Characterization of Antibacterial Bromo-naphthacemycin from Streptomyces sp. N12W1565

doi:10.6023/cjoc202511016

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (5): 2067-2071.DOI: 10.6023/cjoc202511016 Previous Articles Next Articles

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Streptomyces sp. N12W1565中抑菌溴代naphthacemycin的表征

彭淑娅^a^,^b, 路新华^c, 花强^a^,^*(), 唐功利^b^,^*()

^a 华东理工大学生物工程学院上海 200030
^b 中国科学院上海有机化学研究所上海 200032
^c 微生物药物国家工程研究中心石家庄 050015

收稿日期:2025-12-25 修回日期:2026-01-13 发布日期:2026-02-11
基金资助:
国家自然科学基金(22137009)

Characterization of Antibacterial Bromo-naphthacemycin from Streptomyces sp. N12W1565

Shuya Peng^a^,^b, Xinhua Lu^c, Qiang Hua^a^,^*(), Gongli Tang^b^,^*()

^a School of Biotechnology, East China University of Science and Technology, Shanghai 200030
^b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
^c National Microbial Medicine Engineering and Research Center, Shijiazhuang 050015

Received:2025-12-25 Revised:2026-01-13 Published:2026-02-11
Contact: * E-mail: gltang@sioc.ac.cn; qhua@ecust.edu.cn
Supported by:
National Natural Science Foundation of China(22137009)

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Abstract

The halogenated natural product naphthacemycin was isolated from Streptomyces sp. N12W1565 strain associated with the stems of the traditional Chinese medicinal herb Senecio scandens Buch.-Ham. Ex D. Don. Previous studies have established that polychlorination of this metabolite was catalyzed by the multi-site halogenase NatC encoded within the naphthacemycin biosynthetic gene cluster, suggesting that modulation of halide species in the culture medium can enable the generation of diverse halogenated analogues. In this study, brominated naphthacemycins were produced by optimizing the fermentation conditions of this strain. Three novel monobrominated naphthacemycins were successfully characterized by high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) and nuclear magnetic resonance (NMR) spectro- scopy, among which naphthacemycin BB₁ (5) and naphthacemycin BB₃ (7) exhibited significantly enhanced antibacterial activity compared to the non-brominated naphthacemycin B₂ (1).

Key words: type II polyketides natural product, naphthacemycin, halogenation, antibacterial

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Shuya Peng, Xinhua Lu, Qiang Hua, Gongli Tang. Characterization of Antibacterial Bromo-naphthacemycin from Streptomyces sp. N12W1565[J]. Chinese Journal of Organic Chemistry, 2026, 46(5): 2067-2071.

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References 6

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No.	5		6		7
No.	δ_C	δ_H, mult. (J in Hz)	δ_C	δ_H, mult. (J in Hz)	δ_C	δ_H, mult. (J in Hz)
1	107.0	6.79, s	107.0	6.77, t (2.7)	107.3	6.69, d (2.2)
2	163.8		166.1		166.9
3	108.8		102.0	6.29, d (2.3)	102.2	6.22, d (2.2)
4	162.8		166.5		169.4
4a	108.8		108.2		108.6
5	191.0		191.1		191.6
5a	107.4		107.3		107.9
6	167.1		166.5		166.5
6a	118.0		117.5		119.0
7	141.2		142.4		140.2
8	122.4	6.66, d (2.5)	122.0	6.77, t (2.7)	121.5	6.77, s
9	160.3		159.7		158.1
10	110.0	7.04, d (2.5)	110.2	7.20, d (2.5)	105.6
10a	143.0		140.2		139.8
11	116.3	7.37, s	116.0	7.50, s	115.2	7.92, s
11a	146.1		146.2		148.1
12	39.6		39.4		40.2
12a	153.9		155.5		155.8
13	34.6	1.72^a, s	34.7	1.73, s	35.0	1.76^a, s
14	34.5	1.72^a, s	34.2	1.74, s	34.9	1.76^a, s
15	125.8		126.6		125.3
16	158.8		157.4		158.7
17	97.3	6.34^a, s	98.1	6.63, s	97.3	6.34^a, s
18	157.4		154.2		157.0
19	109.2	6.34^a, s	104.1		109.2	6.34^a, s
20	137.9		136.6		137.7
21	20.6	1.89, s	21.3	1.97, s	20.3	1.90, s
16-OMe	56.0	3.60, s	55.9	3.58, s	56.0	3.59, s

No.	5		6		7
No.	δ_C	δ_H, mult. (J in Hz)	δ_C	δ_H, mult. (J in Hz)	δ_C	δ_H, mult. (J in Hz)
1	107.0	6.79, s	107.0	6.77, t (2.7)	107.3	6.69, d (2.2)
2	163.8		166.1		166.9
3	108.8		102.0	6.29, d (2.3)	102.2	6.22, d (2.2)
4	162.8		166.5		169.4
4a	108.8		108.2		108.6
5	191.0		191.1		191.6
5a	107.4		107.3		107.9
6	167.1		166.5		166.5
6a	118.0		117.5		119.0
7	141.2		142.4		140.2
8	122.4	6.66, d (2.5)	122.0	6.77, t (2.7)	121.5	6.77, s
9	160.3		159.7		158.1
10	110.0	7.04, d (2.5)	110.2	7.20, d (2.5)	105.6
10a	143.0		140.2		139.8
11	116.3	7.37, s	116.0	7.50, s	115.2	7.92, s
11a	146.1		146.2		148.1
12	39.6		39.4		40.2
12a	153.9		155.5		155.8
13	34.6	1.72^a, s	34.7	1.73, s	35.0	1.76^a, s
14	34.5	1.72^a, s	34.2	1.74, s	34.9	1.76^a, s
15	125.8		126.6		125.3
16	158.8		157.4		158.7
17	97.3	6.34^a, s	98.1	6.63, s	97.3	6.34^a, s
18	157.4		154.2		157.0
19	109.2	6.34^a, s	104.1		109.2	6.34^a, s
20	137.9		136.6		137.7
21	20.6	1.89, s	21.3	1.97, s	20.3	1.90, s
16-OMe	56.0	3.60, s	55.9	3.58, s	56.0	3.59, s

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Streptomyces sp. N12W1565中抑菌溴代naphthacemycin的表征

Characterization of Antibacterial Bromo-naphthacemycin from Streptomyces sp. N12W1565

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