Study on Secondary Metabolites from Fusarium graminearum

doi:10.6023/cjoc202305031

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (11): 4003-4007.DOI: 10.6023/cjoc202305031 Previous Articles Next Articles

禾谷镰刀菌次级代谢产物研究

张炳文^c, 林雨琦^b, 薛彦青^b, 王婧^b, 杨文超^c, 王晓峰^a^,^b^,^*(), 刘文^b^,^*()

a 国科大杭州高等研究院化学与材料科学学院杭州 310024
b 中国科学院上海有机化学研究所生命有机化学国家重点实验室上海 200032
c 华中师范大学化学学院农药与化学生物学教育部重点实验室武汉 430079

收稿日期:2023-05-25 修回日期:2023-06-20 发布日期:2023-06-26
基金资助:
科技部重大专项(2022YFC2303100); 国家自然科学基金(22193070); 国家自然科学基金(32030002); 浙江省博士后科研择优资助项目

Study on Secondary Metabolites from Fusarium graminearum

Bingwen Zhang^c, Yuqi Lin^b, Yanqing Xue^b, Jing Wang^b, Wenchao Yang^c, Xiaofeng Wang^a^,^b(), Wen Liu^b()

a School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024
b State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
c National Key Laboratory of Green Pesticide, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079

Received:2023-05-25 Revised:2023-06-20 Published:2023-06-26
Contact: * E-mail: xfwang@sioc.ac.cn; wliu@sioc.ac.cn
Supported by:
National Key Research and Development Program of China(2022YFC2303100); National Natural Science Foundation of China(22193070); National Natural Science Foundation of China(32030002); Postdoctoral Science Preferential Funding of Zhejiang Province

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Abstract

Fusarium species are able to produce structurally diverse secondary metabolites which exhibit different biological functions. Based on the epigenetic research strategy, the global negative regulator, kmt6 gene, which is related to the expression of the secondary metabolite gene cluster, was knocked out to activate the silent gene. A chemical investigation on the cultures extract of the mutant strain led to the isolation of compounds 1~4. Among them, fusarane B (1) and fusarane C (2) are two new compounds. Furthermore, the antitumor activities of 1~4 were assayed. Compounds 1 and 3 exhibited moderate inhibitory effect on two human cancer cells of Hela and Mia PaCa2. In addition, the biosynthetic pathways of two polyketones 2 and 4 were proposed based on in vivo examination and molecular docking experiment.

Key words: Fusarium graminearum, secondary metabolites, anti-tumor, biosynthesis

Cite this article

Bingwen Zhang, Yuqi Lin, Yanqing Xue, Jing Wang, Wenchao Yang, Xiaofeng Wang, Wen Liu. Study on Secondary Metabolites from Fusarium graminearum[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 4003-4007.

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References 19

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Position	1		2
Position	δ_H mult. (J in Hz)	δ_C, type	δ_H mult. (J in Hz)	δ_C, type
1	—	173.9, C	—	171.9, C
2	2.51 m	33.0, CH₂	—	126.3, C
3	2.51 m	27.3, CH₂	7.26 d (11.5)	139.8, CH
4	—	144.4, C	6.66 dd (15.2, 11.5)	123.9, CH
5	5.98 d (15.9)	133.3, CH	6.17 d (15.2)	145.0, CH
6	5.40 d (15.9, 9.4)	132.0, CH	—	75.7, C
7	1.76 m	49.7, CH	4.14 s	82.3, CH
8	1.77 m	26.4, CH₂	—	140.2, C
	1.49 m
9	2.38 m	42.2, CH₂	6.02 br s	122.6, CH
	2.32 m
10	—	209.6, C	—	126.3, C
11	2.11 s	30.3, CH₃	6.95 q (7.2)	140.4, CH
12	4.93 s	114.2, CH₂	1.68 s (3H)	15.9, CH₃
	4.88 s
13	1.60 m	32.5, CH	1.96 s (3H)	12.6, CH₃
14	0.88 d (6.8)	20.9, CH₃	—	—
15	0.84 d (6.8)	19.4, CH₃	1.43 s (3H)	26.0, CH₃
16	3.68 s (OMe)	51.8, CH₃	1.54 s (3H)	15.7, CH₃
17	—	—	—	167.7, C
18	—	—	3.73 s (3H)	52.1, CH₃

Position	1		2
Position	δ_H mult. (J in Hz)	δ_C, type	δ_H mult. (J in Hz)	δ_C, type
1	—	173.9, C	—	171.9, C
2	2.51 m	33.0, CH₂	—	126.3, C
3	2.51 m	27.3, CH₂	7.26 d (11.5)	139.8, CH
4	—	144.4, C	6.66 dd (15.2, 11.5)	123.9, CH
5	5.98 d (15.9)	133.3, CH	6.17 d (15.2)	145.0, CH
6	5.40 d (15.9, 9.4)	132.0, CH	—	75.7, C
7	1.76 m	49.7, CH	4.14 s	82.3, CH
8	1.77 m	26.4, CH₂	—	140.2, C
	1.49 m
9	2.38 m	42.2, CH₂	6.02 br s	122.6, CH
	2.32 m
10	—	209.6, C	—	126.3, C
11	2.11 s	30.3, CH₃	6.95 q (7.2)	140.4, CH
12	4.93 s	114.2, CH₂	1.68 s (3H)	15.9, CH₃
	4.88 s
13	1.60 m	32.5, CH	1.96 s (3H)	12.6, CH₃
14	0.88 d (6.8)	20.9, CH₃	—	—
15	0.84 d (6.8)	19.4, CH₃	1.43 s (3H)	26.0, CH₃
16	3.68 s (OMe)	51.8, CH₃	1.54 s (3H)	15.7, CH₃
17	—	—	—	167.7, C
18	—	—	3.73 s (3H)	52.1, CH₃

禾谷镰刀菌次级代谢产物研究

Study on Secondary Metabolites from Fusarium graminearum

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