Graviola

1. 1. Novel cytotoxic annonaceous acetogenins from Annona muricata.
J Nat Prod. 1995 Sep;58(9):1430-7. Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907, USA.

2. Isolation and characterization of a lectin from Annona muricata seeds.
Damico DC, Freire MG, Gomes VM, Toyama MH, Marangoni S, Novello JC, Macedo ML.
Departamento de Bioquimica, Instituto de Biologia, Universidade Estadual de Campinas, Campinas (SP), Brazil.
J Protein Chem. 2003 Nov;22(7-8):655-61.

3. Effect of the extract of Annona muricata and Petunia nyctaginiflora on Herpes simplex virus.
Padma P, Pramod NP, Thyagarajan SP, Khosa RL.
Department of Pharmaceutics, IT, Banaras Hindu University, Varanasi, India.
Annona muricata (Annonaceae) and Petunia nyctaginiflora (Solanaceae) were screened for their activity against Herpes simplex virus-1 (HSV-1) and clinical isolate (obtained from the human keratitis lesion). We have looked at the ability of extract(s) to inhibit the cytopathic effect of HSV-1 on vero cells as indicative of anti-HSV-1 potential. The minimum inhibitory concentration of ethanolic extract of A. muricata and aqueous extract of P. nyctaginiflora was found to be 1 mg/ml.

4. Novel cytotoxic annonaceous acetogenins from Annona muricata.
Chang FR, Wu YC.
Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan, Republic of China.
J Nat Prod. 2001 Jul;64(7):925-31.
PMID: 11473425 [PubMed - indexed for MEDLINE]

5. Isolation and characterization of a lectin from Annona muricata seeds.
Damico DC, Freire MG, Gomes VM, Toyama MH, Marangoni S, Novello JC, Macedo ML.
Departamento de Bioquimica, Instituto de Biologia, Universidade Estadual de Campinas, Campinas (SP), Brazil.
J Protein Chem. 2003 Nov;22(7-8):655-61.
PMID: 14714732 [PubMed - in process]

6. [Studies on the chemical constituents of Annona muricata] [Article in Chinese]
Yu JG, Gui HQ, Luo XZ, Sun L, Zhu P, Yu ZL.
Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100094.
Yao Xue Xue Bao. 1997 Jun;32(6):431-7.
PMID: 11596323 [PubMed - indexed for MEDLINE]

7. New cytotoxic monotetrahydrofuran annonaceous acetogenins from Annona muricata.
Liaw CC, Chang FR, Lin CY, Chou CJ, Chiu HF, Wu MJ, Wu YC.
Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan, Republic of China.
J Nat Prod. 2002 Apr;65(4):470-5.

8. Additional bioactive acetogenins, annomutacin and (2,4-trans and cis)-10R-annonacin-A-ones, from the leaves of Annona muricata.
Wu FE, Zhao GX, Zeng L, Zhang Y, Schwedler JT, McLaughlin JL, Sastrodihardjo S.
Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907, USA.
J Nat Prod. 1995 Sep;58(9):1430-7.

1. Novel cytotoxic annonaceous acetogenins from Annona muricata.
Chang FR, Wu YC.
Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan, Republic of China.
J Nat Prod. 2001 Jul;64(7):925-31.
Seven new annonaceous acetogenins, muricins A-G (1-7), as well as five known compounds, a mixture of muricatetrocin A (8) and muricatetrocin B (9), longifolicin (10), corossolin (11), and corossolone (12), were isolated from the seeds of Annona muricata. The structures of all isolates were elucidated and characterized by spectral and chemical methods. These acetogenins showed significantly selective in vitro cytotoxicities toward the human hepatoma cell lines Hep G(2) and 2,2,15.
PMID: 11473425 [PubMed - indexed for MEDLINE]

2. Isolation and characterization of a lectin from Annona muricata seeds.
Damico DC, Freire MG, Gomes VM, Toyama MH, Marangoni S, Novello JC, Macedo ML.
Departamento de Bioquimica, Instituto de Biologia, Universidade Estadual de Campinas, Campinas (SP), Brazil.
J Protein Chem. 2003 Nov;22(7-8):655-61.
A lectin with a high affinity for glucose/mannose was isolated from Annona muricata seeds (Annonaceae) by gel filtration chromatography on Sephacryl S-200, ion exchange chromatography on a DEAE SP-5 PW column, and molecular exclusion on a Protein Pak Glass 300 SW column. Sodium dodecyl sulfate polyacrylamide gel electrophoresis (PAGE) yielded two protein bands of approximately 14 kDa and 22 kDa. However, only one band was seen in native PAGE. The Mr of the lectin estimated by fast-performance liquid chromatography-gel filtration on Superdex 75 was 22 kDa. The lectin was a glycoprotein with 8% carbohydrate (neutral sugar) and required divalent metal cations (Ca2+, Mg2+, and Mn2+) for full activity. Amino acid analysis revealed a large content of Glx, Gly, Phe, and Lys. The lectin agglutinated dog, chicken, horse, goose, and human erythrocytes and inhibited the growth of the fungi Fusarium oxysporum, Fusarium solani, and Colletotrichum musae.
PMID: 14714732 [PubMed - in process]

3. [Studies on the chemical constituents of Annona muricata] [Article in Chinese]
Yu JG, Gui HQ, Luo XZ, Sun L, Zhu P, Yu ZL.
Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100094.
Yao Xue Xue Bao. 1997 Jun;32(6):431-7.
Annonaceous acetogenin (or polyketide) is a kind of potential antineoplastic agents from Annonaceae plants. Two new acetogenins, Muricatalicin (I) and muricatalin (VI), a mesitoate of a new acetogenin, annonacin-B mesitoate (Vb), and three known acetogenins, annonacin (II), annonacin-A (III) and annonacin-10-one (IV) have been isolated from Annona muricata L. The structures and relative stereochemistry of I, VI and Vb were elucidated on the basis of spectral analysis and examination of their acetates and/or mesitoate.
PMID: 11596323 [PubMed - indexed for MEDLINE]

4. Effect of the extract of Annona muricata and Petunia nyctaginiflora on Herpes simplex virus.
Padma P, Pramod NP, Thyagarajan SP, Khosa RL.
Department of Pharmaceutics, IT, Banaras Hindu University, Varanasi, India.
J Ethnopharmacol. 1998 May;61(1):81-3.
Annona muricata (Annonaceae) and Petunia nyctaginiflora (Solanaceae) were screened for their activity against Herpes simplex virus-1 (HSV-1) and clinical isolate (obtained from the human keratitis lesion). We have looked at the ability of extract(s) to inhibit the cytopathic effect of HSV-1 on vero cells as indicative of anti-HSV-1 potential. The minimum inhibitory concentration of ethanolic extract of A. muricata and aqueous extract of P. nyctaginiflora was found to be 1 mg/ml.
PMID: 9687085 [PubMed - indexed for MEDLINE]

5. New cytotoxic monotetrahydrofuran annonaceous acetogenins from Annona muricata.
Liaw CC, Chang FR, Lin CY, Chou CJ, Chiu HF, Wu MJ, Wu YC.
Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan, Republic of China.
J Nat Prod. 2002 Apr;65(4):470-5.
Three new monotetrahydrofuran annonaceous acetogenins, muricin H (1), muricin I (2), and cis-annomontacin (3), along with five known acetogenins, annonacin, annonacinone, annomontacin, murisolin, and xylomaticin, were isolated from the seeds of Annona muricata. Additionally, two new monotetrahydrofuran annonaceous acetogenins, cis-corossolone (4) and annocatalin (5), together with four known ones, annonacin, annonacinone, solamin, and corossolone, were isolated from the leaves of this species. The structures of all new isolates were elucidated and characterized by spectral and chemical methods. These new acetogenins exhibited significant activity in in vitro cytotoxic assays against two human hepatoma cell lines, Hep G(2) and 2,2,15. Compound 5 showed a high selectivity toward the Hep 2,2,15 cell line.

6. Additional bioactive acetogenins, annomutacin and (2,4-trans and cis)-10R-annonacin-A-ones, from the leaves of Annona muricata.
Wu FE, Zhao GX, Zeng L, Zhang Y, Schwedler JT, McLaughlin JL, Sastrodihardjo S.
Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907, USA.
J Nat Prod. 1995 Sep;58(9):1430-7.
In a continuation of our research on bioactive components from the leaves of Annona muricata, three novel monotetrahydrofuran Annonaceous acetogenins, namely, annomutacin [1], (2,4-trans)-10R-annonacin-A-one [2], and (2,4-cis)-10R- annonacin-A-one [3], have been identified. Their structures were deduced by ms, nmr, ir, and uv spectral and chemical methods, and the absolute configurations were determined by Mosher ester methodology. A known bioactive amide, N-p-coumaroyl tyramine, was also found. Compound 1 and the mixture of compounds 2 and 3 showed selective cytotoxicities against the human A-549 lung tumor cell line.