A New Protoilludane Sesquiterpene Aryl Ester from Armillaria sp. YUD17010

doi:10.6023/cjoc202107006

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4493-4497.DOI: 10.6023/cjoc202107006 Previous Articles Next Articles

NOTES

蜜环菌YUD17010中一个新的原伊鲁烷型倍半萜芳基酯

李洪涛^a^,^b, 谢飞^a, 孙岳^a, 王萌^a, 陈静圆^a, 周皓^a^,^*(), 丁中涛^a^,^c^,^*()

a 云南大学化学科学与工程学院云南省高校功能分子分析与生物转化重点实验室昆明 650091
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
c 大理大学药学院云南大理 671000

收稿日期:2021-07-02 修回日期:2021-07-21 发布日期:2021-08-09
通讯作者: 周皓, 丁中涛
基金资助:
国家自然科学基金(81860623); 云岭学者计划资助项目

A New Protoilludane Sesquiterpene Aryl Ester from Armillaria sp. YUD17010

Hongtao Li^a^,^b, Fei Xie^a, Yue Sun^a, Meng Wang^a, Jingyuan Chen^a, Hao Zhou^a(), Zhongtao Ding^a^,^c()

a Key Laboratory of Functional Molecules Analysis and Biotransformation, Yunnan Provincial Department of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091
b Yunnan Key Laboratory of Pharmacology for Natural Products, School of Pharmaceutical Science, Kunming Medical University, Kunming 650500
c College of Pharmacy, Dali University, Dali, Yunnan 671000

Received:2021-07-02 Revised:2021-07-21 Published:2021-08-09
Contact: Hao Zhou, Zhongtao Ding
Supported by:
National Natural Science Foundation of China(81860623); Project of Yunling Scholars of Yunnan Province

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Abstract

A chemical investigation on the cultures extract of the basidiomycete Armillaria sp. YUD17010 led to the isolation of three protoilludane-type sesquiterpene aryl esters, including a new one armilaroma (1), along with two known ones 4-dehydrodihydromelleolide (2) and armillarivin (3). Their structures and relative configurations were established on the basis of spectroscopic data analysis, and the absolute configurations were assigned by electronic circular dichroism (ECD) spectra aided by quantum chemical calculations. Armilaroma (1) exhibited moderate acetylcholinesterase (AChE) inhibitory activity with an IC₅₀ value of 9.03 μmol/L. Moreover, cytotoxicities against the MCF-7, SW480, HL-60, A-549, and SMMC-7721 human cancer cell lines were also evaluated for compound 1, with the IC₅₀ values ranging from 13.73 μmol/L to 17.92 μmol/L.

Key words: Armillaria sp., fungal metabolite, cytotoxicity, sesquiterpene aryl ester

Cite this article

Hongtao Li, Fei Xie, Yue Sun, Meng Wang, Jingyuan Chen, Hao Zhou, Zhongtao Ding. A New Protoilludane Sesquiterpene Aryl Ester from Armillaria sp. YUD17010[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4493-4497.

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Fig. & Tab. 5

References 24

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Position	δ_H (J in Hz)^a	δ_C (type)^b
1	3.93 (s)	66.4 (CH₂)
2		133.5 (C)
3	5.69 (s)	130.3 (CH)
4	2.88 (d, 6.8)	43.2 (CH)
5	5.72 (overlap)	70.7 (CH)
6	2.13 (d, 7.6)	38.7 (CH₂)
7		32.9 (C)
8	1.25 (s)	27.0 (CH₃)
9	2.07 (overlap)	45.5 (CH)
10	1.33 (dd, 12.0, 6.4)	41.9 (CH₂)
	1.09 (d, 12.0)
11		37.8 (C)
12	1.83 (dd, 9.2, 8.8)	48.0 (CH₂)
	1.49 (d, 13.2)
13	2.77 (s)	39.3 (CH)
14	1.00 (s)	32.2 (CH₃)
15	0.98 (s)	32.4 (CH₃)
1'		105.2 (C)
2'		165.2 (C)
3'	6.20 (s)	101.5 (CH)
4'		161.2 (C)
5'	6.13 (s)	111.9 (CH)
6'		144.1 (C)
7'	2.35 (s)	24.2 (CH₃)
8'		171.3 (C)

Position	δ_H (J in Hz)^a	δ_C (type)^b
1	3.93 (s)	66.4 (CH₂)
2		133.5 (C)
3	5.69 (s)	130.3 (CH)
4	2.88 (d, 6.8)	43.2 (CH)
5	5.72 (overlap)	70.7 (CH)
6	2.13 (d, 7.6)	38.7 (CH₂)
7		32.9 (C)
8	1.25 (s)	27.0 (CH₃)
9	2.07 (overlap)	45.5 (CH)
10	1.33 (dd, 12.0, 6.4)	41.9 (CH₂)
	1.09 (d, 12.0)
11		37.8 (C)
12	1.83 (dd, 9.2, 8.8)	48.0 (CH₂)
	1.49 (d, 13.2)
13	2.77 (s)	39.3 (CH)
14	1.00 (s)	32.2 (CH₃)
15	0.98 (s)	32.4 (CH₃)
1'		105.2 (C)
2'		165.2 (C)
3'	6.20 (s)	101.5 (CH)
4'		161.2 (C)
5'	6.13 (s)	111.9 (CH)
6'		144.1 (C)
7'	2.35 (s)	24.2 (CH₃)
8'		171.3 (C)

Compound	MCF-7	SW480	HL-60	A-549	SMMC-7721
1	16.59±0.16	17.32±0.32	15.98±0.99	17.92±0.74	13.73±0.58
Cisplatin	4.28±0.36	13.78±0.25	11.23±0.61	21.65±0.68	18.17±0.15

Compound	MCF-7	SW480	HL-60	A-549	SMMC-7721
1	16.59±0.16	17.32±0.32	15.98±0.99	17.92±0.74	13.73±0.58
Cisplatin	4.28±0.36	13.78±0.25	11.23±0.61	21.65±0.68	18.17±0.15

蜜环菌YUD17010中一个新的原伊鲁烷型倍半萜芳基酯

A New Protoilludane Sesquiterpene Aryl Ester from Armillaria sp. YUD17010

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