Cytotoxic Activity of Moronic Acid and Identification of the New Triterpene 3,4-seco-Olean-18-ene-3,28-dioic Acid from Phoradendron reichenbachianum

Abstract

The cytotoxic compound moronic acid (1) and the new tetracyclic triterpene 3,4-seco-olean-18-ene-3,28-dioic acid (2), were isolated from the aerial parts of the medicinal plant Phoradendron reichenbachianum (mistletoe, Loranthaceae) through a bioassay-guided fractionation. In addition, squalene, glycerol trilinoleate, morolic acid, betulonaldehyde, betulinaldehyde, α-germanicol, lupeol, β-sitosterol and β-sitosteril glucopyranoside, were identified in this plant species. The structures were elucidated on the basis of chemical and spectroscopic evidence.

Key words

Phoradendron reichenbachianum - Loranthaceae - mistletoe - cytotoxic compound - moronic acid - 3,4-seco-olean-18-ene-3,28-dioic acid - triterpenes - sterols - glycerol trilinoleate

References

• 1 Chazaro M, Oliva H. Dendrophthora costaricensis (Loranthaceae), un Nuevo Registro para la flora de México.  Acta Botánica Mexicana. 1991;  13 31-8
• 2 Chazaro M, Huerta F M, Patiño R M, Sánchez R, Lomelí E, Flores A. Los muerdagos (Loranthaceae) de Jalisco, parásitas poco conocidas.  Ciencia y Desarrollo. 1992;  17 70-85
• 3 Waizel J, Herrera J, Alonso D, Villarreal M L. Estudios preliminares de la actividad citotóxica de muérdagos mexicanos: Cladocolea grahami, Phoradendron reichenbachianum y Phoradendron galeotii (Loranthaceae).  Revista del Instituto Nacional de Cancerología. 1994;  40 133-7
• 4 Geran R I, Greenberg N H, Mc Donald M N, Schumacher A M, Abbot B J. Protocols for screening chemical agents and natural products against animal tumors and other biological systems. Cancer Chemotherapy Reports 1972; Part 3,: 1-17
• 5 Biellmann J F, Ducep J B. Synthese du squalene et d’analogues.  Tetrahedron. 1971;  27 5861-72
• 6 Frost D J, Bus J, Keuning R, Sies I. PMR analysis of unsaturated triglycerides using shift reagents.  Chemistry and Physics of Lipids. 1975;  14 189-92
• 7 Bohlmann F, Knoll K H, Zdero C, Mahanta P K, Grenz M, Suwita A, Ehlers D, LeVan N, Abraham W R, Natu A A. Terpen-derivate aus Senecio-Arten.  Phytochemistry. 1977;  16 965-85
• 8 González A G, Amaro J, Fraga B M, Luis J G. 3-Oxo-6-β-hydroxyolean-18-en-28-oic acid from Orthopterygium huanay .  Phytochemistry. 1983;  22 1828-30
• 9 Zhong S M, Waterman P G, Jeffreys J AD. Naphthoquinones and triterpenes from African Diospyros species.  Phytochemistry. 1984;  23 1067-72
• 10 Sholichin M, Yamasaki K, Kasai R, Tanaka O. Carbon-13 nuclear magnetic resonance of lupane-type triterpenes, lupeol, betulin and betulinic acid.  Chemical Pharmaceutical Bulletin. 1980;  28 1006-8
• 11 Majumder P L, Maiti R N, Panda S K, Mal D, Raju M S, Wenkert E. Structure of moronic acid.  Journal of Organic Chemistry. 1979;  44 2811-2
• 12 Hostettmann-Kaldas M, Nakanishi K. Moronic acid, a simple triterpenoid keto acid with antimicrobial activity isolated from Ozoroa mucronata .  Planta Medica. 1979;  37 358-60
• 13 González A G, Amaro J, Fraga B M, Luis J G. 3-Oxo-6-β-hydroxyolean-18-en-28-oic acid from Orthopterygium huanay .  Phytochemistry. 1983;  22 1828-30
• 14 Barton D HR, Brooks C JW. Triterpenoid. Part I. Morolic acid a new triterpenoid sapogenin.  Journal Chemical Society. 1951;  257-77
• 15 Atta-ur-Rahman V UA. Handbook of Natural Products Data: Vol. 2, Pentacyclic Triterpenoids. Elsevier Science BV Netherlands,; 1994
• 16 Rees H H, Mercer E I, Goodwin T W. The stereospecific biosynthesis of plant sterols and α- and β-amyrin.  The Biochemical Journal. 1966;  99 726-34
• 17 Rees H H, Britton G, Goodwin T W. The biosynthesis of β-amyrin.  The Biochemical Journal. 1968;  106 659-65