Alkaloids from Alangium javanicum and Alangium grisolleoides that mediate Cu2+-dependent DNA strand scission

Van Cuong Pham, Ji Ma, Shannon J. Thomas, Zhidong Xu, Sidney Hecht

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Crude CH2Cl2-MeOH extracts prepared from Alangium javanicum and A. grisolleoides were found to induce DNA strand breakage in the presence of Cu2+ and were subjected to bioassay-guided fractionation to permit identification of the active principle(s). Javaniside (1), a novel alkaloid possessing an unusual monoterpenoid oxindole skeleton, was identified as an active principle contributing to the DNA cleavage activity observed for the crude extract of A. javanicum. Alangiside (2), a tetrahydroisoquinoline monoterpene glucoside widely distributed in the genus Alangium, was also isolated from A. grisolleoides as a new type of Cu2+-dependent DNA cleavage agent. The relative configuration of the asymmetric centers in javaniside was established by analysis of 1H-1H coupling constants and NOESY correlations. Semisynthesis of javaniside from secologanin (3) established the absolute stereochemistry of javaniside.

Original languageEnglish (US)
Pages (from-to)1147-1152
Number of pages6
JournalJournal of Natural Products
Volume68
Issue number8
DOIs
StatePublished - Aug 2005
Externally publishedYes

Fingerprint

Alangiaceae
Alangium
Alkaloids
alkaloids
monoterpenoids
DNA Cleavage
Monoterpenes
DNA
tetrahydroisoquinolines
stereochemistry
extracts
Tetrahydroisoquinolines
Stereochemistry
glucosides
skeleton
Bioassay
fractionation
Glucosides
Fractionation
bioassays

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Alkaloids from Alangium javanicum and Alangium grisolleoides that mediate Cu2+-dependent DNA strand scission. / Pham, Van Cuong; Ma, Ji; Thomas, Shannon J.; Xu, Zhidong; Hecht, Sidney.

In: Journal of Natural Products, Vol. 68, No. 8, 08.2005, p. 1147-1152.

Research output: Contribution to journalArticle

Pham, Van Cuong ; Ma, Ji ; Thomas, Shannon J. ; Xu, Zhidong ; Hecht, Sidney. / Alkaloids from Alangium javanicum and Alangium grisolleoides that mediate Cu2+-dependent DNA strand scission. In: Journal of Natural Products. 2005 ; Vol. 68, No. 8. pp. 1147-1152.
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