TY - JOUR
T1 - New antitumor sesquiterpenoids from Santalum album of Indian origin
AU - Kim, Tae Hoon
AU - Ito, Hideyuki
AU - Hatano, Tsutomu
AU - Takayasu, Junko
AU - Tokuda, Harukuni
AU - Nishino, Hoyoku
AU - Machiguchi, Takahisa
AU - Yoshida, Takashi
N1 - Funding Information:
The authors thank Kannonshoji Temple for kind donation of sandalwood chips used in this research. We are grateful to the SC-NMR Laboratory of Okayama University for performing the NMR spectroscopy. This study was supported in part by the U.S. National Cancer Institute, M.D. (CA17625). One of the authors (T.H.K.) acknowledges the Ministry of Education, Culture, Sports, Science and Technology of Japan for a scholarship.
PY - 2006/7/17
Y1 - 2006/7/17
N2 - 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.
AB - 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.
KW - Campherenane-type sesquiterpene
KW - Cancer chemoprevention
KW - Epstein-Barr virus
KW - Mouse skin two-stage carcinogenesis
KW - Santalaceae
KW - Santalane-type sesquiterpene
KW - Santalum album
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U2 - 10.1016/j.tet.2006.04.072
DO - 10.1016/j.tet.2006.04.072
M3 - Article
AN - SCOPUS:33744938948
SN - 0040-4020
VL - 62
SP - 6981
EP - 6989
JO - Tetrahedron
JF - Tetrahedron
IS - 29
ER -
