Three New Polyketides from the Culture of Mangrove-Derived FungusEupenicilliumsp. HJ002

doi:10.6023/cjoc202102052

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2905-2909.DOI: 10.6023/cjoc202102052 Previous Articles Next Articles

NOTES

红树来源真菌Eupenicillium sp. HJ002发酵产物中三个新的聚酮类化合物

蔡瑾^a^,^b, 农旭华^a^,^b, 王斌^a^,^b, 曾尾女^a^,^b, 黄国雷^a^,^b, 张子怡^a^,^b, 郑彩娟^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 海南师范大学海南省热带药用植物化学重点实验室海口 571158

收稿日期:2021-02-28 修回日期:2021-03-29 发布日期:2021-04-25
通讯作者: 郑彩娟
基金资助:
海南省重点研发计划(ZDYF2019183); 国家自然科学基金(31760093); 海南省自然科学基金(220RC593); 海南省自然科学基金(218MS045)

Three New Polyketides from the Culture of Mangrove-Derived FungusEupenicilliumsp. HJ002

Jin Cai^a^,^b, Xuhua Nong^a^,^b, Bin Wang^a^,^b, Weinü Zeng^a^,^b, Guolei Huang^a^,^b, Ziyi Zhang^a^,^b, Caijuan Zheng^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, Hainan Normal University, Haikou 571158

Received:2021-02-28 Revised:2021-03-29 Published:2021-04-25
Contact: Caijuan Zheng
Supported by:
Key Research and Development Program of Hainan Province(ZDYF2019183); National Natural Science Foundation of China(31760093); National Natural Science Foundation of Hainan Province(220RC593); National Natural Science Foundation of Hainan Province(218MS045)

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Abstract

A pair of novel isochroman epimers eupenicilchromans A, B, and one new isocoumarin derivative eupenicilmarin A, together with five known compounds were isolated from the culture of mangrove-derived fungusEupenicilium sp. HJ002. The structures of the new compounds, including the absolute configurations, were determined by comprehensive spectroscopic methods, experimental and calculated electronic circular dichroism (ECD) methods. Eupenicilchromans A, B showed potent antioxidant activeties with the IC₅₀ values of 0.6 and 2.6 mmol/L, respectively, and eupenicilchroman A displayed better antioxidant activity than the positive control trolox (IC₅₀=1.6 mmol/L).

Key words: Eupenicillium sp., isochroman, isocoumarin, antioxidant activity

Cite this article

Jin Cai, Xuhua Nong, Bin Wang, Weinü Zeng, Guolei Huang, Ziyi Zhang, Caijuan Zheng. Three New Polyketides from the Culture of Mangrove-Derived FungusEupenicilliumsp. HJ002[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2905-2909.

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Fig. & Tab. 5

References 17

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Position	1^a		2^a		3^b
Position	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C
1	5.18 (d, 6.0)	68.3 (CH)	5.38 (d, 6.6)	68.5 (CH)	1.36, (d, 6.4)	164.9 (C)
3	4.45~4.53 (m)	73.9 (CH)	4.51~4.61 (m)	73.8 (CH)	4.50~4.58 (m)	74.3 (CH)
4	2.63~2.69 (m)	31.7 (CH₂)	2.90 (dd, 16.4, 3.0, H-4eq) 2.66 (dd, 16.4, 11.4, H-4ax)	31.6 (CH₂)	2.81 (dd, 16.8, 3.2) 2.72 (dd, 16.8, 11.4)	32.3 (CH₂)
4a		136.5 (C)		136.8 (C)		139.4 (C)
5		116.1 (C)		116.9 (C)		127.3 (C)
6	7.78 (d, 8.6)	131.8 (CH)	7.97 (d, 8.6)	132.2 (CH)		160.2 (C)
7	6.77 (d, 8.6)	117.5 (CH)	6.87 (d, 8.6)	117.3, (CH)	6.93 (d, 8.6)	115.8 (CH)
8		161.6 (C)		161.4 (C)	7.85 (d, 8.6)	133.3 (CH)
8a		124.6 (C)		124.0 (C)		116.2 (C)
9	1.54 (d, 6.6)	22.1 (CH₃)	1.53 (d, 6.6)	22.9 (CH₃)	1.36 (d, 6.4)	32.4 (CH₃)
10	1.50 (d, 6.4)	21.1 (CH₃)	1.49 (d, 6.4)	21.1 (CH₃)		203.4 (C)
11		166.6 (C)		165.9 (C)	2.49 (s)	20.9 (CH₃)
8-OH	9.40 (s)		9.39 (s)

Position	1^a		2^a		3^b
Position	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C
1	5.18 (d, 6.0)	68.3 (CH)	5.38 (d, 6.6)	68.5 (CH)	1.36, (d, 6.4)	164.9 (C)
3	4.45~4.53 (m)	73.9 (CH)	4.51~4.61 (m)	73.8 (CH)	4.50~4.58 (m)	74.3 (CH)
4	2.63~2.69 (m)	31.7 (CH₂)	2.90 (dd, 16.4, 3.0, H-4eq) 2.66 (dd, 16.4, 11.4, H-4ax)	31.6 (CH₂)	2.81 (dd, 16.8, 3.2) 2.72 (dd, 16.8, 11.4)	32.3 (CH₂)
4a		136.5 (C)		136.8 (C)		139.4 (C)
5		116.1 (C)		116.9 (C)		127.3 (C)
6	7.78 (d, 8.6)	131.8 (CH)	7.97 (d, 8.6)	132.2 (CH)		160.2 (C)
7	6.77 (d, 8.6)	117.5 (CH)	6.87 (d, 8.6)	117.3, (CH)	6.93 (d, 8.6)	115.8 (CH)
8		161.6 (C)		161.4 (C)	7.85 (d, 8.6)	133.3 (CH)
8a		124.6 (C)		124.0 (C)		116.2 (C)
9	1.54 (d, 6.6)	22.1 (CH₃)	1.53 (d, 6.6)	22.9 (CH₃)	1.36 (d, 6.4)	32.4 (CH₃)
10	1.50 (d, 6.4)	21.1 (CH₃)	1.49 (d, 6.4)	21.1 (CH₃)		203.4 (C)
11		166.6 (C)		165.9 (C)	2.49 (s)	20.9 (CH₃)
8-OH	9.40 (s)		9.39 (s)

红树来源真菌Eupenicillium sp. HJ002发酵产物中三个新的聚酮类化合物

Three New Polyketides from the Culture of Mangrove-Derived FungusEupenicilliumsp. HJ002

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