Chemical constituents of the volatile oil from leaves of Annona coriacea and in vitro antiprotozoal activity

Revista Brasileira de Farmacognosia

Volumn 21, Issue 1, 2011, Pages 33-40

  Siqueira, Carlos A T ^a   Oliani, Jocimar ^a   Sartoratto, Adilson ^b   Queiroga, Carmen L ^b   Moreno, Paulo R H ^a   Reimão, Juliana Q ^c   Tempone, André G ^c   Fischer, Dominique C H ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b UNIVERSITY OF CAMPINAS   (Brazil)

^c INSTITUTO ADOLFO LUTZ   (Brazil)

Author keywords

Annona coriacea Mart; Annonaceae; GC MS GC FID analysis; In vitro antiprotozoal activity; Volatile oil

Indexed keywords

ALPHA EUDESMOL; ALPHA THUJENE; ANNONA CORIACEA EXTRACT; AROMADENDRENE; BENZNIDAZOLE; BETA ELEMENE; BETA EUDESMOL; BETA IONONE; BETA ISOCOMENE; BETA PINENE; BICYCLOGERMACRENE; BOURBONENE; CARYOPHYLLENE; CYCLOSATIVENE; DELTA CADINENE; EREMOPHILANE DERIVATIVE; ESSENTIAL OIL; GAMMA MUUROLENE; HUMULENE; LIMONENE; MYRCENE; PENTAMIDINE; PLANT EXTRACT; SABINENE; SESQUITERPENE DERIVATIVE; SPATHULENOL; TERPENE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VERBENONE; VIRIDIFLOROL;

ANNONA CORIACEA; ANNONACEAE; ANTIPROTOZOAL ACTIVITY; ARTICLE; BIOCHEMICAL COMPOSITION; CONTROLLED STUDY; DISTILLATION; IC 50; IN VITRO STUDY; LEISHMANIA; LEISHMANIA BRAZILIENSIS; LEISHMANIA CHAGASI; MASS FRAGMENTOGRAPHY; NONHUMAN; PLANT LEAF; PLANT YIELD; PROMASTIGOTE; TRYPANOSOMA CRUZI;

EID: 79954550427     PISSN: 0102695X     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0102-695X2011005000004     Document Type: Article

References (60)

1. Adams RP 2007. Identification of essential oil components by gas chromatography/mass spectrometry. Carol Stream: Allured Publ.
2. Andrade EHA, Oliveira J, Zoghbi MGB 2007. Volatiles of Anaxagorea dolichocarpa Spreng. & Sandw. and Annona densicoma Mart. growing wild in the State of Pará, Brazil. Flavour Fragrance J 22: 158-160.
3. Arruda DC, D'Alexandri FL, Katzin AM, Uliana SRB 2005. Antileishmanial activity of the terpene nerolidol. Antimicrob Agents Chemother 49: 1679-1687.
4. Bermejo A, Figadère B, Zafra-Polo MC, Barrachina I, Estornell E, Cortes D 2005. Acetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of action. Nat Prod Rep 22: 269-303.
5. Boyom FF, Zollo PHA, Menut C, Lamaty G, Bessière JM 1996. Aromatic plants of tropical Central Africa. Part XXVII. Comparative study of the volatile constituents of five Annonaceae species growing in Cameroon. Flavour Fragrance J 11: 333-338.
6. Camacho MDR, Phillipson JD, Croft SL, Solis PN, Marshall SJ, Ghazanfar SA 2003. Screening of plant extracts for antiprotozoal and cytotoxic activities. J Ethnopharmacol 89: 185-191.
7. Carollo CA, Hellmann AR, Máximo de Siqueira J 2005. Sesquiterpenoids from the essential oil from leaves of Duguetia furfuracea (Annonaceae). Biochem Syst Ecol 33: 647-649.
8. Carvalho PL 2009. A proteção da biodiversidade brasileira: o caso das plantas medicinais. http://www.infobibos.com/Artigos/2009_2/Biodiversidade/index.htm. Access June 2010.
9. Coelho MB, De Souza IA, Freire MGM, Marangoni S, Antunes E, Macedo MLR 2003. Neutrophil migration in mice induced by a mannose-binding lectin isolated from Annona coriacea seeds. Toxicon 48: 529-535.
10. Costa EV, Pinheiro MLB, Silva JRA, Maia BHLNS, Duarte MCT, Amaral ACF, Machado GMC, Leon LL 2009. Antimicrobial and antileishmanial activity of essential oil from leaves of Annona foetida (Annonaceae). Quim Nova 32: 78-81.
11. Costa EV, Pinheiro MLB, Xavier CM, Silva JRA, Amaral ACF, Souza ADL, Barison A, Campos FR, Ferreira AG, Machado GMC, Leon LLP 2006. A pyrimidine-β-carboline and other alkaloids from Annona foetida with antileishmanial activity. J Nat Prod 69: 292-294.
12. Costa EV, Teixeira SD, Marques FA, Duarte MCT, Delarmelina C, Pinheiro MALB, Trigo JR, Sales Maia BHLN 2008. Chemical composition and antimicrobial activity of the essential oils of the Amazon Guatteriopsis species. Phytochemistry 69: 1895-1899.
13. Cruz GL 1985. Dicionário de plantas úteis do Brasil. 3 ed. Rio de Janeiro: Civilização Brasileira.
14. Darko LL, Nakanishi K, Nakagawa M 1983. Physiologically active pterocarpan compounds, their isolation and therapeutically active compositions containing them. Eur Pat Appl EP 0,089,229. apud SciFinder Scholar.
15. Ferrari M, Pelizzoni F, Ferrari G 1971. New diterpenoids with clerodane skeleton. Phytochemistry 10: 3267-3269.
16. Ferreira L, Perestrelo R, Camara JS 2009. Comparative analysis of the volatile fraction from Annona cherimola Mill. cultivars by solid-phase microextraction and gas chromatography-quadrupole mass spectrometry detection. Talanta 77: 1087-1096.
17. Fischer DCH, Gualda NCA, Bachiega D, Carvalho CS, Lupo FN, Bonoto SV, Alves MO, Yogi A, Di Santi SM, Ávila PE, Kirchgatter K, Moreno PRH 2004. In vitro screening for antiplasmodial activity of isoquinoline alkaloids from Brazilian plant species. Acta Trop 92: 261-266.
18. Fournier G, Leboeuf M, Cave A 1999. Annonaceae essential oils: a review. J Essent Oil Res 11: 131-142.
19. Garg SN, Gupta D 2005. Composition of the leaf oil of Annona squamosa L. from the North Indian plains. J Essent Oil Res 17: 257-258.
20. Heywood VH (ed.) 1993. Flowering plants of the world. Oxford: University Press, p.30-31.
21. Hoehne FC 1946. Frutas indígenas. São Paulo: Instituto de Botânica.
22. Judd W, Campbell CS, Kellog EA, Stevens PF, Donogahue MJ 2002. Plant systematics: a phylogenetic approach. 2. ed. Sunderland: Sinauer, p.576.
23. Kossouoh C, Moudachirou M, Adjakidje V, Chalchat JC, Figuérédo G 2007. Essential oil chemical composition of Annona muricata L. leaves from Benin. J Essent Oil Res 19: 307-309.
24. Lane JE, Ribeiro-Rodrigues R, Suarez CC, Bogitsh BJ, Jones MM, Singh PK, Carter CE 1996. In vitro trypanocidal activity of tetraethylthiuram disulfide and sodium dietylamine-N-carbodithioate on Trypanosoma cruzi. Am J Trop Med Hyg 55: 263-266.
25. Leboeuf M, Cave A, Bhaumik PK, Mukherjee B, Mukherjee R 1982. The phytochemistry of the Annonaceae. Phytochemistry 21: 2783-2813.
26. Lima MA, Barbosa-Filho JM, Merlic CA, Doroh BC, Maia JGS, Silva MS, Cunha EVL 2004. Alkaloids and volatile constituents from Guatteria poeppigiana. Biochem Syst Ecol 32: 347-349.
27. Mello-Silva R, Pontes AF 2005. Annonaceae do Parque Nacional da Serra da Canastra, Minas Gerais, Brasil. Bol Bot Univ. São Paulo 23: 71-84.
28. Mussini P, Orsini F, Pelizzoni F, Buckwalter BL, Wenkert E 1973a. Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. XXII. Carbon-13 configuration of annonalide. Tetrahedron Lett 49: 4849-4851.
29. Mussini P, Orsini F, Pelizzoni F, Ferrari G 1973b. Constituents of Annona coriacea: structure of a new diterpenoid. J Chem Soc, Perkin Trans I: 2551-2557.
30. Nakagawa M, Nakanishi K, Darko LL, Vick JA 1982. Structures of cabenegrins A-I and A-II, potent antisnake venoms. Tetrahedron Lett 23: 3855-3858.
31. Nebié RHC, Yaméogo RT, Bélanger A, Sib SF 2005. Chemical composition of leaf essential oil of Annona senegalensis Pers. from Burkina Faso. J Essent Oil Res 17: 331-332.
32. Newman DJ, Cragg GM 2007. Natural products as sources of new drugs over the last 25 years. J Nat Prod 70: 461-477.
33. NIST 2005. NIST/EPA/HIH Mass Spectral Library, NIST Mass Spectral Search Program (NIST 05). Version 2.0d. Gaithersburg: NIST Mass Spectrometry Data Center.
34. Onan KD, McPhail AT 1978. Crystal and molecular structure of annonalide, a 9ß H-pimaradienic diterpenoid from Annona coriacea. J Chem Res, Synop 1: 15.
35. Orsini F, Pellizoni F, McPhail AT, Onan KD, Wenkert E 1977. The structure of annonalide. Tetrahedron Lett 12: 1085-1088
36. Osorio EJ, Robledo SM, Bastida J 2008. Alkaloids with antiprotozoal activity: chapter 2. Alkaloids: Chem Biol 66: 113-190.
37. Palazzo MC, Wright HL, Agius BR, Wright BS, Moriarity DM, Haber WA, Setzer WN 2009. Chemical compositions and biological activities of leaf essential oils of six species of Annonaceae from Monteverde, Costa Rica. Rec Nat Prod 3: 153-160.
38. Pontes AL, Barbosa MRV, Maas PJM 2004. Flora paraibana: Annonaceae Juss. Acta Bot Brasilica 18: 281-293.
39. Santoro GF, Cardoso MG, Guimaraes LGL, Freire JM, Soares MJ 2007. Anti-proliferative effect of the essential oil of Cymbopogon citratus (DC) Stapf (lemongrass) on intracellular amastigotes, bloodstream trypomastigotes and culture epimastigotes of Trypanosoma cruzi (Protozoa: Kinetoplastida). Parasitology 134: 1649-1656.
40. Sartorelli P, Andrade SP, Melhem MSC, Prado FO, Tempone AG 2007. Isolation of antileishmanial sterol from the fruits of Cassia fistula using bioguided fractionation. Phytother Res 21: 644-647
41. Savioli L 2010. Neglected tropical diseases. http://www.who.int/neglected_diseases/director/en/index.html. Access June 2010.
42. Silva DB, Matos MFC, Nakashita ST, Misu CK, Yoshida NC, Carollo CA, Fabri JR, Miglio HS, Siqueira JM 2007. Isolamento e avaliação da atividade citotóxica de alguns alcalóides oxaporfínicos obtidos de Annonaceae. Quim Nova 30: 1809-1812.
43. Silva ELM, Roblot F, Hocquemiller R, Serani L, Laprevote O 1998. Structure elucidation of annoheptocins, two new heptahydroxylated C37 acetogenins by highenergy collision-induced dissociation tandem mass spectrometry. Rapid Commun Mass Spectrom 12: 1936-1944.
44. Silva ELM, Roblot F, Laprévote O, Sérani L, Cave A 1997a. Coriaheptocins A and B, the first heptahydroxylated acetogenins, isolated from the roots of Annona coriacea. J Nat Prod 60: 162-167.
45. Silva ELM, Roblot F, Laprevote O, Varenne P, Cave, A 1995. Acetogenins from Annonaceae. Part 40. Coriacin and 4-deoxycoriacin, two new mono-THF acetogenins from the roots of Annona coriacea. Nat Prod Lett 7: 235-242.
46. Silva ELM, Roblot F, Mahuteau J, Cave A 1996. Coriadienin, the first Annonaceous acetogenin with two double bonds isolated from Annona coriaceae. J Nat Prod 59: 528-530.
47. Silva L, Oniki GH, Agripino DG, Moreno PRH, Young MCM, Mayworm MAS, Ladeira AM 2007. Bicyclogermacrene, resveratrol e atividade antifúngica em extratos de folhas de Cissus verticullatta (L.) Nicolson & Jarvis (Vitaceae). Rev Bras Farm 17: 361-367.
48. Silva, ELM, Roblot F, Cave A 1997b. Acetogenin from Annonaceae. 57. Coriacyclodienin and coriacycloenin: two new annonaceous acetogenins from Annona coriacea. Heterocycles 45: 915-925.
49. Smith N, Mori SA, Henderson A, Stevenson DW, Heald SV (eds.) 2004. Flowering plants of the Neotropics. Princeton: Princeton University Press, p.18.
50. Sonnet PE, Jacobson M 1971. Tumor inhibitors. II. Cytotoxic alkaloids from Annona purpurea. J Pharm Sci 60: 1254-1256.
51. Souza VC, Lorenzi H 2008. Botânica sistemática: guia ilustrado para identificação das famílias de Fenerógamas nativas e exóticas no Brasil, baseado em APG II. 2. ed. Nova Odessa: Instituto Plantarum.
52. Tada H, Shiho O, Kuroshima K, Koyama M, Tsukamoto K 1986. An improved colorimetric assay for interleukin-2. J Immunol Methods 93: 157-165.
53. Tempone AG, Treiger Borborema SE, Andrade Jr HF, Amorim Gualda NC, Yogi A, Salerno Carvalho C, Bachiega D, Lupo FN, Bonotto SV, Fischer DCH 2005. Antiprotozoal activity of Brazilian plant extracts from isoquinoline alkaloid-producing families. Phytomedicine 12: 382-390.
54. Valter JL, Alencar KMC, Sartori ALB, Nascimento EA, Chang R, Morais SAL, Laura VA, Yoshida NC, Carollo CA, Silva DB, Grassi RF, Fabri JR, Siqueira JM 2008. Variação química no óleo essencial das folhas de seis indivíduos de Duguetia furfuracea (Annonaceae). Rev Bras Farmacogn 18: 373-378.
55. Van Den Dool H, Kratz PD 1963. A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J Chromatogr 11: 463-471.
56. Villar Del Fresno A, Mares Arambul M, Rios Canavate JL 1984. Propriétés antimicrobiennes des feuilles d'Annona cherimolia Mill. Plant Med Phytother 17: 230-235.
57. Savioli L 2010. http://www.who.int/neglected_diseases/director/en/index.html, access June 2010.
58. 2 extraction and simultaneous determination of eight annonaceous acetogenins in Annona genus plant seeds by HPLC-DAD method. J Pharm Biomed Anal 49: 140-144.
59. Yu JG, Hu, XE, Ho DK, Bean MF, Stephens RE, Cassady, JM, Brinen, LS, Clardy J 1994. Absolute stereochemistry of (+)-gigantecin from Annona coriacea (Annonaceae) J Org Chem 59: 1598-1599.
60. Zheljazkov VD, Cantrell CL, Tekwani B, Khan SI 2008. Content, composition, and bioactivity of the essential oils of three basil genotypes as a function of harvesting. J Agric Food Chem 56: 380-385