棕榈花中两个新的莽草酸类化合物

doi:10.6023/cjoc202109048

有机化学 ›› 2022, Vol. 42 ›› Issue (4): 1248-1251.DOI: 10.6023/cjoc202109048 上一篇下一篇

研究简报

棕榈花中两个新的莽草酸类化合物

林芳霞^a^,^c, 王治鸿^a^,^c, 代德财^b, 周学明^a^,^c^,^*(), 吴禄勇^a^,^c^,^*()

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 海南科技职业大学海南省药食同源植物资源重点实验室海口 571126
c 海南师范大学化学与化工学院热带药用植物化学海南省重点实验室海口 571158

收稿日期:2021-09-29 修回日期:2021-11-22 发布日期:2021-12-22
通讯作者: 周学明, 吴禄勇
作者简介:
† 共同第一作者
基金资助:
海南省自然科学基金(220QN252); 海南省自然科学基金(218QN234)

Two New Shikimic Acid Derivatives from the Flower of Trachycarpus fortunei

Fangxia Lin^a^,^c, Zhihong Wang^a^,^c, Decai Dai^b, Xueming Zhou^a^,^c(), Luyong Wu^a^,^c()

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 Medicinal and Edible Plants Resources of Hainan Province, Hainan Vocational University of Science and Technology, Haikou 571126
c Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158

Received:2021-09-29 Revised:2021-11-22 Published:2021-12-22
Contact: Xueming Zhou, Luyong Wu
About author:
† These authors contributed equally to this work.
Supported by:
Hainan Provincial Natural Science Foundation(220QN252); Hainan Provincial Natural Science Foundation(218QN234)

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摘要/Abstract

从棕榈花中分离鉴定了2个新的莽草酸衍生物以及4个生源相关的莽草酸衍生物. 综合运用多种波谱技术以及化学反应确定了所得化合物的结构. 所有分离得到的化合物均具有α-葡萄糖苷酶抑制活性, 其中trachshikimic B (2), 3-feruloylquinic acid (5)和chlorogenic acid (6)的活性强于阳性对照阿卡波糖.

关键词: 棕榈, 莽草酸衍生物, α-葡萄糖苷酶抑制活性

Two new shikimic acid-derived trachshikimics A and B, together with four known biogenetically related shikimic acid derivatives, were isolated from the flower of Trachycarpus fortunei (Hook.) H. Wendl. Their structures were elucidated using comprehensive spectroscopic methods and chemical reaction. All isolated compounds showed α-glucosidase inhibitory activities, while Trachshikimic B (2), 3-feruloylquinic acid (5) and chlorogenic acid (6) were more active than the positive control acarbose.

Key words: Trachycarpus fortunei, shikimic acid derivative, α-glucosidase inhibitory activity

引用此文

林芳霞, 王治鸿, 代德财, 周学明, 吴禄勇. 棕榈花中两个新的莽草酸类化合物[J]. 有机化学, 2022, 42(4): 1248-1251.

Fangxia Lin, Zhihong Wang, Decai Dai, Xueming Zhou, Luyong Wu. Two New Shikimic Acid Derivatives from the Flower of Trachycarpus fortunei[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1248-1251.

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参考文献 13

[1]	Zhu, X. S.; Tan, G. W. J. Zhongkai Univ. Agric. Eng. 2018, 31, 65. (in Chinese)
	( 朱炫熹, 谭广文, 仲恺农业工程学院学报, 2018, 31, 65.)
[2]	Lin, X. X.; Chen, Z. D. Chin. J. Trop. Crop. 2007, 28, 115. (in Chinese)
	( 林秀香, 陈振东, 热带作物学报, 2007, 28, 115.)
[3]	Zhang, J.; Fan, H. K.; Sun, C. X. Agric. Res. Appl. 2013, (06), 52. (in Chinese)
	( 张军, 范海阔, 孙程旭, 农业研究与应用, 2013, (06), 52.)
[4]	Kuang, X.; Yang, J. Y.; Cai, J.; Liao, Q. Y.; Liao, S.; Zhou, X. M. J. Chin. Med. Mater. 2019, 42, 2557. (in Chinese)
	( 匡鑫, 杨静雨, 蔡瑾, 廖启英, 廖珊, 周学明, 中药材, 2019, 42, 2557.)
[5]	Gui, L. L.; Chen, L.; Dong, J. X. Mil. Med. Sci. 2017, 41, 62. (in Chinese)
	( 桂利利, 陈立, 董俊兴, 军事医学, 2017, 41, 62.)
[6]	Lu, R. M.; Zhang, H. J.; Tan, X. W.; Li, B. Chin. J. Exp. Tradit. Med. Formulae 2011, 17, 97. (in Chinese)
	( 卢汝梅, 张宏建, 谭新武, 李兵, 中国实验方剂学杂志, 2011, 17, 97.)
[7]	Arunagirinathan, G.; Khwaja, N. U. D. Curr. Drug Saf. 2021, 16, 122. doi: 10.2174/1574886315666201217100445 pmid: 33334296
[8]	Eguchi, K.; Komori, T.; Saito, T.; Hoshide, S.; Kario, K. J. Electrocardiol. 2018, 51, 21. doi: S0022-0736(17)30257-1 pmid: 28918212
[9]	Wang, C.; Zhu, L. P.; Yang, J. Z.; Li, C. J.; Zhang, D. M. China J. Chin. Mater. Med. 2010, 35, 714. (in Chinese)
	( 王超, 朱丽萍, 杨敬芝, 李创军, 张东明, 中国中药杂志, 2010, 35, 714.)
[10]	Ulbrich, B.; Zenk, M. H. Phytochemistry 1980, 19, 1625. doi: 10.1016/S0031-9422(00)83782-6
[11]	Van Bragt, J.; Rohrbaugh, L. M.; Wender, S. H. Phytochemistry 1965, 4, 977. doi: 10.1016/S0031-9422(00)86278-0
[12]	Liu, F. L.; Chen, D. J.; Feng, X. L.; Wu, C.; Lin, C. Z.; Zhu, C. C. Tradit. Chin. Drug Res. Clin. Pharmacol. 2016, 27, 242. (in Chinese)
	( 刘方乐, 陈德金, 冯秀丽, 吴冲, 林朝展, 祝晨蔯, 中药新药与临床药理, 2016, 27, 242.)
[13]	Ma, K.; Han, J. J.; Bao, L.; Wei, T. Z.; Liu, H. W. J. Nat. Prod. 2014, 77, 942. doi: 10.1021/np401026b

Position	1 (DMSO-d₆)		2 (DMSO-d₆)
Position	δ_H (J in Hz, 400 MHz)	δ_C (100 MHz)	δ_H (J in Hz, 600 MHz)	δ_C (150 MHz)
1	–	167.5	–	174.9
2	–	128.0	–	73.5
3	6.73 (d, 1.6, 1H)	138.7	2.01 (d, overlap, Hα, 1H) 1.77 (dd, 19.2, 11.4, Hβ, 1H)	37.2
4	4.28 (br s, 1H)	65.5	3.92 (br s, 1H)	68.2
5	3.78 (dd, 6.8, 4.0, 1H)	67.8	3.56 (dd, 9.0, 4.2, 1H)	70.5
6	5.11 (dt, 6.8, 5.2, 1H)	69.9	5.06 (td, 9.0, 7.8, 1H)	70.9
7	2.66 (dd, 18.0, 4.0, Hα, 1H) 2.20 (dd, 18.0, 5.2, Hβ, 1H)	27.7	2.01 (overlap, Hα, 1H) 1.93 (dd, 19.2, 7.8, Hβ, 1H)	36.3
1'	—	166.1	—	165.7
2'	7.53 (d, 16.0, 1H)	114.1	7.47 (d, 16.0, 1H)	114.8
3'	6.30 (d, 16.0, 1H)	145.6	6.20 (d, 16.0, 1H)	145.6
4'	—	128.7	—	128.8
5'	7.06 (d, 2.0, 1H)	106.7	7.09 (d, 2.4, 1H)	106.8
6'	6.81 (d, 8.0, 1H)	148.5	6.81 (d, 8.4, 1H)	148.3
7'	7.02 (dd, 8.0, 2.0, 1H)	149.4	7.03 (dd, 8.4, 2.4, 1H)	149.7
8'	—	108.6	—	108.7
9'	—	124.6	—	125.6
10'	6.02 (s, 2H)	101.5	6.00 (s, 2H)	101.5

Position	1 (DMSO-d₆)		2 (DMSO-d₆)
Position	δ_H (J in Hz, 400 MHz)	δ_C (100 MHz)	δ_H (J in Hz, 600 MHz)	δ_C (150 MHz)
1	–	167.5	–	174.9
2	–	128.0	–	73.5
3	6.73 (d, 1.6, 1H)	138.7	2.01 (d, overlap, Hα, 1H) 1.77 (dd, 19.2, 11.4, Hβ, 1H)	37.2
4	4.28 (br s, 1H)	65.5	3.92 (br s, 1H)	68.2
5	3.78 (dd, 6.8, 4.0, 1H)	67.8	3.56 (dd, 9.0, 4.2, 1H)	70.5
6	5.11 (dt, 6.8, 5.2, 1H)	69.9	5.06 (td, 9.0, 7.8, 1H)	70.9
7	2.66 (dd, 18.0, 4.0, Hα, 1H) 2.20 (dd, 18.0, 5.2, Hβ, 1H)	27.7	2.01 (overlap, Hα, 1H) 1.93 (dd, 19.2, 7.8, Hβ, 1H)	36.3
1'	—	166.1	—	165.7
2'	7.53 (d, 16.0, 1H)	114.1	7.47 (d, 16.0, 1H)	114.8
3'	6.30 (d, 16.0, 1H)	145.6	6.20 (d, 16.0, 1H)	145.6
4'	—	128.7	—	128.8
5'	7.06 (d, 2.0, 1H)	106.7	7.09 (d, 2.4, 1H)	106.8
6'	6.81 (d, 8.0, 1H)	148.5	6.81 (d, 8.4, 1H)	148.3
7'	7.02 (dd, 8.0, 2.0, 1H)	149.4	7.03 (dd, 8.4, 2.4, 1H)	149.7
8'	—	108.6	—	108.7
9'	—	124.6	—	125.6
10'	6.02 (s, 2H)	101.5	6.00 (s, 2H)	101.5

棕榈花中两个新的莽草酸类化合物

Two New Shikimic Acid Derivatives from the Flower of Trachycarpus fortunei

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