Five new monotetrahydrofuran ring acetogenins from the leaves of Annona muricata

Journal of Natural Products
L ZengS Sastrodihadjo

Abstract

Bioactivity-directed fractionation of the leaves of Annona muricata resulted in the isolation of annopentocins A (1), B (2), and C(3), and cis- and trans-annomuricin-D-ones (4, 5). Compounds 1-3 are the first acetogenins reported bearing a mono-tetrahydrofuran (THF) ring with one flanking hydroxyl, on the hydrocarbon side, and another hydroxyl, on the lactone side, that is one carbon away from the THF ring. Compounds 4 and 5 were obtained in a mixture and are new mono-THF ring acetogenins bearing two flanking hydroxyls and an erythro-diol located between the THF and the ketolactone rings. Compound 1 was selectively cytotoxic to pancreatic carcinoma cells (PACA-2), and 2 and 3 were selectively cytotoxic to lung carcinoma cells (A-549); the mixture of 4 and 5 was selectively cytotoxic for the lung (A-549), colon (HT-29), and pancreatic (PACA-2) cell lines with potencies equal to or exceeding those of Adriamycin.

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Citations

Jun 19, 2010·International Journal of Molecular Sciences·Orlando Vieira de SousaMaria Silvana Alves
Jun 30, 2014·BMC Complementary and Alternative Medicine·Rafaele C P AraujoJulio Croda
Aug 17, 2014·BMC Complementary and Alternative Medicine·Soheil Zorofchian MoghadamtousiHamed Karimian
Jul 18, 2015·International Journal of Molecular Sciences·Soheil Zorofchian MoghadamtousiHabsah Abdul Kadir
Jan 2, 2016·Journal of Ethnopharmacology·Nadia J Jacobo-HerreraCarlos Pérez-Plasencia
Sep 4, 2012·Asian Pacific Journal of Cancer Prevention : APJCP·Sulaiman HamizahC I Tan
Dec 15, 2010·Journal of Ethnopharmacology·Angel Josabad Alonso-CastroAlejandro Garcia-Carranca
Dec 16, 1998·Current Opinion in Neurology·G Román
Apr 22, 2016·Journal of Complementary & Integrative Medicine·Hugh A SempleFrancis H Y Green
Aug 8, 2020·International Journal of Molecular Sciences·Manikandan MuthuJae-Wook Oh
Aug 6, 2019·Frontiers in Pharmacology·Nadia Jacobo-HerreraAlejandro Zentella-Dehesa
Sep 25, 2017·Zeitschrift Für Naturforschung. C, a Journal of Biosciences·Christian Anabí Riley-SaldañaAlma Rosa González-Esquinca
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Jun 28, 2011·Pathology Oncology Research : POR·Govindasamy SugunadeviJagadeesan Sathiyapriya
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Sep 18, 2020·Protein and Peptide Letters·Loganayaki PeriyasamySridhar Muthusami
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