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

29 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

Fingerprint

Santalum
Carcinogenesis
Chemical activation
Vanillic Acid
Lignans
Glycosides
Metabolites
Assays
Skin
Nuclear magnetic resonance
Acids
Epstein-Barr virus early antigen

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
  • Organic Chemistry
  • Drug Discovery

Cite this

Kim, T. H., Ito, H., Hatano, T., Takayasu, J., Tokuda, H., Nishino, H., ... 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

New antitumor sesquiterpenoids from Santalum album of Indian origin. / Kim, Tae Hoon; Ito, Hideyuki; Hatano, Tsutomu; Takayasu, Junko; Tokuda, Harukuni; Nishino, Hoyoku; Machiguchi, Takahisa; Yoshida, Takashi.

In: Tetrahedron, Vol. 62, No. 29, 17.07.2006, p. 6981-6989.

Research output: Contribution to journalArticle

Kim, TH, 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, vol. 62, no. 29, pp. 6981-6989. https://doi.org/10.1016/j.tet.2006.04.072
Kim TH, Ito H, Hatano T, Takayasu J, Tokuda H, Nishino H et al. New antitumor sesquiterpenoids from Santalum album of Indian origin. Tetrahedron. 2006 Jul 17;62(29):6981-6989. https://doi.org/10.1016/j.tet.2006.04.072
Kim, Tae Hoon ; Ito, Hideyuki ; Hatano, Tsutomu ; Takayasu, Junko ; Tokuda, Harukuni ; Nishino, Hoyoku ; Machiguchi, Takahisa ; Yoshida, Takashi. / New antitumor sesquiterpenoids from Santalum album of Indian origin. In: Tetrahedron. 2006 ; Vol. 62, No. 29. pp. 6981-6989.
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