New Fusarins from Fusarium graminearum

doi:10.6023/cjoc202106047

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4504-4509.DOI: 10.6023/cjoc202106047 Previous Articles Next Articles

NOTES

禾谷镰刀菌中的新镰刀菌素

林月婷^a, 杨谦^b, 王婉秋^c, 李秋菊^c, 汤志军^b, 唐威华^c, 陶疆^a^,^*(), 刘文^b^,^d^,^*()

a 上海交通大学医学院附属第九人民医院口腔综合科上海交通大学口腔医学院国家口腔医学中心国家口腔疾病临床医学中心上海市口腔医学重点实验室上海 200011
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 中国科学院植物生理生态研究所分子植物科学创新中心上海 200032
d 中国科学院上海有机化学研究所湖州生物制造中心浙江湖州 313000

收稿日期:2021-06-25 修回日期:2021-07-09 发布日期:2021-07-26
通讯作者: 陶疆, 刘文
作者简介:
† 共同第一作者.
基金资助:
国家自然科学基金(81974495); 国家自然科学基金(32030002); 国家自然科学基金(21977109); 国家自然科学基金(21621002); 科技部重大专项(2018YFA090100); 科技部重大专项(2019YFA0905400)

New Fusarins from Fusarium graminearum

Yueting Lin^a, Qian Yang^b, Wanqiu Wang^c, Qiuju Li^c, Zhijun Tang^b, Weihua Tang^c, Jiang Tao^a(), Wen Liu^b^,^d()

a Department of General Dentistry, Shanghai Ninth People's Hospital, Shanghai Jiao Tong University School of Medicine,College of Stomatology, Shanghai Jiao Tong University, National Center for Stomatology; National Clinical Research Center for Oral Diseases; Shanghai Key Laboratory of Stomatology, Shanghai 200011
b State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
c CAS Center for Excellence in Molecular Plant Sciences, Institute of Plant Physiology and Ecology, Chinese Academy of Sciences, Shanghai 200032
d Huzhou Center of Bio-synthetic Innovation, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Huzhou, Zhejiang 313000

Received:2021-06-25 Revised:2021-07-09 Published:2021-07-26
Contact: Jiang Tao, Wen Liu
About author:
† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(81974495); National Natural Science Foundation of China(32030002); National Natural Science Foundation of China(21977109); National Natural Science Foundation of China(21621002); and the National Key Research and Development Program of China(2018YFA090100); and the National Key Research and Development Program of China(2019YFA0905400)

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Abstract

Fusarins as a group of polyketide-nonribosomal peptide hybrid mycotoxins, are produced by the plant pathogenic fungus Fusarium. The building of core framework depends on an unusual iterative type I polyketide synthase (PKS) fused to a non-ribosomal peptide synthetase (NRPS). Two new compounds, fusarins X1 (1) and Y (2), were isolated from Fusarium graminearum. Fusarin X1 (1) possesses a PKS-NRPS hybrid framework, and fusarin Y (2) is a polyketide. It is demonstrate that they are the main and shunt products in fusarins biosynthetic pathway, respectively, by gene inactivation and HRESIMS analyses. These findings not only lay the foundation for understanding of the fusarins biosynthetic logic, but also provide chemical diversity to further explore the concerning infect mechanism.

Key words: Fusarium graminearum, fusarins, biosynthesis, gene knockout

Cite this article

Yueting Lin, Qian Yang, Wanqiu Wang, Qiuju Li, Zhijun Tang, Weihua Tang, Jiang Tao, Wen Liu. New Fusarins from Fusarium graminearum[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4504-4509.

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Fig. & Tab. 6

References 9

[1]	Goswami, R. S.; Kistler, H. C. Mol. Plant Pathol. 2004, 5, 515. doi: 10.1111/j.1364-3703.2004.00252.x
[2]	Cuomo, C. A.; Güldener, U.; Xu, J. R.; Trail, F.; Turgeon, B. G.; Di Pietro, A.; Walton, J. D.; Ma, L. J.; Baker, S. E.; Rep, M.; Adam, G.; Antoniw, J.; Baldwin, T.; Calvo, S.; Chang, Y. L.; Decaprio, D.; Gale, L. R.; Gnerre, S.; Goswami, R. S.; Hammond-Kosack, K.; Harris, L. J.; Hilburn, K.; Kennell, J. C.; Kroken, S.; Magnuson, J. K.; Mannhaupt, G.; Mauceli, E.; Mewes, H. W.; Mitterbauer, R.; Muehlbauer, G.; Münsterkötter, M.; Nelson, D.; O'Donnell, K.; Ouellet, T.; Qi, W.; Quesneville, H.; Roncero, M. I.; Seong, K. Y.; Tetko, I. V.; Urban, M.; Waalwijk, C.; Ward, T. J.; Yao, J.; Birren, B. W.; Kistler, H. C. Science 2007, 317, 1400. doi: 10.1126/science.1143708
[3]	Kimura, M.; Tokai, T.; Takahashi-Ando, N.; Ohsato, S.; Fujimura, M. Biosci., Biotechnol., Biochem. 2007, 71, 2105. doi: 10.1271/bbb.70183
[4]	Kim, Y.-T.; Lee, Y.-R.; Jin, J.; Han, K.-H.; Kim, H.; Kim, J.-C.; Lee, T.; Yun, S.-H.; Lee, Y.-W. Molecular Microbiology. 2005, 58, 1102. doi: 10.1111/j.1365-2958.2005.04884.x
[5]	Wiebe, L. A.; Bjeldanes, L. F. J. Food Sci. 1981, 46, 1424. doi: 10.1111/jfds.1981.46.issue-5
[6]	Niehaus, E.-M.; Kleigrewe, K.; Wiemann, P.; Studt, L.;Sieber, Christian, M. K.; Connolly, Lanelle, R.; Freitag, M.; Güldener, U.; Tudzynski, B.; Humpf, H.-U. Chem. Biol. 2013, 20, 1055. doi: 10.1016/j.chembiol.2013.07.004
[7]	Wang, C.-X.; Chen, G.-D.; Feng, C.-C.; He, R.-R.; Qin, S.-Y.; Hu, D.; Chen, H.-R.; Liu, X.-Z.; Yao, X.-S.; Gao, H. Chem. Commun. 2016, 52, 1250. doi: 10.1039/C5CC07141K
[8]	Yang, Q.; Wang, W.; Lin, Y.; Lin, Y.; Tang, Z.; Wang, J.; Tao, J.; Tang, W.; Liu, W. Org. Biomol. Chem. 2021.
[9]	Adpressa, D. A.; Connolly, L. R.; Konkel, Z. M.; Neuhaus, G. F.; Chang, X. L.; Pierce, B. R.; Smith, K. M.; Freitag, M.; Loesgen, S. Fungal Genet. Biol. 2019, 132, 103256. doi: S1087-1845(19)30236-1 pmid: 31344458

No.	Fusarin X1 (1)			Fusarin Y (2)
No.	δ_H (mult, J/Hz)	δ_C, type		δ_H (mult, J/Hz)	δ_C, type
1	1.74 (dd, 7.2, 1.4)	15.0 s			167.8 s
2	6.85~6.90 (m)	138.8 d	6.88 (br s)		139.7 d
3		130.3 s			140.0 s
4	6.00~6.03 (m)	121.1 d	6.16~6.18 (m)		120.8 d
5		141.0 s			141.4 s
6	4.16 (d, 2.9)	81.9 d	4.65 (s)		80.9 d
7		75.6 s			150.4 s
8	6.67 (d, 15.1)	151.3 d	6.47~6.50 (m)		124.1 d
9	6.85~6.90 (m)	123.7 d	7.53 (dd, 15.5, 11.5)		139.5 d
10	7.58 (dd, 11.1, 1.2)	144.4 d	6.15 (d, 15.5)		131.0 d
11		133.8 s			198.3 s
12		197.6 s	2.25 (s, 3H)		27.3 q
13	4.34 (d, 1.1)	56.6 d	1.88 (d, 1.3)		15.7 q
14	4.24 (d, 1.0)	86.1 d	1.38 (d, 1.3)		13.8 q
15		94.1 s	1.88 (d, 1.3)		13.8 q
16	7.97 (s, NH)		3.68 (s, 3H)		51.9 q
17		169.9 s
18	2.26~2.28 (m, overlap, H-18a); 2.26~2.28 (m, overlap, H-18b)	38.1 t
19	4.03~4.05 (m); 3.93~3.96 (m)	67.7 t
20		167.0 s
21	3.69 (s)	51.0 q
22	1.59 (d, 1.4)	14.8 q
23	1.37 (s)	24.5 q
24	1.91 (d, 1.2)	10.7 q

No.	Fusarin X1 (1)			Fusarin Y (2)
No.	δ_H (mult, J/Hz)	δ_C, type		δ_H (mult, J/Hz)	δ_C, type
1	1.74 (dd, 7.2, 1.4)	15.0 s			167.8 s
2	6.85~6.90 (m)	138.8 d	6.88 (br s)		139.7 d
3		130.3 s			140.0 s
4	6.00~6.03 (m)	121.1 d	6.16~6.18 (m)		120.8 d
5		141.0 s			141.4 s
6	4.16 (d, 2.9)	81.9 d	4.65 (s)		80.9 d
7		75.6 s			150.4 s
8	6.67 (d, 15.1)	151.3 d	6.47~6.50 (m)		124.1 d
9	6.85~6.90 (m)	123.7 d	7.53 (dd, 15.5, 11.5)		139.5 d
10	7.58 (dd, 11.1, 1.2)	144.4 d	6.15 (d, 15.5)		131.0 d
11		133.8 s			198.3 s
12		197.6 s	2.25 (s, 3H)		27.3 q
13	4.34 (d, 1.1)	56.6 d	1.88 (d, 1.3)		15.7 q
14	4.24 (d, 1.0)	86.1 d	1.38 (d, 1.3)		13.8 q
15		94.1 s	1.88 (d, 1.3)		13.8 q
16	7.97 (s, NH)		3.68 (s, 3H)		51.9 q
17		169.9 s
18	2.26~2.28 (m, overlap, H-18a); 2.26~2.28 (m, overlap, H-18b)	38.1 t
19	4.03~4.05 (m); 3.93~3.96 (m)	67.7 t
20		167.0 s
21	3.69 (s)	51.0 q
22	1.59 (d, 1.4)	14.8 q
23	1.37 (s)	24.5 q
24	1.91 (d, 1.2)	10.7 q

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禾谷镰刀菌中的新镰刀菌素

New Fusarins from Fusarium graminearum

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