A Histochemical Technique for the Detection of Annonaceous Acetogenins

Abstract

Annonaceous acetogenins (ACGs) are molecules with carbon numbers C35-C37, usually with tetrahydrofuran and tetrahydropyran rings and one terminal γ-lactone (usually α,β-unsaturated), in a large aliphatic chain that is varyingly hydroxylated, acetoxylated or ketonized. ACGs have ecological functions as insecticides and are pharmacologically promising due to their cytotoxic and antitumoral properties. They are found in the seeds, leaves, roots, flowers and fruits of annonaceous plants and can be detected during isolation via thin-layer chromatography using Kedde's reagent, which reacts with the unsaturated lactone. This chapter describes the location in situ of ACGs in fresh sections of annonaceous seeds using Kedde's reagent.The acetogenins are located in the idioblasts, in the endosperm and in the embryonic axis during differentiation. This method can aid in the detection of ACGs with a terminal unsaturated γ-lactone in organs and tissues.

Screening of antidiabetic and antioxidant potential along with phytochemicals of Annona genus: a review

“…Annona squamosa Leaves, tender stem, Bark, Seeds, Stem bark. Anonaine,Anolobine,Aporphine,Corydine,Isocorydine,Norcorydine,Norisocorydine, Glaucine,Liriodenine,Norlaureline,Norushinsunine,Reticuline,Roemerine,Samoquasine A, Annosqualine,Cyclosqamosin A, Cyclosqamosin B, Cyclosqamosin C, Cyclosqamosin D, Cyclosqamosin E, Cyclosqamosin F, Cyclosqamosin G, Cyclosqamosin H, Cyclosqamosin I, Squamtin A, Annosquamosin A, Annonacin, AnnonacinA, Annonastatin, Squamocin, Squamocin-O1, Squamocin-O2, Bullatacin, Bullatacinone, 4-deoxyannoreticuin, cis-4deoxyannoreticuin(2,4-cis and trans)-squamoxinone, (2,4-cis and trans)-Mosinone A, Mosin B, Mosin C, Squamotacin, Molvizarin, (2,4-cis and trans)-squamolinone, (2,4-cis and trans)-9-oxoasimicinone, Bullacin B, Squamostatin D, (2,4-cis-and trans)-bullatacinone, Squamostatin C, Annonin I, Annonin VI, Squamostene-A, Reticulacin-1, Squamosinin-A, Annotemoyin-1, Annotemoyin-2, Annomosin A, Annosquamosins A,Annosquamosins B, Annosquamosin C, Annosquamosin D, Annosquamosin E, Annosquamosin F, Annosquamosin G.[36]Annona macroprophyllataSeedsLaherradurin; rolliniastin-2; cherimolin-2[37] Annona muricata Annonaine, nornuciferine, asimilobine, epomusenin-A, epomusenin-B, epomurinin-A, epomurinin-B, cis-annoreticuin, muricin J, muricin K, muricin L, cinnamic acid derivative, coumaric acid hexose, 5-caffeoylquinic acid, dihydrokaempferol-hexoside, p-coumaric acid, caffeic acid derivative, e, dicaffeoylquinic acid, feruloylglycoside, 4-feruloyl-5-caffeoylquinic acid, p-coumaric acid methyl ester,annomuricin A, annomuricin B, annomuricin C, annomuricin E, annomutacin, (2,4-cis)-10R-annonacin-A-one, (2,4-trans)-10Rannonacin-A-one, annohexocin, muricapentocin, (2,4-cis)-isoannonacin, (2,4-trans)-isoannonacin, muricatocin A, muricatocin B, muricatocin C, gigantetronenin,annopentocin A, annopentocin B,annopentocin C, cisannomuricin-D-one, trans-annomuricin-D-one,murihexocin A, murihexocin B, murihexocin C ,muricoreacin, Cis-corossolone, annocatalin, annocatacin B, anonaine, isolaureline, xylopine,Quercetin 3-O-α-rhamnosyl-(1→6)-βsophoroside, gallic acid,epicatechine, quercetin 3-O-rutinosid, quercetin 3-O, neohispredoside, quercetin 3-O-robinoside, catechine, chlorogenic acid, argentinine (1-N,Ndimethylethanyl-4,6-dimethoxy-3,8-dihydroxy-phenanthrene), kaempferol 3-O-rutinoside, quercetin 3-O-glucoside, quercetin, kaempferol, annonamine, (S)-norcorydine, (R)-4′-Omethylcoclaurine (R)-O,O-dimethylcoclaurine, ,annoionol A, annoionol B, annoionol C, annoionoside,, vomifoliol, roseoside,turpinionoside A,citroside A, blumenol C, (+)-epiloliolide, loliolide, ,rutin, kaempferol 3-O-rutinoside, kaempferol 3-O-robinobioside, kaempferol 3-O-β-D-(2′ ′-O-β-D-glucopyranosyl,6′′-O-α-L-rhamnopyranosylglucopyranoside, montecristin, cohibin A, cohibin B, cis-solamin, cis-panatellin,cis-uvariamicin IV, cis-uvariamicin I, cis-reticulatacin, cis-reticulatacin-10-one, chatenaytrienin 1, chatenaytrienin 2, chatenaytrienin 3, muridienin 3, muridienin 4, muricadienin, coronin, sabadelin, murisolin, muricatacin, donhexocin, cohibin C, cohibin D, muricatenol, 2,4-cis-gigantetrocinone, 2,4-trans-gigantetrocinone, 2,4-trans-isoannonacin-10-one, annomontacin, longifolicin,muricin A, muricin B, muricin C, muricin D,muricin E,muricin F, muricin G, muricin H, muricin I, cisannomontacin, annonacinone, xylomaticin, N-fatty acyl tryptamines, annoreticuin-9-one, epoxymurin A epoxymurin B, corepoxylone, annonacin-10-one, isoannonacin, isoannonacin-10-one, goniothalamicin, gigantetrocin, gigantetrocin A gigantetrocin B, muricatetrocin A, muricatetrocin B,epomuricenin A epomuricenin B, annomuricatin A, annocatacin A, annomuricatin C, annonacin [38] Annona reticulata Leaf, Bark, Stem bark, Root, Root bark, Seed, Fruit Dopamine, Salsolinol, Coclaurine, Sesquiterpenes mainly Spathenelol, Muurolene, Copaene, Eudesmol, Acetogenin -Squamone, Solamin, Annomonicin, Rolliniastatin 2, Annoreticuin-9-one. Triterpenoidannonaretin A, Monotetrahydrofuron acetogenins, Ret...…”

Current Situation and Perspectives of Fruit Annonaceae in Mexico: Biological and Agronomic Importance and Bioactive Properties

“…Table 2 and Table 3 show some phytochemicals (quantitative or qualitative) identified in pulp, leaf, peel, seeds, roots, and stem bark of fruit Annona species: A. muricata, A. cherimola, A. squamosa, A. reticulata, and A. macroprophyllata [ 83 , 84 , 85 , 86 , 87 , 88 , 89 ]. These compounds include phenolic compounds, alkaloids, fatty acids, cyclopeptides, alkaloids, and acetogenins.…”

“…In the seeds of some Annona species bioactive compounds named cyclopeptides have been reported that in recent years have been of much pharmaceutical interest. Annomuricin A-C has been extracted and identified from A. muricata seeds ( Table 3 ) [ 89 , 101 , 102 ]. Two other cyclopeptides (cherimolacyclopeptide E and F) were obtained from A. cherimola seeds [ 103 , 104 ].…”

“…In the same way, annonacin and bullatacin have been identified in the pulp and stem bark of A. squamosa [ 135 , 138 ]. In A. macroprophyllata, the principal reported acetogenins from seeds are rolliniastatin-2, laherradurin, and cherimolin-2 [ 88 , 89 ].…”

Enhanced Solubility and Antitumor Activity of Annona Squamosa Seed Oil via Nanoparticles Stabilized with TPGS: Preparation and In Vitro and In Vivo Evaluation

“…Annonaceous acetogenins are mainly extracted from seeds of Annonaceae plants [13], and ASSO is separated during the extraction process, which is generally discarded. However, it has been reported that Annona squamosa seed oil (ASSO) has anti-oxidant activity [14], anti-psoriatic activity [15], lipoxygenase inhibitory activity [16], and antitumor activity.…”