Advanced Search

Citation: Mengmeng Lan, Tongxu Cui, Kaichun Xia, Guodong Cui, Yiwen Chu, Peng Fu, Weiming Zhu. (±)-Pyriindolin with a 2, 2′-bipyridine-spiro[furan-3, 3′-indoline] chimeric skeleton from the endophytic Streptomyces albolongus EA12432[J]. Chinese Chemical Letters, ;2022, 33(1): 508-510. doi: 10.1016/j.cclet.2021.05.028 shu

(±)-Pyriindolin with a 2, 2′-bipyridine-spiro[furan-3, 3′-indoline] chimeric skeleton from the endophytic Streptomyces albolongus EA12432

Mengmeng Lan ^{a, 1} ,
Tongxu Cui ^{a, 1} ,
Kaichun Xia ^a ,
Guodong Cui ^a ,
Yiwen Chu ^c ,
Peng Fu ^{a, b, *,} ,
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 266003, China
b.
Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology (Qingdao), Qingdao 266237, China
c.
School of Pharmacy, Chengdu University, Chengdu 610106, China

^*

fupeng@ouc.edu.cn

weimingzhu@ouc.edu.cn

¹

Received Date: 16 March 2021
Revised Date: 28 April 2021
Accepted Date: 12 May 2021
Available Online: 24 May 2021

Figures(4)

(±)-Pyriindolin (1) with a rare molecular backbone formed by fusing a 2, 2′-bipyridine nucleus into a spiro[furan-3, 3′-indoline] skeleton, was isolated from the Streptomyces albolongus EA12432. The constitution and the relative configuration of (±)-1 were determined by extensive spectroscopic analyses, ¹³C calculation and DP4+ probability analysis. The absolute configurations of optically pure (+)-1 and (−)-1 which were obtained after a chiral high performance liquid chromatography (HPLC) separation were further identified by electronic circular dichroism (ECD) calculations. (+)- and (−)-Pyriindolins displayed moderate cytotoxicity against HCT-116 cell line with the half-maximal inhibitory concentration (IC₅₀) values of 2.89 ± 0.17 µmol/L and 4.47 ± 0.26 µmol/L, respectively.
- Pyrisulfoxins,
- Spiroindolone,
- Streptomyces sp.,
- Endophyte,
- Cytotoxicity
1. [1]
  X. Mei, M. Lan, Y. Jin, W. Zhu, Chin. J. Mar. Drugs. 36 (2017) 83–92.
2. [2]
  A. Funk, P.V. Divekar, Can. J. Microbiol. 5 (1959) 317–321. doi: 10.1139/m59-039
3. [3]
  (a) K. Shindo, Y. Yamagishi, Y. Okada, H. Kawai, J. Antibiot. 47 (1994) 1072–1074;
  (b)S. Gomi, S. Amano, E. Sato, et al., J. Antibiot. 47 (1994) 1385–1394.
4. [4]
  (a) N. Tsuge, K. Furihata, K. Shin-Ya, et al., J. Antibiot. 52 (1999) 505–507;
  (b) Y. Du, C. Wang, G. Cui, et al., Front. Chem. 8 (2020) 248.
5. [5]
  (a) P. Fu, P. Liu, X. Li, et al., Org. Lett. 13 (2011) 5948–5951;
  (b) P. Fu, Y. Zhu, X. Mei, et al., Org. Lett. 16 (2014) 4264–4267;
  (c) X. Mei, M. Lan, G. Cui, et al., Org. Chem. Front. 6 (2019) 3566–3574;
  (d) A. Lahoum, N. Sabaou, C. Bijani, et al., Saudi Pharm. J. 27 (2019) 56–65.
6. [6]
  P. Fu, S. Wang, K. Hong, et al., J. Nat. Prod. 74 (2011) 1751–1756. doi: 10.1021/np200258h
7. [7]
  H. Yin, J. Lin, Y. Chu, Chin. J. Antibiot. 41 (2016) 653–657.
8. [8]
  (a) P. Fu, C. Yang, Y. Wang, et al., Org. Lett. 14 (2012) 2422–2425;
  (b) P. Fu, F. Kong, X. Li, et al., Org. Lett. 16 (2014) 3708–3711.
9. [9]
  N. Grimblat, M.M. Zanardi, A.M. Sarotti, J. Org. Chem. 80 (2015) 12526–12534. doi: 10.1021/acs.joc.5b02396
10. [10]
  P.J. Stephens, J. Pan, F.J. Devlin, et al., J. Org. Chem. 72 (2007) 2508–2524. doi: 10.1021/jo062567p
11. [11]
  Y. Zhu, P. Fu, Q. Lin, et al., Org. Lett. 14 (2012) 2666–2669. doi: 10.1021/ol300589r
1. [1]
  Chuan Li , Yangyang Han , Yanan Zhai , Ke Li , Xingzhong Liu , Zhuan Zhang , Cai Jia , Yongsheng Che . Phomaketals A and B, pentacyclic meroterpenoids from a eupC overexpressed mutant strain of Phoma sp.. Chinese Chemical Letters, 2024, 35(7): 109019-. doi: 10.1016/j.cclet.2023.109019
2. [2]
  Jin Wang , Xiaoyan Pan , Junyu Zhang , Qingqing Zhang , Yanchen Li , Weiwei Guo , Jie Zhang . Active molecule-based theranostic agents for tumor vasculature normalization and antitumor efficacy. Chinese Chemical Letters, 2024, 35(8): 109187-. doi: 10.1016/j.cclet.2023.109187
3. [3]
  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
4. [4]
  Hong Zhang , Cui-Ping Li , Li-Li Wang , Zhuo-Da Zhou , Wen-Sen Li , Ling-Yi Kong , Ming-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351
5. [5]
  Jing JIN , Zhuming GUO , Zhiyin XIAO , Xiujuan JIANG , Yi HE , Xiaoming LIU . Tuning the stability and cytotoxicity of fac-[Fe(CO)₃I₃]^- anion by its counter ions: From aminiums to inorganic cations. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 991-1004. doi: 10.11862/CJIC.20230458
6. [6]
  Qi Tan , Run-Zhu Fan , Wencong Yang , Ge Zou , Tao Chen , Jianying Wu , Bo Wang , Sheng Yin , Zhigang She . (+)/(−)-Mycosphatide A, a pair of highly oxidized polyketides with lipid-lowering activity from the mangrove endophytic fungus Mycosphaerella sp. SYSU-DZG01. Chinese Chemical Letters, 2024, 35(9): 109390-. doi: 10.1016/j.cclet.2023.109390
7. [7]
  Lei Wan , Yizhou Tong , Xi Lu , Yao Fu . Cobalt-catalyzed reductive alkynylation to construct C(sp)-C(sp³) and C(sp)-C(sp²) bonds. Chinese Chemical Letters, 2024, 35(7): 109283-. doi: 10.1016/j.cclet.2023.109283
8. [8]
  Huiju Cao , Lei Shi . sp¹-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
9. [9]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
10. [10]
  Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp³)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
11. [11]
  Yujia Shi , Yan Qiao , Pengfei Xie , Miaomiao Tian , Xingwei Li , Junbiao Chang , Bingxian Liu . Rhodium-catalyzed enantioselective in situ C(sp³)−H heteroarylation by a desymmetrization approach. Chinese Chemical Letters, 2024, 35(10): 109544-. doi: 10.1016/j.cclet.2024.109544
12. [12]
  Yuan Liu , Zhu Yin , Xintuo Yang , Jiajia Cheng . Advances in photocatalytic deracemization of sp³-hybridized chiral centers via hydrogen atom transfer. Chinese Chemical Letters, 2025, 36(5): 110521-. doi: 10.1016/j.cclet.2024.110521
13. [13]
  Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
14. [14]
  Weixu Li , Yuexin Wang , Lin Li , Xinyi Huang , Mengdi Liu , Bo Gui , Xianjun Lang , Cheng Wang . Promoting energy transfer pathway in porphyrin-based sp2 carbon-conjugated covalent organic frameworks for selective photocatalytic oxidation of sulfide. Chinese Journal of Structural Chemistry, 2024, 43(7): 100299-100299. doi: 10.1016/j.cjsc.2024.100299
15. [15]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
16. [16]
  Shouchao Zhong , Yue Wang , Mingshu Xie , Yiqian Wu , Jiuqiang Li , Jing Peng , Liyong Yuan , Maolin Zhai , Weiqun Shi . Radiation reduction modification of sp² carbon-conjugated covalent organic frameworks for enhanced photocatalytic chromium(VI) removal. Chinese Chemical Letters, 2025, 36(5): 110312-. doi: 10.1016/j.cclet.2024.110312
17. [17]
  Jian Han , Li-Li Zeng , Qin-Yu Fei , Yan-Xiang Ge , Rong-Hui Huang , Fen-Er Chen . Recent advances in remote C(sp³)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction. Chinese Chemical Letters, 2024, 35(11): 109647-. doi: 10.1016/j.cclet.2024.109647

Metrics

PDF Downloads(9)
Abstract views(617)
HTML views(67)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

Powered By info@rhhz.net

/

DownLoad: Full-Size Img PowerPoint