Studies on the Highly Oxidized Cadinane Sesquiterpenes from Alangium salviifolium and Their Bioactivities

doi:10.6023/cjoc202309005

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (4): 1363-1367.DOI: 10.6023/cjoc202309005 Previous Articles Next Articles

土坛树中高度氧化的杜松烷型倍半萜及其生物活性研究

魏艳梅^a^,^b, 余章昕^a^,^b, 杜怡益^a^,^b, 王平淑^a^,^b, 岑福凌^a^,^b, 李小宝^a^,^b, 陈光英^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海南省热带药用植物化学重点实验室海口 571158

收稿日期:2023-09-04 修回日期:2023-10-31 发布日期:2023-11-15
作者简介:† 共同第一作者.
基金资助:
海南省重点研发项目(ZDYF2022SHFZ286); 海南省重点研发项目(ZDYF2021SHFZ072); 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”(202311658005)

Studies on the Highly Oxidized Cadinane Sesquiterpenes from Alangium salviifolium and Their Bioactivities

Yanmei Wei^a^,^b, Zhangxin Yu^a^,^b, Yiyi Du^a^,^b, Pingshu Wang^a^,^b, Fuling Cen^a^,^b, Xiaobao Li^a^,^b, Guangying Chen^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:2023-09-04 Revised:2023-10-31 Published:2023-11-15
Contact: * E-mail: chgying123@163.com
About author:† The authors contributed equally to this work.
Supported by:
Key R&D Projects in Hainan Province-Social Development(ZDYF2022SHFZ286); Key R&D Projects in Hainan Province-Social Development(ZDYF2021SHFZ072); 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”(202311658005)

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Abstract

Two new highly oxidized cadinane sesquiterpenes of alansalene A (1) and 2,7-dihydroxy-4-isopropyl-1-methyl- 6-naphthaldehyde (5), and five known analogues were isolated from the barks of Alangium salviifolium, which is a folk medicinal plant in Hainan. The structures were elucidated by spectroscopic methods (1D and 2D NMR, HR-ESI-MS). Compound alangene D (2) exhibited stronger anti-inflammatory activity in vitro with IC₅₀ value of (2.98±0.11) μmol/L to that of dexamethasone [IC₅₀=(39.62±0.12) μmol/L]. Alangene F (3) and 2,7-dihydroxy-4-isopropyl-6-methylnaphthalene-1- carbaldehyde (6) displayed potential α-glucosidase inhibitory activities with IC₅₀ values of (111.85±1.80) and (18.55±0.68) μmol/L, respectively, which were stronger than that of acarbose [IC₅₀=(478.75±27.14) μmol/L].

Key words: Alangium salviifolium, highly oxidization, sesquiterpene, anti-inflammatory, α-glucosidase inhibitory

Cite this article

Yanmei Wei, Zhangxin Yu, Yiyi Du, Pingshu Wang, Fuling Cen, Xiaobao Li, Guangying Chen. Studies on the Highly Oxidized Cadinane Sesquiterpenes from Alangium salviifolium and Their Bioactivities[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1363-1367.

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Fig. & Tab. 6

References 15

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No.	1^a		5^b
No.	δ_H(J in Hz)	δ_C	δ_H(J in Hz)	δ_C
1		128.5 (C)		142.1 (C)
2		143.0 (C)	7.19, s	108.2 (CH)
3		154.3 (C)		157.1 (C)
4		110.2 (C)		120.8 (C)
5		148.2 (C)	8.47, s	134.1 (CH)
6		115.1 (C)		122.3 (C)
7		141.2 (C)		148.0 (C)
8	6.34, s	105.2 (CH)	6.95, s	113.9 (CH)
9		170.1 (C)		157.4 (C)
10		110.2 (C)		112.8 (C)
11		112.7 (C)	3.71~3.73, m	29.5 (CH)
12	7.07, d (1.4)	144.1 (CH)	1.37, d (6.8)	24.1 (CH₃)
13	1.95, d (1.3)	13.4 (CH₃)	1.37, d (6.8)	24.1 (CH₃)
14	5.28, s	56.0 (CH₂)	10.10, s	197.4 (CH)
15	10.96, s	196.5 (CH)	2.34, s	10.6 (CH₃)
1'		171.2 (C)
2'	2.08, s	21.2 (CH₃)
2-OCH₃	3.81, s	59.2 (CH₃)
3-OCH₃	4.02, s	61.9 (CH₃)
OH-9	14.77, s

No.	1^a		5^b
No.	δ_H(J in Hz)	δ_C	δ_H(J in Hz)	δ_C
1		128.5 (C)		142.1 (C)
2		143.0 (C)	7.19, s	108.2 (CH)
3		154.3 (C)		157.1 (C)
4		110.2 (C)		120.8 (C)
5		148.2 (C)	8.47, s	134.1 (CH)
6		115.1 (C)		122.3 (C)
7		141.2 (C)		148.0 (C)
8	6.34, s	105.2 (CH)	6.95, s	113.9 (CH)
9		170.1 (C)		157.4 (C)
10		110.2 (C)		112.8 (C)
11		112.7 (C)	3.71~3.73, m	29.5 (CH)
12	7.07, d (1.4)	144.1 (CH)	1.37, d (6.8)	24.1 (CH₃)
13	1.95, d (1.3)	13.4 (CH₃)	1.37, d (6.8)	24.1 (CH₃)
14	5.28, s	56.0 (CH₂)	10.10, s	197.4 (CH)
15	10.96, s	196.5 (CH)	2.34, s	10.6 (CH₃)
1'		171.2 (C)
2'	2.08, s	21.2 (CH₃)
2-OCH₃	3.81, s	59.2 (CH₃)
3-OCH₃	4.02, s	61.9 (CH₃)
OH-9	14.77, s

Compound^a	IC₅₀^b/(μmol•L^–1)
2	2.98±0.11
Dexamethasone^c	39.62±0.12

Compound^a	IC₅₀^b/(μmol•L^–1)
2	2.98±0.11
Dexamethasone^c	39.62±0.12

Compd.^a	SGC-7901^b	K562^b	A549^b	BEL^b
1	59.49±3.07	30.60±1.38	61.18±0.65	72.88±1.64
5	55.18±3.11	45.27±0.63	39.20±1.40	49.62±0.57
Doxorubicin hydrochloride^c	0.06±0.01	0.55±0.01	1.51±0.06	3.79±0.22

土坛树中高度氧化的杜松烷型倍半萜及其生物活性研究

Studies on the Highly Oxidized Cadinane Sesquiterpenes from Alangium salviifolium and Their Bioactivities

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Compound^a	IC₅₀^b/(μmol•L^–1)
3	111.85±1.80
6	18.55±0.68
Acarbose^c	478.75±27.14

Compound^a	IC₅₀^b/(μmol•L^–1)
3	111.85±1.80
6	18.55±0.68
Acarbose^c	478.75±27.14