海洋本草软珊瑚共附生真菌Aspergillus sp. EGF7-0-1中酚酸类化学成分研究(Ⅱ)

doi:10.11978/2022241

热带海洋学报 ›› 2023, Vol. 42 ›› Issue (5): 171-177.doi: 10.11978/2022241CSTR: 32234.14.2022241

海洋本草软珊瑚共附生真菌Aspergillus sp. EGF7-0-1中酚酸类化学成分研究(Ⅱ)

樊浩¹(), 何嘉鸿¹, 韦霞², 陈乐怡¹, 陈欣琪¹, 张翠仙¹()

1. 广州中医药大学中药学院, 广东广州 510006
2. 广西医科大学药学院, 广西南宁 530021

收稿日期:2022-11-09 修回日期:2022-11-29 出版日期:2023-09-10 发布日期:2022-12-06
作者简介:
樊浩(1994—), 男, 陕西省西安市人, 博士研究生, 研究方向为天然药物化学。email: 20212110040@stu.gzucm.edu.cn
基金资助:
广东省自然资源厅专项(GDNRC[2021]048); 广东省自然资源厅专项(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); 广东省大学生创新创业项目(S202010572122)

Phenolic acids from soft coral-associated symbiotic and epiphytic fungi Aspergillus sp. EGF7-0-1 (Ⅱ)

FAN Hao¹(), HE Jiahong¹, WEI Xia², CHEN Leyi¹, CHEN Xinqi¹, ZHANG Cuixain¹()

1. School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
2. Pharmaceutical college, Guangxi Medicinal University, Nanning 530021, China

Received:2022-11-09 Revised:2022-11-29 Online:2023-09-10 Published:2022-12-06
Supported by:
Special fund of Guangdong Provincial Department of Natural Resources(GDNRC[2021]048); Special fund of Guangdong Provincial Department of Natural Resources(GDNRC[2020]039); National Natural Science Foundation of China(82273845); National Natural Science Foundation of China(81741160); Innovation and Entrepreneurship Program for College Students in Guangdong Province(S202010572122)

摘要/Abstract

摘要：

为寻找海洋来源结构新颖的次生代谢产物, 采用大米培养基对海洋本草软珊瑚(Sinularia sp.)共附生真菌Aspergillus sp. EGF7-0-1进行规模发酵, 利用高效液相色谱等多种柱色谱技术对其乙酸乙酯提取物进行分离纯化; 采用核磁共振波谱、高分辨质谱、旋光光谱等现代光谱学方法, 并结合文献数据比对等对其进行结构鉴定, 获得10个简单芳香酚酸化合物, 分别为4-hydroxy-3-(3'-methyl-2'-butenyl) phenylacetic acid (1)、asperulosin C (2)、对羟基苯乙酸(3)、对羟基苯乙酸甲酯(4)、4-hydroxy-3-prenyl-benzoic acid (5)、4-hydroxy-3-(3-methylbut-2-enyl) benzaldehyde (6)、对羟基苯甲醛(7)、对羟基苯甲酸甲酯(8)、间羟基苯乙酸(9)和2,2'-oxybis(1,4)-ditert-butylbenzene (10), 其中化合物1是新发现的天然产物。抗肿瘤活性研究表明, 化合物1~10对人结肠癌细胞、人乳腺癌细胞、人肝癌细胞、小鼠肝癌细胞、小鼠乳腺癌细胞、小鼠黑色素瘤细胞和小鼠皮肤黑色素瘤细胞等肿瘤细胞均无活性。

关键词: 海洋本草软珊瑚, Aspergillus sp. EGF7-0-1, 酚酸类, 新天然产物, 结构鉴定

Abstract:

In order to discover the novel and bioactive secondary metabolites, the soft coral-associated (Sinularia sp.) symbiotic and epiphytic fungi Aspergillus sp. EGF7-0-1 was fermented by using rice medium. The metabolites were isolated by the chromatography technology and high performance liquid chromatography (HPLC). Ten phenolic acids compounds were obtained. According to the 1D and 2D nuclear magnetic resonance (NMR), high resolution electrospray ionization mass spectroscopy (HR-ESI-MS), optical rotatory dispersion (ORD), and comparison with the literature, their structures were determined as 4-hydroxy-3-(3'-methyl-2'-butenyl) phenylacetic acid (1), asperulosin C (2), 4-hydroxyphenylacetic acid (3), methyl 4-hydroxyphenylacetate (4), 4-hydroxy-3-prenyl-benzoic acid (5), 4-hydroxy-3-(3-methylbut-2-enyl) benzaldehyde (6), p-Hydroxybenzaldehyde (7), methyl 4-hydroxybenzoate (8), 3-hydroxyphenylacetic acid (9) and 2,2'-oxybis(1,4)-ditert-butylbenzene (10). Among them, compound 1 was a new natural product. Antitumor activity studies showed that compounds 1~10 were not active against HCT116, MCF7, Huh 7, Hepa 1-6, 4T1, B16 and F10 tumor cells.

Key words: traditional marine Chinese medicine soft coral, Aspergillus sp. EGF7-0-1, phenolic acids, new natural product, identification

樊浩, 何嘉鸿, 韦霞, 陈乐怡, 陈欣琪, 张翠仙. 海洋本草软珊瑚共附生真菌Aspergillus sp. EGF7-0-1中酚酸类化学成分研究(Ⅱ)[J]. 热带海洋学报, 2023, 42(5): 171-177.

FAN Hao, HE Jiahong, WEI Xia, CHEN Leyi, CHEN Xinqi, ZHANG Cuixain. Phenolic acids from soft coral-associated symbiotic and epiphytic fungi Aspergillus sp. EGF7-0-1 (Ⅱ)[J]. Journal of Tropical Oceanography, 2023, 42(5): 171-177.

图/表 6

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参考文献 15

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仪器/试剂	型号/规格	品牌
核磁共振波谱仪	400MHz AVANCE Ⅲ型	德国 Bruker公司
高分辨液质联用仪	Triple TOF^TM 5600⁺	美国 AB SCIEX公司
高效液相色谱	QuikSep半制备型	北京慧德易科技有限公司
旋转蒸发器	XHRE-2000A	上海霄汉实业发展有限公司
低温冷却液循环泵	DLSB-5/20	上海霄汉实业发展有限公司
单人单面超净工作台	SW-CJ-1FD	苏州净化设备厂
高压蒸汽灭菌器	LX-B75L型	合肥华泰医疗设备有限公司
Kromasil C18半制备柱	10mm×250mm, 5μm	瑞典Akzo Nobel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 500 G	瑞典cytiva公司
乙酸乙酯、甲醇、等常规试剂	分析纯	广东光华科技股份有限公司
氘代甲醇	25 G	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
海盐、大米、土豆		市场采购
荧光多功能酶标仪		美国Beckman Coulter公司 DTX 880
噻唑蓝粉末		美国Amresco公司
RPMI-1640培养基		美国Gibco公司
DMEM 培养基		武汉普诺赛生命科技有限公司
0.25%胰蛋白酶		美国Gibco公司
胎牛血清		上海依科赛生物制品有限公司
青-链霉素		美国Hyclone公司

No.	1		2		3		4		5
No.	δ_H, 裂分 (偶合常数)	δ_C, 类型	δ_H, 裂分 (偶合常数)	δ_C, 类型	δ_H, 裂分 (偶合常数)	δ_C, 类型	δ_H, 裂分 (偶合常数)	δ_C, 类型	δ_H, 裂分 (偶合常数)	δ_C, 类型
1		126.9, C		126.2, C		129.0, C		126.3, C			123.6, C
2	6.56, m	132.9, CH	6.92, m	131.3, CH	7.10, d (8.0)	131.3, CH	7.07, d (8.1)	131.3, CH	7.76, m		132.5, CH
3		129.2, C		129.3, C	6.70, d (8.0)	116.0, CH	6.72, d (8.1)	116.3, CH			129.0, C
4		155.0, C		155.2, C		156.9, C		157.5, C			160.2, C
5	6.66, dd (8.2, 2.4)	115.7, CH	6.88, dd (8.4, 2.5)	115.9, CH	6.70, d (8.0)	116.0, CH	6.72, d (8.1)	116.3, CH	7.69, dd (8.6, 2.0)		115.2, CH
6	6.67, d (8.2)	131.3, CH	6.68, d (8.4)	131.1, CH	7.10, d (8.0)	131.3, CH	7.07, d (8.1)	131.3, CH	6.76, d (8.6)		130.3, CH
7	3.49, m	41.6, CH₂	3.49, m	41.1, CH₂	3.69, s	40.1, CH₂	3.52, s	40.9, CH₂			169.3, C
8		176.8, C		177.2, C		175.7, C		174.6, C
9			3.78, s	52.4, CH			3.65, s	52.4, q
1'	3.07, d (3.3)	29.2, CH₂	3.27, d (7.43)	29.2, CH₂					3.30, d (1.6)		29.1, CH₂
2'	5.07, m	124.0, CH	5.30, m	123.9, CH					5.32, m		123.5, CH
3'		132.9, C		133.1, C							133.4, C
4'		17.8, CH₃		17.8, CH₃							17.8, CH₃
5'		25.9, CH₃		25.9, CH₃							26.0, CH₃

No.	6		7		8		9
No.	δ_H, 裂分(偶合常数)	δ_C, 类型	δ_H, 裂分(偶合常数)	δ_C, 类型	δ_H, 裂分(偶合常数)	δ_C, 类型	δ_H, 裂分(偶合常数)	δ_C, 类型
1		122.9, C		128.9, C		123.9, C	6.69, d (8.0)	123.1, CH
2	7.63, m	132.3, CH	7.71, d (8.1)	132.3, CH	7.56, d (8.2)	131.3, CH		132.1, C
3		130.1, C	6.89, d (8.1)	116.0, CH	6.66, d (8.2)	115.9, CH	7.02, d (8.5)	116.1, CH
4		163.3, C		164.3, C		162.7, C		156.8, C
5	7.59, dd (8.1, 2.1)	116.0, CH	6.89, d (8.1)	116.0, CH	6.66, d (8.2)	115.9, CH	6.72, m	114.7, CH
6	6.89, d (8.1)	130.5, CH	7.71, d (8.1)	132.3, CH	7.56, d (8.2)	131.3, CH	7.02, d (8.5)	129.2, CH
7	9.72, s	193.1, CH	9.98, s	191.1, CH		165.8, C	3.51, s	37.9, CH₂
8					3.79, s	52.7, CH₃		176.2, C
9
1'	3.34, s	28.9, CH₂
2'	5.34, m	123.0, CH
3'		134.0, C
4'		17.8, CH₃
5'		25.9, CH₃

海洋本草软珊瑚共附生真菌Aspergillus sp. EGF7-0-1中酚酸类化学成分研究(Ⅱ)

Phenolic acids from soft coral-associated symbiotic and epiphytic fungi Aspergillus sp. EGF7-0-1 (Ⅱ)

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