Radermachol and naphthoquinone derivatives from Tecomella undulata: Complete 1H and 13C NMR assignments of radermachol with the aid of computational 13C shift prediction

Pahup Singh, Poonam Khandelwal, Noriyuki Hara, Teigo Asai, Yoshinori Fujimoto

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Petroleum ether extract of the heartwood of Tecomella undulata affords radermachol, an unusual rare pigment and 2-isopropenylnaphtho[2,3-b]furan-4,9- quinone along with lapachol, tecomaquinone-I, dehydro-α-lapachone, α-lapachone, β-lapachone, cluytyl ferulate, stigmasterol and β-sitosterol. Radermachol and 2-isopropenylnaphtho [2,3-b]furan-4,9-quinone are being reported for the first time from genus Tecomella. Complete assignments of 1H and 13C NMR signals of polyketide, radermachol 1, have been achieved by the 13C NMR chemical shift prediction using ab initio MO and DFT/GIAO methods in addition to 2D-NMR techniques.

Original languageEnglish
Pages (from-to)1865-1870
Number of pages6
JournalIndian Journal of Chemistry - Section B Organic and Medicinal Chemistry
Volume47
Issue number12
Publication statusPublished - 2008 Dec 1
Externally publishedYes

Keywords

  • 2-Isopropenylnaphtho[2,3-b]furan-4,9-quinone
  • Chemical shift prediction
  • Computational chemistry
  • Radermachol
  • Tecomella undulata

ASJC Scopus subject areas

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry

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