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

Abstract

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

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.

Figures/Tables 6

Fig. 1

Tab. 1

Fig. 2

Tab. 2

Tab. 3

Fig. 3

References 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

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

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