	3323 [R_int=0.0283, Rs_igma=0.0195]
α/(°)	90	Data/restraints/parameters	3323/1/241
β/(°)	90.0340 (10)	Goodness-of-fit on F²	1.047
γ/(°)	90	Final R indexes [I≥2σ (I)]	R₁ = 0.0247, wR2 = 0.0640
Volume/Å³	1664.27 (4)	Final R indexes [all data]	R₁ = 0.0254, wR2 = 0.0644
Z	4	Largest diff. peak/hole / e Å^-3	0.15/-0.14
ρcalc/(g·cm-3)	1.410	Flack parameter	-0.06 (5)

鲸鱼骨来源真菌Penicillium sp. S2014503化学成分及其生物活性研究

Bioactive natural compounds from a whale bone-derived fungus Penicillium sp. S2014503

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