Discovery of a New Polycyclic Tetramate Macrolactam 3-Hydroxycombamide I

doi:10.6023/cjoc202110001

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (5): 1557-1561.DOI: 10.6023/cjoc202110001 Previous Articles Next Articles

NOTES

新多环特特拉姆酸大环内酰胺3-Hydroxycombamide I的发现

颜雅倩^a, 王浩鑫^b, 李瑶瑶^a^,^*()

a 山东大学药学院天然产物化学生物学教育部重点实验室济南 250012
b 山东大学微生物技术国家重点实验室山东青岛 266237

收稿日期:2021-10-02 修回日期:2022-01-14 发布日期:2022-01-20
通讯作者: 李瑶瑶
基金资助:
国家自然科学基金(81773598); 山东大学青年学者计划(2016WLJH31); 长江学者和创新团队发展计划(IRT_17R68)

Discovery of a New Polycyclic Tetramate Macrolactam 3-Hydroxycombamide I

Yaqian Yan^a, Haoxin Wang^b, Yaoyao Li^a()

a Key Laboratory of Chemical Biology, Ministry of Education, School of Pharmaceutical Sciences, Shandong University, Jinan 250012
b State Key Laboratory of Microbial Technology, Shandong University, Qingdao, Shandong 266237

Received:2021-10-02 Revised:2022-01-14 Published:2022-01-20
Contact: Yaoyao Li
Supported by:
National Natural Science Foundation of China(81773598); Young Scholars Program of Shandong University(2016WLJH31); Program for Changjiang Scholars and Innovative Research Team in University(IRT_17R68)

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Abstract

3-Hydroxycombamide I (2), a new polycyclic tetramate macrolactam (PoTeM) bearing a 5/5/6 cyclization pattern was isolated from the recombinant strain S001-cbm-OX4-ikaD, which is derived from Streptomyces sp. S001 by integration of the modified combamides biosynthetic gene cluster. The chemical structure of 2 was determined by analysis of 1D and 2D-NMR and HRMS data. The hydroxylation of compound 2 at C-3 was deduced to be catalyzed by a hydroxylase of Streptomyces sp. S001. The antibacterial and cytotoxic activity of compound 2 was evaluated by filter paper disc diffusion and methyl thiazolyl tetrazolium (MTT) assay, respectively. The effect of compound 2 on inhibition of the T3SS (type III secretion system) of Salmonella enterica serovar Typhimurium was also investigated. However, compound 2 was inactivity in all assays. The results indicated that the hydroxylation at C-3 may occurs after the oxidative modifictions of the polycyclic system in the biosynthesis of PoTeMs.

Key words: natural products, biotransformations, Streptomyces, polycyclic tetramate macrolactams

Cite this article

Yaqian Yan, Haoxin Wang, Yaoyao Li. Discovery of a New Polycyclic Tetramate Macrolactam 3-Hydroxycombamide I[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1557-1561.

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Fig. & Tab. 5

References 18

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Position	¹H NMR	¹³C NMR	Position	¹H NMR	¹³C NMR
1		193.0s	17	1.41~1.36 (m)	48.9d
2	3.69 (br s)	67.4d	18	1.60 (t, J=9.0)	66.8d
3	3.79 (d, J=6.6)	70.4d	19	1.06~0.96 (m)	53.3d
4	1.45~1.39 (m) 1.17~1.12 (m)	31.1t	20	1.90~1.85 (m) 1.21~1.17 (m)	30.1t
5	3.30~3.24 (m) 2.62~2.52 (m)	36.2t	21	1.66~1.60 (m) 1.31~1.21 (m)	32.2t
6	7.93 (t, J=5.0)		22	1.96~1.89 (m)	45.2d
7		165.4s	23	6.40~6.35 (m)	146.5d
8	5.76 (br d, J=10.7)	124.2d	24	7.15~7.02 (m)	126.0d
9	5.96 (td, J=11.1, 2.3)	138.7d	25
10	3.49~3.41 (m) 1.88~1.80 (m)	28.4t	26
11	1.24~1.18 (m)	43.8d	27		176.0s
12	1.93~1.85 (m)	46.6d	28
13	1.86~1.76 (m) 1.24~1.11 (m)	44.6t	29	0.92 (d, J=6.7)	13.5q
14		87.2s	30	1.51~1.44 (m) 1.27~1.18 (m)	29.7t
15	1.82~1.76 (m) 1.53 (d, J=13.6)	50.3t	31	0.84 (t, J=7.2)	9.0q
16		85.9s

Position	¹H NMR	¹³C NMR	Position	¹H NMR	¹³C NMR
1		193.0s	17	1.41~1.36 (m)	48.9d
2	3.69 (br s)	67.4d	18	1.60 (t, J=9.0)	66.8d
3	3.79 (d, J=6.6)	70.4d	19	1.06~0.96 (m)	53.3d
4	1.45~1.39 (m) 1.17~1.12 (m)	31.1t	20	1.90~1.85 (m) 1.21~1.17 (m)	30.1t
5	3.30~3.24 (m) 2.62~2.52 (m)	36.2t	21	1.66~1.60 (m) 1.31~1.21 (m)	32.2t
6	7.93 (t, J=5.0)		22	1.96~1.89 (m)	45.2d
7		165.4s	23	6.40~6.35 (m)	146.5d
8	5.76 (br d, J=10.7)	124.2d	24	7.15~7.02 (m)	126.0d
9	5.96 (td, J=11.1, 2.3)	138.7d	25
10	3.49~3.41 (m) 1.88~1.80 (m)	28.4t	26
11	1.24~1.18 (m)	43.8d	27		176.0s
12	1.93~1.85 (m)	46.6d	28
13	1.86~1.76 (m) 1.24~1.11 (m)	44.6t	29	0.92 (d, J=6.7)	13.5q
14		87.2s	30	1.51~1.44 (m) 1.27~1.18 (m)	29.7t
15	1.82~1.76 (m) 1.53 (d, J=13.6)	50.3t	31	0.84 (t, J=7.2)	9.0q
16		85.9s

Compound	HeLa	HCT116	SW480
2	>20	>20	>20
多柔比星	0.83±0.19	0.85±0.27	1.05±0.13

Compound	HeLa	HCT116	SW480
2	>20	>20	>20
多柔比星	0.83±0.19	0.85±0.27	1.05±0.13

新多环特特拉姆酸大环内酰胺3-Hydroxycombamide I的发现

Discovery of a New Polycyclic Tetramate Macrolactam 3-Hydroxycombamide I

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