Cyclopropane- and spirolimonoids and related compounds from Hortia oreadica

• Published in: Phytochemistry (Oxford) Vol. 76; pp. 52 - 59
• Main Authors: Severino, Vanessa G.P., Braga, Patrícia A.C., da Silva, Maria Fátima das G.F., Fernandes, João B., Vieira, Paulo C., Theodoro, Jahyr E., Ellena, Javier A.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.04.2012; Elsevier
• Subjects: Biochemistry & Molecular Biology; Chemical Fractionation - methods; Chemosystematics; Cyclopropanes - chemistry; Cyclopropanes - isolation & purification; Hortia oreadica; Hortiolides; Life Sciences & Biomedicine; Limonins - chemistry; Limonins - isolation & purification; Limonoids; Magnetic Resonance Spectroscopy; Methylene Chloride - chemistry; Molecular Structure; Optical Rotation; Plant Extracts - chemistry; Plant Roots - chemistry; Plant Sciences; Plant Stems - chemistry; Rutaceae; Rutaceae - chemistry; Rutaceae - classification; Science & Technology; X-ray crystal diffraction; X-Ray Diffraction; Chemosystematics; Hortiolides; X-ray crystal diffraction; Hortia oreadica; Rutaceae; Limonoids; PHYLOGENY; CEDRELOPSIS-GREVEI; NMR-SPECTROSCOPY; PTAEROXYLACEAE; COLOMBIANA; CHEMOSYSTEMATIC SIGNIFICANCE; GUYANIN; DERIVATIVES; ALKALOIDS
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2011.12.016

A study of Hortia oreadica afforded nine limonoids, whose chemosystematic significance is discussed. [Display omitted] ► Limonoids of unprecedented structural type were isolated. ► Limonoids were isolated, and their chemotaxonomical significance is discussed. ► Cyclopropanelimonoids were isolated from Hortia oreadica. ► Spirolimonoids were isolated from H. oreadica. ► The biogenesis of cyclopropane- and spirolimonoids is discussed. The dichloromethane extract from taproots of Hortia oreadica afforded six limonoids, these are 9,11-dehydro-12α-acetoxyhortiolide A, hortiolide C, 11α-acetoxy-15-deoxy-6-hydroxyhortiolide C, hortiolide D, hortiolide E, 12β-hydroxyhortiolide E, in addition to the known limonoid, guyanin. The dichloromethane extract from stems of H. oreadica also afforded two limonoids 9,11-dehydro-12α-hydroxyhortiolide A and 6-hydroxyhortiolide C. As a result of this study and literature data, Hortia has been shown to produce highly specialized limonoids that are similar to those from the Flindersia (Flindersioideae). The taxonomy of Hortia has been debatable, with most authors placing it in the Toddalioideae. Considering the complexity of the isolated limonoids, Hortia does not show any close affinity to the genera of Toddalioideae. That is, the limonoids appear to be of little value in resolving the taxonomic situation of Hortia.