Three New Secondary Metabolites from the Mangrove-Derived Fungus Daldinia eschscholtzii HJ004

doi:10.6023/cjoc202205041

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (1): 332-337.DOI: 10.6023/cjoc202205041 Previous Articles Next Articles

NOTES

红树来源真菌Daldinia eschscholtzii HJ004发酵产物中三个新的次级代谢产物

王斌^a^,^b, 曾尾女^a^,^b, 李杲钰^a^,^b, 肖媚^a^,^b, 韦方芳^a^,^b, 罗由萍^a^,^b, 钮智刚^a^,^b, 黄国雷^a^,^b, 郑彩娟^a^,^b^,^*()

a 海南师范大学化学与化工学院热带药用资源化学教育部重点实验室海口 571158
b 海南师范大学化学与化工学院海南省热带药用植物化学重点实验室海口 571158

收稿日期:2022-05-23 修回日期:2022-07-11 发布日期:2022-08-25
通讯作者: 郑彩娟
基金资助:
海南省重点研发计划(ZDYF2021SHFZ270); 国家自然科学基金(32160108); 国家自然科学基金(41866005); 海南省自然科学基金(220RC593); 海南省科技攻关计划(ZDKJ202008); 海南省院士创新平台海南省专项(YSPTZX202030)

Three New Secondary Metabolites from the Mangrove-Derived Fungus Daldinia eschscholtzii HJ004

Wang Bin^a^,^b, Zeng Weinv^a^,^b, Li Gaoyu^a^,^b, Xiao Mei^a^,^b, Wei Fangfang^a^,^b, Luo Youping^a^,^b, Niu Zhigang^a^,^b, Huang Guolei^a^,^b, Zheng Caijuan^a^,^b()

a Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158
b Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158

Received:2022-05-23 Revised:2022-07-11 Published:2022-08-25
Contact: Zheng Caijuan
Supported by:
Key Research and Development Program of Hainan Province(ZDYF2021SHFZ270); National Natural Science Foundation of China(32160108); National Natural Science Foundation of China(41866005); Natural Science Foundation of Hainan Province(220RC593); Key Science and Technology Program of Hainan Province(ZDKJ202008); Specific Research Fund of the Innovation Platform for Academicians of Hainan Province(YSPTZX202030)

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Abstract

Three new compounds, together with eight known compounds, were isolated from the mangrove-derived fungus Daldinia eschscholtzii HJ004. The structure of 8-ethyl-7-hydroxy-5-carboxyl-2,3-dimethylchromone (1) was extensively elucidated and characterized by HRESIMS, 1D and 2D NMR, and single-crystal X-ray crystallography. The absolute configurations of felinone C (2) and helicascolide G (3) were determined by using electronic circular dichroism (ECD) method or comparing circular dichroism (CD) data with the literature. The radical scavenging capabilities of the 11 compounds obtained were tested by total antioxidant capacity assay kit with a rapid ABTS method. Among them 4 compounds exhibited stronger antioxidant activity with IC₅₀ values range from 5.57 μmol/L to 195.03 μmol/L, than the positive control trolox (IC₅₀=292.12 μmol/L). These results indicate that chromones have the potential values of developing antioxidants.

Key words: Daldinia eschscholtzii, chromone, lactone, antioxidant activity

Cite this article

Wang Bin, Zeng Weinv, Li Gaoyu, Xiao Mei, Wei Fangfang, Luo Youping, Niu Zhigang, Huang Guolei, Zheng Caijuan. Three New Secondary Metabolites from the Mangrove-Derived Fungus Daldinia eschscholtzii HJ004[J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 332-337.

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References 23

[1]	Chen, S. H.; Cai, R. L.; Liu, Z. M.; Cui, H.; She, Z. G. Nat. Prod. Rep. 2022, 39, 560. doi: 10.1039/D1NP00041A
[2]	Deshmukh, S. K.; Gupta, M. K.; Prakash, V.; Reddy, M. S. J. Fungi 2018, 4, 101. doi: 10.3390/jof4030101
[3]	Li, S. J.; Jiao, F. W.; Li, W.; Zhang, X.; Yan, W.; Jiao, R. H. J. Nat. Prod. 2020, 83, 2976. doi: 10.1021/acs.jnatprod.0c00523
[4]	Carroll, A. R.; Copp, B. R.; Davis, R. A.; Keyzers, R. A.; Prinsep, M. R. Nat. Prod. Rep. 2021, 38, 362. doi: 10.1039/D0NP00089B
[5]	Guo, H. X.; Huang, C. Y.; Yan, Z. Y.; Chen, T.; Hong, K.; Long, Y. H. Chin. J. Nat. Med. 2020, 18, 855.
[6]	Zhang, Y. L.; Zhang, J.; Jiang, N.; Lu, Y. H.; Wang, L.; Xu, S. H.; Wang, W.; Zhang, G. F.; Xu, Q.; Ge, H. M.; Ma, J.; Song, Y. C.; Tan, R. X. J. Am. Chem. Soc. 2011, 133, 5931. doi: 10.1021/ja110932p pmid: 21434637
[7]	Zhang, A. H.; Jiang, N.; Wang, X. Q.; Tan, R. X. Sci. Rep. 2019, 9, 1. doi: 10.1038/s41598-018-37186-2
[8]	Du, L.; King, J. B.; Cichewicz, R. H. J. Nat. Prod. 2014, 77, 2454. doi: 10.1021/np500522z
[9]	Lin, L. P.; Tan, R. X. Chin. J. Chem. 2018, 36, 749. doi: 10.1002/cjoc.201800160
[10]	Qin, X. D.; Dong, Z. J.; Liu, J. K.; Yang, L. M.; Wang, R. R.; Zheng, Y. T.; Lu, Y.; Wu, Y. S.; Zheng, Q. T. Helv. Chim. Acta 2006, 89, 127. doi: 10.1002/hlca.200690004
[11]	Mei, R. Q.; Huang, G. L.; Wang, B.; Bai, M.; Luo, Y. P.; Chen, G. Y.; Zheng, C. J. Chin. J. Org. Chem. 2019, 39, 1479. (in Chinese) doi: 10.6023/cjoc201812008
	(梅荣清, 黄国雷, 王斌, 白猛, 罗由萍, 陈光英, 郑彩娟, 有机化学, 2019, 39, 1479.)
[12]	Bai, M.; Zheng, C. J.; Huang, G. L.; Mei, R. Q.; Wang, B.; Luo, Y. P.; Zheng, C.; Niu, Z. G.; Chen, G. Y. J. Nat. Prod. 2019, 82, 1155. doi: 10.1021/acs.jnatprod.8b00866
[13]	Liao, H. X.; Shao, T. M.; Mei, R. Q.; Huang, G. L.; Zhou, X. M.; Zheng, C. J.; Wang, C. Y. Mar. Drugs 2019, 17, 710. doi: 10.3390/md17120710
[14]	Liao, H. X.; Zheng, C. J.; Huang, G. L.; Mei, R. Q.; Nong, X. H.; Shao, T. M.; Chen, G. Y.; Wang, C. Y. J. Nat. Prod. 2019, 82, 2211. doi: 10.1021/acs.jnatprod.9b00241
[15]	Du, F. Y.; Li, X. M.; Zhang, P.; Li, C. S.; Wang, B. G. Mar. Drugs 2014, 12, 2816. doi: 10.3390/md12052816
[16]	Poch, G. K.; Gloer, J. B. J. Nat. Prod. 1989, 52, 257. pmid: 2746255
[17]	Rao, C. R.; Venkateswarlu, V. Recl. Trav. Chim. Pays-Bas 1956, 75, 1321. doi: 10.1002/recl.19560751113
[18]	Dai, J. Q.; Krohn, K.; Floerke, U.; Draeger, S.; Schulz, B.; Kiss-Szikszai, A.; Antus, S.; Kurtan, T.; Van Ree, T. Eur. J. Org. Chem. 2006, 2006, 3498.
[19]	Yang, W. C.; Chen, Y.; Cai, R. L.; Zou, G.; Wang, B.; She, Z. G. Chem. Biodiversity 2020, 17, e2000192.
[20]	Kato, H.; Li, W.; Koike, M.; Wang, Y. H.; Koike, K. Phytochemistry 2010, 71, 1925. doi: 10.1016/j.phytochem.2010.08.007
[21]	Cao, F.; Yang, Q.; Shao, C. L.; Kong, C. J.; Zheng, J. J.; Liu, Y. F.; Wang, C. Y. Mar. Drugs 2015, 13, 4171. doi: 10.3390/md13074171
[22]	Zhang, P.; Meng, L. H.; Attila, M.; Li, X. M.; Tibor, K.; Wang, B. G. RSC Adv. 2015, 5, 39870. doi: 10.1039/C5RA02203G
[23]	Chen, Y.; Meng, G. L.; Bai, W. L.; Ma, Y.; Xie, L. P.; Altaf, N.; Qian, Y. N.; Han, Y.; Ji, Y. Clin. Exp. Pharmacol. Physiol. 2017, 44, 266. doi: 10.1111/1440-1681.12692

No.	1 (in DMSO-d₆)		2 (in CDCl₃)		3 (in CDCl₃)
No.	δ_H (J in Hz)	δ_C (type)	δ_H (J in Hz)	δ_C (type)	δ_H (J in Hz)	δ_C (type)
1				161.3 (C)		176.9 (C)
2		161.3 (C)	6.48 (s)	102.5 (CH)		44.2 (C)
3		114.9 (C)		128.9 (C)	3.51 (d,1.6)	77.3 (CH)
4		175.8 (C)	7.50 (s)	119.4 (CH)	2.12 (ddq, 1.6, 6.8, 10.8)	34.4 (CH)
4a		111.0 (C)
5		154.8 (C)		135.6 (C)	4.68 (dd, 8.4, 10.8)	82.8 (CH)
6	6.92 (s)	113.0 (CH)	7.23 (d,8.4)	123.2 (CH)	5.44 (ddd, 1.6, 8.4, 15.2)	128.6 (CH)
7		159.0 (C)	7.40 (d,8.4)	111.1 (CH)	5.79 (dq, 6.8, 15.2)	131.9 (CH)
8		117.5 (C)		154.5 (C)	1.73 (dd, 1.6, 6.8)	17.8 (CH₃)
8a		154.8 (C)
9	2.41 (s)	18.1 (CH₃)	3.13~3.21 (m)	36.8 (CH)	1.27 (s)	26.6 (CH₃)
10	1.90 (s)	9.6 (CH₃)	1.37 (d, 6.8)	15.2 (CH₃)	1.33 (s)	22.7 (CH₃)
11		169.6 (C)	3.80~3.89 (m)	66.4 (CH₂)	1.00 (d, 6.8)	14.0 (CH₃)
12	2.75 (q, 7.2)	15.9 (CH₂)	4.74 (s)	65.8 (CH₂)
13	1.11 (t,7.2)	13.3 (CH₃)

No.	1 (in DMSO-d₆)		2 (in CDCl₃)		3 (in CDCl₃)
No.	δ_H (J in Hz)	δ_C (type)	δ_H (J in Hz)	δ_C (type)	δ_H (J in Hz)	δ_C (type)
1				161.3 (C)		176.9 (C)
2		161.3 (C)	6.48 (s)	102.5 (CH)		44.2 (C)
3		114.9 (C)		128.9 (C)	3.51 (d,1.6)	77.3 (CH)
4		175.8 (C)	7.50 (s)	119.4 (CH)	2.12 (ddq, 1.6, 6.8, 10.8)	34.4 (CH)
4a		111.0 (C)
5		154.8 (C)		135.6 (C)	4.68 (dd, 8.4, 10.8)	82.8 (CH)
6	6.92 (s)	113.0 (CH)	7.23 (d,8.4)	123.2 (CH)	5.44 (ddd, 1.6, 8.4, 15.2)	128.6 (CH)
7		159.0 (C)	7.40 (d,8.4)	111.1 (CH)	5.79 (dq, 6.8, 15.2)	131.9 (CH)
8		117.5 (C)		154.5 (C)	1.73 (dd, 1.6, 6.8)	17.8 (CH₃)
8a		154.8 (C)
9	2.41 (s)	18.1 (CH₃)	3.13~3.21 (m)	36.8 (CH)	1.27 (s)	26.6 (CH₃)
10	1.90 (s)	9.6 (CH₃)	1.37 (d, 6.8)	15.2 (CH₃)	1.33 (s)	22.7 (CH₃)
11		169.6 (C)	3.80~3.89 (m)	66.4 (CH₂)	1.00 (d, 6.8)	14.0 (CH₃)
12	2.75 (q, 7.2)	15.9 (CH₂)	4.74 (s)	65.8 (CH₂)
13	1.11 (t,7.2)	13.3 (CH₃)

红树来源真菌Daldinia eschscholtzii HJ004发酵产物中三个新的次级代谢产物

Three New Secondary Metabolites from the Mangrove-Derived Fungus Daldinia eschscholtzii HJ004

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