深海真菌Diaporthe phaseolorum FS459的聚酮类化合物研究

doi:10.6023/cjoc202010046

有机化学 ›› 2021, Vol. 41 ›› Issue (4): 1591-1598.DOI: 10.6023/cjoc202010046 上一篇下一篇

研究论文

深海真菌Diaporthe phaseolorum FS459的聚酮类化合物研究

胡彩云^a^,^b, 李赛妮^a, 陈玉婵^a, 高晓霞^b, 刘昭明^a^,^*(), 章卫民^a^,^*()

a 广东省微生物研究所广东省科学院华南应用微生物国家重点实验室广东省菌种保藏与应用重点实验东省微生物应用新技术公共实验室广州 510070
b 广东药科大学药学院广州 510070

收稿日期:2020-10-31 修回日期:2020-12-14 发布日期:2020-12-31
通讯作者: 刘昭明, 章卫民
基金资助:
国家自然科学基金(41906106); 国家自然科学基金(31272087); 广东省海洋经济发展专项基金(GDNRC[2020]042); 广东省科学院建设国内一流研究机构行动专项(2019GDASYL-0103007); 广东省自然科学基金(2016A030312014)

Polyketides from the Deep-Sea-Derived FungusDiaporthe phaseolorum FS459

Caiyun Hu^a^,^b, Saini Li^a, Yuchan Chen^a, Xiaoxia Gao^b, Zhaoming Liu^a^,^*(), Weimin Zhang^a^,^*()

a State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangdong Academy of Sciences, Guangzhou 510070
b College of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006

Received:2020-10-31 Revised:2020-12-14 Published:2020-12-31
Contact: Zhaoming Liu, Weimin Zhang
About author:
* Corresponding authors. E-mail: wmzhang@gdim.cn;
E-mail: liuzm@gdim.cn
Supported by:
National Natural Science Foundation of China(41906106); National Natural Science Foundation of China(31272087); Guangdong Provincial Special Fund for Marine Economic Development Project(GDNRC[2020]042); Guangdong Academy of Sciences Project of Science and Technology Development(2019GDASYL-0103007); Natural Science Foundation of Guangdong Province(2016A030312014)

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摘要/Abstract

从深海真菌Diaporthe phaseolorum FS459中分离出10个聚酮化合物,包括3个新的色酮衍生物(1、2和5),一对新的差向异构体混合物(3和4), 1个新的Azaphilone类似物(6)及4个已知的化合物(7~10). 它们的结构是基于综合波谱分析进行确定, 同时其绝对构型通过对比实测电子圆二色谱(ECD)曲线与量子化学计算得出的理论值来确定. 化合物1~4具有罕见的2?,3?-二甲基二氧戊环结构单元. 此外, 本研究还评估了化合物1~10的体外细胞毒性、抗菌活性及NO产生的抑制效果.

关键词: 聚酮, 深海真菌, Diaporthe phaseolorum, 细胞毒

Ten polyketides, including three new chromone derivatives (1, 2 and 5), a pair of new epimer mixtures (3 and 4), a new azaphilone analogue (6) and four known compounds (7~10) were isolated from the deep-sea-derived fungus Diaporthe phaseolorumFS459. Their structures were elucidated by extensive spectroscopic analysis, while the absolute configurations were established by comparison of experimental and quantum chemical calculated electronic circular dichroism (ECD) spectra. Compounds 1~4 possessed a rare 2?,3?-dimethyl-dioxolane moiety. Thein vitro cytotoxicity, antibacterial activities and NO production inhibitory effects of compounds 1~10 were evaluated.

Key words: polyketides, deep-sea-derived fungus, Diaporthe phaseolorum, cytotoxicity

引用此文

胡彩云, 李赛妮, 陈玉婵, 高晓霞, 刘昭明, 章卫民. 深海真菌Diaporthe phaseolorum FS459的聚酮类化合物研究[J]. 有机化学, 2021, 41(4): 1591-1598.

Caiyun Hu, Saini Li, Yuchan Chen, Xiaoxia Gao, Zhaoming Liu, Weimin Zhang. Polyketides from the Deep-Sea-Derived FungusDiaporthe phaseolorum FS459[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1591-1598.

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图/表 8

参考文献 21

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Position	1^a		2^a
Position	δ_C, type	δ_H(J/Hz)	δ_C, type	δ_H(J/Hz)
2	67.9, CH₂	4.70, dd (11.4, 8.3)	67.9, CH₂	4.71, dd (11.9, 7.8)
2	67.9, CH₂	4.58, dd (11.4, 4.5)	4.57, dd (11.5, 4.3)	4.71, dd (11.9, 7.8)
3	51.4, CH	2.62, ddd (8.3, 6.4, 4.5)	51.5, CH	2.58, ddd (8.0, 7.8, 4.3)
4	190.0, C		190.0, C
4a	112.1, C		112.0, C
5	136.2, C		136.2, C
6	109.2, CH	6.54, d (2.4)	109.2, CH	6.54, d (2.4)
7	165.4, C		165.1, C
8	102.0, CH	6.46, d (2.4)	102.0, CH	6.47, d (2.4)
8a	163.8, C		163.8, C
9	64.4, CH	4.45, ddd (10.1, 6.4, 2.0)	64.5, CH	4.44, m
10	44.1, CH₂	2.02, dd (14.4, 2.0)	43.8, CH₂	2.03, dd (14.6, 1.9)
10	44.1, CH₂	1.85 dd (14.4, 10.1)	43.8, CH₂	1.89, dd (14.6, 10.4)
11	109.2, C		109.3, C
12	25.8, CH₃	1.39, s	26.1, CH₃	1.38, s
13	169.7, C		169.7, C
14	52.9, CH₃	3.93, s	52.9, CH₃	3.93, s
15	55.9, CH₃	3.83, s	55.9, CH₃	3.83, s
1?	16.4, CH₃	1.25, d (5.9)	16.3, CH₃	1.27, d (5.8)
2?	78.3, CH	3.71, dq (8.3, 5.9)	78.0, CH	3.72, dq (9.4, 5.8)
3?	78.7, CH	3.65, dq (8.3, 5.9)	80.4, CH	3.68, dq (9.4, 5.8)
4?	17.1, CH₃	1.24, d (5.9)	17.2, CH₃	1.24, d (5.8)

Position	1^a		2^a
Position	δ_C, type	δ_H(J/Hz)	δ_C, type	δ_H(J/Hz)
2	67.9, CH₂	4.70, dd (11.4, 8.3)	67.9, CH₂	4.71, dd (11.9, 7.8)
2	67.9, CH₂	4.58, dd (11.4, 4.5)	4.57, dd (11.5, 4.3)	4.71, dd (11.9, 7.8)
3	51.4, CH	2.62, ddd (8.3, 6.4, 4.5)	51.5, CH	2.58, ddd (8.0, 7.8, 4.3)
4	190.0, C		190.0, C
4a	112.1, C		112.0, C
5	136.2, C		136.2, C
6	109.2, CH	6.54, d (2.4)	109.2, CH	6.54, d (2.4)
7	165.4, C		165.1, C
8	102.0, CH	6.46, d (2.4)	102.0, CH	6.47, d (2.4)
8a	163.8, C		163.8, C
9	64.4, CH	4.45, ddd (10.1, 6.4, 2.0)	64.5, CH	4.44, m
10	44.1, CH₂	2.02, dd (14.4, 2.0)	43.8, CH₂	2.03, dd (14.6, 1.9)
10	44.1, CH₂	1.85 dd (14.4, 10.1)	43.8, CH₂	1.89, dd (14.6, 10.4)
11	109.2, C		109.3, C
12	25.8, CH₃	1.39, s	26.1, CH₃	1.38, s
13	169.7, C		169.7, C
14	52.9, CH₃	3.93, s	52.9, CH₃	3.93, s
15	55.9, CH₃	3.83, s	55.9, CH₃	3.83, s
1?	16.4, CH₃	1.25, d (5.9)	16.3, CH₃	1.27, d (5.8)
2?	78.3, CH	3.71, dq (8.3, 5.9)	78.0, CH	3.72, dq (9.4, 5.8)
3?	78.7, CH	3.65, dq (8.3, 5.9)	80.4, CH	3.68, dq (9.4, 5.8)
4?	17.1, CH₃	1.24, d (5.9)	17.2, CH₃	1.24, d (5.8)

Position	3^a		4^a
Position	δ_C, type	δ_H(J in Hz)	δ_C, type	δ_H(J in Hz)
2	68.5, CH₂	4.53, overlap	68.4, CH₂	4.53, overlap
		4.55, overlap		4.55, overlap
3	50.5, CH	2.89, ddd (9.2, 4.7, 4.7)	50.5, CH	2.89, ddd (9.2, 4.7, 4.7)
4	190.0, C		189.9, C
4a	112.7, C		112.7, C
5	136.1, C		136.1, C
6	109.5, CH	6.55, brs	109.5, CH	6.55, brs
7	165.1, C		165.1, C
8	102.1, CH	6.46, brs	102.1, CH	6.47, brs
8a	163.8, C		163.8, C
9	67.1, CH	4.47, overlap	67.2, CH	4.47, overlap
10	42.7, CH₂	2.00, overlap	42.2, CH₂	2.00, overlap
		1.83 overlap		1.83, overlap
11	109.3, C		109.3, C
12	25.6, CH₃	1.40, s	25.9, CH₃	1.39, s
13	169.7, C		169.7, C
14	52.9, CH₃	3.93, s	52.9, CH₃	3.93, s
15	55.9, CH₃	3.83, s	55.9, CH₃	3.83, s
1?	16.4, CH₃	1.27, overlap	16.3, CH₃	1.27, overlap
2?	78.3, CH	3.72, overlap	77.9, CH	3.72, overlap
3?	78.7, CH	3.65, overlap	79.5, CH	3.65, overlap
4?	17.1, CH₃	1.24, overlap	17.2, CH₃	1.24, overlap

Position	3^a		4^a
Position	δ_C, type	δ_H(J in Hz)	δ_C, type	δ_H(J in Hz)
2	68.5, CH₂	4.53, overlap	68.4, CH₂	4.53, overlap
		4.55, overlap		4.55, overlap
3	50.5, CH	2.89, ddd (9.2, 4.7, 4.7)	50.5, CH	2.89, ddd (9.2, 4.7, 4.7)
4	190.0, C		189.9, C
4a	112.7, C		112.7, C
5	136.1, C		136.1, C
6	109.5, CH	6.55, brs	109.5, CH	6.55, brs
7	165.1, C		165.1, C
8	102.1, CH	6.46, brs	102.1, CH	6.47, brs
8a	163.8, C		163.8, C
9	67.1, CH	4.47, overlap	67.2, CH	4.47, overlap
10	42.7, CH₂	2.00, overlap	42.2, CH₂	2.00, overlap
		1.83 overlap		1.83, overlap
11	109.3, C		109.3, C
12	25.6, CH₃	1.40, s	25.9, CH₃	1.39, s
13	169.7, C		169.7, C
14	52.9, CH₃	3.93, s	52.9, CH₃	3.93, s
15	55.9, CH₃	3.83, s	55.9, CH₃	3.83, s
1?	16.4, CH₃	1.27, overlap	16.3, CH₃	1.27, overlap
2?	78.3, CH	3.72, overlap	77.9, CH	3.72, overlap
3?	78.7, CH	3.65, overlap	79.5, CH	3.65, overlap
4?	17.1, CH₃	1.24, overlap	17.2, CH₃	1.24, overlap

Position	5^a		Position	6^a
Position	δ_C, type	δ_H(J/Hz)	Position	δ_C, type	δ_H(J/Hz)
			1	143.6, CH	7.35, s
2	159.5, C		2	158.3, C
3	102.4, C		3	107.0, CH	6.05, s
4	172.2, C		4	105.9, CH	5.34, s
4a	115.3, C		5	192.6, C
5	134.3, C		6	82.5, C
6	112.2, CH	6.86, s	7	43.4, CH	3.54, dd (12.9, 1.9)
7	162.7, C		8	117.0, C
8	102.0, CH	6.86, s	9	145.7, C
8a	156.9, C		10	44.9, CH	3.26, dd (12.9, 2.1)
9	94.4, CH	5.41, s	11	73.6, CH₃	3.72, d (8.9)
10	167.8, C		12	37.6, CH	1.92, m
11	20.4, CH₃	2.01, s	13	25.1, CH₂	1.73, m
12	64.7, CH₂	5.27, s		1.24, m
13	169.7, C	–	14	10.5, CH₃	0.94, t (7.4)
14	53.1, CH₃	3.99, s	15	19.5, CH₃	2.18, s
15	56.0, CH₃	3.89, s	16	18.3, CH₃	1.32, s
			17	15.9, CH₃	0.96, d (6.6)
			18	192.6, C

深海真菌Diaporthe phaseolorum FS459的聚酮类化合物研究

Polyketides from the Deep-Sea-Derived FungusDiaporthe phaseolorum FS459

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