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Limonoids from Azadirachta excelsa

B Cui1, H Chai, H L Constant

  • 1Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago 60612, USA.

Phytochemistry
|June 5, 1998
PubMed
Summary
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Researchers isolated novel limonoids from Azadirachta excelsa. Two known compounds, nimbolide and 28-deoxonimbolide, showed broad cytotoxicity against cancer cell lines, while the new compounds were inactive.

Area of Science:

  • Natural Product Chemistry
  • Pharmacology
  • Medicinal Chemistry

Background:

  • Azadirachta excelsa is a medicinal plant with potential therapeutic compounds.
  • Meliacins are a class of limonoids found in Meliaceae family plants, known for diverse biological activities.

Purpose of the Study:

  • To isolate and characterize novel meliacin-type limonoids from Azadirachta excelsa stem extract.
  • To evaluate the cytotoxic potential of isolated compounds against human cancer cell lines.

Main Methods:

  • Activity-directed fractionation of plant extract using KB cells.
  • Structure elucidation of isolated compounds using spectroscopic methods.
  • Cytotoxicity screening against a panel of human cancer cell lines.
  • Electrospray Liquid Chromatography-Mass Spectrometry (LC/MS) for dereplication.

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Main Results:

  • Four meliacin-type limonoids were isolated: two novel (2,3-dihydronimbolide, 3-deoxymethylnimbidate) and two known (nimbolide, 28-deoxonimbolide).
  • Nimbolide and 28-deoxonimbolide exhibited broad cytotoxicity against tested cancer cell lines.
  • The novel compounds, 2,3-dihydronimbolide and 3-deoxymethylnimbidate, were found to be inactive in cytotoxicity assays.

Conclusions:

  • Nimbolide and 28-deoxonimbolide are the primary cytotoxic meliacins in Azadirachta excelsa stem extract.
  • The novel limonoids 2,3-dihydronimbolide and 3-deoxymethylnimbidate do not possess significant cytotoxic activity.
  • LC/MS dereplication is an effective method for identifying active constituents in complex natural product mixtures.