A New Polyketide from Fusarium graminearum

doi:10.6023/cjoc202303033

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (9): 3319-3322.DOI: 10.6023/cjoc202303033 Previous Articles Next Articles

禾谷镰刀菌中一个新的聚酮类化合物

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

a 中国科学技术大学化学系合肥 230026
b 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
c 国科大杭州高等研究院化学与材料科学学院杭州 310024
d 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

收稿日期:2023-03-22 修回日期:2023-04-25 发布日期:2023-05-05
作者简介:^† 共同第一作者.
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); 浙江省博士后科研项目择优资助项目

A New Polyketide from Fusarium graminearum

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

a Department of Chemistry, University of Science and Technology of China, Hefei 230026
b Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079
c School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024
d State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032

Received:2023-03-22 Revised:2023-04-25 Published:2023-05-05
Contact: * E-mail: xfwang@sioc.ac.cn;wliu@sioc.ac.cn
About author:^† These authors contributed equally to this work.
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

The fungus Fusarium species is well known for producing bioactive natural products with diverse structures. A chemical investigation on the cultures extract of the Fusarium graminearum led to the isolation of one new polyketide, fusarane A (1). Its structure was elucidated on the basis of extensive HRESIMS, 1D and 2D-NMR spectra data analysis, and single-crystal X-ray diffraction. Structurally, compound 1 has a rare conjugated polyene moiety in which configurations of all double bonds were determined to be E. Furthermore, 1 showed potent inhibitory activity against S. aureus ATCC 29213 with the MIC value of 32 μg/mL when assayed in combination with disulfram (10 μg/mL), an established antibiotic adjuvant that augmented the activity of antibiotics.

Key words: Fusarium graminearum, natural product, polyketide, antibacterial activity

Cite this article

Weizhong Ding, Bingwen Zhang, Yanqing Xue, Yuqi Lin, Zhijun Tang, Jing Wang, Wenchao Yang, Xiaofeng Wang, Wen Liu. A New Polyketide from Fusarium graminearum[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3319-3322.

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Fig. & Tab. 5

Figure 1. Chemical structure of compound 1

Figure 2. Key 1H-1H COSY and HMBC correlations of compound 1

Figure 3. Key NOESY correlations of 1

Figure 4. X-ray ORTEP drawing of 1

Compd.	MIC/(μg•mL^–1)
1	>128
Disulfram	>128
Chloramphenicol	6
Compound+Disulfram	32
Compound+Chloramphenicol	128

Table 2. Activities of compound 1 against S. aureus ATCC 29213 in the presence of disulfram (10 μg/mL) or chloramphenicol (4 μg/mL)

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禾谷镰刀菌中一个新的聚酮类化合物

A New Polyketide from Fusarium graminearum

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