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

doi:10.6023/cjoc202205041

有机化学 ›› 2023, Vol. 43 ›› Issue (1): 332-337.DOI: 10.6023/cjoc202205041 上一篇下一篇

研究简报

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)

文章分享

1. 332.pdf(2778KB)

摘要/Abstract

从红树来源真菌Daldinia eschscholtzii HJ004中分离得到3个新化合物以及8个已知化合物. 通过高分辨质谱、一维和二维核磁共振波谱以及X射线单晶衍射数据确定了8-乙基-7-羟基-5-羧基-2,3-二甲基色酮(1)的结构. 通过电子圆二色谱(ECD)量子化学计算以及圆二色谱(CD)数据与文献进行比较, 确定了felinone C (2)和螺旋霉素G (3)的绝对构型. 利用总抗氧化能力检测试剂盒(ABTS快速法)测试了所得11个化合物的自由基清除能力, 其中4个化合物表现出显著的抗氧化活性, IC₅₀值的范围为5.57~195.03 μmol/L, 强于阳性对照水溶性维生素E (trolox)的抗氧化活性(IC₅₀=292.12 μmol/L), 具有开发为抗氧剂的潜力.

关键词: Daldinia eschscholtzii, 色原酮, 内酯类化合物, 抗氧化活性

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

引用此文

王斌, 曾尾女, 李杲钰, 肖媚, 韦方芳, 罗由萍, 钮智刚, 黄国雷, 郑彩娟. 红树来源真菌Daldinia eschscholtzii HJ004发酵产物中三个新的次级代谢产物[J]. 有机化学, 2023, 43(1): 332-337.

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 7

参考文献 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

RichHTML

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

图/表 7

参考文献 23

相关文章 8

编辑推荐

相关统计

本文评价

[1]	赵婷, 农旭华, 王佳莉, 许宽毓, 唐敏敏, 易继凌, 韩长日, 陈光英. 长花龙血树茎中抗氧化活性的木脂素类成分研究[J]. 有机化学, 2023, 43(8): 2968-2972.
[2]	蔡瑾, 农旭华, 王斌, 曾尾女, 黄国雷, 张子怡, 郑彩娟. 红树来源真菌Eupenicillium sp. HJ002发酵产物中三个新的聚酮类化合物[J]. 有机化学, 2021, 41(7): 2905-2909.
[3]	张强健, 王芸芸, 赵雨珣, 马崇慧, 徐徐, 谷文, 杨益琴, 王石发. 樟脑磺酸噻唑腙类化合物的设计、合成及抗氧化应用[J]. 有机化学, 2019, 39(9): 2616-2624.
[4]	吴建章, 李物兰, 陈玲姿, 楚生辉, 赵承光, 卫涛, 杨树林, 李校堃. 查尔酮及其螺杂环衍生物的合成、晶体结构、抗氧化活性研究[J]. 有机化学, 2012, 32(11): 2141-2147.
[5]	傅晓钟, 邢凤晶, 蓝燕宇, 王爱民, 王永林, 李靖, 周雯, 张伟, 刘影. 灯盏乙素苷元4-N-取代氨甲基苯甲酸酯的合成及体外抗氧化活性研究[J]. 有机化学, 2011, 31(07): 1043-1048.
[6]	张培全,曾和平. 5-[2-(8-羟基喹啉-2-基)乙烯基]-2-甲基-8-羟基喹啉的合成、抗氧化活性及促进鼠骨髓间质干细胞增殖的研究[J]. 有机化学, 2008, 28(06): 1035-1039.
[7]	蒋柳云,刘玉明. 两种槲皮素-Zn配合物的抗氧化活性及其结构的量子化学研究[J]. 有机化学, 2005, 25(06): 684-689.
[8]	周应军,李波,梁建宁, 徐绥绪孙启时,郭虹,吴璐, 谭桂山. 槲树叶中的5种酚性成分[J]. 有机化学, 2005, 25(01): 109-112.