Triterpene Constituents from the Stem Bark of Pinus luchuensis and their DNA Topoisomerase II Inhibitory Effect

Abstract

Nine lanostane and serratane-type triterpenes including two unknown compounds were isolated from the stem bark of Pinus luchuensis. These new compounds were characterized as 3-oxolanost-9(11)-ene-24S,25-diol (1) and 29-acetoxy-3β-methoxyserrat-14-en-21α-ol (2) on the basis of spectroscopic evidence. Some of these triterpenes were tested for the inhibitory effect on DNA topoisomerase II activity. Compound 1 showed a slightly less potent inhibitory activity with an IC₅₀ value of 186 μM.

Pinus luchuensis - Pinaceae - triterpene, 3-oxolanost-9 (11)-ene-24S,25-diol, 29-acetoxy-3β-methoxyserrat-14-en-21α-ol - DNA topoisomerase II

References

• 1 Tanaka R, Matsunaga S. Terpenoids and steroids from several Euphorbiaceae and Pinaceae plants. J. Pharm. Soc.  Jpn. 1999;  119 319-39
• 2 Takayasu J, Tanaka R, Matsunaga S, Ueyama H, Tokuda H, Hasegawa T, Nishino A, Nishino H, Iwashima A. Anti-tumor-promoting activity of derivatives of abieslactone, a natural triterpenoid isolated from several Abies genus.  Cancer Lett.. 1990;  53 141-4
• 3 Wada S, Tanaka R, Iida A, Matsunaga S. In vitro inhibitory effects of DNA topoisomerase II by fernane-type triterpenoids isolated from a Euphorbia genus. Bioorg. Med. Chem.  Lett.. 1998;  8 2829-32
• 4 Wada S, Tanaka R. Four new tris-nor-lanostene-type triterpenoids from the stem bark of Pinus luchuensis. J. Nat.  Prod.. 2000;  63 1055-7
• 5 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
• 6 Kutney J P, Eigendorf G, Worth B R, Rowe J W, Conner A H, Nagasampagi B A. 111. New triterpenes from the stem bark of western white pine (Pinus monticola Dougl.). Helv. Chim.  Acta. 1981;  64 1183-207
• 7 Ohtsu H, Tanaka R, Michida T, Shingu T, Matsunaga S. Tetracyclic triterpenes and other constituents from the leaves and bark of Larix kaempferi .  Phytochemistry. 1998;  49 1761-9
• 8 Tanaka R, Ohmori K, Minoura K, Matsunaga S. Two new epoxyserratanes from the cuticle of Picea jezoensis. J. Nat.  Prod.. 1996;  59 237-41
• 9 Tanaka R, Tsujimoto K, Matsunaga S. Two serratane triterpenes from the stem bark of Picea jezoensis var. hondoensis .  Phytochemistry. 1999;  52 1581-5
• 10 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
• 11 Tanaka R, Tsuboi R, Matsunaga S. Serratanes from the stem bark of Picea jezoensis Carr. hondoensis .  Phytochemistry. 1994;  37 209-11
• 12 Moriarity D M, Huang J, Yancey C A, Zhang P, Setzer W N, Lawton R O, Bates R B, Caldera S. Lupeol is the cytotoxic principle in the leaf extract of Dendropanax cf. querceti .  Planta Medica. 1998;  64 370-2
• 13 Ma Z Z, Hano Y, Nomura T, Chen Y J. Three new triterpenoids from Peganum nigellastrum. J. Nat.  Prod.. 2000;  63 390-2