New antitumor sesquiterpenoids from Santalum album of Indian origin

Tae Hoon Kim, Hideyuki Ito, Tsutomu Hatano, Junko Takayasu, Harukuni Tokuda, Hoyoku Nishino, Takahisa Machiguchi, Takashi Yoshida

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

Three new campherenane-type (1, 4, 7) and three new santalane-type (9, 11, 12) sesquiterpenoids, and two aromatic glycosides (21, 22) together with 12 known metabolites including α,β-santalols (14, 18), (E)-α,β-santalals (15, 19), α,β-santaldiols (16, 20), α-santalenoic acid (17), and vanillic acid 4-O-neohesperidoside were isolated from Santalum album chips of Indian origin. The structures of the new compounds, including absolute configurations, were elucidated by 1D- and 2D-NMR spectroscopic and chemical methods. The antitumor promoting activity of these isolates along with several neolignans previously isolated from the same source was evaluated for both in vitro Epstein-Barr virus early antigen (EBV-EA) activation and in vivo two-stage carcinogenesis assays. Among them, compound 1 exhibited a potent inhibitory effect on EBV-EA activation, and also strongly suppressed two-stage carcinogenesis on mouse skin.

Original languageEnglish
Pages (from-to)6981-6989
Number of pages9
JournalTetrahedron
Volume62
Issue number29
DOIs
Publication statusPublished - Jul 17 2006

Keywords

  • Campherenane-type sesquiterpene
  • Cancer chemoprevention
  • Epstein-Barr virus
  • Mouse skin two-stage carcinogenesis
  • Santalaceae
  • Santalane-type sesquiterpene
  • Santalum album

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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  • Cite this

    Kim, T. H., Ito, H., Hatano, T., Takayasu, J., Tokuda, H., Nishino, H., Machiguchi, T., & Yoshida, T. (2006). New antitumor sesquiterpenoids from Santalum album of Indian origin. Tetrahedron, 62(29), 6981-6989. https://doi.org/10.1016/j.tet.2006.04.072