海南红树红榄李内生真菌Penicillium sclerotiorum HLL113次级代谢产物研究

doi:10.6023/cjoc202109021

有机化学 ›› 2022, Vol. 42 ›› Issue (3): 896-900.DOI: 10.6023/cjoc202109021 上一篇下一篇

研究简报

海南红树红榄李内生真菌Penicillium sclerotiorum HLL113次级代谢产物研究

杨静雨^a^,^b, 唐敏敏^a^,^b, 陈丽^a^,^b, 赖心怡^a^,^b, 卓欣^a^,^b, 周学明^a^,^b^,^*(), 陈光英^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

收稿日期:2021-09-15 修回日期:2021-10-23 发布日期:2021-11-09
通讯作者: 周学明, 陈光英
基金资助:
国家自然科学基金(41866005); 国家自然科学基金(22177023); 海南省重大科技计划(ZDKJ202008); 海南省研究生创新研究(Hys2020-307)

Study on the Secondary Metabolites of Endophytic Penicillium sclerotiorum HLL113

Jing-Yu Yang^a^,^b, Min-Min Tang^a^,^b, Li Chen^a^,^b, Xin-Yi Lai^a^,^b, Xin Zhuo^a^,^b, Xue-Ming Zhou^a^,^b(), Guang-Ying 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

Received:2021-09-15 Revised:2021-10-23 Published:2021-11-09
Contact: Xue-Ming Zhou, Guang-Ying Chen
Supported by:
National Natural Science Foundation of China(41866005); National Natural Science Foundation of China(22177023); Key Science and Technology Program of Hainan Province(ZDKJ202008); Innovative Research Projects of Postgraduates in Hainan Universities(Hys2020-307)

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摘要/Abstract

从红树红榄李来源内生真菌Penicillium sclerotiorum HLL113中分离纯化得到两个新的呋喃衍生物(2S,3S,5S)-2- (2-hydroxyethyl)-3-hydroxy-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran (1), (2S,3S,5S)-2-allyl-3-hydroxy-5-(2-hydroxy- propan-2-yl)-2-methyltetrahydrofuran (2)和6个已知的甾体化合物, 其中6,9-epoxy-ergosta-7,22-dien-3-ol (5)为首次从青霉属中分离得到, 它们的结构经多种现代波谱技术确定. 对所有化合物进行了α-葡萄糖苷酶抑制活性测试, 活性测试结果表明(22E,4R)-ergosta-7,9(11),22-triene-3β,5α,6β-triol (7)和derrisisoflavone K (8)对α-葡萄糖苷酶具有显著的抑制活性.

关键词: 红榄李, Penicillium sclerotiorum, 次级代谢产物, 呋喃衍生物, α-葡萄糖苷酶抑制活性

Two new furan derivatives, (2S,3S,5S)-2-(2-hydroxyethyl)-3-hydroxy-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran (1) and (2S,3S,5S)-2-allyl-3-hydroxy-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran (2), together with six known steroid compounds were isolated from Penicillium sclerotiorum HLL113. 6,9-Epoxy-ergosta-7,22-dien-3-ol (5) was isolated from the genus Penicillium for the first time. Their structures were elucidated on the basis of extensive spectroscopic methods. The test results of α-glucosidase inhibitory activity showed that (22E,4R)-ergosta-7,9(11),22-triene-3β,5α,6β-triol (7) and derrisisoflavone K (8) have significant inhibitory activity.

Key words: Lumnitzera littorea, Penicillium sclerotiorum, secondary metabolite, furan derivative, inhibitory activity against α-glucosidase

引用此文

杨静雨, 唐敏敏, 陈丽, 赖心怡, 卓欣, 周学明, 陈光英. 海南红树红榄李内生真菌Penicillium sclerotiorum HLL113次级代谢产物研究[J]. 有机化学, 2022, 42(3): 896-900.

Jing-Yu Yang, Min-Min Tang, Li Chen, Xin-Yi Lai, Xin Zhuo, Xue-Ming Zhou, Guang-Ying Chen. Study on the Secondary Metabolites of Endophytic Penicillium sclerotiorum HLL113[J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 896-900.

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Position	1		2
Position	δ_H (MeOH-d₄)	δ_C (CDCl₃)	δ_H (MeOH-d₄)	δ_C (CDCl₃)
2	—	84.5 (C)	—	87.6 (C)
3	3.61 (dd, J=10.0, 2.0 Hz)	77.6 (CH)	3.83 (dd, J=8.4, 5.6 Hz)	75.5 (CH)
4	1.20~1.26 (m), 1.81~1.89 (m)	26.4 (CH₂)	1.84~1.90 (m), 2.18~2.25 (m)	34.7 (CH₂)
5	3.78 (dd, J=9.2, 6.0 Hz)	87.4 (CH)	3.92 (dd, J=5.6, 3.2 Hz)	83.4 (CH)
6	1.66~1.72 (m), 2.01~2.09 (m)	34.8 (CH₂)	5.88 (dd, J=17.2, 10.8 Hz)	142.1 (CH)
7	3.44 (dd, J=11.2, 9.6 Hz) 3.86 (dd, J=11.2, 1.6 Hz)	47.2 (CH₂)	5.04 (dd, J=10.8, 1.6 Hz) 5.24 (dd, J=17.2, 1.6 Hz)	112.9 (CH₂)
8	1.12 (s)	24.2 (CH₃)	1.24 (s)	21.1 (CH₃)
9	—	70.7 (C)	—	71.8 (C)
10	1.18 (s)	22.5 (CH₃)	1.14 (s)	26.2 (CH₃)
11	1.21 (s)	27.7 (CH₃)	1.26 (s)	27.7 (CH₃)

Position	1		2
Position	δ_H (MeOH-d₄)	δ_C (CDCl₃)	δ_H (MeOH-d₄)	δ_C (CDCl₃)
2	—	84.5 (C)	—	87.6 (C)
3	3.61 (dd, J=10.0, 2.0 Hz)	77.6 (CH)	3.83 (dd, J=8.4, 5.6 Hz)	75.5 (CH)
4	1.20~1.26 (m), 1.81~1.89 (m)	26.4 (CH₂)	1.84~1.90 (m), 2.18~2.25 (m)	34.7 (CH₂)
5	3.78 (dd, J=9.2, 6.0 Hz)	87.4 (CH)	3.92 (dd, J=5.6, 3.2 Hz)	83.4 (CH)
6	1.66~1.72 (m), 2.01~2.09 (m)	34.8 (CH₂)	5.88 (dd, J=17.2, 10.8 Hz)	142.1 (CH)
7	3.44 (dd, J=11.2, 9.6 Hz) 3.86 (dd, J=11.2, 1.6 Hz)	47.2 (CH₂)	5.04 (dd, J=10.8, 1.6 Hz) 5.24 (dd, J=17.2, 1.6 Hz)	112.9 (CH₂)
8	1.12 (s)	24.2 (CH₃)	1.24 (s)	21.1 (CH₃)
9	—	70.7 (C)	—	71.8 (C)
10	1.18 (s)	22.5 (CH₃)	1.14 (s)	26.2 (CH₃)
11	1.21 (s)	27.7 (CH₃)	1.26 (s)	27.7 (CH₃)

Compound	IC₅₀/(µmol•mL^–1)
1	2009.566
2	1851.642
3	1910.011
4	1467.279
5	1791.437
6	1472.091
7	861.211
8	940.376
阿卡波糖	1954.935

Compound	IC₅₀/(µmol•mL^–1)
1	2009.566
2	1851.642
3	1910.011
4	1467.279
5	1791.437
6	1472.091
7	861.211
8	940.376
阿卡波糖	1954.935

海南红树红榄李内生真菌Penicillium sclerotiorum HLL113次级代谢产物研究

Study on the Secondary Metabolites of Endophytic Penicillium sclerotiorum HLL113

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