PARTE UTILIZADA= Used part: Semillas. 

ACCIÓN FARMACOLÓGICA= Pharmacological action: Antihelmíntica, antirreumática. 

COMPOSICIÓN QUÍMICA= Chemical composition: Se ha reportado la presencia de los siguientes compuestos químicos en diferentes partes de la planta: alcaloides isoquinolínicos : (-)-N-metilactinodafrina, anonanaína, (-)-analobina, asimilobina, atherospermidina, isoboldina, liriodenina, nornuciferina, reticulina, roemerina y norushinsunina; lactonas; asimicina, squamocina y desacetiluvaricina; diterpeno: ácido kaur-16-en-16-óico. El screening fitoquímico demuestra la presencia de alcaloides, HCN, y leucoantocianinas. 

ZONA GEOGRÁFICA= Geografical zone: Brasil. 

DIVERSIDAD GENÉTICA Y MEJORAMIENTO DE PLANTAS MEDICINALES= Medicinal plants and improvement of medicinal herbs
:

PCR-RFLP of 14 accessions of six Annona species namely A. cherimola Mill., A. squamosa L., A. reticulata L., A. glabra L., A. muricata L. and A. montana Macfad. and A. cherimola x A. squamosa were studied. One set of Sequence Tagged Site (STS) primers was used in order to amplify the position of cpDNA fragment: "rbc L-ORF106". The amplified fragment was digested with six kinds of restriction enzymes (four base cutter). Enzymes av. generated two to eight bands in each sample. Seven different restriction patterns were obsd. when digested with Rsa I, but other enzymes showed four to six. The pair-wise distance values ranged from 0.017 to 0.607 with the min. between A. squamosa and A. cherimola x A. squamosa and the max. between A. glabra and A. cherimola x A. squamosa. Eight most parsimonious trees were obtained using Swofford parsimony method, and 50 % majority-rule consensus tree was obtained from them. These results indicated that the cultivated and wild species grouped sep. and the A. cherimola x A. squamosa was placed between its parents in the cultivated species. A. glabra clustered singly in the dendrogram demonstrating that this species is different from the others. We believe that these results would give basic information in the phylogenetic studies of Annona species using a large no. of species. 

ÚLTIMOS AVANCES EN LA QUÍMICA Y ACTIVIDADES BACTERIOLÓGICAS EN LAS PLANTAS MEDICINALES= Medicinal plants, last advances on chemistry and bacteria activities on the medicinal herbs

1) The active fraction of the EtOH ext. of the stem of Annona glabra against acetylcholinesterase (AChE) was analyzed by combining HPLC microfractionation with a bioassay.  The anal.-scale sample was fractionated by HPLC-DAD into 96-well microplates, which, after evapn., were assayed against AChE.  The active subfractions were scaled up by sepn. over semi-preparative HPLC to give 20 compds.  Four of these, (7S,14S)-(-)-N-methyl-10-O-demethylxylopinine salt (3), S-(-)-7,8-didehydro-10-O-demethylxylopininium salt (10), S-(-)-7,8-didehydrocorydalminium salt (11), and 5-O-methylmarcanine D (17), were assigned as new natural products.  In addn., compds. 10 and 11 represent the first natural occurrence of 7,8-didehydroprotoberberines.  Compd. 3, pseudocolumbamine (12), palmatine (15), and pseudopalmatine (16) showed anti-AChE IC50 values of 8.4, 5.0, 0.4, and 1.8 mM, resp.

2) AIM: To study the inhibitory effect of two diterpenoid compds. isolated from Annona glabra Linn (Cunabic acid and ent-kauran-19-al-17-oic acid) on the proliferation of Human Liver Cancer (HLC) cell line SMMC-7721 and its mechanism.  METHODS: Inhibition of cell proliferation was measured by MTT assay.  The morphol. changes of SMMC-7721 cells were obsd. under inverted phase-contrast microscope, fluorescent microscope, transmission electron microscope (TEM), and scanning electron microscope (SEM).  Flow cytometer (FCM) was used to calc. the cell apoptotic rate, and immunohistochem. staining was used to observe the regulation of gene expression.  RESULTS: The proliferation of SMMC-7721 cells was obviously inhibited after being treated with Cunabic acid at the concn. >5 mmol/L and ent-kauran-19-al-17-oic acid >10 mmol/L.  The biggest inhibitory effect was 81.05 % when treated with Cunabic acid at the concn. of 25 mmol/L.  The effect had a linear relation with concn.  The result indicated that drug-treated cells exhibit typical morphol. changes of apoptosis, including condensed chromatin and a redn. in vol.  Sub-G0/G1 peak was found by FCM anal. and the cell cycle was arrested at G0/G1 stage.  The apoptotic rates of the cells treated by Cunabic acid and ent-kauran-19-al-17-oic acid were 43.31 % and 24.95 %, resp.  It was visualized by immunohistochem. staining that the drugs down-regulated the gene expression of bcl-2 gene and up-regulated that of bax gene.  CONCLUSION: The two diterpenoid compds. isolated from Annona glabra Linn, Cunabic acid and ent-kauran-19-al-17-oic acid can obviously inhibit the proliferation of HLC cell line SMMC-7721.  The mechanism is correlated with the induction of cell apoptosis by down-regulating the gene expression of bcl-2 gene and upregulating that of bax gene.

3) Bio-assay guided fraction of the methanolic ext. of Annona glabra seeds (Annonaceae), cultivated in Egypt, revealed to the isolation of three bis-tetrahydrofuran acetogenins; squamocin-C (1), squamocin-D (2), and annonin I (3).  Compds. 1 and 2 were obtained as stereoisomeric mixt.  All isolates were assayed for their cytotoxicity towards brine shrimp and five in vitro cancer cell lines (A549, HT29, MCF 7, RPMI, and U251), and showed significant activity.  The structures of all compds. were detd. by interpretation of their NMR and MS analyses.

Stem and Leaf: In Guyana, boiled for a tea (and sometimes mixed with a whole plant of Passiflora foetida), which is drunk to destroy flatworms and nematodes.

Bark and Leaf: Mixed with the bark and leaves of Annona squamosa for a sedative and cardiotonic infusion.

1) 270 (doscientos setenta) plantas medicinales iberoamericanas. Santiago de Bogotá : CYTED-SECAB, 1995, p.25-28.

2) MAHBUBUR RAHMAN, S. M.; YAMADA, Masahiko; YOSHIDA, Masao. Relationship of Annona species as revealed by PCR-RFLP analysis. Breeding Science.1997, vol.47, nº4, p.335-339.
 
3) TSAI, Sheng-Fa; LEE, Shoei-Sheng. Characterization of Acetylcholinesterase Inhibitory Constituents from Annona glabra Assisted by HPLC Microfractionation. Journal of Natural Products. 2010, vol.73, nº10, p.1632-1635.
 
4) ZHANG, Yong-hong, et al.  Anticancer effect of two diterpenoid compounds isolated from Annona glabra Linn.     
Acta Pharmacologica Sinica. 2004, vol.25, nº7, p.937-942.
 
5) ABDEL-LATEFF, Ahmed, et al. Cytotoxic acetogenins from Annona glabra cultivated in Egypt. Pharmacognosy Research. 2009, vol.1, nº3, p.130-135.

6) Robertt, A., et al.. Medicinal Plants of the Guianas (Guyana, Suriname, French Guyana)/Smithsonian NMNH. cited online: 17-08-2017