Two New Nor-Labdane Diterpenoids from Hedychium spcatum Rhizomes

doi:10.6023/cjoc202412008

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (7): 2605-2611.DOI: 10.6023/cjoc202412008 Previous Articles Next Articles

草果药根茎中两个新的降半日花烷型二萜

史路利^a, 董俊芳^b, 钱启超^a, 乔温皓^a, 胡炜彦^b, 李来伟^b, 张荣平^a, 陈兴龙^a^,^*()

^a 云南中医药大学中药学院云南省南药可持续利用研究重点实验室昆明 650500
^b 昆明医科大学药学院云南省天然药物药理重点实验室昆明 650500

收稿日期:2024-12-08 修回日期:2025-01-20 发布日期:2025-02-02
基金资助:
云南省兴滇英才-青年人才项目(XDYC-QNRC-2022-0271); 国家自然科学基金(32160107); “云岭学者”支持计划(YNWR-YLXZ-2019-019); 云南省科技厅社会发展专项-重点研发计划(202303AC100025); 云南省南药可持续利用研究重点实验室开放课题(202105AG-070012XS23088)

Two New Nor-Labdane Diterpenoids from Hedychium spcatum Rhizomes

Luli Shi^a, Junfang Dong^b, Qichao Qian^a, Wenhao Qiao^a, Weiyan Hu^b, Laiwei Li^b, Rongping Zhang^a, Xinglong Chen^a^,^*()

^a School of Chinese Materia Medica & Yunnan Key Laboratory of Southern Medicine Utilization, Yunnan University of Chinese Medicine, Kunming 650500
^b School of Pharmaceutical Science & Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming 650500

Received:2024-12-08 Revised:2025-01-20 Published:2025-02-02
Contact: *E-mail: chxlkib@163.com
Supported by:
Yunnan Xingdian Talent-Youth Talent Project(XDYC-QNRC-2022-0271); National Natural Science Foundation of China(32160107); Program of Yunling Scholarship(YNWR-YLXZ-2019-019); Social Development Special Projects-Key Research and Development Plan of Science and Technology Department of Yunnan Province(202303AC100025); Open Foundation of Yunnan Key Laboratory of Southern Medicine Utilization(202105AG-070012XS23088)

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Abstract

This study aimed to investigate the chemical constituents with anti-neuroinflammation effect from Hedychium spicatu rhizomes in which four compounds were isolated by various chromatographic techniques, such as MCI and silica gel column chromatography and semi-preparative high performance liquid chromatography. They were identified by high reso- lution mass spectrometry, nuclear magnetic resonance, and electronic circular dichroism (ECD) methods as (10R,11E)-6- hydroxy-15,16-bisnor-labda-5,8,11-triene-7,13-dione (1), (5S,9S,10R,11E)-14,15,16-trinor-labda-7,11-diene-6-one-13-acid me- thyl ester (2), (11E)-15,16-bisnor-labda-7,11-diene-6,13-dione (3), (11E)-6α-hydroxy-15,16-bisnor-labda-8(17),11-diene-13- one (4). Compouns 1 and 2 are two new nor-labdane diterpenoids. Their anti-neuro-inflammatory effects were evaluated via lipopolysaccharide (LPS) induced mouse microglial (BV2) cells. The results showed that the four compounds could inhibit the production of NO induced by LPS to displayed anti-neuroinflammatory effect. The IC₅₀ values of compounds 1~4 were (17.12±5.59), (28.66±7.82), (22.24±8.02), and (16.81±5.62) μmol/L, respectively.

Key words: Hedychium spicatum, chemical constituents, nor-labdane diterpenoids, anti-neuroinflammatory effect

Cite this article

Luli Shi, Junfang Dong, Qichao Qian, Wenhao Qiao, Weiyan Hu, Laiwei Li, Rongping Zhang, Xinglong Chen. Two New Nor-Labdane Diterpenoids from Hedychium spcatum Rhizomes[J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2605-2611.

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Position	Compound 1		Compound 2
Position	δ_H (J in Hz)^a	δ_C^b	δ_H (J in Hz)^a	δ_C^b
1	1.91~1.78 (m); 1.53~1.49 (m)	32.0 (CH₂)	1.22~1.17 (m); 1.56~1.47 (m)	40.2 (CH₂)
2	1.74~1.62 (m); 1.91~1.78 (m)	17.4 (CH₂)	1.44~1.38 (m); 1.56~1.47 (m)	18.1 (CH₂)
3	1.43~1.40 (m); 1.91~1.78 (m)	37.5 (CH₂)	1.12 (overlapped); 1.38~1.34 (m)	43.2 (CH₂)
4	—	36.0 (C)	—	32.6 (C)
5	—	141.7 (C)	2.04 (s)	63.2 (CH)
6	—	143.8 (C)	—	199.4 (C)
7	—	181.5 (C)	5.85 (s)	128.7 (CH)
8	—	128.4 (C)	—	154.6 (C)
9	—	160.3 (C)	2.98 (d, J=10.9)	60.1 (CH)
10	—	42.7 (C)	—	42.8 (C)
11	7.30 (d, 16.4)	139.6 (CH)	6.80 (dd, J=15.5/10.8)	145.4 (CH)
12	6.26 (d, 16.4)	134.6 (CH)	5.95 (d, J=15.5)	126.0 (CH)
13	—	197.4 (C)	—	166.0 (C)
14	2.36 (s)	28.4 (CH₃)	—	—
17	2.00 (s)	13.5 (CH₃)	1.73 (s)	22.9 (CH₃)
18	1.39 (s)	28.2 (CH₃)	1.11 (s)	33.6 (CH₃)
19	1.39 (s)	27.7 (CH₃)	1.15 (s)	21.7 (CH₃)
20	1.48 (s)	30.2 (CH₃)	0.96 (s),	15.9 (CH₃)
6-OH	6.94 (s)	—	—	—
-OCH₃	—	—	3.74 (s)	51.8 (CH₃)

Position	Compound 1		Compound 2
Position	δ_H (J in Hz)^a	δ_C^b	δ_H (J in Hz)^a	δ_C^b
1	1.91~1.78 (m); 1.53~1.49 (m)	32.0 (CH₂)	1.22~1.17 (m); 1.56~1.47 (m)	40.2 (CH₂)
2	1.74~1.62 (m); 1.91~1.78 (m)	17.4 (CH₂)	1.44~1.38 (m); 1.56~1.47 (m)	18.1 (CH₂)
3	1.43~1.40 (m); 1.91~1.78 (m)	37.5 (CH₂)	1.12 (overlapped); 1.38~1.34 (m)	43.2 (CH₂)
4	—	36.0 (C)	—	32.6 (C)
5	—	141.7 (C)	2.04 (s)	63.2 (CH)
6	—	143.8 (C)	—	199.4 (C)
7	—	181.5 (C)	5.85 (s)	128.7 (CH)
8	—	128.4 (C)	—	154.6 (C)
9	—	160.3 (C)	2.98 (d, J=10.9)	60.1 (CH)
10	—	42.7 (C)	—	42.8 (C)
11	7.30 (d, 16.4)	139.6 (CH)	6.80 (dd, J=15.5/10.8)	145.4 (CH)
12	6.26 (d, 16.4)	134.6 (CH)	5.95 (d, J=15.5)	126.0 (CH)
13	—	197.4 (C)	—	166.0 (C)
14	2.36 (s)	28.4 (CH₃)	—	—
17	2.00 (s)	13.5 (CH₃)	1.73 (s)	22.9 (CH₃)
18	1.39 (s)	28.2 (CH₃)	1.11 (s)	33.6 (CH₃)
19	1.39 (s)	27.7 (CH₃)	1.15 (s)	21.7 (CH₃)
20	1.48 (s)	30.2 (CH₃)	0.96 (s),	15.9 (CH₃)
6-OH	6.94 (s)	—	—	—
-OCH₃	—	—	3.74 (s)	51.8 (CH₃)

草果药根茎中两个新的降半日花烷型二萜

Two New Nor-Labdane Diterpenoids from Hedychium spcatum Rhizomes

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Compound	IC₅₀^a/(μmol•L^－1)
1	17.12±5.59
2	28.66±7.82
3	22.24±8.02
4	16.81±5.62
MINO^b	16.26±4.97

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