Antileishmanial Sesquiterpenes from the Brazilian Red Alga Laurencia dendroidea

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

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