LC-MS- and 1H NMR Spectroscopy-Guided Identification of Antifungal Diterpenoids from Sagittaria latifolia

Ranga Rao Ravu, Melissa R. Jacob, Cynthia Jeffries, Ying Tu, Shabana I. Khan, Ameeta K. Agarwal, R. Kiplin Guy, Larry A. Walker, Alice M. Clark, Xing Cong Li

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10 Scopus citations


Antifungal screening of small-molecule natural product libraries showed that a column fraction (CF) derived from the plant extract of Sagittaria latifolia was active against the fungal pathogen Cryptococcus neoformans. Dereplication analysis by liquid chromatography-mass spectrometry (LC-MS) and proton nuclear magnetic resonance spectroscopy (1H NMR) indicated the presence of new compounds in this CF. Subsequent fractionation of the plant extract resulted in the identification of two new isopimaradiene-type diterpenoids, 1 and 2. The structures of 1 and 2 were determined by chemical methods and spectroscopic analysis as isopimara-7,15-dien-19-ol 19-O-α-l-arabinofuranoside and isopimara-7,15-dien-19-ol 19-O-α-l-(5′-acetoxy)arabinofuranoside, respectively. Compound 1 exhibited IC50 values of 3.7 and 1.8 μg/mL, respectively, against C. neoformans and C. gattii. Its aglycone, isopimara-7,15-dien-19-ol (3), resulting from acid hydrolysis of 1, was also active against the two fungal pathogens, with IC50 values of 9.2 and 6.8 μg/mL, respectively. This study demonstrates that utilization of the combined LC-MS and 1H NMR analytical tools is an improved chemical screening approach for hit prioritization in natural product drug discovery.

Original languageEnglish
Pages (from-to)2255-2259
Number of pages5
JournalJournal of Natural Products
Issue number9
StatePublished - Sep 25 2015

Bibliographical note

Publisher Copyright:
© 2015 The American Chemical Society and American Society of Pharmacognosy.

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry


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