RSS-Feed abonnieren
DOI: 10.1055/s-2000-8886
Georg Thieme Verlag Stuttgart · New York
Bioactive Triterpenoids from the Stem Bark of Picea glehni
Publikationsverlauf
November 8, 1999
January 23, 2000
Publikationsdatum:
31. Dezember 2000 (online)
Abstract
Two new triterpenoids, 3α-methoxyserrat-14-en-21β-yl formate (1), and 24-methylcycloartenone (2), were isolated from the stem bark of Picea glehni (Fr. Schm.) Masters together with three known triterpenoids, 3α-methoxyserrat-14-en-21β-ol, 3β-methoxyserrat-14-en-21β-ol, and piceanonol A. Compounds 1, 2, and a synthetic sample, 3α-methoxyserrat-13-en-21β-yl formate showed potent inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA).
Key words
Picea glehni - Pinaceae - serratane - cycloartane - 2D NMR - in vitro anti-tumor-promoting activity
References
- 1 Norin T.. Some aspects of the chemistry of the order pinales. Phytochemistry. 1972;; 11 1231-42
- 2 Samejima J.. Asahi Encyclopedia, Plants of the World,. Asahi Shinbunsha Tokyo. 1972;; 16 2500
- 3 Tanaka R,, Mun C,, Usami Y,, Matsunaga S.. 3-Oxo-serratene triterpenoids from the stem bark of Picea jezoensis var. hondoensis. . Phytochemistry. 1994;; 35 1517-22
- 4 Tanaka R,, Tsuboi R,, Matsunaga S.. Serratenes from the stem bark of Picea jezoensis var. hondoensis. Phytochemistry. 1994;; 37 209-11
- 5 Tanaka R,, Tsujimoto K,, Muraoka O,, Matsunaga S.. Two serratane triterpenes from the stem bark of Picea jezoensis var. hondoensis. Phytochemistry. 1998;; 47 839-43
- 6 Tanaka R,, Kumagai T,, In Y,, Ishida T,, Nishino H,, Matsunaga S.. Piceanonols A, and B, Triterpenoids bearing a novel skeletal system isolated from the bark of Picea jezoensis var. hondoensis. Tetrahedron Letters. 1999;; 40 6415-8
- 7 Tanaka R,, Senba H,, Minematsu T,, Muraoka O,, Matsunaga S.. 21α-Hydroxy-3β-methoxyserrat-14-en-30-al and other triterpenoids from the cuticle of Picea jezoensis. Phytochemistry. 1995;; 38 1467-71
- 8 Tanaka R,, Ohmori K,, Minoura K,, Matsunaga S.. Two new epoxyserratanes from the cuticle of Picea jezoensis. . Journal of Natural Products. 1996;; 59 237-41
- 9 Tanaka R,, Tsujimoto K., In Y,, Matsunaga S.. New methoxytriterpene dione from the cuticle of Picea jezoensis var. jezoensis. . Journal of Natural Products. 1997;; 60 319-22
- 10 Kurvyakov P I,, Gatilov Yu V,, Khan V A,, Dubovenko Zh V,, Pentegova V A.. Structure of gleenol - a C15H26O sesquiterpenic alcohol with a new type of carbon skeleton. Khimiia Prirodnykh Soedinenii. 1979;; 2 164-8
- 11 Konoshima T,, Takasaki M,, Kozuka M,, Tokuda H.. Studies on inhibitors of skin-tumor promotion, I. Inhibitory effects of triterpenes from Euptelea polyandra on Epstein-Barr virus activation. Journal of Natural Products. 1987;; 50 1167-70
- 12 Kremen L J.. Acetic formic anhydride. Organic Syntheses. 1988;; VI 8
- 13 Ringold H J,, Loken B,, Rosenkranz G,, Sondhimer F.. The direct Oppenauer oxidation of steroidal formate esters. A new synthesis of 17α-hydroxyprogesterone. Journal of American Chemical Society. 1956;; 78 816-9
- 14 Ito K,, Lai J.. Studies on the constituents of Marsdenia formosana Masamune. I. Isolation of triterpenoids and structure of marsformol. Yakugaku Zasshi. 1978;; 98 249-56
- 15 Tanaka R,, Matsunaga S.. Triterpene constituents from Euphorbia supina. . Phytochemistry. 1988;; 27 3579-84
- 16 Aplin R T,, Hornby G M.. Application of mass spectrometry to the structual investigation of 9,19-cyclosterols and triterpenes. Journal of Chemical Society (B). 1966; 1078-9
- 17 Nes W D,, Koike K,, Jia Z,, Sakamoto Y,, Satou T,, Nikaido T,, Griffin J F.. 9β,19-Cyclosterol: analysis by 1H and 13C NMR, crystallographic observation, and molecular mechanics calculations. Journal of American Chemical Society. 1998;; 120 5970-80
- 18 Budzynska-Topolowska J,, Rutkowski A.. Nonsaponifiable triterpene alcohols. Rapeseed oil. Revue Francaise des Corps Gras. 1969;; 16 695-9
Reiko Tanaka
Department of Medicinal Chemistry Osaka University of Pharmaceutical Sciences
4-20-1 Nasahara Takatsuki Osaka 569-1094 Japan
eMail: E-mail: tanakar@oysun01.oups.ac.jp
Fax: Fax: +81-726-90-1084