海绵来源真菌Aspergillus sp. SCSIO 41018的次级代谢产物及其自由基清除活性研究

doi:10.11978/2024011

Abstract

Abstract:

This paper reported the identification of seven compounds from the rice ferment of Aspergillus sp. fungus SCSIO 41018 isolated from sponge Callyspongia sp. in the Xuwen County, Guangdong Province, China. These compounds were purified by silica gel column chromatography, Sephadex LH-20 gel column chromatography and semi-preparative high performance liquid chromatography. The seven compounds were identified by nuclear magnetic resonance spectroscopy and mass spectrometry to determine their structures, in combination with the reported data, as: cycloechinulin (1), 4-methyl-1H-pyrazole-3-carboxylic acid (2), diorcinol (3), methyl-4-hydroxy-2-(3-hydroxy-5-methylphenoxy)-6-methylbenzoate (4), benzeneacetic acid (5), protocatechuic acid (6), indole-3-carboxaldehyde (7), wherein compound 2 was first isolated from Aspergillus sp. fungi. The free radical scavenging activity was evaluated, and the results showed that compounds 5 and 6 had stronger free radical scavenging ability and antioxidants potential than the positive control ascorbic acid (Vc, vitamin C).

Key words: Aspergillussp., fungus, secondary metabolites, free radical scavenging activity

CLC Number:

Q936

YUAN Yuan, ZHANG Yuanyuan, XU Fuquan, LIU Qingchao, WANG Junfeng. Secondary metabolites from the sponge-derived fungus Aspergillus sp. SCSIO 41018 and their free radical scavenging activity[J].Journal of Tropical Oceanography, 2024, 43(6): 196-200.

Figures/Tables 4

References 14

[1]	金嘉悦, 方淼森, 尹凯波, 等, 2023. OSMAC策略探索海洋真菌次生代谢产物的研究进展[J]. 中国抗生素杂志, 48(5): 481-491.
	JIN JIAYUE, FANG MIAOSEN, YIN KAIBO, et al, 2023. Research progress of secondary metabolites of marine fungi by OSMAC strategy[J]. Chinese Journal of Antibiotics, 48(5): 481-491 (in Chinese with English abstract).
[2]	李骅轩, 崔淑君, 肖朝江, 等, 2019. 厚皮香酚性成分及其镇痛活性[J]. 中成药, 41(7): 1582-1586.
	LI HUAXUAN, CUI SHUJUN, XIAO CHAOJIANG, et al, 2019. Phenolic constituents from Ternstroemia gymnanthera and their analgesic activities[J]. Chinese Traditional Patent Medicine, 41(7): 1582-1586 (in Chinese with English abstract).
[3]	李艳, 巩士磊, 车影, 等, 2015. Fenton反应考察抗坏血酸清除羟基自由基能力及动力学[J]. 应用化学, 32(8): 948-954. doi: 10.11944/j.issn.1000-0518.2015.08.140427
	LI YAN, GONG SHILEI, CHE YING, et al, 2015. Hydroxyl radical scavenging activity and kinetics of vitamin C[J]. Chinese Journal of Applied Chemistry, 32(8): 948-954 (in Chinese with English abstract). doi: 10.11944/j.issn.1000-0518.2015.08.140427
[4]	刘永宏, 杨斌, 董俊德, 2008. 美丽属海绵次生代谢产物及其生物活性[J]. 热带海洋学报, 27(6): 73-80.
	LIU YONGHONG, YANG BIN, DONG JUNDE, 2008. Secondary metabolites and their bioactivities of marine sponge Callyspongia[J]. Journal of Tropical Oceanography, 27(6): 73-80 (in Chinese with English abstract).
[5]	孙彩霞, 唐旭利, 李凯, 等, 2022. 1株海洋来源真菌Aspergillus alabamensis次级代谢产物研究[J]. 中国海洋药物, 41(1): 63-69.
	SUN CAIXIA, TANG XULI, LI KAI, et al, 2022. Study on the secondary metabolites of a marine fungus Aspergillus alabamensis[J]. Chinese Journal of Marine Drugs, 41(1): 63-69 (in Chinese with English abstract).
[6]	杨君泽, 吴小凯, 何山, 2017. 海绵来源真菌天然产物的研究进展[J]. 天然产物研究与开发, 29(4): 695-704.
	YANG JUNZE, WU XIAOKAI, HE SHAN, 2017. Review on natural products from sponge-associated fungi[J]. Natural Product Research and Development, 29(4): 695-704 (in Chinese with English abstract). doi: 10.16333/j.1001-6880.2017.4.027
[7]	张浩, 陈艳, 李晓波, 等, 2022. 荨麻抑制前列腺增生作用物质基础研究[J]. 中国中药杂志, 47(2): 419-427.
	ZHANG HAO, CHEN YAN, LI XIAOBO, et al, 2022. Active constituents of Urtica fissa in inhibition of benign prostatic hyperplasia[J]. China Journal of Chinese Materia Medica, 47(2): 419-427 (in Chinese with English abstract).
[8]	CARROLL A R, COPP B R, DAVIS R A, et al, 2023. Marine natural products[J]. Natural Product Reports, 40(2): 275-325. doi: 10.1039/d2np00083k pmid: 36786022
[9]	DAO D Q, PHAN T T T, NGUYEN T L A, et al, 2020. Insight into antioxidant and photoprotective properties of natural compounds from marine fungus[J]. Journal of Chemical Information and Modeling, 60(3): 1329-1351. doi: 10.1021/acs.jcim.9b00964 pmid: 31999921
[10]	DE GUZMAN F S, GLOER J B, WICKLOW D T, et al, 1992. New diketopiperazine metabolites from the sclerotia of Aspergillus ochraceus[J]. Journal of Natural Products, 55(7): 931-939.
[11]	PARAMESWARAN P S, NAIK C G, HEGDE V R, 1997. Secondary metabolites from the sponge Tedania anhelans: isolation and characterization of two novel pyrazole acids and other metabolites[J]. Journal of Natural Products, 60(8): 802-803.
[12]	RAMADAN M A, AHMAD A S, NAFADY A M, et al, 2009. Chemical composition of the stem bark and leaves of Ficus pandurata hance[J]. Natural Product Research, 23(13): 1218-1230.
[13]	TIAN YONGQI, LIN XIUPING, ZHOU XUEFENG, et al, 2018. Phenol derivatives from the sponge-derived fungus Didymellaceae sp. SCSIO F46[J]. Frontiers in Chemistry, 6: 536.
[14]	YURCHENKO A N, SMETANINA O F, KALINOVSKY A I, et al, 2010. A new meroterpenoid from the marine fungus Aspergillus versicolor (Vuill.) Tirab[J]. Russian Chemical Bulletin, 59(4): 852-856.

化合物	IC₅₀ (μg·mL^-1)
1	1 272.00
2	-
3	108.40
4	448.20
5	4.69
6	10.36
Vc	12.75

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Secondary metabolites from the sponge-derived fungus Aspergillus sp. SCSIO 41018 and their free radical scavenging activity

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