深海放线菌Streptomyces koyangensis SCSIO 5802中次级代谢产物neoabyssomicin H的分离鉴定*

doi:10.11978/2022107

热带海洋学报 ›› 2023, Vol. 42 ›› Issue (3): 169-173.doi: 10.11978/2022107CSTR: 32234.14.2022107

深海放线菌Streptomyces koyangensis SCSIO 5802中次级代谢产物neoabyssomicin H的分离鉴定^*

宋永相¹^,²^,³^,⁴(), 李晓悦¹^,³, 鞠建华¹^,²^,³^,⁴

1.中国科学院热带海洋生物资源与生态重点实验室(中国科学院南海海洋研究所), 广东省海洋药物重点实验室, 广东广州 510301
2.南方海洋科学与工程广东省实验室(广州), 广东广州 511458
3.中国科学院大学, 北京 100049
4.三亚中科海洋研究院, 海南三亚, 572000

收稿日期:2022-05-12 修回日期:2022-06-13 出版日期:2023-05-10 发布日期:2022-06-16
作者简介:
宋永相(1980—), 男, 河南省濮阳市人, 副研究员, 从事海洋微生物活性物质的发掘与应用研究。email: songx@scsio.ac.cn
*感谢中国科学院南海海洋研究所分析测试中心的肖志会老师、郑晓红老师在核磁数据测试, 孙爱君老师、马宣老师、张云老师在质谱和X-Ray晶体数据测试方面给予的帮助。
基金资助:
海南省重大科技资助计划(ZDKJ202018); 南方海洋科学与工程广东省实验室(广州)人才团队引进重大专项(GML2019ZD0406); 广东省本土创新创业团队项目(2019BT02Y262); 广东省海洋经济发展(海洋六大产业)专项资金(GDNRC[2021]54); 国家自然科学基金面上项目(41676151)

The isolation and identification of neoabyssomicin H from the deep-sea derived Streptomyces koyangensis SCSIO 5802^*

SONG Yongxiang¹^,²^,³^,⁴(), LI Xiaoyue¹^,³, JU Jianhua¹^,²^,³^,⁴

1. CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China
2. Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), Guangzhou 511453, China
3. University of Chinese Academy of Sciences, Beijing 100049, China
4. Sanya Institute of Oceanology, SCSIO, Sanya 572000, China

Received:2022-05-12 Revised:2022-06-13 Online:2023-05-10 Published:2022-06-16
Supported by:
Finance Science and Technology Project of Hainan Province(ZDKJ202018); Key Special Project for Introduced Talents Team of Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou)(GML2019ZD0406); Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program(2019BT02Y262); Guangdong Provincial Marine Economic Development (Six Major Marine Undertakings) Special Fund Project(GDNRC[2021]54); National Natural Science Foundation of China(41676151)

摘要/Abstract

摘要：

深渊霉素类化合物具有抗结核分枝杆菌、抗MRSA (methicillin-resistant Staphylococcus aureus)、选择性激活潜伏HIV病毒等生物活性, 具有显著的开发利用潜力。本文在前期研究基础上, 进一步对深海链霉菌Streptomyces koyangensis SCSIO 5802新型深渊霉素类化合物的生产潜力进行发掘, 综合利用多种色谱分离手段, 获得一个结构新颖的深渊霉素硫醚二聚体化合物, 命名为neoabyssomicin H。该化合物的结构通过UV、IR、HR-ESI-MS, 1D和2D NMR及X-Ray单晶铜靶衍射等进行了鉴定。活性测试结果表明, neoabyssomicin H对金黄色葡萄球菌和系列临床MRSA的MIC(minimum inhibitory concentration)值大于128μg·mL^-1。该研究进一步丰富了深渊霉素类化合物, 为硫醚二聚体类深渊霉素活性化合物的研究提供了新的分子实体。

关键词: 深海放线菌, 深渊霉素, 抗菌, 硫醚二聚体

Abstract:

Abyssomicins have attracted much attention for their potential of being developed into novel lead compounds by virtue of their antimicrobial and antiviral activities. The deep-sea derived strain of Streptomyces koyangensis SCSIO 5802 produces a series of abyssomicins. In order to further expand the library of abyssomicins, the fermentation fractions of this strain have been thoroughly investigated, which led to the first isolation of a new thioether dimer of abyssomicin with a macrolide moiety named neoabyssomicin H. Its structure was elucidated by using UV, IR, HR-ESI-MS, 1D and 2D NMR, and X-ray single crystal using Cu Kα radiation, etc. In antibacterial activity assays, the compound was found inactive against Staphylococcus aureus ATCC 29213 and a panel of MRSA clinical isolates at 128 μg·mL^-1. This study has expanded the scope of abyssomicins with a new molecular entity for study on this class of lead compounds.

Key words: deep-sea derived actinomycete, abyssomicin, antibacteria, thioether dimerization

宋永相, 李晓悦, 鞠建华. 深海放线菌Streptomyces koyangensis SCSIO 5802中次级代谢产物neoabyssomicin H的分离鉴定^*[J]. 热带海洋学报, 2023, 42(3): 169-173.

SONG Yongxiang, LI Xiaoyue, JU Jianhua. The isolation and identification of neoabyssomicin H from the deep-sea derived Streptomyces koyangensis SCSIO 5802^*[J]. Journal of Tropical Oceanography, 2023, 42(3): 169-173.

图/表 4

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图3

参考文献 10

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[5]	JI XIAOQI, TU JIAJIA, SONG YONGXIANG, et al, 2020. A luciferase-like monooxygenase and flavin reductase pair abme2/abmz catalyzes baeyer-villiger oxidation in neoabyssomicin biosynthesis[J]. ACS Catalysis, 10(4): 2591-2595. doi: 10.1021/acscatal.9b05488
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原子序号	碳谱化学位移δ_C	氢谱化学位移δ_H	HMBC相关数据
1/1', C	170.9
2/2', C	100.9
3/3', C	194.4
4/4', CH₂	37.4	2.97, ddd (13.1, 6.5, 3.5)	5/5',
		2.64, m	6/6', 3/3'
5/5', CH₂	32.9	2.08, m	3/3'
		2.02, m	4/4', 3/3'
6/6', CH	73.2	4.85, overlapped
7/7', C	170.2
8/8', CH₂	37.2	2.81, overlapped	7/7', 9/9', 10/10'
		2.66, overlapped	9/9'
9/9', CH	38.8	2.79, overlapped	7/7', 8/8', 9'/9, 15/15'
10/10', CH	51.4	2.68, dd (5.0, 4.3)	9/9', 11/11', 15/15', 16/16'
11/11', CH	71.1	4.51, d (4.3)	10/10', 9/9', 12/12', 18/18', 13/13'
12/12', C	90.6
13/13', CH	27.8	2.62, m	15/15', 19/19'
14/14', CH₂	37.1	2.81, overlapped	19/19', 13/13', 10/10', 15/15', 16/16'
		2.40, dd (17.5, 5.5)	1/1', 2/2', 13/13'
15/15', C	77.0
16/16', C	186.6
17/17', CH₃	18.9	1.22, d (6.2)	5/5', 6/6'
18/18', CH₃	18.1	1.57, s	11/11', 12/12', 13/13'
19/19', CH₃	15.5	1.01, d (7.1)	12/12', 13/13', 14/14'

深海放线菌Streptomyces koyangensis SCSIO 5802中次级代谢产物neoabyssomicin H的分离鉴定^*

The isolation and identification of neoabyssomicin H from the deep-sea derived Streptomyces koyangensis SCSIO 5802^*

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