A New Steroid from Armillaria gallica

doi:10.6023/cjoc202407037

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (4): 1411-1416.DOI: 10.6023/cjoc202407037 Previous Articles Next Articles

高卢蜜环菌中一个新的甾体类化合物

张晶晶^†,a^,^c^,^e, 李慧琼^†,a^,^d, 张兴杰^†,a^,^d, 王永朋^a^,^d, 周学梅^a^,^d, 肖伟烈^a^,^c^,^d^,^e^,^*(), 程立君^b^,^*(), 李晓莉^a^,^d^,^*()

a 云南大学药学院教育部自然资源药物化学重点实验室云南省特色植物提取实验室有限公司昆明 650500
b 昭通学院农学与生命科学学院云南省天麻与真菌共生生物学重点实验室云南昭通 657000
c 云南大学国际河流与生态安全研究院昆明 650500
d 云南大学化学科学与工程学院昆明 650500
e 西南联合研究生院昆明 650092

收稿日期:2024-07-24 修回日期:2024-09-06 发布日期:2024-10-17
作者简介:^† 共同第一作者
基金资助:
国家自然科学基金(82260682); 昭通学院云南天麻与真菌共生生物学重点实验室(TMKF2023A01); 云南特色植物筛选与研发服务CXO平台(2022YKZY001); 云岭学者计划资助项目

A New Steroid from Armillaria gallica

Jingjing Zhang^†,a^,^c^,^e, Huiqiong Li^†,a^,^d, Xingjie Zhang^†,a^,^d, Yongpeng Wang^a^,^d, Xuemei Zhou^a^,^d, Weilie Xiao^a^,^c^,^d^,^e(), Lijun Cheng^b(), Xiaoli Li^a^,^d()

a Yunnan Characteristic Plant Extraction Laboratory Co. Ltd., Key Laboratory of Medicinal Chemistry for Natural Resource (Ministry of Education), School of Pharmacy, Yunnan University, Kunming 650500
b Yunnan Key Laboratory of Gastrodia and Fungi Symbiotic Biology, College of Agriculture and Life Sciences, Zhaotong University, Zhaotong, Yunnan 657000
c Institute of International Rivers and Eco-Security, Yunnan University, Kunming 650500
d School of Chemical Science and Technology, Yunnan University, Kunming 650500
e Southwest United Graduate School, Kunming 650092

Received:2024-07-24 Revised:2024-09-06 Published:2024-10-17
Contact: * E-mail: xiaoweilie@ynu.edu.cn; chenglijun224@ztu.edu.cn; lixiaoli@ynu.edu.cn
About author:^† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(82260682); Yunnan Key Laboratory of Gastrodia and Fungi Symbiotic Biology of Zhaotong University(TMKF2023A01); Yunnan Characteristic Plant Screening and R & D Service CXO Platform(2022YKZY001); Project of Yunling Scholars of Yunnan Province

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Abstract

A chemical investigation on the cultures extract of the basidiomycete Armillaria gallica Marxm. & Romagn. led to the isolation of eight compounds, including a new steroid armillanal D (1), a new natural product VD2-1 (8) and six known compounds. The structure of 1 was elucidated on the basis of extensive 1D and 2D-NMR spectra analysis, HR-ESI-MS, and electronic circular dichroism (ECD) spectra. The inhibitory activity of these compounds except 8 on NLRP3 inflammasome activation in Nigericin-induced mouse macrophage (J774A.1) cells was evaluated. Chaxine C (6) exhibited potential anti- inflammatory activity in vitro with IC₅₀ value of (4.97±0.81) μmol/L.

Key words: Armillaria gallica, fungal metabolite, steroid, anti-inflammatory activity

Cite this article

Jingjing Zhang, Huiqiong Li, Xingjie Zhang, Yongpeng Wang, Xuemei Zhou, Weilie Xiao, Lijun Cheng, Xiaoli Li. A New Steroid from Armillaria gallica[J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1411-1416.

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Fig. & Tab. 6

References 22

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Position	δ_C (type)	δ_H (J in Hz)	Position	δ_C (type)	δ_H (J in Hz)
1	35.5 (CH₂)	1.93~1.97 (m, 1H)			1.26 (overlap)
		1.76 (overlap)	16	29.8 (CH₂)	1.76 (overlap)
2	27.2 (CH₂)	1.84~1.89 (m, 1H)			1.37~1.42 (m, 1H)
		1.65~1.69 (m, 1H)	17	57.5 (CH)	1.26 (overlap)
3	71.3 (CH)	4.92~4.98 (m, 1H)	18	13.3 (CH₃)	0.86 (s, 3H)
4	34.0 (CH₂)	2.04~2.13 (m, 2H)	19	18.5 (CH₃)	0.93 (s, 3H)
5	83.2 (C)		20	41.2 (CH)	2.02~2.07 (m, 1H)
6	136.3 (CH)	6.28 (d, 8.5, 1H)	21	21.4 (CH₃)	1.02 (d, 6.6, 3H)
7	131.9 (CH)	6.55 (d, 8.5, 1H)	22	136.8 (CH)	5.18 (dd, 15.3, 8.3, 1H)
8	80.8 (C)		23	133.5 (CH)	5.25 (dd, 15.3, 7.7, 1H)
9	52.7 (CH)	1.47 (overlap)	24	44.3 (CH)	1.82~1.87 (m, 1H)
10	38.2 (C)		25	20.1 (CH₃)	0.84 (d, 6.8, 3H)
11	21.5 (CH₂)	1.53 (overlap)	26	34.4 (CH)	1.47 (overlap)
		1.49 (overlap)	27	20.5 (CH₃)	0.86 (d, 6.7, 3H)
12	40.6 (CH₂)	1.97~2.00 (m, 1H)	28	18.2 (CH₃)	0.93 (d, 6.7, 3H)
		1.26 (overlap)	1'	175.7 (C)
13	45.8 (C)		2'	67.9 (CH)	4.20 (q, 6.9, 1H)
14	53.0 (CH)	1.53 (overlap)	3'	20.6 (CH₃)	1.35 (d, 6.9, 3H)
15	24.4 (CH₂)	1.54~1.58 (m, 1H)

Position	δ_C (type)	δ_H (J in Hz)	Position	δ_C (type)	δ_H (J in Hz)
1	35.5 (CH₂)	1.93~1.97 (m, 1H)			1.26 (overlap)
		1.76 (overlap)	16	29.8 (CH₂)	1.76 (overlap)
2	27.2 (CH₂)	1.84~1.89 (m, 1H)			1.37~1.42 (m, 1H)
		1.65~1.69 (m, 1H)	17	57.5 (CH)	1.26 (overlap)
3	71.3 (CH)	4.92~4.98 (m, 1H)	18	13.3 (CH₃)	0.86 (s, 3H)
4	34.0 (CH₂)	2.04~2.13 (m, 2H)	19	18.5 (CH₃)	0.93 (s, 3H)
5	83.2 (C)		20	41.2 (CH)	2.02~2.07 (m, 1H)
6	136.3 (CH)	6.28 (d, 8.5, 1H)	21	21.4 (CH₃)	1.02 (d, 6.6, 3H)
7	131.9 (CH)	6.55 (d, 8.5, 1H)	22	136.8 (CH)	5.18 (dd, 15.3, 8.3, 1H)
8	80.8 (C)		23	133.5 (CH)	5.25 (dd, 15.3, 7.7, 1H)
9	52.7 (CH)	1.47 (overlap)	24	44.3 (CH)	1.82~1.87 (m, 1H)
10	38.2 (C)		25	20.1 (CH₃)	0.84 (d, 6.8, 3H)
11	21.5 (CH₂)	1.53 (overlap)	26	34.4 (CH)	1.47 (overlap)
		1.49 (overlap)	27	20.5 (CH₃)	0.86 (d, 6.7, 3H)
12	40.6 (CH₂)	1.97~2.00 (m, 1H)	28	18.2 (CH₃)	0.93 (d, 6.7, 3H)
		1.26 (overlap)	1'	175.7 (C)
13	45.8 (C)		2'	67.9 (CH)	4.20 (q, 6.9, 1H)
14	53.0 (CH)	1.53 (overlap)	3'	20.6 (CH₃)	1.35 (d, 6.9, 3H)
15	24.4 (CH₂)	1.54~1.58 (m, 1H)

Compound	IC₅₀ (means±SD)/(μmol•L^－1)
6	4.97±0.81
Andrographolide	8.11±0.71

Compound	IC₅₀ (means±SD)/(μmol•L^－1)
6	4.97±0.81
Andrographolide	8.11±0.71

高卢蜜环菌中一个新的甾体类化合物

A New Steroid from Armillaria gallica

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