Polyketides from the Deep-Sea-Derived FungusDiaporthe phaseolorum FS459

doi:10.6023/cjoc202010046

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1591-1598.DOI: 10.6023/cjoc202010046 Previous Articles Next Articles

ARTICLES

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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Abstract

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

Cite this article

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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Fig. & Tab. 8

References 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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