Staurosporine Natural Products Derived from Marine Streptomyces sp. OUCMDZ-5522

doi:10.6023/cjoc202411022

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (7): 2486-2500.DOI: 10.6023/cjoc202411022 Previous Articles Next Articles

ARTICLES

源自海洋链霉菌OUCMDZ-5522的十字孢碱类天然产物

卜淑甜^a, 王永^a, 殷文剑^a, 温青云^a, 王佩^c, 朱伟明^a^,^b^,^*()

^a 中国海洋大学医药学院海洋药物教育部重点实验室山东青岛 266003
^b 青岛海洋科技中心海洋药物与生物制品功能实验室山东青岛 266237
^c 广西民族大学化学化工学院林产化学与工程国家民委重点实验室南宁 530006

收稿日期:2024-11-27 修回日期:2025-01-11 发布日期:2025-02-14
基金资助:
国家自然科学基金(82473838); 国家自然科学基金(30572246); 国家自然科学基金-山东联合基金(U1906213)

Staurosporine Natural Products Derived from Marine Streptomyces sp. OUCMDZ-5522

Shutian Bu^a, Yong Wang^a, Wenjian Yin^a, Qingyun Wen^a, Pei Wang^c, Weiming Zhu^a^,^b^,^*()

^a Key Laboratory of Marine Drugs, Ministry of Education of Chin, School of Medicine and Pharmacy, Ocean University of China, Qingdao, Shandong 266003
^b Laboratory for Marine Drugs and Bioproducts, Marine Science and Technology Center, Qingdao, Shandong 266237
^c Key Laboratory of Chemistry and Engineering of Forest Products (State Ethnic Affairs Commission), School of Chemistry and Chemical Engineering, Guangxi Minzu University, Nanning 530006

Received:2024-11-27 Revised:2025-01-11 Published:2025-02-14
Contact: *E-mail: weimingzhu@ouc.edu.cn
Supported by:
National Natural Science Foundation of China(82473838); National Natural Science Foundation of China(30572246); National Natural Science Foundation of China-Shandong Fund Joint Project(U1906213)

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Abstract

The marine-derived Streptomyces OUCMDZ-5522 was fermented in a carbazole liquid medium. Guided by the distinctive UV absorption of the indolocarbazole core of staurosporine, 11 staurosporine alkaloids were isolated from the fermentation broth. Using nuclear magnetic resonance (NMR), specific rotation, and electronic circular dichroism (ECD) techniques, their structures were identified as 7-oxo-3'-N-carbamoyl staurosporine (1), 3'-N-mesylstaurosporine (2), 7-oxostauro- sporine (3), staurosporine (4), 3'-demethylamino-2'α,3'α-dihydroxy staurosporine (MLR-52, 5), K252d (6), K252a (7), 3'-methylamino-3'-deoxy K252a (8), holyrine A (9), 3'-N-acetylholyrine A (10) and 7-oxo-3'-N-acetylholyrine A (13G-31G, 11), respectively. Notably, compound 1 is a new compound, and compound 2 is a new naturally occurring discovery. Antibacterial activities were observed for compound 1 against Edwardsiella tarda, compound 6 against Vibrio vulnificus, compound 9 against Vibrio parahaemolyticus, and compound 10 against Vibrio vulnificus, Enterobacter aerogenes, Bacillus cereus and Bacillus thuringiensis, each with a minimum inhibitory concentration (MIC) of 32 μg•mL^－1.

Key words: marine Streptomyces, staurosporine alkaloids, structure identification, antibacterial activity

Cite this article

Shutian Bu, Yong Wang, Wenjian Yin, Qingyun Wen, Pei Wang, Weiming Zhu. Staurosporine Natural Products Derived from Marine Streptomyces sp. OUCMDZ-5522[J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2486-2500.

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Fig. & Tab. 12

References 36

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Position	δ_C (type)	δ_H (mult. J in Hz)	COSY	HMBC	NOESY
1	109.9 (CH)	7.75 (d, 8.2)	2	3, 4a
2	127.2 (CH)	7.61 (t, 7.4)	1, 3	4, 13a
3	120.7 (CH)	7.43 (t, 7.8)	2, 4	1, 4a
4	124.9 (CH)	9.07 (d, 8.1)	3	2, 4b, 13a
4a	121.4 (C)
4b	115.2 (C)
4c	119.5 (C)
5	171.2 (C)
6	—	11.1 (s)		4c
7	170.9 (C)
7a	120.9 (C)
7b	116.1 (C)
7c	122.8 (C)
8	124.9 (CH)	9.25 (d, 7.9)	9	10, 7b, 11a	10
9	120.6 (CH)	7.39 (t, 7.3)	8, 10	11, 7c
10	126.9 (CH)	7.56 (t, 7.8)	9, 11	8, 11a	8
11	113.7 (CH)	7.71 (d, 8.1)	10	9, 7c
11a	139.9 (C)
12a	130.5 (C)
12b	128.8 (C)
13a	137.7 (C)
1'	82.6 (CH)	7.03 (td, 5.8, 2.1)	2'	12b 13a, 5'	3'
2'	27.4 (CH₂)	2.68~2.71 (m); 2.22 (td, 5.8, 12.8)	1', 3'	3', 4'
3'	48.3 (CH)	4.85 (d, 12.8)	2', 4'	4'	1', 6'
4'	84.0 (CH)	4.22 (d, 3.0)	3'	2', 6', 4'-OCH₃	11
5'	95.2 (C)
6'	29.2 (CH₃)	2.35 (s)		4'	3'
3'-NCH₃	30.2 (CH₃)	2.63 (s)		3', 3'-NCO
4'-OCH₃	60.2 (CH₃)	2.68 (d, 3.0)		4'
3'-NCO	158.9 (C)			3'-NCH₃
NH₂		6.02 (s)			3', 3'-NCH₃

Position	δ_C (type)	δ_H (mult. J in Hz)	COSY	HMBC	NOESY
1	109.9 (CH)	7.75 (d, 8.2)	2	3, 4a
2	127.2 (CH)	7.61 (t, 7.4)	1, 3	4, 13a
3	120.7 (CH)	7.43 (t, 7.8)	2, 4	1, 4a
4	124.9 (CH)	9.07 (d, 8.1)	3	2, 4b, 13a
4a	121.4 (C)
4b	115.2 (C)
4c	119.5 (C)
5	171.2 (C)
6	—	11.1 (s)		4c
7	170.9 (C)
7a	120.9 (C)
7b	116.1 (C)
7c	122.8 (C)
8	124.9 (CH)	9.25 (d, 7.9)	9	10, 7b, 11a	10
9	120.6 (CH)	7.39 (t, 7.3)	8, 10	11, 7c
10	126.9 (CH)	7.56 (t, 7.8)	9, 11	8, 11a	8
11	113.7 (CH)	7.71 (d, 8.1)	10	9, 7c
11a	139.9 (C)
12a	130.5 (C)
12b	128.8 (C)
13a	137.7 (C)
1'	82.6 (CH)	7.03 (td, 5.8, 2.1)	2'	12b 13a, 5'	3'
2'	27.4 (CH₂)	2.68~2.71 (m); 2.22 (td, 5.8, 12.8)	1', 3'	3', 4'
3'	48.3 (CH)	4.85 (d, 12.8)	2', 4'	4'	1', 6'
4'	84.0 (CH)	4.22 (d, 3.0)	3'	2', 6', 4'-OCH₃	11
5'	95.2 (C)
6'	29.2 (CH₃)	2.35 (s)		4'	3'
3'-NCH₃	30.2 (CH₃)	2.63 (s)		3', 3'-NCO
4'-OCH₃	60.2 (CH₃)	2.68 (d, 3.0)		4'
3'-NCO	158.9 (C)			3'-NCH₃
NH₂		6.02 (s)			3', 3'-NCH₃

Position	3		4
Position	δ_C (type)	δ_H (mult. J in Hz)	δ_C (type)	δ_H (mult. J in Hz)
1	110.0 (CH)	7.60 (d, 8.0)	108.4 (CH)	7.57 (d, 8.2)
2	125.2 (CH)	7.45 (dd, 8.0, 7.4)	124.9 (CH)	7.42 (dd, 8.2, 7.4)
3	119.3 (CH)	7.63 (dd, 8.2, 7.4)	118.8 (CH)	7.27 (dd, 7.9, 7.4)
4	125.0 (CH)	9.25 (d, 8.2)	125.6 (CH)	9.29 (d, 7.9)
4a	122.9 (C)		122.5 (C)
4b	115.0 (C)		113.5 (C)
4c	121.0 (C)		119.0 (C)
5	171.1 (C)		172.3 (C)
6		11.1 (s)		8.54 (s)
7	170.9 (C)		45.4 (CH₂)	4.95 (s)
7a	131.0 (C)		132.1 (C)
7b	114.9 (C)		114.1 (C)
7c	121.0 (C)		123.9 (C)
8	121.5 (CH)	9.05 (d, 8.0)	120.9 (CH)	7.97 (d, 8.6)
9	121.1 (CH)	7.45 (dd, 8.0, 7.4)	119.8 (CH)	7.27 (dd, 8.6, 8.2)
10	127.2 (CH)	7.63 (dd, 8.5, 7.4)	124.4 (CH)	7.45 (dd, 7.9, 8.2)
11	112.7 (CH)	8.05 (d, 8.5)	115.3 (CH)	7.96 (d, 7.9)
11a	138.9 (C)		139.5 (C)
12a	129.8 (C)		130.0 (C)
12b	127.3 (C)		126.7 (C)
13a	137.6 (C)		136.4 (C)
1'	81.0 (CH)	6.95 (dd, 2.7, 9.3)	80.0 (CH)	6.69 (t, 3.7)
2'	27.0 (CH₂)	2.13 (td, 1.8, 2.7); 3.33~3.35 (m)	29.4 (CH₂)	3.17~3.20 (m); 2.49~2.51 (m)
3'	53.2 (CH)	4.04~4.06 (m)	50.1 (CH)	3.22~3.25 (m)
4'	79.3 (CH)	4.46 (d, 2.0)	82.8 (CH)	4.04 (d, 3.4)
5'	93.3 (C)		91.1 (C)
6'	27.8 (CH₃)	2.48 (s)	29.8 (CH₃)	2.30 (s)
3'-NH		9.01~9.04 (m)
3'-NCH₃	30.7 (CH₃)	2.20 (s)	33.4 (CH₃)	1.44 (s)
4'-OCH₃	59.9 (CH₃)	2.71 (s)	57.3 (CH₃)	3.32 (s)

Position	3		4
Position	δ_C (type)	δ_H (mult. J in Hz)	δ_C (type)	δ_H (mult. J in Hz)
1	110.0 (CH)	7.60 (d, 8.0)	108.4 (CH)	7.57 (d, 8.2)
2	125.2 (CH)	7.45 (dd, 8.0, 7.4)	124.9 (CH)	7.42 (dd, 8.2, 7.4)
3	119.3 (CH)	7.63 (dd, 8.2, 7.4)	118.8 (CH)	7.27 (dd, 7.9, 7.4)
4	125.0 (CH)	9.25 (d, 8.2)	125.6 (CH)	9.29 (d, 7.9)
4a	122.9 (C)		122.5 (C)
4b	115.0 (C)		113.5 (C)
4c	121.0 (C)		119.0 (C)
5	171.1 (C)		172.3 (C)
6		11.1 (s)		8.54 (s)
7	170.9 (C)		45.4 (CH₂)	4.95 (s)
7a	131.0 (C)		132.1 (C)
7b	114.9 (C)		114.1 (C)
7c	121.0 (C)		123.9 (C)
8	121.5 (CH)	9.05 (d, 8.0)	120.9 (CH)	7.97 (d, 8.6)
9	121.1 (CH)	7.45 (dd, 8.0, 7.4)	119.8 (CH)	7.27 (dd, 8.6, 8.2)
10	127.2 (CH)	7.63 (dd, 8.5, 7.4)	124.4 (CH)	7.45 (dd, 7.9, 8.2)
11	112.7 (CH)	8.05 (d, 8.5)	115.3 (CH)	7.96 (d, 7.9)
11a	138.9 (C)		139.5 (C)
12a	129.8 (C)		130.0 (C)
12b	127.3 (C)		126.7 (C)
13a	137.6 (C)		136.4 (C)
1'	81.0 (CH)	6.95 (dd, 2.7, 9.3)	80.0 (CH)	6.69 (t, 3.7)
2'	27.0 (CH₂)	2.13 (td, 1.8, 2.7); 3.33~3.35 (m)	29.4 (CH₂)	3.17~3.20 (m); 2.49~2.51 (m)
3'	53.2 (CH)	4.04~4.06 (m)	50.1 (CH)	3.22~3.25 (m)
4'	79.3 (CH)	4.46 (d, 2.0)	82.8 (CH)	4.04 (d, 3.4)
5'	93.3 (C)		91.1 (C)
6'	27.8 (CH₃)	2.48 (s)	29.8 (CH₃)	2.30 (s)
3'-NH		9.01~9.04 (m)
3'-NCH₃	30.7 (CH₃)	2.20 (s)	33.4 (CH₃)	1.44 (s)
4'-OCH₃	59.9 (CH₃)	2.71 (s)	57.3 (CH₃)	3.32 (s)

Position	δ_C (type)	δ_H (mult. J in Hz)	COSY	HMBC	NOESY
1	109.0 (CH)	7.61 (d, 8.4)	2	3, 4a	1'
2	125.1 (CH)	7.50 (dd, 8.4, 7.5)	1, 3	4, 13a
3	119.6 (CH)	7.31 (dd, 8.0, 7.5)	2, 4	1, 4a
4	125.8 (CH)	9.29 (d, 8.0)	3	2, 4b, 13a
4a	122.7 (C)
4b	115.2 (C)
4c	119.5 (C)
5	172.0 (C)
6		8.60 (s)		5, 7, 7a, 4c
7	45.5 (CH₂)	5.00 (s)		5, 4c, 7a, 7b	8
7a	132.7 (C)
7b	114.2 (C)
7c	123.8 (C)
8	121.6 (CH)	8.04 (d,7.6)	9	10, 7a, 11a	7, 10
9	120.5 (CH)	7.37 (dd, 7.6, 7.5)	8, 10	11, 7c
10	125.1 (CH)	7.50 (dd, 8.3, 7.5)	9, 11	8, 11a	8
11	113.7 (CH)	8.06 (d, 8.3)	10	9, 7c
11a	138.8 (C)
12a	129.2 (C)
12b	125.4 (C)
13a	136.3 (C)
1'	82.3 (CH)	7.04 (dd, 8.5, 5.9)	2'	12b, 2', 5'	1, 3'
2'	26.9 (CH₂)	2.22 (dt, 12.7, 5.9), 2.81~2.83 (m)	1', 3'	3'	4'-CH₃
3'	51.4 (CH)	4.40 (dt, 12.7, 3.5)	2'	3'-NCH₃	1'
4'	85.2 (CH)	4.29 (brs)		2', 4'-OCH₃	4'-OCH₃
5'	94.9 (C)			6'
6'	29.2 (CH₃)	2.36 (s)		5'	4'
3'-NCH₃	30.4 (CH₃)	2.67 (s)		3'
4'-OCH₃	60.5 (CH₃)	2.78 (s)		4'
3'-NSO₂CH₃	36.8 (CH₃)	3.12 (s)

源自海洋链霉菌OUCMDZ-5522的十字孢碱类天然产物

Staurosporine Natural Products Derived from Marine Streptomyces sp. OUCMDZ-5522

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培养基名称	配方
A1	可溶性淀粉10 g, 酵母浸膏4 g, 蛋白胨2 g, Fe₂(SO₄)₃•4H₂O 0.04 g, KBr 0.1 g, 海水1 L, 自然pH
Kazuo	可溶性淀粉25 g, 酵母浸膏2 g, 豆粉15 g, CaCO₃ 2 g, Amberlite XAD-16N 10 g, 海水1 L, 自然pH
LB	胰蛋白胨10 g, NaCl 5 g, 酵母浸膏5 g, 自来水1 L, 自然pH
YPD	酵母浸膏10 g, 蛋白胨20 g, 葡萄糖20 g, 海水1 L, 自然pH
分离培养基	可溶性淀粉10 g, 干酪素0.3 g, 硝酸钾2 g, 七水合硫酸镁0.05 g, 氯化钠2.0 g, 磷酸氢二钾2.0 g, 碳酸钙0.02 g, 七水合硫酸亚铁0.01 g, 海水500 L, 水500 L, 琼脂20 g, 重铬酸钾50 mg, pH 7.2~7.4
纯化培养基	葡萄糖4.0 g, 酵母膏4.0 g, 麦芽浸粉10.0 g, 海盐27.0 g, 水1000 mL, pH 7.0

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