Three New Phenolic Derivatives from the Fruits of Rubus idaeus Linnaeus and Their Anti-inflammatory Activity

doi:10.6023/cjoc202409022

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (7): 2620-2624.DOI: 10.6023/cjoc202409022 Previous Articles Next Articles

覆盆子果实中三个新的酚类衍生物及其抗炎活性

张玉^a^,^b^,^*(), 徐雪峰^a^,^b, 闫浩^a^,^b, 代德财^a^,^b

^a 海南科技职业大学化学与材料工程学院海口 571126
^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

收稿日期:2024-10-31 修回日期:2024-11-21 发布日期:2024-12-26
基金资助:
海南科技职业大学科学研究(HKD20220418)

Three New Phenolic Derivatives from the Fruits of Rubus idaeus Linnaeus and Their Anti-inflammatory Activity

Yu Zhang^a^,^b^,^*(), Xuefeng Xu^a^,^b, Hao Yan^a^,^b, Decai Dai^a^,^b

^a College of Chemical and Material Engineering, Hainan Vocational University of Science and Technology, Haikou 571126
^b Key Laboratory of Medicinal and Edible Plants Resources of Hainan Province, Hainan Vocational University of Science and Technology, Haikou 571126

Received:2024-10-31 Revised:2024-11-21 Published:2024-12-26
Contact: *E-mail: 938463421@qq.com
Supported by:
Hainan Vocational University of Science and Technology Scientific Research Project(HKD20220418)

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Abstract

Silica gel column chromatography (CC), Sephadex LH-20 CC and high performance liquid chromatography (HPLC) were used to study the chemical constituents of the fruits of the medicine-food plant Rubus idaeus Linnaeus. A new tetrahydrogenated naphthol syringic acid ester, named rubusnolicester (1), two new phenolic glycoside derivatives, 4-chloro- 2,6-dimethoxylphenol-1-O-β-D-glucopyranoside (2) and salicylic acid-2-O-(6'-O-acetyl)-β-D-glucopyranoside (3), together with one known salicylic acid glycoside derivative (4) and three known flavonoids derivatives (5~7), were isolated. Their structures were elucidated by HRESI-MS, NMR spectroscopy, and a comparison of optical rotation (OR). Compounds 1~7 were evaluated the inhibitory activities against the nitric oxide (NO) production induced by lipopolysaccharide (LPS) in mouse macrophage RAW264.7 cells in vitro. Compound 1 exhibited inhibitory effect with the IC₅₀ value of (12.28±1.25) μmol/L.

Key words: Rubus, Rubus idaeus, phenolic glycoside, anti-inflammatory

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Yu Zhang, Xuefeng Xu, Hao Yan, Decai Dai. Three New Phenolic Derivatives from the Fruits of Rubus idaeus Linnaeus and Their Anti-inflammatory Activity[J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2620-2624.

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References 16

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Position	1 (CD₃OD)		2 (CD₃OD)		3 (DMSO-d₆)
Position	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C
1	2.94 (dd, 15.6, 5.2, H-1a) 2.59 (dd, 15.6, 8.4, H-1b)	38.4	—	137.8	—	122.0
2	3.97~4.05 (m)	76.0	—	154.8	—	155.7
3	1.98~2.04 (m, H-3a) 1.67~1.75 (m, H-3b)	32.6	7.01 (s)	103.3	7.17 (d, 8.4)	116.8
4	2.82~2.88 (m, H-4a) 2.70~2.78 (m, H-4b)	28.5	—	128.2	7.48 (dd, 8.4, 7.6)	133.7
5	—	137.9	7.01 (s)	103.3	7.05 (dd, 7.6, 7.6)	122.3
6	6.50 (d, 2.4)	115.6	—	154.8	7.59 (d, 7.6)	130.8
7	—	156.3			—	167.6
8	6.54 (dd, 8.4, 2.4)	114.3
9	6.86 (d, 8.4)	131.1
10	—	127.4
1'	—	126.6	4.67 (d, 7.2)	106.2	4.91 (d, 6.0)	101.1
2'	7.34 (s)	108.3	3.46 (dd, 9.2, 7.2)	75.8	3.24 (overlap)	73.7
3'	—	148.7	3.39 (dd, 9.2, 7.6)	77.9	3.26 (overlap)	76.7
4'	—	140.9	3.41 (dd, 8.4, 7.6)	71.4	3.15 (dd, 11.2, 7.6)	70.2
5'	—	148.7	3.18~3.21 (m)	78.3	3.56 (dd, 11.2, 6.8)	74.1
6'	7.34 (s)	108.3	3.80 (dd, 12.0, 6.4, H-6'a) 3.67 (dd, 12.0, 5.2, H-6'b)	62.7	4.19 (d, 12.0, Ha) 4.04 (dd, 12.0, 6.8, Hb)	63.8
7'	——	166.6			—	170.7
8'					1.96 (s)	21.1
3'/5'-OMe	3.89 (s)	56.7
2/6-OMe			3.81 (s)	56.8

Position	1 (CD₃OD)		2 (CD₃OD)		3 (DMSO-d₆)
Position	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C
1	2.94 (dd, 15.6, 5.2, H-1a) 2.59 (dd, 15.6, 8.4, H-1b)	38.4	—	137.8	—	122.0
2	3.97~4.05 (m)	76.0	—	154.8	—	155.7
3	1.98~2.04 (m, H-3a) 1.67~1.75 (m, H-3b)	32.6	7.01 (s)	103.3	7.17 (d, 8.4)	116.8
4	2.82~2.88 (m, H-4a) 2.70~2.78 (m, H-4b)	28.5	—	128.2	7.48 (dd, 8.4, 7.6)	133.7
5	—	137.9	7.01 (s)	103.3	7.05 (dd, 7.6, 7.6)	122.3
6	6.50 (d, 2.4)	115.6	—	154.8	7.59 (d, 7.6)	130.8
7	—	156.3			—	167.6
8	6.54 (dd, 8.4, 2.4)	114.3
9	6.86 (d, 8.4)	131.1
10	—	127.4
1'	—	126.6	4.67 (d, 7.2)	106.2	4.91 (d, 6.0)	101.1
2'	7.34 (s)	108.3	3.46 (dd, 9.2, 7.2)	75.8	3.24 (overlap)	73.7
3'	—	148.7	3.39 (dd, 9.2, 7.6)	77.9	3.26 (overlap)	76.7
4'	—	140.9	3.41 (dd, 8.4, 7.6)	71.4	3.15 (dd, 11.2, 7.6)	70.2
5'	—	148.7	3.18~3.21 (m)	78.3	3.56 (dd, 11.2, 6.8)	74.1
6'	7.34 (s)	108.3	3.80 (dd, 12.0, 6.4, H-6'a) 3.67 (dd, 12.0, 5.2, H-6'b)	62.7	4.19 (d, 12.0, Ha) 4.04 (dd, 12.0, 6.8, Hb)	63.8
7'	——	166.6			—	170.7
8'					1.96 (s)	21.1
3'/5'-OMe	3.89 (s)	56.7
2/6-OMe			3.81 (s)	56.8

覆盆子果实中三个新的酚类衍生物及其抗炎活性

Three New Phenolic Derivatives from the Fruits of Rubus idaeus Linnaeus and Their Anti-inflammatory Activity

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