New limonoids from hortia oreadica and unexpected coumarin from h. superba using chromatography over cleaning sephadex with sodium hypochlorite
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2014-08
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Resumo
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
9α-hydroxyhortiolide A, 11β-hydroxyhortiolide C and 1(S*)-acetoxy-7(R*)-hydroxy-7-
deoxoinchangin. 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
13C 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.
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Hortia oreadica, H. brasiliana, H. superba, Rutaceae, Limonoids, Alkaloids, Coumarins, Dihydrocinnamic acids, Sephadex LH-20, Chlorination
Citação
SEVERINO, Vanessa G. P. et al. New limonoids from hortia oreadica and unexpected coumarin from h. superba using chromatography over cleaning sephadex with sodium hypochlorite. Molecules, Basel, v. 19, p. 12031-12047, Aug. 2014.