New Limonoids from Hortia oreadica and Unexpected Coumarin from H. superba Using Chromatography over Cleaning Sephadex with Sodium Hypochlorite

作者：Severino Vanessa G P; de Freitas Samya D L; Braga Patricia A C; Forim Moacir Rossi; da Silva M Fatima das G F^*; Fernandes Joao B; Vieira Paulo C; Venancio Tiago

来源：Molecules, 2014, 19(8): 12031-12047.

DOI：10.3390/molecules190812031

• Hortia oreadica
• H. brasiliana
• H. superba
• Rutaceae
• limonoids
• alkaloids
• coumarins
• dihydrocinnamic acids
• Sephadex LH-20
• chlorination

Previous investigations of H. oreadica reported the presence of a wide spectrum of complex limonoids and dihydrocinnamic acids. Our interest in the Rutaceae motivated a reinvestigation of H. oreadica, H. brasiliana and H. superba searching for other secondary metabolites present in substantial amounts for taxonomic analysis. In a continuation of the investigation of the H. oreadica, three new limonoids have now been isolated 9 alpha-hydroxyhortiolide A, 11 beta-hydroxyhortiolide C and 1(S*)-acetoxy-7-(R*)-hydroxy-7deoxoinchangin. All the isolated compounds from the Hortia species reinforce its position in the Rutaceae. With regard to limonoids the genus produces highly specialized compounds, whose structural variations do not occur in any other member of the Rutaceae, thus, it is evident from limonoid data that Hortia takes an isolated position within the family. In addition, H. superba afforded the unexpected coumarin 5-chloro-8-methoxy-psoralen, which may not be a genuine natural product. Solid-state cross-polarisation/magic-anglespinning C-13 nuclear magnetic resonance, X-Ray fluorescence and Field-emission gun scanning electron microscopy experiments show that the Sephadex LH-20 was modified after treatment with NaOCl, suggesting that when xanthotoxin (8-methoxy-psoralen) was extracted from cleaning of the gel column, chlorination of the aromatic system occurred.

• 出版日期2014-8