Two New Shikimic Acid Derivatives from the Flower of Trachycarpus fortunei

doi:10.6023/cjoc202109048

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (4): 1248-1251.DOI: 10.6023/cjoc202109048 Previous Articles Next Articles

NOTES

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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Abstract

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

Cite this article

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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References 13

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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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