Anti-inflammatory Clerodane Diterpenoids from Polyalthia longifolia

doi:10.6023/cjoc202208019

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (2): 751-755.DOI: 10.6023/cjoc202208019 Previous Articles Next Articles

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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Abstract

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

Cite this article

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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Fig. & Tab. 6

References 14

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	(余章昕, 王灿红, 郑威, 陈德力, 杨云, 刘洋洋, 魏建和, 中国药学杂志, 2019, 54, 1946.)

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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