Subscribe to RSS
DOI: 10.1055/s-0030-1250526
© Georg Thieme Verlag KG Stuttgart · New York
Antileishmanial Sesquiterpenes from the Brazilian Red Alga Laurencia dendroidea
Publication History
received September 22, 2010
revised October 10, 2010
accepted October 13, 2010
Publication Date:
05 November 2010 (online)
![](https://www.thieme-connect.de/media/plantamedica/201107/lookinside/thumbnails/10.1055-s-0030-1250526-1.jpg)
Abstract
Investigation of the bioactive crude extracts from two populations of the red alga Laurencia dendroidea from the southeastern Brazilian coast led to the identification of five sesquiterpenes: (+)-obtusane (1), a triquinane derivative (2), (−)-elatol (3), obtusol (4), and cartilagineol (5). An antileishmanial bioassay against Leishmania amazonensis was conducted for crude lipophilic extracts and for sesquiterpenes 2, 3, and 4. Compounds 3 and 4 displayed in vitro and in vivo leishmanicidal activity and very low cytotoxicity.
Key words
antileishmanial activity - halogenated sesquiterpenes - Laurencia dendroidea J. Agardh - Rhodomelaceae - Leishmania amazonensis Lainson & Shaw
- Supporting Information for this article is available online at
- Supporting Information .
References
- 1 Blunt J W, Copp B R, Hu W P, Munro M H G, Northcote P T, Prinsep M R. Marine natural products. Nat Prod Rep. 2007; 24 31-86
- 2 Souto M L, Manriquez C P, Norte M, Fernandez J J. Novel marine polyethers. Tetrahedron. 2002; 58 8119-8125
- 3 Pereira R C, Da Gama B A, Teixeira V L, Yoneshigue-Valentin Y. Ecological roles of natural products of the Brazilian red seaweed Laurencia obtusa. Braz J Biol. 2003; 63 665-672
- 4 Konig G M, Wright A D. Laurencia rigida: chemical investigations of its antifouling dichloromethane extract. J Nat Prod. 1997; 60 967-970
- 5 Mohammed K A, Hossain C F, Zhang L, Bruick R K, Zhou Y D. Laurediterpineol, a new diterpene from the tropical marine alga Laurencia intricata that potently inhibits HIF-1 mediated hypoxic signaling in breast tumor cells. J Nat Prod. 2004; 67 2002-2007
- 6 Vairappan C S, Kawamoto T, Miwa H, Suzuki M. Potent antibacterial activity of halogenated compounds against antibiotic-resistant bacteria. Planta Med. 2004; 70 1087-1090
- 7 Morales J L, Cantillo-Ciau Z O, Sanchez-Molina I, Mena-Rejon G J. Screening of antibacterial and antifungal activities of six marine macroalgae from coasts of Yucatan peninsula. Pharm Biol. 2006; 44 632-635
- 8 Sakemi S, Higa T, Jefford C W, Bernardinelli G. Venustatriol – a new, antiviral, triterpene tetracyclic ether from Laurencia venusta. Tetrahedron Lett. 1986; 27 4287-4290
- 9 Gray C A, Lira S P, Silva M, Pimenta E F, Thiemann O H, Oliva G, Hajdu E, Andersen R J, Berlinck R G. Sulfated meroterpenoids from the Brazilian sponge Callyspongia sp. are inhibitors of the antileishmaniasis target adenosine phosphoribosyl transferase. J Org Chem. 2006; 71 8685-8690
- 10 Rao K V, Donia M S, Peng J, Garcia-Palomero E, Alonso D, Martínez A, Medina M, Franzblau S G, Tekwani B L, Khan S I, Wahyuono S, Willet K L, Hamann M T. Manzamine B and E and ircinal A related alkaloids from an Indonesian Acanthostrongylophora sponge and their activity against infectious, tropical parasitic, and Alzheimer's diseases. J Nat Prod. 2006; 69 1034-1040
- 11 Dube A, Singh N, Saxena A, Lakshmi V. Antileishmanial potential of a marine sponge, Haliclona exigua (Kirkpatrick) against experimental visceral leishmaniasis. Parasitol Res. 2007; 101 317-324
- 12 Freile-Pelegrin Y, Robledo D, Chan-Bacab M J, Ortega-Morales B O. Antileishmanial properties of tropical marine algae extracts. Fitoterapia. 2008; 79 374-377
- 13 Genovese G, Tedone L, Hamann M T, Morabito M. The Mediterranean red alga Aparagopsis: a source of compounds against Leishmania. Marine Drugs. 2009; 7 361-366
- 14 González A G, Martín J D, Martín V S, Norte M. Carbon 13 NMR application to Laurencia polyhalogenated sesquiterpenes. Tetrahedron Lett. 1979; 29 2719-2722
- 15 Furasaki A, Matsumoto T, Kurata K, Suzuki T, Suzuki M, Kurosawa E. X-ray structure determination of (−)-obtusane, a new sesquiterpene from the red alga Laurencia nipponica Yamada. Bull Chem Soc Jpn. 1983; 56 3501-3502
- 16 Coll J C, Wright A D. Tropical marine algae III. New sesquiterpenes from Laurencia majuscule (Rhodophyta, Rhodophyceae, Ceramiales, Rhodomelaceae). Austr J Chem. 1989; 42 1591-1603
- 17 Weyerstahl P, Marschall H, Seelmann I, Jakupovic J. Cameroonane, prenopsane and nopsane, three new tricyclic sesquiterpene skeletons. Eur J Org Chem. 1998; 6 1205-1212
- 18 Kennedy D J, Selby I A, Thomson R H. Chamigrane metabolites from Laurencia obtusa and L. scoparia. Phytochemistry. 1988; 27 1761-1766
- 19 Juagdan E G, Kalidindi R, Scheuer P. Two new chamigranes from an Hawaiian red alga Laurencia cartilaginea. Tetrahedron. 1997; 53 521-528
- 20 Vairappan C S, Daitoh M, Suzuki M, Abe T, Masuda M. Antibacterial halogenated metabolites from the Malaysian Laurencia species. Phytochemistry. 2001; 58 291-297
- 21 Brennan M R, Erickson K L, Minoti D A, Pascoe K O. Chamigrane metabolites from a Jamaican variety of Laurencia obtuse. Phytochemistry. 1987; 26 1053-1057
- 22 Wessels M, Konig G M, Wright A D. New natural product isolation and comparison of the secondary metabolite content of three distinct samples of the sea hare Aplysia dactylomela from Tenerife. J Nat Prod. 2000; 63 920-928
- 23 Francisco M E, Turnbull M M, Erickson K L. Cartilagineol, the fourth lineage of Laurencia derived polyhalogenated chamigrene. Tetrahedron Lett. 1998; 39 5289-5292
- 24 Liew F Y, Millot S, Parkinson C, Palmer R M J, Moncada S. Macrophage killing of Leishmania parasite in vivo is mediated by nitric oxide from L-arginine. J Immunol. 1990; 144 4794-4797
Angélica Ribeiro Soares
Núcleo de Estudos em Ecologia e Desenvolvimento Sócio-Ambiental de Macaé
Universidade Federal do Rio de Janeiro
Rua Rotary Club s/n° Bairro São José do Barreto
Macaé 27901-000 RJ
Brazil
Phone: +55 22 27 59 34 31
Fax: +55 22 27 62 93 13
Email: angelica.r.soares@gmail.com
- www.thieme-connect.de/ejournals/toc/plantamedica