Bioactive Compounds of Annona

Living reference work entry
Part of the Reference Series in Phytochemistry book series (RSP)


Evaluation of phytochemicals from extract of different plant parts has results in the identification of numerous important bioactive constituents in various Annona species. The major phytochemical constituents include acetogenins, alkaloids, essential oils, phenolic compounds, cyclopeptides, amino acids, pigments, and vitamins. These phytochemicals contribute toward several pharmacological activities such as antitumoral, antidiabetic, anxiolytic, analgesic, anti-inflammatory, infectious, and parasitic diseases. The aim of this review is to discuss the major phytochemicals like acetogenins, alkaloids, and essential oils and their pharmacological in various Annona species including A. squamosa, A. reticulata, A. cherimola, A. glabra, A. senegalensis, A. crassiflora, and A. coriacea.


Acetogenins Alkaloids Annona Bioactive compounds Essential oils Pharmacological studies Phytochemicals 

List of Abbreviations










Essential oils


gamma-aminobutyric acid


Gas chromatography-mass spectrometry


High-performance liquid chromatography-mass spectrometry


Half-maximal inhibitory concentration


Median lethal dose


Nicotinamide adenine dinucleotide


Oxygen radical absorbance




  1. 1.
    Pareek S, Yahia EM, Pareek OP, Kaushik RA (2011) Postharvest physiology and technology of Annona fruits. Food Res Int 44(7):1741–1751CrossRefGoogle Scholar
  2. 2.
    Pinto AC, Cordeiro MCR, de Andrade SRM, Ferreira FR, Filgueiras HA, Alves HA, Kinpara DI (2005) Annona species. International center for underutilised crops. University of Southampton, SouthamptonGoogle Scholar
  3. 3.
    Léon J (1987) Botánica de los cultivos tropicales. II CA, San JoséGoogle Scholar
  4. 4.
    González Vega ME (2013) Chirimoya (Annona cherimola Miller), Frutal tropical y sub-tropical de valores promisorios. Cultiv Trop 34:52–63Google Scholar
  5. 5.
    Le Ven J, Schmitz-Afonso I, Lewin G, Brunelle A, Touboul D, Champy P (2014) Identification of the environmental neurotoxins annonaceous acetogenins in an Annona cherimola Mill. alcoholic beverage using HPLC-ESI-LTQ-Orbitrap. J Agric Food Chem 62:8696–8704PubMedCrossRefGoogle Scholar
  6. 6.
    Alique R, Oliveira GS (1994) Changes in sugars and organic acids in cherimoya (Annona cherimola Mill.) fruit under controlled atmosphere storage. J Agric Food Chem 42:799–803CrossRefGoogle Scholar
  7. 7.
    Bermejo A, Figadère B, Zafra-Polo M-C, Barrachina I, Estornell E, Cortes D (2005) Acetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of action. Nat Prod Rep 22:269–303PubMedCrossRefGoogle Scholar
  8. 8.
    Chen Y, Chen JW, Zhai JH, Wang Y, Wang SL, Li X (2013) Antitumor activity and toxicity relationship of annonaceous acetogenins. Food Chem Toxicol 58:394–400PubMedCrossRefGoogle Scholar
  9. 9.
    Wang DS, Rizwani GH, Guo H et al (2014) Annona squamosa Linn: cytotoxic activity found in leaves extract against human tumour cell lines. Pak J Pharm Sci 27:1559–1563PubMedGoogle Scholar
  10. 10.
    Siqueira CA, Oliani J, Sartoratto A et al (2011) Chemical constituents of the volatile oil from leaves of Annona coriacea and in vitro antiprotozoal activity. Braz J Pharmacogn 21:33–40Google Scholar
  11. 11.
    Singh N, Kaushik NK, Mohanakrishnan D, Tiwari SK, Sahal D (2015) Antiplasmodial activity of medicinal plants from Chhota Nagpur plateau, Jharkhand, India. J Ethnopharmacol 165:152–162PubMedCrossRefGoogle Scholar
  12. 12.
    Jamkhande PG, Wattamwar AS (2015) Annona reticulata Linn. (Bullock’s heart): plant profile, phytochemistry and pharmacological properties. J Tradit Complement Med 5:144–152PubMedPubMedCentralCrossRefGoogle Scholar
  13. 13.
    Rocha RS, Kassuya CA, Formagio AS et al (2015) Analysis of the anti-inflammatory and chemopreventive potential and description of the antimutagenic mode of action of the Annona crassiflora methanolic extract. Pharm Biol 17:1–13Google Scholar
  14. 14.
    Thattakudian Sheik Uduman MS, Sundarapandian R, Muthumanikkam A et al (2011) Protective effect of methanolic extract of Annona squamosa Linn in isoniazidrifampicin induced hepatotoxicity in rats. Pak J Pharm Sci 24:129–134PubMedGoogle Scholar
  15. 15.
    Chavan MJ, Kolhe DR, Wakte PS, Shinde DB (2012) Analgesic and antiinflammatory activity of kaur-16-en-19-oic acid from Annona reticulata L. bark. Phytother Res 26:273–276PubMedCrossRefGoogle Scholar
  16. 16.
    Chavan MJ, Wakte PS, Shinde DB (2012) Analgesic and anti-inflammatory activities of the sesquiterpene fraction from Annona reticulata L. bark. Nat Prod Res 26:1515–1518PubMedCrossRefGoogle Scholar
  17. 17.
    González-Trujano ME, Martínez AL, Reyes-Ramírez A, Reyes-Trejo B, Navarrete A (2006) Palmitone isolated from Annona diversifolia induces an anxiolytic-like effect in mice. Planta Med 72:703–707PubMedCrossRefGoogle Scholar
  18. 18.
    Alali FQ, Xiao-Xi L, McLaughlin JL (1999) Annonaceous acetogenins: recent progress. J Nat Prod 62:504–540PubMedCrossRefGoogle Scholar
  19. 19.
    Gleye C, Raynaud S, Hocquemiller R et al (1998) Muricadienin, muridienins and chatenaytrienins, the early precursors of annonaceous acetogenins. Phytochemistry 47:749–754CrossRefGoogle Scholar
  20. 20.
    Zafra-Polo MC, Figadère B, Gallardo T, Tormo J, Cortes D (1998) Natural acetogenins from Annonaceae, synthesis and mechanisms of action. Phytochemistry 48:1087–1117CrossRefGoogle Scholar
  21. 21.
    Egydio-Brandão A, Novaes P, Santos D (2017) Alkaloids from Annona: review from 2005 to 2017. JSM Biochem Mol Biol 4:1031–1043Google Scholar
  22. 22.
    Lima JPS, Pinheiro MLB, Santos AMG, Costa EV (2012) In vitro antileishmanial and cytotoxic activities of Annona mucosa (Annonaceae). Rev Virtual Quimica 4:692–702Google Scholar
  23. 23.
    Costa EV, Pinheiro MLB, Souza ADLD et al (2011) Trypanocidal activity of oxoaporphine and pyrimidine-β-carboline alkaloids from the branches of Annona foetida Mart. (Annonaceae). Molecules 16:9714–9720PubMedPubMedCentralCrossRefGoogle Scholar
  24. 24.
    Cruz-Chacón IDL, González-Esquinca AR, Fefer PG, Garcia LFJ (2011) Liriodenine, early antimicrobial defence in Annona diversifolia. Z Naturforsch C 66:377–384PubMedCrossRefGoogle Scholar
  25. 25.
    Johns T, Windust A, Jurgens T, Mandor SM (2011) Antimalarial alkaloids isolated from Annona squamosa. Phytopharmacology 1:49–53Google Scholar
  26. 26.
    Hasrat JA, De Bruyne T, De Backer JP, Vauquelin G, Vlietinck AJ (1997) Isoquinoline derivatives isolated from the fruit of Annona muricata as 5-HTergic 5-HT1A receptor agonists in rats: unexploited antidepressive (lead) products. J Pharm Pharmacol 49:1145–1149PubMedCrossRefGoogle Scholar
  27. 27.
    Hasrat JA, Pieters L, de Backer JP, Vauquelin G, Vlietinck AJ (1997) Screening of medicinal plants from Suriname for 5-HT1A ligands: bioactive isoquinoline alkaloids from fruit of Annona muricata. Phytomedicine 4:133–140PubMedCrossRefGoogle Scholar
  28. 28.
    Corrêa MP (1984) Dicionário das plantas úteis do Brasil e das exóticas cultivadas. Imprensa Nacional 3:238–239. IBDF, Rio de JaneiroGoogle Scholar
  29. 29.
    Costa EV, Dutra LM, de Jesus HCR, Nogueira PCL, Moraes VRS, Salvador MJ, Prata APN (2011) Chemical composition and antioxidant, antimicrobial, and larvicidal activities of the essential oils of Annona salzmannii and A. pickelii (Annonaceae). Nat Prod Commun 6:907–912PubMedGoogle Scholar
  30. 30.
    Costa EV, Dutra LM, Salvador MJ, Ribeiro LH, Gadelha FR, Carvalho JE (2013) Chemical composition of the essential oils of Annona pickelii and Annona salzmannii (Annonaceae), and their antitumor and trypanocidal activities. Nat Prod Res 27:997–1001CrossRefGoogle Scholar
  31. 31.
    Li X, Chen XL, Chen JW, Sun DD (2010) Annonaceous acetogenins from the seeds of Annona squamosa. Chem Nat Compd 46:101–105CrossRefGoogle Scholar
  32. 32.
    Chen Y, Chen JW, Li X (2012) Monotetrahydrofuran annonaceous acetogenins from the seeds of Annona squamosa. Phytochem Lett 5:33–36CrossRefGoogle Scholar
  33. 33.
    Yuan F, Bai GG, Chen Y, Miao YJ, Chen JW, Li X (2015) Structure-activity relationships of diverse ACGs against multidrug resistant human lung cancer cell line A549/Taxol. Bioorg Med Chem Lett 25:787–790CrossRefGoogle Scholar
  34. 34.
    Chen Y, Chen JW, Li X (2011) Cytotoxic bistetrahydrofuran annonaceous acetogenins from the seeds of Annona squamosa. J Nat Prod 74:2477–2481PubMedCrossRefGoogle Scholar
  35. 35.
    Rahman MM, Parvin S, Haque ME, Islam ME, Mosaddik MA (2005) Antimicrobial and cytotoxic constituents from the seeds of Annona squamosa. Fitoterapia 76:484–489CrossRefGoogle Scholar
  36. 36.
    Araya H (2004) Studies on annonaceous tetrahydrofuranic acetogenins from Annona squamosa L. seeds. Bull Natl Inst Agro-Environ Sci (Japan) 23:77–149Google Scholar
  37. 37.
    Dang QL, Kim WK, Nguyen CM et al (2011) Nematicidal and antifungal activities of annonaceous acetogenins from Annona squamosa against various plant pathogens. J Agric Food Chem 59:11160–11167CrossRefGoogle Scholar
  38. 38.
    Ndob IBB, Champy P, Gleye C, Lewin G, Akendengue B (2009) Annonaceous acetogenins: precursors from the seeds of Annona squamosa. Phytochem Lett 2:72–76CrossRefGoogle Scholar
  39. 39.
    Oberlies NH, Chang CJ, McLaughlin JL (1997) Structure-activity relationships of diverse annonaceous acetogenins against multidrug resistant human mammary adenocarcinoma (Mcf-7/Adr) cells. J Med Chem 40:2102–2106PubMedCrossRefGoogle Scholar
  40. 40.
    Liaw CC, Yang YL, Chen M et al (2008) Mono-tetrahydrofuran annonaceous acetogenins from Annona squamosa as cytotoxic agents and calcium ion chelators. J Nat Prod 71:764–771PubMedCrossRefGoogle Scholar
  41. 41.
    Yu JG, Luo XZ, Sun L, Li DY, Huang WH, Liu CY (2005) Chemical constituents from the seeds of Annona squamosa. Acta Pharm Sin 40:153–158Google Scholar
  42. 42.
    Xu SS, Li X, Chen JW, Chen Y (2012) Chemical constituents from seeds of Annona squamosa. Chin Trad Herbal Drugs 43:255–258Google Scholar
  43. 43.
    Jayendra M, Kumar Y (2013) New compound 6,7-dimethoxy-2-methylisoquinolinium from Indian medicinal plant Annona squamosa L. Int J Chem Anal Sci 4:161–168CrossRefGoogle Scholar
  44. 44.
    Miao YJ, Xu XF, Yuan F et al (2015) Four cytotoxic annonaceous acetogenins from the seeds of Annona squamosa. Nat Prod Res 30:1273–1279PubMedCrossRefGoogle Scholar
  45. 45.
    Araya H, Sahai M, Singh S et al (2002) Squamocin-O-1 and squamocin-O-2, new adjacent bis-tetrahydrofuran acetogenins from the seeds of Annona squamosa. Phytochemistry 61:999–1004PubMedCrossRefGoogle Scholar
  46. 46.
    Yang HJ, Li X, Zhang N, Chen JW, Wang MY (2009) Two new cytotoxic acetogenins from Annona squamosa. J Asian Nat Prod Res 11:250–256PubMedCrossRefGoogle Scholar
  47. 47.
    Xie HH, Wei XY, Wang JD, Liu MF, Yang RZ (2003) A new cytotoxic acetogenin from the seeds of Annona squamosa. Chin Chem Lett 14:588–590Google Scholar
  48. 48.
    Tormo JR, Gallardo T, Aragón R, Cortes D, Estornell E (1999) Specific interactions of monotetrahydrofuranic annonaceous acetogenins as inhibitors of mitochondrial complex I. Chem Biol Interact 122:171–183PubMedCrossRefGoogle Scholar
  49. 49.
    Yang YL, Hua KF, Chuang PH et al (2008) New cyclic peptides from the seeds of Annona squamosa L. and their anti-inflammatory activities. J Agric Food Chem 56:386–392PubMedCrossRefGoogle Scholar
  50. 50.
    Morita H, Sato Y, Kobayashi J (1999) Cyclosquamosins A-G, cyclic peptides from the seeds of Annona squamosa. Tetrahedron 55:7509–7518CrossRefGoogle Scholar
  51. 51.
    Mazahery ARF, Dator RP, Concepcion GP, Jacinto SD (2009) Murihexocin C from the leaves of Annona squamosa Linn. induces apoptosis in human colon carcinoma col 2 cell line. Philipp Agric Sci 92:122–132Google Scholar
  52. 52.
    Hopp DC, Alali FQ, Gu ZM, McLaughlin JL (1998) Three new bioactive bis-adjacent THF-ring acetogenins from the bark of Annona squamosa. Bioorg Med Chem 6:569–575PubMedCrossRefGoogle Scholar
  53. 53.
    Hopp DC (1997) New bioactive annonaceous acetogenins from the bark of Annona squamosa, and the use of countercurrent chromatography for their isolation. Dissertation, Purdue University, West LafayetteGoogle Scholar
  54. 54.
    Lima LARS, Pimenta LPS, Boaventura MAD (2010) Acetogenins from Annona cornifolia and their antioxidant capacity. Food Chem 122:1129–1138CrossRefGoogle Scholar
  55. 55.
    Silva ELMD, Roblot F, Cave A (1997) Coriacyclodienin and coriacycloenin: two new annonaceous acetogenins from Annona coriacea. Heterocycles 45:915–925CrossRefGoogle Scholar
  56. 56.
    da C Alves T, Gonçalves MRS, Correia FCS et al (2014) New acetogenins from the seeds of Annona coriacea. Helv Chim Acta 97:1469–1474CrossRefGoogle Scholar
  57. 57.
    Chen CY, Chang FR, Chiu HF, Wu MJ, Wu YC (1999) Aromin-A, an annonaceous acetogenin from Annona cherimola. Phytochemistry 51:429–433PubMedCrossRefGoogle Scholar
  58. 58.
    Kim DH, Ma ES, Suk KD, Son JK, Lee JS, Woo MH (2001) Annomolin and annocherimolin, new cytotoxic annonaceous acetogenins from Annona cherimola seeds. J Nat Prod 64:502–506PubMedCrossRefGoogle Scholar
  59. 59.
    Nirmal SA, Gaikwad SB, Dhasade VV, Dhikale RS, Kotkar PV, Dighe SS (2010) Anthelmintic activity of Annona reticulata leaves. Res J Pharm Biol Chem Sci 1:115–118Google Scholar
  60. 60.
    Bhalke RD, Chavan MJ (2011) Analgesic and CNS depressant activities of extracts of Annona reticulata Linn. bark. Phytopharmacology 1:160–165Google Scholar
  61. 61.
    Wele A, Mayer C, Dermigny Q, Zhang Y, Blond A, Bodo B (2008) Sequence and three dimensional structure of cycloreticulins A and B new cyclooctapeptides from the seeds of Annona reticulata. Tetrahedron 64:154–162CrossRefGoogle Scholar
  62. 62.
    Duval RA, Duret P, Lewin G, Peris E, Hocquemiller R (2005) Semisynthesis and biological activity aminoacyl trimesters of squamocin, an annonaceous acetogenin. Bioorg Med Chem 13:3773–3781PubMedCrossRefGoogle Scholar
  63. 63.
    Dong L, Jingguang Y, Lan S, Xiuzhen L, Shaorong G, Jitian L (1998) Studies on chemical constituents of the seeds from Annona reticulata (Annonaceae). Nat Prod Res Dev 10:1–7Google Scholar
  64. 64.
    Sahpaz S, Carmen González M, Hocquemiller R, Zafra-Polo M, Cortes D (1996) Annosenegalin and annogalene: two cytotoxic monotetrahydrofuran acetogenins from Annona senegalensis and Annona cherimola. Phytochemistry 42:103–107PubMedCrossRefGoogle Scholar
  65. 65.
    Zeng L, Ye Q, Oberlies N, Shi G, Gu Z, He K, McLaughlin JL (1996) Recent advances in Annonaceous acetogenins. Nat Prod Rep 13:275–306PubMedCrossRefGoogle Scholar
  66. 66.
    Fall D, Sambou B, Seck M, Wélé A, Ndoye I, Gleye C, Laurens A (2008) Enhancing the anthelminthic activity roots of Annona senegalensis. Dakar Med 53:61–67PubMedGoogle Scholar
  67. 67.
    Laguna-Hernández G, Brechú-Franco AE, De la Cruz-Chacón I, González-Esquinca AR (2017) A histochemical technique for the detection of Annonaceous acetogenins. In: Pellicciari C, Biggiogera M (eds) Histochemistry of single molecules, methods in molecular biology. Human Press, New York, pp 331–338CrossRefGoogle Scholar
  68. 68.
    Rabêlo SV, Costa EV, Barison A, Dutra LM, Nunes XP, Tomaz JC (2015) Alkaloids isolated from the leaves of atemoya (Annona cherimola × Annona squamosa). Rev Bras Farmacogn 25:419–421CrossRefGoogle Scholar
  69. 69.
    Martínez-Vázquez M, Diana G, Estrada-Reyes R, González-Lugo M, Apan TR, Heinze G (2005) Bio-guided isolation of the cytotoxic corytenchine and isocoreximine from roots of Annona cherimola. Fitoterapia 76:733–736PubMedCrossRefGoogle Scholar
  70. 70.
    Egydio APM, Valvassoura TA, Santos DYA (2013) Geographical variation of isoquinoline alkaloids of Annona crassiflora Mart. from cerrado, Brazil. Biochem Syst Ecol 46:145–151CrossRefGoogle Scholar
  71. 71.
    Campos FR, Batista RL, Batista CL (2008) Isoquinoline alkaloids from leaves of Annona sericea (Annonaceae). Biochem Syst Ecol 36:804–806CrossRefGoogle Scholar
  72. 72.
    Costa EV, Pinheiro MLB, Xavier CM et al (2006) A pyrimidine-β-carboline and other alkaloids from Annona foetida with antileishmanial activity. J Nat Prod 69:292–294PubMedCrossRefGoogle Scholar
  73. 73.
    Lee SS, Wu DY, Tsai SF, Chen CK (2015) Anti-acetylcholinesterase alkaloids from Annona glabra leaf. Nat Prod Commun 10:891–893PubMedGoogle Scholar
  74. 74.
    Rinaldi MVN, Díaz IEC, Suffredini IB, Moreno PRH (2017) Alkaloids and biological activity of beribá (Annona hypoglauca). Rev Bras Farmacogn 1:77–83CrossRefGoogle Scholar
  75. 75.
    Costa EV, Sampaio MFC, Salvador MJ, Nepel A, Barison A (2015) Chemical constituents from the stem bark of Annona pickelii (Annonaceae). Quim Nova 38:769–776Google Scholar
  76. 76.
    Dutra LM, Costa EV, Souza Moraes VRS, Nogueira PCL, Vendramin ME, Barison A (2012) Chemical constituents from the leaves of Annona pickelii (Annonaceae). Biochem Syst Ecol 41:115–118CrossRefGoogle Scholar
  77. 77.
    Nakano D, Ishitsuka K, Hatsuse T et al (2011) Screening of promising chemotherapeutic candidates against human adult T-cell leukemia/lymphoma from plants: active principles from Physalis pruinosa and structure–activity relationships with withanolides. J Nat Med 65:559–567PubMedCrossRefGoogle Scholar
  78. 78.
    Li HT, Wu HM, Chen H, Liu CM, Chen CY (2013) The pharmacological activities of (−)-anonaine. Molecules 18:8257–8263PubMedPubMedCentralCrossRefGoogle Scholar
  79. 79.
    Cruz PEO, Costa EV, Moraes VRS et al (2011) Chemical constituents from the bark of Annona salzmannii (Annonaceae). Biochem Syst Ecol 39:872–875CrossRefGoogle Scholar
  80. 80.
    Fofana S, Keita A, Balde S, Ziuaev R, Aripova SF (2012) Alkaloids from leaves of Annona muricata. Chem Nat Compd 48:714CrossRefGoogle Scholar
  81. 81.
    Magadula JJ, Innocent E, Otieno JN (2009) Mosquito larvicidal and cytotoxic activities of Annona species and isolation of active principles. J Med Plant Res 3:674–680Google Scholar
  82. 82.
    Lall N, Kishore N, Bodiba D, More G, Tshikalange E, Kikuchi H, Oshima Y (2017) Alkaloids from aerial parts of Annona senegalensis against Streptococcus mutans. Nat Prod Res 31:1944–1947PubMedCrossRefGoogle Scholar
  83. 83.
    Vendramin ME, Costa EV, Santos EP, Campos FR (2013) Chemical constituents from the leaves of Annona rugulosa (Annonaceae). Biochem Syst Ecol 49:152–155CrossRefGoogle Scholar
  84. 84.
    Dholvitayakhun A, Trachoo N, Sakee U, Cushnie TP (2013) Potential applications for Annona squamosa leaf extract in the treatment and prevention of foodborne bacterial disease. Nat Prod Commun 8:385–388PubMedGoogle Scholar
  85. 85.
    Nakano D, Ishitsuka K, Kamikawa M et al (2013) Screening of promising chemotherapeutic candidates from plants against human adult T-cell leukemia/lymphoma (III). J Nat Med 67:894–903PubMedCrossRefGoogle Scholar
  86. 86.
    Baskar R, Rajeswari V, Kumar TS (2007) In vitro antioxidant studies in leaves of Annona species. Ind J Exp Biol 45:480–485Google Scholar
  87. 87.
    Lebrini M, Robert F, Roos C (2010) Inhibition effect of alkaloids extract from Annona squamosa plant on the corrosion of C38 steel in normal hydrochloric acid medium. Int J Electrochem Sci 5:1698–1712Google Scholar
  88. 88.
    Vila Verde GM, Paula JR, Carneiro DM (2003) Levantamento etnobotânico das plantas medicinais do cerrado utilizadas pela população de Mossâmedes (GO). Rev Bras Farmacogn 13:64–66CrossRefGoogle Scholar
  89. 89.
    Bicas JL, Molina G, Dionísio AP et al (2011) Volatile constituents of exotic fruits from Brazil. Food Res Int 44:1843–1855CrossRefGoogle Scholar
  90. 90.
    Pino JA (2000) Volatile components of Cuban Annona fruits. J Essent Oil Res 12:613–616CrossRefGoogle Scholar
  91. 91.
    Costa EV, Pinheiro MLB, Silva JRA et al (2009) Antimicrobial and antileishmanial activity of essential oil from the leaves of Annona foetida (Annonaceae). Quim Nova 32:78–81CrossRefGoogle Scholar
  92. 92.
    Pino JA (2010) Annona fruits. In: Hui YH (ed) Handbook of fruit and vegetable flavors. Wiley, Hoboken, pp 231–246Google Scholar
  93. 93.
    Jirovetz L, Buchbauer G, Shafi PM, Saidutty A (1998) Analysis of the essential oils of the leaves and roots of Annona reticulata (Annonaceae) from South-India. Ernaehrung 22:9–10Google Scholar
  94. 94.
    Pino JA, Marbots R, Fuentes V (2003) Characterization of volatiles in bullock’s heart (Annona reticulata L.) fruit cultivars from Cuba. J Agric Food Chem 51:3826–3839CrossRefGoogle Scholar
  95. 95.
    Bartley JP (1987) Volatile constituents of custard apple. Chromatographia 23:129–131CrossRefGoogle Scholar
  96. 96.
    Augusto F, Valente ALP, Tada ES, Rivellino SR (2000) Screening of Brazilian fruit aromas using solid-phase microextraction gas chromatography-mass spectrometry. J Chromatogr A 873:117–127PubMedCrossRefGoogle Scholar
  97. 97.
    Ogunwande IA, Ekundayo O, Olawore NO, Kasali AA (2006) Essential oil of Annona reticulata L. leaves from Nigeria. J Essent Oil Res 18:374–376CrossRefGoogle Scholar
  98. 98.
    Nébié RHC, Yaméogo RT, Bélanger A, Sib FS (2005) Chemical composition of leaf essential oil of Annona senegalensis Pers. from Burkina Faso. J Essent Oil Res 17:331–332CrossRefGoogle Scholar
  99. 99.
    Andrade EHA, Zoghbi MGB, Maia JHGS, Fabricius H, Marx F (2001) Chemical characterization of the fruit of Annona squamosa L. occurring in the Amazon. J Food Compos Anal 14:227–232CrossRefGoogle Scholar
  100. 100.
    Joy B, Rao JM (1997) Essential oil of the leaves of Annona squamosa L. J Essent Oil Res 9:349–350CrossRefGoogle Scholar
  101. 101.
    Correa-Gordillo J, Ortiz J, Sanchez-Mejía M, Pachón H (2012) Soursop (Annona muricata L.) antioxidant activity: a literature review. Bol Latinoam Caribe Plant Med Aromat 11:111–126Google Scholar
  102. 102.
    Vijayameena C, Sabhashini G, Loganayagi M, Ramesh B (2013) Phytochemical screening and assessment of antibacterial activity for the bioactive compounds in Annona muricata. Int J Curr Microbiol Appl Sci 2:1–8Google Scholar
  103. 103.
    Okhale SE, Akpan E, Fatokun OT, Esievo KB, Kunle OF (2016) Annona senegalensis Persoon (Annonaceae): a review of its ethnomedicinal uses, biological activities and phytocompounds. J Pharmacog Phytochem 5:211–219Google Scholar
  104. 104.
    Andrade-Cetto A, Heinrich M (2005) Mexican plants with hypoglycaemic effect used in the treatment of diabetes. J Ethnopharmacol 99:325–348PubMedCrossRefGoogle Scholar
  105. 105.
    Guillopé R, Escobar-Khondiker M, Guérineau V, Laprévote O, Höglinger GU, Champy P (2011) Kaurenoic acid from pulp of Annona cherimola in regard to Annonaceae-induced Parkinsonism. Phytother Res 25:1861–1864PubMedCrossRefGoogle Scholar
  106. 106.
    Silva MV, Costa TR, Ferreira EC et al (2001) Growth inhibition effect of Brazilian Cerrado plant extracts on Candida species. Pharm Biol 39:138–141CrossRefGoogle Scholar
  107. 107.
    Navarro-García VM, Gonzalez A, Fuentes M et al (2003) Antifungal activities of nine traditional Mexican medicinal plants. J Ethnopharmacol 87:85–88PubMedCrossRefGoogle Scholar
  108. 108.
    Saez J, Granados H, Torres B, Velez ID, Munoz D (1998) Leishmanicidal activity of Annona aff. spraguei seeds. Fitoterapia 69:478–479Google Scholar
  109. 109.
    Vila-Nova NS, Morais SM, Falcão MJ et al (2011) Leishmanicidal activity and cytotoxicity of compounds from two Annonacea species cultivated in Northeastern Brazil. Rev Soc Bras Med Trop 44:567–571PubMedCrossRefGoogle Scholar
  110. 110.
    Camacho MD, Phillipson JD, Croft SL, Solis PN, Marshall SJ, Ghazanfar SA (2003) Screening of plant extracts for antiprotozoal and cytotoxic activities. J Ethnopharmacol 89:185–191PubMedCrossRefGoogle Scholar
  111. 111.
    Ajaiyeoba E, Falade M, Ogbole O, Okpako L, Akinboye D (2006) In vivo antimalarial and cytotoxic properties of Annona senegalensis extract. Afr J Tradit Complement Altern Med 3:137–141Google Scholar
  112. 112.
    De Omena MC, Navarro DM, De Paula JE, Luna JS, Ferreira de Lima MR, Sant’Ana AE (2007) Larvicidal activities against Aedes aegypti of some Brazilian medicinal plants. Bioresour Technol 98:2549–2556PubMedCrossRefGoogle Scholar
  113. 113.
    Rodrigues AM, De Paula JE, Degallier N, Molez JE, Espindola LS (2006) Larvicidal activity of some Cerrado plant extracts against Aedes aegypti. J Am Mosq Control Assoc 22:314–317PubMedCrossRefGoogle Scholar
  114. 114.
    De Mendonça FA, Da Silva KF, Dos Santos KK, Ribeiro Júnior KA, Sant’Ana AE (2005) Activities of some Brazilian plants against larvae of the mosquito Aedes aegypti. Fitoterapia 76:629–636PubMedCrossRefGoogle Scholar
  115. 115.
    Grzybowski A, Tiboni M, Silva MA, Chitolina RF, Passos M, Fontana JD (2013) Synergistic larvicidal effect and morphological alterations induced by ethanolic extracts of Annona muricata and Piper nigrum against the dengue fever vector Aedes aegypti. Pest Manag Sci 69:589–601PubMedCrossRefGoogle Scholar
  116. 116.
    Dos Santos AF, Sant’Ana AE (2001) Molluscicidal properties of some species of Annona. Phytomedicine 8:115–120PubMedCrossRefGoogle Scholar
  117. 117.
    Dos Santos AF, Sant’Ana AE (2000) The molluscicidal activity of plants used in Brazilian folk medicine. Phytomedicine 6:431–438PubMedCrossRefGoogle Scholar
  118. 118.
    Yang C, Gundala SR, Mukkavilli R, Vangala S, Reid MD, Aneja R (2015) Synergistic interactions among flavonoids and acetogenins in Graviola (Annona muricata) leaves confer protection against prostate cancer. Carcinogenesis 3:656–665CrossRefGoogle Scholar
  119. 119.
    De Pedro N, Cautain B, Melguizo A, Vicente F, Genilloud O, Peláez F, Tormo JR (2013) Mitochondrial complex I inhibitors, acetogenins, induce HepG2 cell death through the induction of the complete apoptotic mitochondrial pathway. J Bioenerg Biomembr 45:153–164PubMedCrossRefGoogle Scholar
  120. 120.
    Kim DH, Son JK, Woo MH (2001) Annomocherin, annonacin and annomontacin: a novel and two known bioactive mono-tetrahydrofuran annonaceous acetogenins from Annona cherimola seeds. Arch Pharm Res 24:300–306PubMedCrossRefGoogle Scholar
  121. 121.
    Woo MH, Chung SO, Kim DH (1999) Cis-annonacin and (2, 4)-cis-and trans isoannonacins: cytotoxic monotetrahydrofuran Annonaceous acetogenins from the seeds of Annona cherimola. Arch Pharm Res 22:524–528PubMedCrossRefGoogle Scholar
  122. 122.
    Barrachina I, Neske A, Granell S, Bermejo A et al (2004) Tucumanin, a beta-hydroxygamma- lactone bistetrahydrofuranic acetogenin from Annona cherimola, is a potent inhibitor of mitochondrial complex I. Planta Med 70:866–868PubMedCrossRefGoogle Scholar
  123. 123.
    Son JK, Kim DH, Woo MH (2003) Two new epimeric pairs of acetogenins bearing a carbonyl group from Annona cherimola seeds. J Nat Prod 66:1369–1372PubMedCrossRefGoogle Scholar
  124. 124.
    You M, Wickramaratne DB, Silva GL et al (1995) (−)-Roemerine, an aporphine alkaloid from Annona senegalensis that reverses the multidrug-resistance phenotype with cultured cells. J Nat Prod 58:598–604PubMedCrossRefGoogle Scholar
  125. 125.
    Nandhakumar E, Indumathi P (2013) In vitro antioxidant activities of methanol and aqueous extract of Annona squamosa (L.) fruit pulp. J Acupunct Meridian Stud 6:142–148PubMedCrossRefGoogle Scholar
  126. 126.
    Yang YL, Chang FR, Hwang TL, Chang WT, Wu YC (2004) Inhibitory effects of ent-kauranes from the stems of Annona squamosa on superoxide anion generation by human neutrophils. Planta Med 70:256–258PubMedCrossRefGoogle Scholar
  127. 127.
    Panda S, Kar A (2007) Antidiabetic and antioxidative effects of Annona squamosa leaves are possibly mediated through quercetin-3-Oglucoside. Biofactors 31:201–210PubMedCrossRefGoogle Scholar
  128. 128.
    Ajboye TO, Yakubu MT, Salau AK, Oladiji AT, Akanji MA, Okogun JI (2010) Antioxidant and drug detoxification potential of aqueous extract of Annona senegalensis leaves in carbon tetrachloride-induced hepatocellular damage. Pharm Biol 48:1361–1370PubMedCrossRefGoogle Scholar
  129. 129.
    Pathak K, Zaman K (2014) An overview on medicinally important plant - Annona reticulata Linn. Int J Pharmacogn Phytochem Res 5:299–301Google Scholar
  130. 130.
    Damasceno DC, Volpato GT, Sartori TC, Rodrigues PF, Perin EA, Calderon IM, Rudge MV (2002) Effects of Annona squamosa extract on early pregnancy in rats. Phytomedicine 9:667–672PubMedCrossRefGoogle Scholar
  131. 131.
    Castillo-Juárez I, González V, Jaime-Aguilar H, Martínez G, Linares E, Bye R, Romero I (2009) Anti-helicobacter pylori activity of plants used in Mexican traditional medicine for gastrointestinal disorders. J Ethnopharmacol 122:402–405PubMedCrossRefGoogle Scholar
  132. 132.
    Yadav DK, Singh N, Dev K, Sharma R, Sahai M, Palit G, Maurya R (2011) Anti-ulcer constituents of Annona squamosa twigs. Fitoterapia 82:666–675PubMedCrossRefGoogle Scholar
  133. 133.
    Suleiman MM, Dzenda T, Sani CA (2008) Antidiarrhoeal activity of the methanol stem-bark extract of Annona senegalensis Pers. (Annonaceae). J Ethnopharmacol 116:125–130PubMedCrossRefGoogle Scholar
  134. 134.
    Formagio AS, Vieira Mdo C, Dos Santos LA et al (2013) Composition and evaluation of the anti-inflammatory and anticancer activities of the essential oil from Annona sylvatica A. St.-Hil. J Med Food 16:20–25PubMedCrossRefGoogle Scholar
  135. 135.
    Carballo AI, Martínez AL, González-Trujano ME, Pellicer F, Ventura-Martínez R, Díaz-Reval MI, López-Muñoz FJ (2010) Antinociceptive activity of Annona diversifolia Saff. leaves extract and palmitone as a bioactive compound. Pharmacol Biochem Behav 95:6–12PubMedCrossRefGoogle Scholar
  136. 136.
    Wu TY, Yang IH, Tsai YT et al (2012) Isodesacetyluvaricin, an Annonaceous acetogenin, specifically inhibits gene expression of cyclooxygenase-2. J Nat Prod 75:572–576PubMedCrossRefGoogle Scholar
  137. 137.
    Yeh SH, Chang FR, Wu YC, Yang YL, Zhuo SK, Hwang TL (2005) An anti-inflammatory ent-kaurane from the stems of Annona squamosa that inhibits various human neutrophil functions. Planta Med 71:904–909PubMedCrossRefGoogle Scholar
  138. 138.
    Martínez-Vázquez M, Estrada-Reyes R, Araujo Escalona AG et al (2012) Antidepressant-like effects of an alkaloid extract of the aerial parts of Annona cherimola in mice. J Ethnopharmacol 139:164–170PubMedCrossRefGoogle Scholar
  139. 139.
    González-Trujano ME, Tapia E, López-Meraz L, Navarrete A, Reyes-Ramírez A, Martínez A (2006) Anticonvulsant effect of Annona diversifolia Saff. and palmitone on penicillin-induced convulsive activity. A behavioral and EEG study in rats. Epilepsia 47:1810–1817CrossRefGoogle Scholar
  140. 140.
    Cano-Europa E, González-Trujano ME, Reyes-Ramírez A, Hernández-García A, Blas-Valdivia V, Ortiz-Butrón R (2010) Palmitone prevents pentylenetetrazole-caused neuronal damage in the CA3 hippocampal region of prepubertal rats. Neurosci Lett 470:111–114PubMedCrossRefGoogle Scholar
  141. 141.
    Okoye TC, Akah PA, Omeje EO, Okoye FB, Nworu SC (2013) Anticonvulsant effect of kaurenoic acid isolated from the root bark of Annona senegalensis. Pharmacol Biochem Behav 109:38–43PubMedCrossRefGoogle Scholar
  142. 142.
    Khallouki F, Haubner R, Ulrich CM, Owen RW (2011) Ethnobotanical survey, chemical composition, and antioxidant capacity of methanolic extract of the root bark of Annona cuneata Oliv. J Med Food 11:1397–1402CrossRefGoogle Scholar
  143. 143.
    Formagio AS, Kassuya CA, Neto FF, Volobuff CR et al (2013) The flavonoid content and antiproliferative, hypoglycaemic, anti-inflammatory and free radical scavenging activities of Annona dioica St.-Hill. BMC Complement Altern Med 13:14PubMedPubMedCentralCrossRefGoogle Scholar
  144. 144.
    Shokeen P, Ray K, Bala M, Tandon V (2005) Preliminary studies on activity of Ocimum sanctum, Drynaria quercifolia, and Annona squamosa against Neisseria gonorrhoeae. Sex Transm Dis 32:106–111PubMedCrossRefGoogle Scholar
  145. 145.
    Dholvitayakhun A, Cushnie TP, Trachoo N (2012) Antibacterial activity of three medicinal Thai plants against Campylobacter jejuni and other foodborne pathogens. Nat Prod Res 26:356–363PubMedCrossRefGoogle Scholar
  146. 146.
    Waechter AI, Ferreira ME, Fournet A et al (1997) Experimental treatment of cutaneous leishmaniasis with argentilactone isolated from Annona haematantha. Planta Med 63:433–435PubMedCrossRefGoogle Scholar
  147. 147.
    Senthilkumar N, Varma P, Gurusubramanian G (2009) Larvicidal and adulticidal activities of some medicinal plants against the malarial vector, Anopheles stephensi (Liston). Parasitol Res 104:237–244PubMedCrossRefGoogle Scholar
  148. 148.
    Fall D, Badiane M, Ba D, Loiseau P, Bories C, Gleye C, Laurens A, Hocquemiller R (2003) Antiparasitic effect of Senegalese Annonaceae used in traditional medicine. Dakar Med 48:112–116PubMedGoogle Scholar
  149. 149.
    Pandey N, Barve D (2011) Phytochemical and pharmacological review on Annona squamosa Linn. Int J Res Pharm Biomed Sci 2:1404–1412Google Scholar
  150. 150.
    Pardhasaradhi BV, Reddy M, Ali AM, Kumari AL, Khar A (2005) Differential cytotoxic effects of Annona squamosa seed extracts on human tumour cell lines: role of reactive oxygen species and glutathione. J Biosci 30:237–244PubMedCrossRefGoogle Scholar
  151. 151.
    Pardhasaradhi BV, Reddy M, Ali AM, Kumari AL, Khar A (2004) Antitumour activity of Annona squamosa seed extracts is through the generation of free radicals and induction of apoptosis. Indian J Biochem Biophys 41:167–172PubMedGoogle Scholar
  152. 152.
    Durodola JI (1975) Viability and transplantability of developed tumor cells treated with antitumor agent C/M2 isolated from a herbal cancer remedy of Annona senegalensis. Planta Med 28:359–362PubMedCrossRefGoogle Scholar
  153. 153.
    Davis JA, Sharma S, Mittra S, Sujatha S, Kanaujia A, Shukla G, Katiyar C, Lakshmi BS, Bansal VS, Bhatnagar PK (2012) Antihyperglycemic effect of Annona squamosa hexane extract in type 2 diabetes animal model: PTP1B inhibition, a possible mechanism of action? Ind J Pharmacol 44:326–332CrossRefGoogle Scholar
  154. 154.
    Mishra A, Dogra JV, Singh JN, Jha OP (1979) Post–coital antifertility activity of Annona squamosa and Ipomoea fistulosa. Planta Med 35:283–285PubMedCrossRefGoogle Scholar
  155. 155.
    Yeo D, Dinica R, Yapi HF, Furdui B, Praisler M, Djaman AJ, N’Guessan JD (2011) Evaluation of the anti-inflammatory activity and phytochemical screening of Annona senegalensis leaves. Therapie 66:73–80PubMedCrossRefGoogle Scholar
  156. 156.
    Coelho MB, Desouza IA, Freire MG, Marangoni S, Antunes E, Macedo ML (2006) Neutrophil migration in mice induced by a mannose-binding lectin isolated from Annona coriacea seeds. Toxicon 48:529–535PubMedCrossRefGoogle Scholar
  157. 157.
    Rejón-Orantes J d C, González-Esquinca AR, De la Mora MP, Roldan Roldan G, Cortes D (2011) Annomontine, an alkaloid isolated from Annona purpurea, has anxiolytic-like effects in the elevated plus-maze. Planta Med 77:322–327CrossRefGoogle Scholar
  158. 158.
    Champy P, Melot A, Guérineau Eng V et al (2005) Quantification of acetogenins in Annona muricata linked to atypical parkinsonism in guadeloupe. Mov Disord 20:1629–1633PubMedCrossRefGoogle Scholar
  159. 159.
    Tundis R, Xiao J, Loizzo MR (2017) Annona species (Annonaceae): a rich source of potential antitumor agents? Ann N Y Acad Sci 1398:30–36PubMedCrossRefGoogle Scholar
  160. 160.
    Caparros-Lefebvre D, Elbaz A (1999) Possible relation of atypical parkinsonism in the French West Indies with consumption of tropical plants: a case control study. Caribbean Parkinsonism study group. Lancet 354:281–286PubMedCrossRefGoogle Scholar
  161. 161.
    Caparros-Lefebvre D, Steele J, Kotake Y, Ohta S (2006) Geographic isolates of atypical parkinsonism and tauopathy in the tropics: possible synergy of neurotoxins. Mov Disord 21:1769–1771PubMedCrossRefGoogle Scholar
  162. 162.
    Bonneau N, Baloul L, Bajin Ba Ndob I, Sénéjoux F, Champy P (2017) The fruit of Annona squamosa L. as a source of environmental neurotoxins: from quantification of squamocin to annotation of Annonaceous acetogenins by LCMS/MS analysis. Food Chem 226:32–40PubMedCrossRefGoogle Scholar

Authors and Affiliations

  1. 1.Department of Agriculture and Environmental SciencesNational Institute of Food Technology, Entrepreneurship and Management (NIFTEM)KundliIndia

Section editors and affiliations

  • Hosakatte Niranjana Murthy
    • 1
    • 2
  1. 1.Department of BotanyKarnatak UniversityDharwadIndia
  2. 2.Research Center for the Development of Advanced Horticultural TechnologyChungbuk National UniversityCheongjuRepublic of Korea

Personalised recommendations