A New β-Carboline and Its Analogues from Actinoalloteichus cyanogriseus OUCMDZ-413

doi:10.6023/cjoc202509027

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (3): 968-973.DOI: 10.6023/cjoc202509027 Previous Articles Next Articles

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来自海洋异壁放线菌OUCMDZ-413的一种新β-咔啉及其类似物

高谕康^a^,^†, 梅显贵^a^,^c^,^†, 刘樾^a, 付鹏^a^,^b, 刘培培^a^,^*(), 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海洋药物与生物制品功能实验室山东青岛 266237
^c 山东农业大学农学院作物生物学国家重点实验室作物生物学国家重点实验室山东泰安 271018

收稿日期:2025-09-22 修回日期:2025-11-04 发布日期:2025-12-25
通讯作者: 刘培培, 朱伟明
作者简介:
†共同第一作者
基金资助:
国家自然科学基金(82473838); 国家自然科学基金(30572246); 及国家自然科学基金-山东联合基金(U1906213)

A New β-Carboline and Its Analogues from Actinoalloteichus cyanogriseus OUCMDZ-413

Yukang Gao^a, Xiangui Mei^a^,^c, Yue Liu^a, Peng Fu^a^,^b, Peipei Liu^a^,^*(), Weiming Zhu^a^,^b^,^*()

^a Key Laboratory of Marine Drugs, Ministry of Education of China, 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 State Key Laboratory of Crop Biology, Agronomy College, Shandong Agricultural University, Taian, Shandong 271018

Received:2025-09-22 Revised:2025-11-04 Published:2025-12-25
Contact: Peipei Liu, Weiming Zhu
About author:
†These authors contributed equally to this work.
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

A new 1-acetyl-3-hydroxymethyl-β-carboline (1) and a key intermediate (S)-cyanogramide B (2), involved in the biosynthesis of cyanogramide (6), were isolated for the first time from the marine derived Actinoalloteichus cyanogriseus OUCMDZ-413, along with three know analogues. Their structures were fully elucidated through comprehensive nuclear magnetic resonance (NMR), specific rotation, and electronic circular dichroism (ECD) techniques. The isolation of (S)-cyano- gramide B (2), along with the re-isolation of cyanogramide (6), highlights that fermentation optimization is an effective strategy for exploring the metabolic potential of microorganisms. These findings provide valuable insights into the metabolite diversity of Actinoalloteichus cyanogriseus OUCMDZ-413.

Key words: marine actinobacteria, Actinoalloteichus cyanogriseus OUCMDZ-413, β-carboline, structural elucidation, chemodiversity

Cite this article

Yukang Gao, Xiangui Mei, Yue Liu, Peng Fu, Peipei Liu, Weiming Zhu. A New β-Carboline and Its Analogues from Actinoalloteichus cyanogriseus OUCMDZ-413[J]. Chinese Journal of Organic Chemistry, 2026, 46(3): 968-973.

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References 26

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No.	1		2		3		4
No.	δ_C	δ_H	δ_C	δ_H	δ_C	δ_H	δ_C	δ_H
1	134.5 (C)		159.2 (C)		132.5 (C)		133.2 (C)
3	149.9 (C)		99.2 (C)		137.1 (C)	8.36 (d, J=5.3 Hz)	138.2 (CH)	8.36 (d, J=5.3 Hz)
4	116.4 (CH)	8.48 (s)	152.8 (C)		115.8 (CH)	8.06 (d, J=5.3 Hz)	113.7 (CH)	8.06 (d, J=5.3 Hz)
5	121.8 (CH)	8.29 (t, J=7.8 Hz)			122.1 (CH)	8.26 (d, J=8.0 Hz)	121.7 (CH)	8.26 (d, J=8.0 Hz)
6	120.2 (CH)	7.28 (t, J=7.8 Hz)	111.0 (CH)	7.70 (dt, J=8.4, 1.0 Hz)	120.6 (CH)	7.28 (t, J=7.5 Hz)	119.8 (CH)	7.28 (t, J=7.5 Hz)
7	128.9 (CH)	7.57 (dt, J=7.8, 0.8 Hz)	127.1 (CH)	7.56 (ddd, J=8.4, 7.0, 1.0 Hz)	129.0 (CH)	7.59 (t, J=7.5 Hz)	128.5 (CH)	7.59 (t, J=7.5 Hz)
8	113.1 (CH)	7.77 (dd, J=7.8, 0.8 Hz)	120.9 (CH)	7.30 (ddd, J=7.9, 7.0, 1.0 Hz)	112.9 (CH)	7.78 (d, J=8.2 Hz)	112.5 (CH)	7.78 (d, J=8.2 Hz)
9		11.78 (s)	121.8 (CH)	8.25 (dt, J=7.9, 1.0 Hz)		11.29 (s)		11.29 (s)
10	64.6 (CH₂)	4.80 (s)	97.6 (CH)	7.72 (s)	166.5 (C)
11	201.3 (C)		22.5 (CH₃)	2.03 (s)
12	25.8 (CH₃)	2.77 (s)	31.4 (CH₃)	4.30 (s)
4a	120.0 (C)		128.9 (C)		129.9 (C)		129.5 (C)
4b(9b)	132.0 (C)		123.2 (C)		121.0 (C)		120.7 (C)
5a			140.8 (C)
8a(10a)	142.3 (C)		127.5 (C)		141.4 (C)		141.0 (C)
9a	133.3 (C)		121.5 (C)		131.9 (C)		130.5 (C)
1'			40.5 (CH₂)	3.59 (t, J=8.1 Hz)
2'			34.4 (CH₂)	3.01 (t, J=8.1 Hz)	151.3 (C)		152.2 (C)
3'			138.9 (C)		111.1 (CH)	7.20 (d, J=3.2 Hz)	109.7 (CH)	7.20 (d, J=3.2 Hz)
4'(8')			128.5 (CH)	7.30 (m)	109.3 (CH)	6.58 (d, J=3.2 Hz)	109.2 (CH)	6.58 (d, J=3.2 Hz)
5'(7')			128.8 (CH)	7.31 (m)	157.3 (C)		156.8 (C)
6'			126.4 (CH)	7.24 (tt, J=6.8, 1.9 Hz)	56.0 (CH₂)	4.66 (s)	56.0 (CH₂)	4.66 (s)
6'-OH						5.57 (brs)		5.57 (brs)

No.	1		2		3		4
No.	δ_C	δ_H	δ_C	δ_H	δ_C	δ_H	δ_C	δ_H
1	134.5 (C)		159.2 (C)		132.5 (C)		133.2 (C)
3	149.9 (C)		99.2 (C)		137.1 (C)	8.36 (d, J=5.3 Hz)	138.2 (CH)	8.36 (d, J=5.3 Hz)
4	116.4 (CH)	8.48 (s)	152.8 (C)		115.8 (CH)	8.06 (d, J=5.3 Hz)	113.7 (CH)	8.06 (d, J=5.3 Hz)
5	121.8 (CH)	8.29 (t, J=7.8 Hz)			122.1 (CH)	8.26 (d, J=8.0 Hz)	121.7 (CH)	8.26 (d, J=8.0 Hz)
6	120.2 (CH)	7.28 (t, J=7.8 Hz)	111.0 (CH)	7.70 (dt, J=8.4, 1.0 Hz)	120.6 (CH)	7.28 (t, J=7.5 Hz)	119.8 (CH)	7.28 (t, J=7.5 Hz)
7	128.9 (CH)	7.57 (dt, J=7.8, 0.8 Hz)	127.1 (CH)	7.56 (ddd, J=8.4, 7.0, 1.0 Hz)	129.0 (CH)	7.59 (t, J=7.5 Hz)	128.5 (CH)	7.59 (t, J=7.5 Hz)
8	113.1 (CH)	7.77 (dd, J=7.8, 0.8 Hz)	120.9 (CH)	7.30 (ddd, J=7.9, 7.0, 1.0 Hz)	112.9 (CH)	7.78 (d, J=8.2 Hz)	112.5 (CH)	7.78 (d, J=8.2 Hz)
9		11.78 (s)	121.8 (CH)	8.25 (dt, J=7.9, 1.0 Hz)		11.29 (s)		11.29 (s)
10	64.6 (CH₂)	4.80 (s)	97.6 (CH)	7.72 (s)	166.5 (C)
11	201.3 (C)		22.5 (CH₃)	2.03 (s)
12	25.8 (CH₃)	2.77 (s)	31.4 (CH₃)	4.30 (s)
4a	120.0 (C)		128.9 (C)		129.9 (C)		129.5 (C)
4b(9b)	132.0 (C)		123.2 (C)		121.0 (C)		120.7 (C)
5a			140.8 (C)
8a(10a)	142.3 (C)		127.5 (C)		141.4 (C)		141.0 (C)
9a	133.3 (C)		121.5 (C)		131.9 (C)		130.5 (C)
1'			40.5 (CH₂)	3.59 (t, J=8.1 Hz)
2'			34.4 (CH₂)	3.01 (t, J=8.1 Hz)	151.3 (C)		152.2 (C)
3'			138.9 (C)		111.1 (CH)	7.20 (d, J=3.2 Hz)	109.7 (CH)	7.20 (d, J=3.2 Hz)
4'(8')			128.5 (CH)	7.30 (m)	109.3 (CH)	6.58 (d, J=3.2 Hz)	109.2 (CH)	6.58 (d, J=3.2 Hz)
5'(7')			128.8 (CH)	7.31 (m)	157.3 (C)		156.8 (C)
6'			126.4 (CH)	7.24 (tt, J=6.8, 1.9 Hz)	56.0 (CH₂)	4.66 (s)	56.0 (CH₂)	4.66 (s)
6'-OH						5.57 (brs)		5.57 (brs)

Medium name	Medium component
LB	Tryptone 10 g, NaCl 5 g, yeast extract 5 g, sea water 1 L
YPD	Yeast extract 10 g, peptone 20 g, glucose 20 g, sea water 1 L
Medium 1#	Peptone 20 g, soluble starch 20 g, glycerol 20 g, CaCO₃ 2 g, sea water 1 L
Medium 2#	Peptone 20 g, soluble starch 20 g, glycerol 20 g, CaCO₃ 2 g, 2-pyridinecarboxylic acid 0.4 g, XAD-16 macroporous adsorption resin 50 g, sea water 1 L

Medium name	Medium component
LB	Tryptone 10 g, NaCl 5 g, yeast extract 5 g, sea water 1 L
YPD	Yeast extract 10 g, peptone 20 g, glucose 20 g, sea water 1 L
Medium 1#	Peptone 20 g, soluble starch 20 g, glycerol 20 g, CaCO₃ 2 g, sea water 1 L
Medium 2#	Peptone 20 g, soluble starch 20 g, glycerol 20 g, CaCO₃ 2 g, 2-pyridinecarboxylic acid 0.4 g, XAD-16 macroporous adsorption resin 50 g, sea water 1 L

来自海洋异壁放线菌OUCMDZ-413的一种新β-咔啉及其类似物

A New β-Carboline and Its Analogues from Actinoalloteichus cyanogriseus OUCMDZ-413

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