长叶暗罗中克罗烷型二萜及其抗炎作用

doi:10.6023/cjoc202208019

有机化学 ›› 2023, Vol. 43 ›› Issue (2): 751-755.DOI: 10.6023/cjoc202208019 上一篇下一篇

研究简报

长叶暗罗中克罗烷型二萜及其抗炎作用

余章昕^a^,^b, 宋鑫明^a^,^b, 姚远^a^,^b, 杨俊^a^,^b, 杨硕^a^,^b, 李小宝^a^,^b^,^*()

a 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
b 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:2022-08-15 修回日期:2022-10-05 发布日期:2022-10-31
基金资助:
海南省自然科学基金(221MS034); 海南省自然科学基金(220MS036); 海南省重点研发(ZDYF2022SHFZ286); 海南省重点研发(ZDYF2021SHFZ072); 海南省教育厅(Hnky 2021-30); 国家自然科学基金(21662012); 海南省院士创新平台(YSPTZX202030); 及中央引导地方科技发展资金(ZY2022HN08)

Anti-inflammatory Clerodane Diterpenoids from Polyalthia longifolia

Zhangxin Yu^a^,^b, Xinming Song^a^,^b, Yuan Yao^a^,^b, Jun Yang^a^,^b, Shuo Yang^a^,^b, Xiaobao Li^a^,^b()

a Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, 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:2022-08-15 Revised:2022-10-05 Published:2022-10-31
Contact: *E-mail: lixiaobao0797@163.com
Supported by:
Natural Science Foundation of Hainan Province(221MS034); Natural Science Foundation of Hainan Province(220MS036); Key R&D Projects in Hainan Province-Social Development(ZDYF2022SHFZ286); Key R&D Projects in Hainan Province-Social Development(ZDYF2021SHFZ072); Education Department of Hainan Province(Hnky 2021-30); National Natural Science Foundation of China(21662012); Innovation Platform for Academicians of Hainan Province(YSPTZX202030); Central Government Guides Local Science and Technology Development(ZY2022HN08)

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摘要/Abstract

对长叶暗罗茎的化学成分进行研究, 分离得到4个新的克罗烷型二萜类化合物, 通过NMR、HR-ESI-MS等多种现代波谱技术鉴定为: 2-氧代-14,15,16-降三碳克罗烷-3-烯-13-酸(1)、2-氧代-14,15,16-降三碳克罗烷-3-烯-13-甲酯(2)、2-氧代-14,15,16-降三碳克罗烷-3,11E-二烯-13-酸(3)、2-氧代-16-羟基-克罗烷-3,13Z-二烯-15-酸(4). 其中, 化合物1~3为降三碳克罗烷型二萜, 所有化合物均表现出一定的抗炎活性, IC₅₀值范围为9.24~18.82 μmol/L.

关键词: 长叶暗罗, 克罗烷型二萜, 抗炎活性

Four new clerodane diterpenoids (1~4) were obtained from the stems of Polyalthia longifolia during a systematic phytochemical investigation. Their structures were elucidated comprehensive spectroscopic methods as 2-oxo-14,15,16-tri- norclerod-3-en-13-oic acid (1), 2-oxo-14,15,16-trinorclerod-3-en-13-methyl ester (2), 2-oxo-14,15,16-trinorclerod-3,11E- dien-13-oic acid (3), and 2-oxo-cleroda-3,13Z-dien-16-hydroxy-15-oic acid (4). Among them, compounds 1~3 are 14,15,16-norclerodane diterpenoids. The anti-inflammatory activity of mouse leukemia cells of monocyte macrophage (RAW 264.7) cells with lipopolysaccharide-induced was evaluated, and all the compounds showed potential anti-inflammatory activities with IC₅₀ values ranged from 9.24 to18.82 μmol/L.

Key words: Polyalthia longifolia, clerodane diterpenes, anti-inflammatory

引用此文

余章昕, 宋鑫明, 姚远, 杨俊, 杨硕, 李小宝. 长叶暗罗中克罗烷型二萜及其抗炎作用[J]. 有机化学, 2023, 43(2): 751-755.

Zhangxin Yu, Xinming Song, Yuan Yao, Jun Yang, Shuo Yang, Xiaobao Li. Anti-inflammatory Clerodane Diterpenoids from Polyalthia longifolia[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 751-755.

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图/表 6

参考文献 14

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No.	1	2	3	4
1	2.35, dd (11.2, 4.80) 2.33~2.37, m	2.34, dd (11.2, 4.80) 2.36~2.40, m	2.35, br d (11.2) 2.28~2.33, m	2.34, dd (11.2, 4.80) 2.16~2.23, m
3	5.72, s	5.71 s	5.72, s	5.63, s
6	1.35, td (12.4, 5.6) 1.80~1.82, m	1.36, td (12.4, 5.6) 1.79~1.82, m	2.16 td (12.4, 4.8) 1.47~1.52, m, overlap	1.25~1.32, m 1.41~1.48, m, overlap
7	1.50~1.52, m 1.47~1.50, m	1.50~1.53, m 1.47~1.51, m	1.48~1.52, m 1.45~1.50, m, overlap	1.47~1.52, m, overlap
8	1.38~1.42, m	1.37~1.43, m	1.37~1.44, m	1.42~1.47, m, overlap
10	1.77, dd (10.8, 4.4)	1.78, dd (10.8,4.4)	1.93, br d (3.2), overlap	1.79, br d (12.6)
11	1.65, td (6.8, 3.6)	1.66, td (6.8, 3.6)	6.67, d (16.0)	1.48~1.53, m
12	2.13~2.17, m 2.08~2.11, m	2.13~2.18, m 2.07~2.11, m	5.75, d (16.0)	2.08~2.13, m 2.21~2.28, m
14				5.76, s
16				4.66, br s
17	0.85, d (7.2)	0.84, d (7.2)	0.75, d (6.0)	0.79, d (6.4)
18	1.88, d (1.2)	1.88, d (0.8)	1.90, s	1.84, br s
19	1.11, s	1.11, s	1.13, s	1.07, s
20	0.84, s	0.83, s	1.00, s	0.81, s
OCH₃		3.64, s

No.	1	2	3	4
1	2.35, dd (11.2, 4.80) 2.33~2.37, m	2.34, dd (11.2, 4.80) 2.36~2.40, m	2.35, br d (11.2) 2.28~2.33, m	2.34, dd (11.2, 4.80) 2.16~2.23, m
3	5.72, s	5.71 s	5.72, s	5.63, s
6	1.35, td (12.4, 5.6) 1.80~1.82, m	1.36, td (12.4, 5.6) 1.79~1.82, m	2.16 td (12.4, 4.8) 1.47~1.52, m, overlap	1.25~1.32, m 1.41~1.48, m, overlap
7	1.50~1.52, m 1.47~1.50, m	1.50~1.53, m 1.47~1.51, m	1.48~1.52, m 1.45~1.50, m, overlap	1.47~1.52, m, overlap
8	1.38~1.42, m	1.37~1.43, m	1.37~1.44, m	1.42~1.47, m, overlap
10	1.77, dd (10.8, 4.4)	1.78, dd (10.8,4.4)	1.93, br d (3.2), overlap	1.79, br d (12.6)
11	1.65, td (6.8, 3.6)	1.66, td (6.8, 3.6)	6.67, d (16.0)	1.48~1.53, m
12	2.13~2.17, m 2.08~2.11, m	2.13~2.18, m 2.07~2.11, m	5.75, d (16.0)	2.08~2.13, m 2.21~2.28, m
14				5.76, s
16				4.66, br s
17	0.85, d (7.2)	0.84, d (7.2)	0.75, d (6.0)	0.79, d (6.4)
18	1.88, d (1.2)	1.88, d (0.8)	1.90, s	1.84, br s
19	1.11, s	1.11, s	1.13, s	1.07, s
20	0.84, s	0.83, s	1.00, s	0.81, s
OCH₃		3.64, s

No.	1	2	3	4
1	34.9 (CH₂)	35.0 (CH₂)	35.0 (CH₂)	34.5 (CH₂)
2	200.3 (C)	200.1 (C)	199.8 (C)	199.6 (C)
3	125.7 (CH)	125.7 (CH)	126.0 (CH)	125.4 (CH)
4	172.7 (C)	172.5 (C)	171.7 (C)	172.4 (C)
5	40.0 (C)	40.0 (C)	39.2 (C)	39.9 (C)
6	35.7 (CH₂)	35.6 (CH₂)	35.4 (CH₂)	35.4 (CH₂)
7	27.0 (CH₂)	27.0 (CH₂)	26.3 (CH₂)	26.7 (CH₂)
8	36.3 (CH)	36.2 (CH)	40.4 (CH)	36.0 (CH)
9	38.6 (C)	38.6 (C)	44.4 (C)	38.7 (C)
10	46.0 (CH)	45.9 (CH)	48.7 (CH)	45.7 (CH)
11	32.1 (CH₂)	32.3 (CH₂)	160.6 (CH)	34.9 (CH₂)
12	27.6 (CH₂)	27.9 (CH₂)	120.6 (CH)	21.9 (CH₂)
13	177.6 (C)	174.2 (C)	170.1 (C)	170.3 (C)
14				115.1 (CH)
15				173.8 (C)
16				73.0 (CH₂)
17	15.9 (CH₃)	15.9 (CH₃)	16.8 (CH₃)	15.7 (CH₃)
18	19.1 (CH₃)	19.1 (CH₃)	19.0 (CH₃)	19.0 (CH₃)
19	18.4 (CH₃)	18.4 (CH₃)	18.2 (CH₃)	18.3 (CH₃)
20	17.8 (CH₃)	17.8 (CH₃)	12.0 (CH₃)	17.7 (CH₃)
OCH₃		51.8 (CH₃)

No.	1	2	3	4
1	34.9 (CH₂)	35.0 (CH₂)	35.0 (CH₂)	34.5 (CH₂)
2	200.3 (C)	200.1 (C)	199.8 (C)	199.6 (C)
3	125.7 (CH)	125.7 (CH)	126.0 (CH)	125.4 (CH)
4	172.7 (C)	172.5 (C)	171.7 (C)	172.4 (C)
5	40.0 (C)	40.0 (C)	39.2 (C)	39.9 (C)
6	35.7 (CH₂)	35.6 (CH₂)	35.4 (CH₂)	35.4 (CH₂)
7	27.0 (CH₂)	27.0 (CH₂)	26.3 (CH₂)	26.7 (CH₂)
8	36.3 (CH)	36.2 (CH)	40.4 (CH)	36.0 (CH)
9	38.6 (C)	38.6 (C)	44.4 (C)	38.7 (C)
10	46.0 (CH)	45.9 (CH)	48.7 (CH)	45.7 (CH)
11	32.1 (CH₂)	32.3 (CH₂)	160.6 (CH)	34.9 (CH₂)
12	27.6 (CH₂)	27.9 (CH₂)	120.6 (CH)	21.9 (CH₂)
13	177.6 (C)	174.2 (C)	170.1 (C)	170.3 (C)
14				115.1 (CH)
15				173.8 (C)
16				73.0 (CH₂)
17	15.9 (CH₃)	15.9 (CH₃)	16.8 (CH₃)	15.7 (CH₃)
18	19.1 (CH₃)	19.1 (CH₃)	19.0 (CH₃)	19.0 (CH₃)
19	18.4 (CH₃)	18.4 (CH₃)	18.2 (CH₃)	18.3 (CH₃)
20	17.8 (CH₃)	17.8 (CH₃)	12.0 (CH₃)	17.7 (CH₃)
OCH₃		51.8 (CH₃)

化合物	IC₅₀/(μmol•L^-1)
1	15.33±0.4
2	18.82±0.5
3	13.13±0.3
4	9.24±0.3
氨基胍	8.38±0.2

长叶暗罗中克罗烷型二萜及其抗炎作用

Anti-inflammatory Clerodane Diterpenoids from Polyalthia longifolia

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