海洋本草软珊瑚共附生曲霉属真菌EGF7-0-1和EGF15-0-3共培养中甾体类成分研究Ⅱ

doi:10.11978/2022240

热带海洋学报 ›› 2023, Vol. 42 ›› Issue (5): 161-170.doi: 10.11978/2022240CSTR: 32234.14.2022240

海洋本草软珊瑚共附生曲霉属真菌EGF7-0-1和EGF15-0-3共培养中甾体类成分研究Ⅱ

司徒美霞¹(), 雷祖发¹, 杨倩茹², 邓胜毅¹, 吴科键², 陈鸿皓², 韦霞¹^,³, 樊浩¹, 张伟²(), 张翠仙¹()

1. 广州中医药大学, 广东广州 510006
2. 中山大学附属中学, 广东广州 510275
3. 广西医科大学, 广西南宁 530021

收稿日期:2022-11-08 修回日期:2022-12-06 出版日期:2023-09-10 发布日期:2022-12-08
作者简介:
司徒美霞(1997—), 女, 广东省江门市人, 硕士研究生, 从事天然药效物质基础研究。email: 20201120645@stu.gzucm.edu.cn
基金资助:
广东省自然资源厅省级促进经济高质量发展专项资金(海洋经济发展用途)项目(GDNRC[2021]48); 广东省自然资源厅省级促进经济高质量发展专项资金(海洋经济发展用途)项目(GDNRC[2020]039); 国家自然科学基金项目(82273845); 国家自然科学基金项目(81741160); 广州市青少年科技教育项目(KP市2022027)

Research on the steroids from the coculture of soft coral-associated fungi Aspergillus sp. EGF7-0-1 and EGF15-0-3

SITU Meixia¹(), LEI Zufa¹, YANG Qianru², DENG Shengyi¹, WU Kejian², CHEN Honghao², WEI Xia¹^,³, FAN Hao¹, ZHANG Wei²(), ZHANG Cuixian¹()

1. School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
2. The Middle School Attached to Sun Yat-sen University, Guangzhou 510275, China
3. Pharmaceutical college, Guangxi Medicinal University, Nanning 530021, China

Received:2022-11-08 Revised:2022-12-06 Online:2023-09-10 Published:2022-12-08
Supported by:
Special fund of Guangdong Provincial Department of Natural Resources for Promoting High-quality Economic Development (Marine Economic Development)(GDNRC[2021]48); Special fund of Guangdong Provincial Department of Natural Resources for Promoting High-quality Economic Development (Marine Economic Development)(GDNRC[2020]039); National Natural Science Foundation of China(82273845); National Natural Science Foundation of China(81741160); Guangzhou Youth Science and Technology Education Project(KP市2022027)

摘要/Abstract

摘要：

文章模拟微生物自然生长环境, 对两株海洋本草软珊瑚曲霉属真菌Aspergillus sp. EGF7-0-1和Aspergillus sp. EGF15-0-3进行共培养, 以期发现新颖骨架成分。采用硅胶、反相色谱、羟丙基葡聚糖凝胶和高效液相色谱等方法对其次生代谢产物进行分离、纯化; 采用高分辨质谱、核磁共振、旋光及物理常数对照等方法对所分离得到的化合物进行结构鉴定; 采用全球天然产物分子网络(Global Natural Products Social Molecular Networking, GNPS)方法对次生代谢产物进行分析。从两株软珊瑚来源的曲霉属真菌大米共培养中分离得到10个甾体类化合物: Chaxine (1)、Herbarulide (2)、dankasterones A (3)、25-hydroxyergosta-4,6,8(14),22-tetraen3-one (4)、Ganodermasides D (5)、Ergosta-4,6,8(14),22-tetraen-3-one (6)、Ergosta-4,7,22-trien-3-one (7)、Isocyathisterol (8)、Stigmasta-4,22-dien-3-one (9)和β-sitostenone (10)。化合物1~3均为高度氧化重排的甾体类化合物。化合物4、5、7和9首次从曲霉属真菌中分离得到。GNPS分析表明与菌株EGF7-0-1和EGF15-0-3单培养相比, 两株真菌共培养能诱导出更为丰富的甾体类化合物。

关键词: 海洋本草软珊瑚, 共附生曲霉属真菌, 共培养, 甾体

Abstract:

In order to simulate the growth environment of microorganisms to change or increase the production of secondary metabolites in the presence of other microorganisms and protect the ecological environment of marine herbs, soft coral-associated two fungi Aspergillus sp. EGF7-0-1 and EGF15-0-3 were cocultured on rice medium. Firstly, GNPS (Global Natural Products Social Molecular Networking) method was used to analyze secondary metabolites. Then, the secondary metabolites were separated and purified by silica gel, ODS (Octadecylsilyl), Sephadex LH-20 and HPLC (Preparative High Performance Liquid Chromatography). Their structures were identified by HR-ESI-MS (High Resolution Electrospray Ionization Mass Spectroscopy), NMR (Nuclear Magnetic Resonance), ORD (Optical Rotatory Dispersion) and the relative physical constants were compared with the literature. Ten steroids were obtained and identified as Chaxine C (1), Herbarulide (2), dankasterones A (3), 25-hydroxyergosta-4,6,8(14),22-tetraen3-one (4), Ganodermasides D (5), Ergosta-4,6,8(14),22-tetraen-3-one (6), Ergosta-4,7,22-trien-3-one (7), Isocyathisterol (8), Stigmasta-4,22-dien-3-one (9) and β-sitostenone (10). Compounds 1~3 were steroids with oxidative rearrangement and 4, 5, 7 and 9 were firstly acquired from Aspergillus sp. compared with the single culture of EGF7-0-1 and EGF15-0-3. Based on the coculture strategy, the content types of steroids were more abundant.

Key words: soft coral, Aspergillus sp., coculture, steroid

司徒美霞, 雷祖发, 杨倩茹, 邓胜毅, 吴科键, 陈鸿皓, 韦霞, 樊浩, 张伟, 张翠仙. 海洋本草软珊瑚共附生曲霉属真菌EGF7-0-1和EGF15-0-3共培养中甾体类成分研究Ⅱ[J]. 热带海洋学报, 2023, 42(5): 161-170.

SITU Meixia, LEI Zufa, YANG Qianru, DENG Shengyi, WU Kejian, CHEN Honghao, WEI Xia, FAN Hao, ZHANG Wei, ZHANG Cuixian. Research on the steroids from the coculture of soft coral-associated fungi Aspergillus sp. EGF7-0-1 and EGF15-0-3[J]. Journal of Tropical Oceanography, 2023, 42(5): 161-170.

图/表 7

图1

表1

表2

表3

化合物 1~10的 13C NMR数据(100MHz, CDCl3, δC, type)"

No.	1	2	3	4	5	6	7	8	9	10
1	32.1, t	33.9, t	39.0, t	34.1, t	27.6, t	34.3, t	33.2, t	35.2, t	35.7, t	35.7, t
2	24.8, t	33.2, t	34.5, t	34.1, t	34.0, t	34.3, t	34.3, t	33.8, t	34.0, t	32.1, t
3	148.8, d	198.4, s	199.3, s	199.7, s	199.5, s	199.7, t	199.6, s	199.9, s	199.7, s	199.8, s
4	128.1, d	114.7, d	126.7, d	123.2, d	126.4, d	123.1, d	122.8, d	125.3, d	123.8, d	123.7, d
5	195.8, s	173.9, s	156.2, s	124.7, s	161.4, s	124.6, s	169.2, s	163.5, s	171.7, s	171.9, s
6	164.3, d	162.4, s	200.2, s	124.7, d	124.8, d	124.6, d	33.2, t	128.2, d	33.0, t	33.0, t
7	117.5, d	113.3, d	41.0, t	134.1, d	130.9, d	134.2, d	115.7, d	139.4, d	32.0, t	33.9, t
8	156.2, s	159.5, s	62.3, s	164.5, s	126.7, s	164.5, s	139.7, s	71.9, s	35.6, d	35.6, d
9	204.6, s	47.2, d	49.5, d	44.5, d	72.6, s	44.5, d	45.9, d	53.3, d	53.8, d	53.8, d
10	81.2, s	40.4, s	36.1, s	36.9, s	42.4, s	36.9, s	38.2, s	36.3, s	38.6, s	38.7, s
11	39.0, t	25.4, t	25.3, t	19.0, t	25.5, t	19.1, t	22.1, t	18.0, t	21.0, t	21.0, t
12	38.0, t	39.1, t	38.5, t	35.6, t	32.1, t	35.7, t	39.1, t	40.9, t	39.5, t	39.4, t
13	46.5, s	47.0, s	54.1, s	44.2, s	44.6, s	44.1, s	43.5, s	44.2, s	42.3, s	42.5, s
14	57.9, d	58.1, d	215.0, s	155.7, s	158.3, s	156.3, s	55.1, d	57.2, d	56.0, d	56.0, d
15	21.9, t	22.6, t	38.1, t	25.3, t	25.7, t	25.5, t	23.0, t	19.1, t	24.3, t	24.2, t
16	29.1, t	27.7, t	23.3, t	27.7, t	27.8, t	27.9, t	28.2, t	28.2, t	28.9, t	28.2, t
17	55.3, d	56.3, d	49.5, d	55.6, d	55.7, d	55.8, d	55.9, d	56.6, d	55.9, d	55.9, d
18	12.1, q	12.5, q	17.2, q	19.1, q	17.9, q	19.1, q	12.3, s	14.6, q	12.2, q	12.0, s
19	21.9, q	20.0, q	24.2, q	16.8, q	20.9, q	16.8, q	21.4, q	19.0, q	17.4, q	19.0, s
20	40.1, d	40.2, d	37.4, d	39.5, d	39.3, d	39.4, d	40.6, d	39.9, d	40.5, d	36.1, d
21	21.0, q	21.0, q	23.8, q	21.2, q	21.3, q	21.4, q	21.2, q	20.7, q	19.0, q	18.7, q
22	134.6, d	134.7, d	132.5, d	138.4, d	134.9, d	135.2, d	135.6, d	135.4, d	138.1, d	34.0, t
23	132.9, d	132.8, d	135.3, d	129.9, d	132.9, d	132.7, d	132.4, d	132.3, d	129.5, d	29.1, t
24	42.8, d	42.8, d	43.4, d	48.3, d	43.0, d	43.0, d	42.9, d	43.0, d	51.2, d	45.8, d
25	33.0, d	33.1, d	33.2, d	72.5, s	33.2, d	33.2, d	33.0, d	33.2, d	31.9, d	26.1, d
26	19.7, q	20.0, q	19.8, q	27.1, q	19.8, q	20.1, q	20.1, q	19.8, q	21.2, q	17.4, q
27	20.0, q	19.6, q	20.2, q	26.6, q	20.1, q	19.8, q	19.8, q	20.1, q	21.1, q	19.8, q
28	17.6, q	17.6, q	17.1, q	15.8, q	17.8, q	17.8, q	17.7, q	17.8, q	25.4, t	23.1, t
29									12.3, q	12.0, q

表3

图2

图3

图4

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仪器/试剂	型号/规格	品牌
高分辨液质联用仪	Triple TOFTM 5600⁺	美国 AB SCIEX公司
核磁共振波谱仪	400 MHz AVANCE Ⅲ型	德国Bruker公司
高效液相色谱	QuikSep半制备型	北京慧德易科技有限公司
自动旋光仪	MCP 500	安东帕公司
紫外透射反射仪	WFH-201B	上海精科实业有限公司
超净工作台	SW-CJ-1FD	苏州净化设备厂
立式压力蒸汽灭菌器	LS-100H	江阴滨江医疗设备有限公司
电子天平	PWN224ZH	奥豪斯仪器(常州)有限制造公司
旋转蒸发器	XHRE-2000A	上海宵汉实业发展有限公司
低温冷却液循环泵	XHDLSB-5/25	上海宵汉实业发展有限公司
色谱柱a: Luna 分析柱	4.6mm×100mm, 5μm	美国Phenomenex公司
色谱柱b: YMC-Pack ODS-A半制备柱	10mm×250mm, 5μm	日本YMC Co.,Ltd.公司
色谱柱c: H& EC18半制备柱	10mm×250mm, 5μm	北京慧德易科技有限公司
常规柱层析硅胶	200~300目、300~400目	青岛海洋化工厂
Sephadex LH-20	YILIMART 500G	瑞典 cytiva公司
C-18反相色谱填料	YMC*GEL ODS-A-HG	日本 YMC公司
乙酸乙酯、石油醚、甲醇、乙腈、二氯甲烷、三氯甲烷和正丁醇	分析纯	广东光华科技股份有限公司
氘代氯仿	25G	美国剑桥CIT公司
葡萄糖	分析纯	天津致远化学试剂有限公司
技术琼脂粉	分析纯	广东环凯微生物科技有限公司
土豆、大米、海盐		购于市场

No.	1	2	3	4	5
4	6.03, d, 10.1	5.74, s	6.36, s	5.74, s	5.88, s
6				6.04, d, 9.5	6.12, d, 9.6
7	5.64, d, 2.4	5.72, s	2.65, dd, 16.9, 1.5	6.60, d, 9.5	6.49, d, 9.6
9			2.81, t, 9.1
18	0.87, s	0.63, s	0.98, s	0.96, s	0.96, s
19	1.47, s	1.23, s	1.26, s	0.99, s	1.11, s
21	1.02, d, 6.6	1.02, d, 6.6	1.09, d, 7.1	1.08, d, 6.7	1.08, d, 6.7
22	5.14, dd, 15.3, 8.4	5.14, dd, 15.3, 8.4	5.24, dd, 15.2, 6.0	5.34, dd, 15.2, 7.6	5.20, dd, 15.3, 7.9
23	5.26, dd, 15.3, 7.7	5.25, dd, 15.2, 7.6	5.28, d, 15.2, 6.1	5.39, dd, 15.2, 7.8	5.27, dd, 15.3, 7.2
26	0.84, d, 6.8	0.82, d, 6.8	0.81, d, 6.8	1.14, s	0.83, d, 6.8
27	0.82, d, 6.8	0.82, d, 6.8	0.83, d, 6.8	1.17, s	0.85, d, 6.8
28	0.91, d, 6.8	0.91, d, 6.8	0.91, d, 6.8	1.01, d, 6.7	0.93, d, 6.9
No.	6	7	8	9	10
4	5.73, s	5.79, d, 2.0	5.72, s	5.72, s	5.71, s
6	6.03, d, 9.5		6.09, d, 9.6
7	6.61, d, 9.5		6.16, d, 9.6
18	0.96, s	0.60, s	1.02, s	0.73, s	0.70, s
19	0.99, s	1.17, s	1.32, s	1.18, s	1.17, s
21	1.06, d, 6.7	1.03, d, 6.6	0.99, d, 6.6	1.02, d, 6.6	.91, d, 6.5
22	5.26, dd, 15.2,7.1	5.16, dd, 15.2, 7.7	5.12, dd, 15.3, 8.2	5.15, dd, 15.2, 8.5
23	5.20, dd, 15.2,7.8	5.23, dd, 15.2, 6.9	5.22, dd, 15.3, 7.6	5.02, dd, 15.2, 8.5
26	0.83, d, 6.8	0.82, d, 6.5	0.82, d, 6.8	0.84, d, 6.3	0.83, d, 6.8
27	0.85, d, 6.8	0.84, d, 6.5	0.83, d, 6.8	0.79, d, 6.3	0.82, d, 6.8
28	0.93, d, 6.9	0.91, d, 6.5	0.91, d, 6.8
29				0.80, t, 7.3	0.84, t, 7.3

海洋本草软珊瑚共附生曲霉属真菌EGF7-0-1和EGF15-0-3共培养中甾体类成分研究Ⅱ

Research on the steroids from the coculture of soft coral-associated fungi Aspergillus sp. EGF7-0-1 and EGF15-0-3

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