Next Article in Journal
Synthesis and Cytotoxic Activity Evaluation of Novel Arylpiperazine Derivatives on Human Prostate Cancer Cell Lines
Previous Article in Journal
Bioevaluation of Novel Anti-Biofilm Coatings Based on PVP/Fe3O4 Nanostructures and 2-((4-Ethylphenoxy)methyl)-N- (arylcarbamothioyl)benzamides
Article Menu

Export Article

Open AccessArticle
Molecules 2014, 19(8), 12031-12047; doi:10.3390/molecules190812031

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

Departamento de Química, Universidade Federal de São Carlos, CP 676, São Carlos 13565-905, SP, Brazil
*
Author to whom correspondence should be addressed.
Received: 24 May 2014 / Revised: 1 July 2014 / Accepted: 16 July 2014 / Published: 12 August 2014
(This article belongs to the Section Natural Products)
View Full-Text   |   Download PDF [2444 KB, uploaded 12 August 2014]   |  

Abstract

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-angle-spinning 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. View Full-Text
Keywords: Hortia oreadica; H. brasiliana; H. superba; Rutaceae; limonoids; alkaloids; coumarins; dihydrocinnamic acids; Sephadex LH-20; chlorination Hortia oreadica; H. brasiliana; H. superba; Rutaceae; limonoids; alkaloids; coumarins; dihydrocinnamic acids; Sephadex LH-20; chlorination
Figures

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Severino, V.G.; de Freitas, S.D.; Braga, P.A.; Forim, M.R.; da Silva, M.F.G.; Fernandes, J.B.; Vieira, P.C.; Venâncio, T. New Limonoids from Hortia oreadica and Unexpected Coumarin from H. superba Using Chromatography over Cleaning Sephadex with Sodium Hypochlorite. Molecules 2014, 19, 12031-12047.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top