Bis(indolyl)methane Alkaloids: Isolation, Bioactivity, and Syntheses

P. J. Praveen; P. S. Parameswaran; M. S. Majik

doi:10.1055/s-0034-1380415

Synthesis, Table of Contents

Synthesis 2015; 47(13): 1827-1837
DOI: 10.1055/s-0034-1380415

short review

Bis(indolyl)methane Alkaloids: Isolation, Bioactivity, and Syntheses

Authors

P. J. Praveen

^aCSIR-National Institute of Oceanography, Bioorganic Chemistry Laboratory, Dona Paula, Goa 403 004, India

^bCSIR-National Institute of Oceanography Regional Centre, Kochi 682 018, India Email: param@nio.org
P. S. Parameswaran*

^bCSIR-National Institute of Oceanography Regional Centre, Kochi 682 018, India Email: param@nio.org
M. S. Majik*

^cDepartment of Chemistry, Goa University, Goa 403 206, India Email: majikms@gmail.com

Abstract

All articles of this category

Abstract

Bis(indolyl)methane (BIM) alkaloids are an important group of bioactive natural products predominantly found in marine organisms. Thus, compounds like arsindoline A and B, vibrindole A, arundine, and trisindoline are found in marine bacteria, while the related compound, streptindole is obtained from Streptococcus faecium IB 37, found in human feces. In recent years, these molecules, which display a wide range of biological properties (antibacterial, antiviral, anti-oxidant, neurotoxic activity etc.), have attracted the attention of several synthetic and natural product chemists. This review lists selected bis(indolyl)methane analogues reported from different natural sources to date, together with their biological properties and synthesis.

1 Introduction

2 Occurrence, Isolation, Structure Elucidation, and Biological Activity

3 Synthetic Approaches towards Bis(indolyl)methanes

4 Conclusions

Key words

bis(indolyl)methanes - natural products - isolation - synthesis - bioactive metabolites

Full Text

References

References
1 Kochanowska-Karamyan AJ, Hamann MT. Chem. Rev. 2010; 110: 4489
2 Bifulco G, Bruno I, Minale L, Riccio R, Calignano A. J. Nat. Prod. 1994; 57: 1294
3 Fattorusso E, Taglialatela-Scafati O. Modern Alkaloids . Wiley-VCH; Weinheim: 2008
4 Haiwei G, Zhengfeng X. Chin. J. Org. Chem. 2012; 32: 1195
5 Kaishap PP, Dohutia C. Int. J. Pharm. Sci. Rev. Res. 2013; 4: 1312 ; http://ijpsr.com/
6 Osawa T, Namiki M. Tetrahedron Lett. 1983; 24: 4719
7 Bell R, Carmeli S, Sar N. J. Nat. Prod. 1994; 57: 1587
8 Kamal A, Ali Qureshi A. Tetrahedron 1963; 19: 513
9 Zee SH, Chen CS. J. Chin. Chem. Soc. 1974; 21: 229
10 Singh H, Singh K. Tetrahedron 1988; 44: 5897
11 Kobayashi M, Aoki S, Gato K, Matsunami K, Kurosu M, Kitagawa I. Chem. Pharm. Bull. 1994; 42: 2449
12 Veluri R, Oka I, Wagner-Döbler I, Laatsch H. J. Nat. Prod. 2003; 66: 1520
13 Fatima I, Ahmad I, Anis I, Malik A, Afza NI. Molecules 2007; 12: 155 ; http://www.mdpi.com/journal/molecules
14 Khuzhaev BU, Aripova SF, Shakirov RS. Chem. Nat. Compd. 1994; 30: 635
15 Cai S.-X, Li D.-H, Zhu T.-J, Wang F.-P, Xiao X, Gu Q.-Q. Helv. Chim. Acta 2010; 93: 791
16 Hogan IT, Sainsbury M. Synthesis 1984; 872
17 Julia M, Tilly G. Bull. Soc. Chim. Fr. 1965; 2175
18 Meyers AI, Nabeya A, Adickes HW, Politzer IR, Malone GR, Kovelesky AC, Nolen RC, Portnoy RC. J. Org. Chem. 1973; 38: 36
19 Denis JN, Mauger H, Vallée Y. Tetrahedron Lett. 1997; 38: 8515
20 Mauger HC, Denis JN, Pouchot MT. A, Vallée Y. Tetrahedron 2000; 56: 791
21 Bartoli G, Bosco M, Foglia G, Giuliani A, Marcantoni E, Sambri L. Synthesis 2004; 895
22 Sato S, Sato T. Carbohydr. Res. 2005; 340: 2251
23 Chakrabarty M, Ghosh N, Basak R, Harigaya Y. Synth. Commun. 2004; 34: 421
24 Azizi N, Torkian L, Saidi MR. J. Mol. Catal. A: Chem. 2007; 275: 109
25 Chakrabarty M, Ghosh N, Basak R, Harigaya Y. Tetrahedron Lett. 2002; 43: 4075
26 Karthik M, Magesh CJ, Perumal PT, Palanichamy M, Arabindoo B, Murugesan V. Appl. Catal., A 2005; 286: 137
27 Banerjee B, Mandal SK, Roy SC. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2007; 46: 669
28 Kumar S, Grover IS, Sandhu JS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2009; 48: 585
29 Guo X, Pan S, Liu J, Li Z. J. Org. Chem. 2009; 74: 8848
30 Surasani R, Kalita D, Chandrasekhar KB. Green Chem. Lett. Rev. 2013; 6: 113
31 Jella RR, Nagarajan R. Tetrahedron 2013; 69: 10249
32 Abe T, Nakamura S, Yanada R, Choshi T, Hibino S, Ishikura M. Org. Lett. 2013; 15: 3622
33 Beltra J, Gimeno MC, Herrera RP. Beilstein J. Org. Chem. 2014; 10: 2206
34 Xiang J, Wang J, Wang M, Meng X, Wu A. Org. Biomol. Chem. 2015; 13: 4240