Studies on the Chemical Constituents from the Seeds of Noni and Their Anti-inflammatory Bioactivity

doi:10.6023/cjoc202309010

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (4): 1357-1362.DOI: 10.6023/cjoc202309010 Previous Articles Next Articles

诺丽种子的化学成分及其抗炎活性研究

魏琴芝^a^,^b^,^c, 余章昕^b^,^c, 徐盟^a^,^b^,^c, 徐伟^a, 岑福凌^a^,^b^,^c, 张雅琦^b^,^c, 李小宝^b^,^c^,^*(), 陈光英^a^,^b^,^c^,^*()

a 福建中医药大学药学院福州 350122
b 海南师范大学热带药用资源化学教育部重点实验室海口 571158
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:2023-09-11 修回日期:2023-11-16 发布日期:2023-12-07
作者简介:† 共同第一作者.
基金资助:
国家自然科学基金(22367008); 国家自然科学基金(21662012); 海南省院士创新平台(YSPTZX202030); 中央引导地方科技发展专项(ZY2022HN08); 海南师范大学“大学生创新创业训练计划”(HSCX2023-17)

Studies on the Chemical Constituents from the Seeds of Noni and Their Anti-inflammatory Bioactivity

Qinzhi Wei^a^,^b^,^c, Zhangxin Yu^b^,^c, Meng Xu^a^,^b^,^c, Wei Xu^a, Fuling Cen^a^,^b^,^c, Yaqi Zhang^b^,^c, Xiaobao Li^b^,^c(), Guangying Chen^a^,^b^,^c()

a College of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350122
b Key Laboratory of Tropical Medicinal Resources Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158
c Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158

Received:2023-09-11 Revised:2023-11-16 Published:2023-12-07
Contact: * E-mail: lixiaobao0797@163.com; chgying123@163.com
About author:† The authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22367008); National Natural Science Foundation of China(21662012); Innovation Platform for Academicians of Hainan Province(YSPTZX202030); Central Government Guides Local Science and Technology Development(ZY2022HN08); Hainan Normal University “Innovative Entrepreneurship Training Program for College Students”(HSCX2023-17)

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Abstract

A new sesquineolignan moricitan A (1), a new natural product 4-methoxy isoamericanin A (2), a new anthraquinone 1,3-dihydroxy-2,5-dimethoxy-6-(methoxymethyl)anthracene-9,10-dione (7), and seven known compounds 3~6 and 8~10 were obtained from the seeds of Noni. The structures were elucidated using comprehensive spectroscopic methods, and the absolute configuration of 1 was established based on quantum-chemical electronic circular dichroism calculations. The inhibitory activity of all the compounds on NO production in lipopolysaccharide-induced (LPS) mouse leukemia cells of monocyte macrophage (RAW 264.7) cells was evaluated. Compound 1 and 9'-ethyl americanol A (3) exhibited stronger anti-inflam- matory activity in vitro with IC₅₀ values of (2.52±0.22) and (5.46±0.89) μmol/L to that of dexamethasone [IC₅₀=(65.39±1.02) μmol/L], respectively.

Key words: Morinda citrifolia, Noni, lignan, anthraquinone, anti-inflammatory

Cite this article

Qinzhi Wei, Zhangxin Yu, Meng Xu, Wei Xu, Fuling Cen, Yaqi Zhang, Xiaobao Li, Guangying Chen. Studies on the Chemical Constituents from the Seeds of Noni and Their Anti-inflammatory Bioactivity[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1357-1362.

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No.	1		2
No.	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C
1		129.6 (C)		127.7 (C)
2	7.06, d (1.8)	117.6 (CH)	6.93, d (1.8)	109.4 (CH)
3		143.0 (C)		146.6 (C)
4		152.1 (C)		147.2 (C)
5		131.1 (C)	6.97, d (8.1)	114.9 (CH)
6	7.15, d (1.8)	118.8 (CH)	6.96, dd (1.8, 8.1)	121.0 (CH)
7	7.56, d (15.6)	156.3 (CH)	4.97, d (8.3)	76.5 (CH)
8	6.59, dd (7.8, 15.6)	126.8 (CH)	4.09, ddd (2.7, 3.9, 8.3)	78.9 (CH)
9	9.55, dd (1.2, 7.8)	196.2 (CH)	3.83, dd (2.7, 12.6) 3.57, d (12.7)	61.7 (CH₂)
1'		136.0 (C)		128.1 (C)
2'	6.94, d (2.4)	115.5 (CH)	7.21, d (2.1)	117.3 (CH)
3'		145.3 (C)		144.4 (C)
4'		144.8 (C)		146.3 (C)
5'	6.95, d (8.4)	118.2 (CH)	7.02, d (8.4)	117.8 (CH)
6'	6.91, dd (2.4, 8.4)	119.8 (CH)	7.14, dd (2.1, 8.4)	123.0 (CH)
7'	5.62, d (6.0)	89.3 (CH)	7.37, d (15.8)	152.6 (CH)
8'	3.53, dd (6.0, 12.0)	55.1 (CH)	6.57, dd (7.7, 15.8)	127.4 (CH)
9'	3.81, dd (6.6, 11.4) 3.86, dd (4.8, 11.4)	64.8 (CH₂)	9.65, d (7.7)	193.8 (CH)
1''		129.5 (C)
2''	6.84, t (2.4)	115.6 (CH)
3''		146.7 (C)
4''		147.2 (C)
5''	6.80, d (8.4)	116.4 (CH)
6''	6.76, dd (2.4, 8.4)	120.4 (CH)
7''	4.84, d (8.4)	77.6 (CH)
8''	3.98~4.01, m	80.0 (CH)
9''	3.48, dd (4.8, 12.4) 3.53, dd (3.0, 12.4)	62.1 (CH₂)
OCH₃-4			3.93, s	56.2 (CH₃)

No.	1		2
No.	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C
1		129.6 (C)		127.7 (C)
2	7.06, d (1.8)	117.6 (CH)	6.93, d (1.8)	109.4 (CH)
3		143.0 (C)		146.6 (C)
4		152.1 (C)		147.2 (C)
5		131.1 (C)	6.97, d (8.1)	114.9 (CH)
6	7.15, d (1.8)	118.8 (CH)	6.96, dd (1.8, 8.1)	121.0 (CH)
7	7.56, d (15.6)	156.3 (CH)	4.97, d (8.3)	76.5 (CH)
8	6.59, dd (7.8, 15.6)	126.8 (CH)	4.09, ddd (2.7, 3.9, 8.3)	78.9 (CH)
9	9.55, dd (1.2, 7.8)	196.2 (CH)	3.83, dd (2.7, 12.6) 3.57, d (12.7)	61.7 (CH₂)
1'		136.0 (C)		128.1 (C)
2'	6.94, d (2.4)	115.5 (CH)	7.21, d (2.1)	117.3 (CH)
3'		145.3 (C)		144.4 (C)
4'		144.8 (C)		146.3 (C)
5'	6.95, d (8.4)	118.2 (CH)	7.02, d (8.4)	117.8 (CH)
6'	6.91, dd (2.4, 8.4)	119.8 (CH)	7.14, dd (2.1, 8.4)	123.0 (CH)
7'	5.62, d (6.0)	89.3 (CH)	7.37, d (15.8)	152.6 (CH)
8'	3.53, dd (6.0, 12.0)	55.1 (CH)	6.57, dd (7.7, 15.8)	127.4 (CH)
9'	3.81, dd (6.6, 11.4) 3.86, dd (4.8, 11.4)	64.8 (CH₂)	9.65, d (7.7)	193.8 (CH)
1''		129.5 (C)
2''	6.84, t (2.4)	115.6 (CH)
3''		146.7 (C)
4''		147.2 (C)
5''	6.80, d (8.4)	116.4 (CH)
6''	6.76, dd (2.4, 8.4)	120.4 (CH)
7''	4.84, d (8.4)	77.6 (CH)
8''	3.98~4.01, m	80.0 (CH)
9''	3.48, dd (4.8, 12.4) 3.53, dd (3.0, 12.4)	62.1 (CH₂)
OCH₃-4			3.93, s	56.2 (CH₃)

No.	δ_H (J in Hz)	δ_C
1	7.41, s	107.9 (CH)
2		155.4 (C)
3		138.3 (C)
4		155.5 (C)
5	8.14, d (8.0)	123.3 (CH)
6	7.86, d (8.0)	133.7 (CH)
7		141.3 (C)
8		158.7 (C)
9		181.2 (C)
10		187.4 (C)
10a		134.8 (C)
11		125.4 (C)
9a		131.2 (C)
12		111.4 (C)
13	4.65, s	69.2 (CH₂)
OCH₃-3	4.13, s	61.3 (CH₃)
OCH₃-8	3.93, s	62.3 (CH₃)
OCH₃-13	3.50, s	59.1 (CH₃)
OH-4	13.04, s

No.	δ_H (J in Hz)	δ_C
1	7.41, s	107.9 (CH)
2		155.4 (C)
3		138.3 (C)
4		155.5 (C)
5	8.14, d (8.0)	123.3 (CH)
6	7.86, d (8.0)	133.7 (CH)
7		141.3 (C)
8		158.7 (C)
9		181.2 (C)
10		187.4 (C)
10a		134.8 (C)
11		125.4 (C)
9a		131.2 (C)
12		111.4 (C)
13	4.65, s	69.2 (CH₂)
OCH₃-3	4.13, s	61.3 (CH₃)
OCH₃-8	3.93, s	62.3 (CH₃)
OCH₃-13	3.50, s	59.1 (CH₃)
OH-4	13.04, s

化合物	IC₅₀/(μmol•L^–1)
1	2.52±0.22
3	5.46±0.89
5	58.63±12.23
地塞米松	65.39±1.02

诺丽种子的化学成分及其抗炎活性研究

Studies on the Chemical Constituents from the Seeds of Noni and Their Anti-inflammatory Bioactivity

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