Study on the Secondary Metabolites of the Endophytic Fungus Aspergillus terreus HQ100X-1 in Scutellaria formosana

doi:10.6023/cjoc202202016

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (9): 2961-2966.DOI: 10.6023/cjoc202202016 Previous Articles Next Articles

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蓝花黄芩内生真菌Aspergillus terreus HQ100X-1次级代谢产物研究

黄丹^a^,^b, 农旭华^a^,^b, 杨建妮^a^,^b, 李琛^a^,^b, 韩长日^c^,^*(), 陈光英^a^,^b, 宋小平^a^,^b, 孙振范^c, 惠阳^a^,^b^,^*(), 陈文豪^a^,^b^,^*()

a 海南师范大学化学与化工学院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
c 海南科技职业大学药食同源植物资源海南省重点实验室海口 571126

收稿日期:2022-02-13 修回日期:2022-03-28 发布日期:2022-06-22
通讯作者: 韩长日, 惠阳, 陈文豪
作者简介:
^† 共同第一作者
基金资助:
国家自然科学基金(22167013); 海南省重点研发项目(ZDYF2021SHFZ221); 海南省自然科学基金(221RC541); 海南省教育厅项目(Hnky2021ZD-10); 海南省研究生创新科研课题(Hys2021-72); 大学生创新创业训练计划(202111658002); 大学生创新创业训练计划(202111658003)

Study on the Secondary Metabolites of the Endophytic Fungus Aspergillus terreus HQ100X-1 in Scutellaria formosana

Dan Huang^a^,^b, Xuhua Nong^a^,^b, Jianni Yang^a^,^b, Chen Li^a^,^b, Changri Han^c(), Guangying Chen^a^,^b, Xiaoping Song^a^,^b, Zhenfan Sun^c, Yang Hui^a^,^b(), Wenhao Chen^a^,^b()

a Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, 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
c Key Laboratory of Medicinal and Edible Plants Resources of Hainan Province, Hainan Vocational University of Science and Technology, Haikou 571126

Received:2022-02-13 Revised:2022-03-28 Published:2022-06-22
Contact: Changri Han, Yang Hui, Wenhao Chen
About author:
^† These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(22167013); Key Project of Research and Development of Hainan Province(ZDYF2021SHFZ221); Hainan Provincial Natural Science Foundation of China(221RC541); Education Department of Hainan Province(Hnky2021ZD-10); Program for Hainan Provincial Graduate Innovation Research Project(Hys2021-72); Innovation Training Program for College Students(202111658002); Innovation Training Program for College Students(202111658003)

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Abstract

Two new compounds, terrustone (1) and asperteretone G (2) together with ten known compounds were isolated from Scutellaria formosana endophytic fungus Aspergillus terreus HQ100X-1, terrustone (1) is a trihydroxycyclopentanone with four consecutive chiral centers. Their structures were determined by 1D/2D NMR data along with electrostatic circular dichroism (ECD) calculation for configurational assignment. Compound rbrolide R (4) showed antibacterial activity against Staphylococcus aureus with minimum inhibitory concentration (MIC) value of 2.5 μg/mL.

Key words: scutellaria formosana, Aspergillus terreus, antibacterial activity

Cite this article

Dan Huang, Xuhua Nong, Jianni Yang, Chen Li, Changri Han, Guangying Chen, Xiaoping Song, Zhenfan Sun, Yang Hui, Wenhao Chen. Study on the Secondary Metabolites of the Endophytic Fungus Aspergillus terreus HQ100X-1 in Scutellaria formosana[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2961-2966.

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Fig. & Tab. 6

References 23

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Position	1 (in MeOH-d₄)		Position	2 (in MeOH-d₄)
Position	δ_H (J in Hz)	δ_C	Position	δ_H (J in Hz)	δ_C
1		212.5 (C)	1		170.4 (C)
2		84.4 (C)	2		132.3 (C)
3	2.33~2.40 (m)	43.4 (CH)	3		154.5 (C)
4	3.96 (dd, 1.2, 3.6)	73.7 (CH)	4		121.0 (C)
5	3.59 (d, 3.6)	80.1 (CH)	5	3.68 (s)	31.5 (CH₂)
1'	2.08 (ddd, 1.2, 4.0,13.2)	39.7 (CH₂)	6/7	3.26 (s)	51.9 (CH₃)
1'	2.86 (t, 13.2)	39.7 (CH₂)	1'		121.2 (C)
2'	5.51~5.58 (m)	131.8 (CH)	2'/6'	7.31 (d, 8.5)	131.7 (CH×2)
3'	5.58~5.65 (m)	127.5 (CH)	3'/5'	6.83 (d, 8.5)	116.3 (CH×2)
4'	1.70 (d, 5.6)	18.2 (CH₃)	4'		159.6 (C)
1''	2.62 (dd, 6.0, 15.6)	33.4 (CH₂)	1''		127.8 (C)
1''	3.11 (dd, 8.8, 15.6)	33.4 (CH₂)	2''	6.78 (s)	131.3 (CH)
2''	5.00 (dd, 6.0, 8.8)	119.3 (CH)	3''		129.1 (C)
3''		135.2 (C)	4''		154.8 (C)
4''	1.65 (s)	26.1 (CH₃)	5''	6.59 (d, 8.0)	115.6 (CH)
5''	1.63 (s)	18.1 (CH₃)	6''	6.76 (d, 8.0)	128.5 (CH)
			7''	3.17 (d, 7.4)	28.9 (CH₂)
			8''	5.20 (t, 7.4)	123.8 (CH)
			9''		133.1 (C)
			10''	1.64 (s)	17.8 (CH₃)
			11''	1.71 (s)	26.0 (CH₃)

Position	1 (in MeOH-d₄)		Position	2 (in MeOH-d₄)
Position	δ_H (J in Hz)	δ_C	Position	δ_H (J in Hz)	δ_C
1		212.5 (C)	1		170.4 (C)
2		84.4 (C)	2		132.3 (C)
3	2.33~2.40 (m)	43.4 (CH)	3		154.5 (C)
4	3.96 (dd, 1.2, 3.6)	73.7 (CH)	4		121.0 (C)
5	3.59 (d, 3.6)	80.1 (CH)	5	3.68 (s)	31.5 (CH₂)
1'	2.08 (ddd, 1.2, 4.0,13.2)	39.7 (CH₂)	6/7	3.26 (s)	51.9 (CH₃)
1'	2.86 (t, 13.2)	39.7 (CH₂)	1'		121.2 (C)
2'	5.51~5.58 (m)	131.8 (CH)	2'/6'	7.31 (d, 8.5)	131.7 (CH×2)
3'	5.58~5.65 (m)	127.5 (CH)	3'/5'	6.83 (d, 8.5)	116.3 (CH×2)
4'	1.70 (d, 5.6)	18.2 (CH₃)	4'		159.6 (C)
1''	2.62 (dd, 6.0, 15.6)	33.4 (CH₂)	1''		127.8 (C)
1''	3.11 (dd, 8.8, 15.6)	33.4 (CH₂)	2''	6.78 (s)	131.3 (CH)
2''	5.00 (dd, 6.0, 8.8)	119.3 (CH)	3''		129.1 (C)
3''		135.2 (C)	4''		154.8 (C)
4''	1.65 (s)	26.1 (CH₃)	5''	6.59 (d, 8.0)	115.6 (CH)
5''	1.63 (s)	18.1 (CH₃)	6''	6.76 (d, 8.0)	128.5 (CH)
			7''	3.17 (d, 7.4)	28.9 (CH₂)
			8''	5.20 (t, 7.4)	123.8 (CH)
			9''		133.1 (C)
			10''	1.64 (s)	17.8 (CH₃)
			11''	1.71 (s)	26.0 (CH₃)

蓝花黄芩内生真菌Aspergillus terreus HQ100X-1次级代谢产物研究

Study on the Secondary Metabolites of the Endophytic Fungus Aspergillus terreus HQ100X-1 in Scutellaria formosana

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