Citation: Liu Chengli, Yang Chenglong, Zeng Yingjie, Shi Jing, Li Lingyu, Li Wei, Jiao Ruihua, Tan Renxiang, Ge Huiming. Chartrenoline, a novel alkaloid isolated from a marine Streptomyces chartreusis NA02069[J]. Chinese Chemical Letters, ;2019, 30(1): 44-46. doi: 10.1016/j.cclet.2018.10.030 shu

Chartrenoline, a novel alkaloid isolated from a marine Streptomyces chartreusis NA02069

State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecues, School of Life Sciences, Nanjing University, Nanjing 210023, China

Corresponding author: Ge Huiming, hmge@nju.edu.cn
Received Date: 26 September 2018
Revised Date: 24 October 2018
Accepted Date: 25 October 2018
Available Online: 26 January 2018

Figures(4)

A novel alkaloid, chartrenoline (1), featuring an unusual 6/6/5/5-tetracyclic nucleus, was isolated from a marine Streptomyces chartreusis NA02069. The structure of 1 including its absolute configurations was established by extensive analyses of its high resolution mass, NMR and single-crystal X-ray diffraction data. A plausible biosynthetic pathway for chartrenoline (1) is proposed.
- Alkaloid,
- Chartrenoline,
- Streptomyces chartreusis,
- 6/6/5/5-Tetracyclic nucleus,
- Marine-derived microorganism
1. [1]
  J.W. Blunt, A.R. Carroll, B.R. Copp, et al., Nat. Prod. Rep. 35(2018) 8-53. doi: 10.1039/C7NP00052A
2. [2]
  M. Kita, H. Kigoshi, Nat. Prod. Rep. 32(2015) 534-542. doi: 10.1039/C4NP00129J
3. [3]
  L.A. Salvador-Reyes, H. Luesch, Nat. Prod. Rep. 32(2015) 478-503. doi: 10.1039/C4NP00104D
4. [4]
  D.Q. Xue, H.L. Liu, S.H. Chen, et al., Chin. Chem. Lett. 28(2017) 1190-1193. doi: 10.1016/j.cclet.2017.03.040
5. [5]
  R. Montaser, H. Luesch, Future Med. Chem. 3(2011) 1475-1489. doi: 10.4155/fmc.11.118
6. [6]
  Y. Gao, W. Xian, H.C. Liu, et al., Chin. Chem. Lett. 28(2017) 905-908. doi: 10.1016/j.cclet.2017.01.004
7. [7]
  K.A. Reynolds, H. Luhavaya, J. Li, et al., J. Antibiot. 71(2018) 333-338. doi: 10.1038/ja.2017.146
8. [8]
  D. Zhou, C. Wang, M.L. Li, et al., Chin. Chem. Lett. 29(2018) 191-193. doi: 10.1016/j.cclet.2017.06.007
9. [9]
  R.H. Feling, G.O. Buchanan, T.J. Mincer, et al., Angew. Chem. Int. Ed. 42(2003) 355-357. doi: 10.1002/anie.200390115
10. [10]
  T.A.M. Gulder, B.S. Moore, Angew. Chem. Int. Ed. 49(2010) 9346-9367. doi: 10.1002/anie.201000728
11. [11]
  S.K. Davidson, S.W. Allen, G.E. Lim, et al., Appl. Environ. Microb. 67(2001) 4531-4537. doi: 10.1128/AEM.67.10.4531-4537.2001
12. [12]
  B. Zhang, K.B. Wang, W. Wang, et al., Org. Lett. 20(2018) 2967-2971. doi: 10.1021/acs.orglett.8b01006
13. [13]
  A.E. Trindade-Silva, G.E. Lim-Fong, K.H. Sharp, et al., Curr. Opin. Biotech. 21(2010) 834-842. doi: 10.1016/j.copbio.2010.09.018
14. [14]
  Y.S. Wang, B. Zhang, J.P. Zhu, et al., J. Am. Chem. Soc. 140(2018) 10909-10914. doi: 10.1021/jacs.8b06623
15. [15]
  C.L. Yang, Y.S. Wang, C.L. Liu, et al., Mar. Drugs 15(2017) 244. doi: 10.3390/md15080244
16. [16]
  S.F. Bi, F. Li, Y.C. Song, et al., Nat. Prod. Commun. 6(2011) 353-355.
17. [17]
  U.R. Awodi, J.L. Ronan, J. Masschelein, et al., Chem. Sci. 8(2017) 411-415. doi: 10.1039/C6SC02803A
18. [18]
  W. Huang, S.J. Kim, J. Liu, et al., Org. Lett. 17(2015) 5344-5347. doi: 10.1021/acs.orglett.5b02707
19. [19]
  S. Garbley, H. Kluge, H.U. Hope, et al., Angew. Chem. Int. Ed. 26(1987) 664-665.
1. [1]
  Shuige Zhao , Pengcheng Yan , Peipei Liu , Haishan Liu , Ning Li , Peng Fu , Weiming Zhu . Pyridapeptides F‒I, cyclohexapeptides from marine sponge-derived Streptomyces sp. OUCMDZ-4539. Chinese Chemical Letters, 2024, 35(7): 108950-. doi: 10.1016/j.cclet.2023.108950
2. [2]
  Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
3. [3]
  Aimin Fu , Chunmei Chen , Qin Li , Nanjin Ding , Jiaxin Dong , Yu Chen , Mengsha Wei , Weiguang Sun , Hucheng Zhu , Yonghui Zhang . Niduenes A−F, six functionalized sesterterpenoids with a pentacyclic 5/5/5/5/6 skeleton from endophytic fungus Aspergillus nidulans. Chinese Chemical Letters, 2024, 35(9): 109100-. doi: 10.1016/j.cclet.2023.109100
4. [4]
  Jingping Hu , Jing Xu . Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C₁₄–epi-deoxycalyciphylline H. Chinese Chemical Letters, 2024, 35(4): 108733-. doi: 10.1016/j.cclet.2023.108733
5. [5]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
6. [6]
  Ruizhi Yang , Xia Li , Weiping Guo , Zixuan Chen , Hongwei Ming , Zhong-Zhen Luo , Zhigang Zou . New thermoelectric semiconductors Pb5Sb12+xBi6-xSe32 with ultralow thermal conductivity. Chinese Journal of Structural Chemistry, 2024, 43(3): 100268-100268. doi: 10.1016/j.cjsc.2024.100268
7. [7]
  Liang Ming , Dan Liu , Qiyue Luo , Chaochao Wei , Chen Liu , Ziling Jiang , Zhongkai Wu , Lin Li , Long Zhang , Shijie Cheng , Chuang Yu . Si-doped Li₆PS₅I with enhanced conductivity enables superior performance for all-solid-state lithium batteries. Chinese Chemical Letters, 2024, 35(10): 109387-. doi: 10.1016/j.cclet.2023.109387
8. [8]
  Xinyu You , Xin Zhang , Shican Jiang , Yiru Ye , Lin Gu , Hexun Zhou , Pandong Ma , Jamal Ftouni , Abhishek Dutta Chowdhury . Efficacy of Ca/ZSM-5 zeolites derived from precipitated calcium carbonate in the methanol-to-olefin process. Chinese Journal of Structural Chemistry, 2024, 43(4): 100265-100265. doi: 10.1016/j.cjsc.2024.100265
9. [9]
  Qianqian Liu , Xing Du , Wanfei Li , Wei-Lin Dai , Bo Liu . Synergistic Effects of Internal Electric and Dipole Fields in SnNb₂O₆/Nitrogen-Enriched C₃N₅ S-Scheme Heterojunction for Boosting Photocatalytic Performance. Acta Physico-Chimica Sinica, 2024, 40(10): 2311016-. doi: 10.3866/PKU.WHXB202311016
10. [10]
  . . University Chemistry, 2024, 39(6): 0-0.
11. [11]
  Pan Liu , Yanming Sun , Alberto J. Fernández-Carrión , Bowen Zhang , Hui Fu , Lunhua He , Xing Ming , Congling Yin , Xiaojun Kuang . Bismuth-based halide double perovskite Cs₂KBiCl₆: Disorder and luminescence. Chinese Chemical Letters, 2024, 35(5): 108641-. doi: 10.1016/j.cclet.2023.108641
12. [12]
  Zhengzheng LIU , Pengyun ZHANG , Chengri WANG , Shengli HUANG , Guoyu YANG . Synthesis, structure, and electrochemical properties of a sandwich-type {Co₆}-cluster-added germanotungstate. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1173-1179. doi: 10.11862/CJIC.20240039
13. [13]
  Xianghe Kong , Xiaoli Liao , Zhenkun Huang , Lei Mei , Hongqing Wang , Kongqiu Hu , Weiqun Shi . Designed assembly of heterometallic cluster organic frameworks based on Th₆ cluster. Chinese Chemical Letters, 2024, 35(11): 109642-. doi: 10.1016/j.cclet.2024.109642
14. [14]
  Xin Wang , Changzhao Chen , Qishen Wang , Kai Dai . Graphene quantum dot modified Bi2MoO6 nanoflower for efficient degradation of BPA under visible light. Chinese Journal of Structural Chemistry, 2024, 43(12): 100473-100473. doi: 10.1016/j.cjsc.2024.100473
15. [15]
  . . University Chemistry, 2024, 39(5): 0-0.
16. [16]
  Yang Feng , Yang-Qing Tian , Yong-Qiang Zhao , Sheng-Jun Chen , Bi-Feng Yuan . Dynamic deformylation of 5-formylcytosine and decarboxylation of 5-carboxylcytosine during differentiation of mouse embryonic stem cells into mouse neurons. Chinese Chemical Letters, 2024, 35(11): 109656-. doi: 10.1016/j.cclet.2024.109656
17. [17]
  Shiyi WANG , Chaolong CHEN , Xiangjian KONG , Lansun ZHENG , Lasheng LONG . Polynuclear lanthanide compound [Ce₄^ⅢCe₆^Ⅳ(μ₃-O)₄(μ₄-O)₄(acac)₁₄(CH₃O)₆]·2CH₃OH for the hydroboration of amides to amine. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 88-96. doi: 10.11862/CJIC.20240342
18. [18]
  Qiang ZHAO , Zhinan GUO , Shuying LI , Junli WANG , Zuopeng LI , Zhifang JIA , Kewei WANG , Yong GUO . Cu₂O/Bi₂MoO₆ Z-type heterojunction: Construction and photocatalytic degradation properties. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 885-894. doi: 10.11862/CJIC.20230435
19. [19]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
20. [20]
  Meijuan Chen , Liyun Zhao , Xianjin Shi , Wei Wang , Yu Huang , Lijuan Fu , Lijun Ma . Synthesis of carbon quantum dots decorating Bi₂MoO₆ microspherical heterostructure and its efficient photocatalytic degradation of antibiotic norfloxacin. Chinese Chemical Letters, 2024, 35(8): 109336-. doi: 10.1016/j.cclet.2023.109336

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沈阳化工大学材料科学与工程学院沈阳 110142