海洋真菌Phaeosphaeriopsis sp. ZYX-Z-811次生代谢产物研究

doi:10.11978/2023095

Abstract

Abstract:

The secondary metabolites of marine fungus Phaeosporiopsis sp. ZYX-Z-811 were isolated and identified, and their biological activities were evaluated. The compounds were separated and purified by Silica gel, C18, Sephadex LH-20 column chromatography and high performance liquid chromatography (HPLC), ten compounds were separated, and their structures were identified by NMR, IR and UV spectroscopic methods. Ten compounds were identified as 4-epi-lignicol (1), lignicol (2), 6-demethylkigelin (3), 6, 8-dihydroxy-3, 4, 7-trimethylisocoumarin (4), 6, 7-dimethoxymellein (5), musaone A (6), 2-(4-hydroxyphenyl)ethylacetate (7), 3-indole formaldehyde (8), indole-3-acetic acid methyl ester (9), methyl p-hydroxybenzoate (10), among which compound 1 was not published in journal, and the absolute configuration was determined by ECD calculation. These compounds were evaluated for antioxidant activity and α-glucosidase in hibitoryactivity, respectively, compound 10 showed weak antioxidant activities.

Key words: marine-derived fungus, Phaeosphairiopsis sp., secondary metabolites, bioactivity

QUAN Miaomiao, MA Qingyun, YANG Li, XIE Qingyi, DAI Haofu, HAO Yu’e, ZHAO Youxing. Study on the secondary metabolites of marine fungus Phaeospheriopsis sp. ZYX-Z-811[J].Journal of Tropical Oceanography, 2024, 43(2): 121-127.

Figures/Tables 5

Fig.1

Tab. 1

Fig. 2

Fig.3

Tab.2

References 22

[1]	安昶亮, 孔凡栋, 马青云, 等, 2019. 海洋真菌Aspergillus sp. SCS-KFD66的次级代谢产物研究[J]. 中草药, 50(13): 3001-3007.
	AN CHANGLIANG, KONG FANDONG, MA QINGYUN, et al, 2019. Studies on secondary metabolite of marine-derived fungus Aspergillus sp. SCS-KFD66[J]. Chinese Traditional and Herbal Drugs, 50(13): 3001-3007 (in Chinese with English abstract).
[2]	鲍泽安, 2021. 海洋真菌Paraconiothyrium sp. S212B的次级代谢产物和生物活性研究[D]. 咸阳: 西北农林科技大学 (in Chinese).
[3]	蔡健, 梁曼颖, 王健娇, 等, 2021. 长棘海星中含氮类化学成分研究[J]. 中国海洋药物, 40(4): 45-49.
	CAI JIAN, LIANG MANYING, WANG JIANJIAO, et al, 2021. Nitrogenous chemical constituents from Acanthasterplanci[J]. Chinese Journal of Marine Drugs, 40(4): 45-49 (in Chinese with English abstract).
[4]	郭珩, 2019. 深海真菌Diaporthephaseolorum次级代谢产物及其生物活性研究[D]. 广州: 广东药科大学 (in Chinese).
[5]	厉学, 宋少江, 朴淑娟, 等, 2009. 辽宁海绵Aplysinopsis sp.的化学成分研究[J]. 中国海洋药物, 28(4): 21-25.
	LI XUE, SONG SHAOJIANG, PIAO SHUJUAN, et al, 2009. Study on the chemical constituents of marine sponge Aplysinopsis sp.[J]. Chinese Journal of Marine Drugs, 28(4): 21-25 (in Chinese with English abstract).
[6]	娄洁, 李丽梅, 王月德, 等, 2016. 杂色曲霉中的一个具有细胞毒活性的新异香豆素[J]. 中国中药杂志, 41(1): 92-95.
	LOU JIE, LI LIMEI, WANG YUEDE, et al, 2016. A new cytotoxic isocoumarin from endophytic fungus Aspergillus versicolor[J]. China Journal of Chinese Materia Medica, 41(1): 92-95 (in Chinese with English abstract).
[7]	李新爱, 曹钰镁, 巨凤, 等, 2022. 小海马内生菌Fusariumsolani化学成分的研究[J]. 中药与临床, 13(1): 1-5, 31.
	LI XIN’AI, CAO YUMEI, JU FENG, et al, 2022. Study on the chemical constituents of Fusarium solani, an endophytic fungus from Hippocampus japonicas Kaup[J]. Pharmacy and Clinics of Chinese Materia Medica, 13(1): 1-5, 31 (in Chinese with English abstract).
[8]	解飞翔, 袁伟钰, 石佩星, 等, 2019. 竹子内生真菌Fusarium oxysporum次级代谢产物的研究[J]. 安徽农业科学, 47(5): 174-175, 189.
	XIE FEIXIANG, YUAN WEIYU, SHI PEIXING, et al, 2019. Studie on secondary metabolites of endophytic fungus Fusarium oxysporum from bamboo[J]. Journal of Anhui Agricultural Science, 47(5): 174-175, 189 (in Chinese with English abstract).
[9]	王鸿, 冯宇美, 吴祺豪, 等, 2014. 海洋真菌Mucorcircinelloides MNP12010102的次级代谢产物研究[J]. 浙江工业大学学报, 42(5): 487-490.
	WANG HONG, FEN YUMEI, WU QIHAO, et al, 2014. Study on secondary metabolite of marine-derived fungus Mucorcirculalloides MNP12010102[J]. Journal of Zhejiang University of Technology, 42(5): 487-490 (in Chinese with English abstract).
[10]	姚楠, 2014. 海洋芽孢杆菌GS-5次级代谢产物化学成分和生物学活性研究[D]. 杭州: 浙江工商大学 (in Chinese).
[11]	钟晋谦, 2021. 两株真菌Phaeosphaeriopsismusae和Neoroussoella sp. 次级代谢产物研究[D]. 广州: 广东药科大学 (in Chinese).
[12]	甄锦程, 司璐, 于洪佳, 等, 2022. 三株大兴安岭森林凋落物真菌中次生代谢产物及其抗菌活性研究[J]. 天然产物研究与开发, 34(9): 1515-1522.
	ZHEN JINCHENG, SI LU, YU HONGJIA, et al, 2022. Study on the secondary metabolite sand antibacterial activities of three forest litter fungus in the Greater Hinggan Mountains[J]. Natural Product Research and Development, 34(9): 1515-1522 (in Chinese with English abstract).
[13]	ARIEFTA N R, KRISTIANA P, ABOSHI T, et al, 2018. New isocoumarins, naphthoquinones, and a cleistanthane-type diterpene from Nectriapseudotrichia 120-1NP[J]. Fitoterapia, 127: 356-361. doi: 10.1016/j.fitote.2018.03.012
[14]	AYER W A, LU PUPING, ORSZANSKA H, et al, 1993. Deoxyscytalidin and lignicol: new metabolites from Scytalidiumspecies[J]. Journal of Natural Products, 56: 1835-1838. doi: 10.1021/np50100a029
[15]	CARROLL A R, COPPB R, DAVISR A, et al, 2021. Marine natural products[J]. Natural Product Reports, 38(2): 362-413. doi: 10.1039/d0np00089b pmid: 33570537
[16]	CÂMARA M P, RAMALEYA W, CASTLEBURY L A, et al, 2003. Neophaeosphaeria and Phaeosphaeriopsis, segregates of Paraphaeosphaeria[J]. Mycological Research, 107(5): 516-522. doi: 10.1017/S0953756203007731
[17]	CHOUDHARY M I, MUSHARRAF S G, MUKHMOOR T, et al, 2004. Isolation of bioactive compounds from Aspergillus terreus[J]. Zeitschriftfűr Naturforschung, 59(3): 324-328.
[18]	REN ZIMING, YANG LI, MA QINGYUN, et al, 2022. Meroterpenoids and steroids from the marine-derived fungus Trametes sp. ZYX-Z-16[J]. Molecules, 27(24): 8782. doi: 10.3390/molecules27248782
[19]	SHIMADA A, INOKUCHI T, KUSANO M, et al, 2004. 4-Hydroxykigelin and 6-demethylkigelin, root growth promoters, produced by Aspergillus terreus[J]. Zeitschriftfűr Naturforschung C: Journal of Biosciences, 59(3-4): 218-222.
[20]	YANG LI, KONG DEXIAN, XIAO NA, et al, 2022. Antidiabetic lanostane triterpenoids from the fruiting bodies of Ganodermaweberianum[J]. Bioorganic Chemistry, 127: 106025. doi: 10.1016/j.bioorg.2022.106025
[21]	ZHANG XIAOYONG, ZHANG YUN, XU XINYA, et al, 2013. Diverse deep-sea fungi from the South China Sea and their antimicrobial activity[J]. Current Microbiology, 67(5): 525-530. doi: 10.1007/s00284-013-0394-6
[22]	ZHONG JINQIAN, CHEN YNCHAN, LIU ZHAOMING, et al, 2022. Bioactive polyketide derivatives from the endophytic fungus Phaeosphaeriopsismusa[J]. Phytochemistry, 195: 113055. doi: 10.1016/j.phytochem.2021.113055

碳位	化合物1		化合物2
碳位	δ_C	δ_H	δ_C	δ_H
1	169.3		169.0
3	78.1	4.63, qd (J=6.5, 2.0Hz)	80.0	4.45, m
4	65.2	4.34, d (J=2.1Hz)	67.7	4.38, d (J=5.2Hz)
5	138.2		139.8
6	107.4	6.46, s	105.8	6.65, s
7	157.0		158.0
8	134.5		134.4
9	155.6		156.0
10	99.9		99.6
11	15.8	1.35, d (J=6.5Hz)	18.1	1.35, d (J=6.0Hz)
12	59.9	3.71, s	60.3	3.70, s

化合物	清除率/%
4-epi-lignicol	25.2
lignicol	12.7
6-demethylkigelin	16.2
6,8-dihydroxy-3,4,7-trimethylisocoumarin	17.8
6,7-dimethoxymellein	25.8
musaone A	6.9
2-(4-hydroxyphenyl)ethylacetate	25.8
3-吲哚甲醛	18.9
吲哚-3-乙酸甲酯	2.1
对羟基苯甲酸甲酯	50.6
抗坏血酸	96.8

Study on the secondary metabolites of marine fungus Phaeospheriopsis sp. ZYX-Z-811

RichHTML

PDF (PC)

Like

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 5

References 22

Related Articles 11

Metrics

Comments

Recommended 0

[1]	AN Fan, JIANG Yue, WANG Yu, CAO Guangping, GAO Chenghai, LIU Yonghong, YI Xiangxi, BAI Meng. Studies on secondary metabolites of endophytic fungus Aspergillus terreus GXIMD 03158 isolated from mangroves Acanthus ilicifolius L. [J]. Journal of Tropical Oceanography, 2024, 43(5): 41-48.
[2]	LIN Yingting, SUN Ying, HU Jiangnan, DONG Shuai. Study on secondary metabolites of the endophytic fungus Talaromyces sp. XXH006 Isolated from Conus literatus [J]. Journal of Tropical Oceanography, 2024, 43(4): 181-188.
[3]	WANG Jiaxi, LU Humu, QI Xin, GAO Chenghai, LIU Yonghong, LUO Xiaowei. Study on the secondary metabolites from the Weizhou Island coral Acropora austera associated fungus Arachniotus ruber GXIMD 02510 and their antibacterial activity [J]. Journal of Tropical Oceanography, 2024, 43(4): 174-180.
[4]	LIU Ying, XIAO Yang, ZHU Zhenxin, LIU Hongcun, JIANG Mingguo, ZHU Yuzhang, LIN Kun, WU Jincheng, LU Xiaomei, HUANG Xiaoning, LIANG Haina, LU Wensen, YANG Lifang. Study on the Secondary Metabolites of Marine Streptomyces Sporoverrucosus 33510 [J]. Journal of Tropical Oceanography, 2024, 43(2): 128-134.
[5]	FENG Guangfu, HE Jeyi, BAI Meng, YI Xiangxi, LIU Xinming, LUO Lianxiang, GAO Chenghai. Secondary Metabolites from Hydaranth of Coral Goniopora columna in the Beibu Gulf [J]. Journal of Tropical Oceanography, 2024, 43(2): 135-139.
[6]	XING Nannan, REN Runxin, TANG Zhenzhou, LUO Zhihong, XIA Chenxi, LIU Yonghong, PENG Liang, CHEN Xianqiang. Study on the secondary metabolites of fungus Aspergillus sp. GXIMD02003 derived from marine sediment in the Weizhou island [J]. Journal of Tropical Oceanography, 2023, 42(5): 154-160.
[7]	LIANG Hanqiao, CHEN Wenfeng, FAN Yikai, ZHU Zidong, MA Guoxu, CHEN Deli, TIAN Jing. Research progress on the secondary metabolites and activities of endophytic fungi of genus Aspergillus and Trichoderma from mangroves [J]. Journal of Tropical Oceanography, 2023, 42(4): 12-24.
[8]	YE Yuxiu, LUO Xiaowei, YANG Bin, LIN Xiuping, LIU Yonghong, ZHOU Xuefeng. Study on the secondary metabolites of reef habitat algae-derived fungus Pestalotiopsis neglecta SCSIO41403 from the South China Sea [J]. Journal of Tropical Oceanography, 2022, 41(3): 186-190.
[9]	ZHANG Han, TAN Yanhong, YANG Bin, LIU Yonghong, LI Yunqiu. Study on the secondary metabolites from the South China Sea soft coral-derived fungus Acremonium sp. SCSIO41216 [J]. Journal of Tropical Oceanography, 2021, 40(6): 135-139.
[10]	Xiji XIAO,Yun DENG,Lufeng XIE,Qi ZHANG,Xia WEI,Xin YU,Cuixian ZHANG. Research on Sterols from Leptogorgia rigida [J]. Journal of Tropical Oceanography, 2019, 38(4): 64-69.
[11]	Yanhong TAN, Jixing LI, Xiuping LIN, Bin YANG, Yonghong LIU, Yunqiu LI. Study on the secondary metabolites from the South China Sea soft coral-derived fungus Eupenicillium sp. DX-SER3 (KC871024) [J]. Journal of Tropical Oceanography, 2019, 38(2): 43-47.