Abstract
Phytochemical investigation of the leaves and twigs of Acronychia pedunculata has led to the isolation of three new acetophenone monomers 1–3 as well as 1-[2′,4′-dihydroxy-3′,5′-di-(3″-methyl-2″-butenyl)-6′-methoxy]phenylethanone (4), acronyculatin E (5), a mixture of β-sitosterol and stigmasterol, and sesamin. The structures of these new compounds were elucidated spectroscopically. The inhibitory activities of the isolated acetophenone derivatives against mammalian DNA polymerases and human cancer cell growth were also assessed.
References
Kumar V, Karunaratne V, Sanath MR, Meegalle K (1989) 1-[2′,4′-Dihydroxy-3′,5′-di-(3″-methylbut-2″-enyl)-6′-methoxy]phenylethanone from Acronychia pedunculata root bark. Phytochemistry 28:1278–1279
Arthur HR, Chan RK, Loo SN, Tam SW, Tung S (1966) New alkaloids from Hong Kong plants. Phytochemistry 5:379–383
Kouloura E, Halabalaki M, Lallemand MC, Nam S, Jove R, Litaudon M, Awang K, Hadi HA, Skaltsounis AL (2012) Cytotoxic prenylated acetophenone dimers from Acronychia pedunculata. J Nat Prod 75:1270–1276
de Silva LB, de Silva ULL, Mahendran M, Jenings R (1979) Kokusaginine and evolitrine from Acronychia pedunculata. Phytochemistry 18:1255–1256
Cui B, Chai H, Horgen FD, Hansen B, Madulid DA, Soejarto DD, Farnsworth NR, Cordell GA, Pezzuto JM, Kinghorn AD (1999) Quinoline alkaloids from Acronychia laurifolia. Phytochemistry 52:95–98
de Silva LB, Herath WM, Liyanage C, Kumar V, Ahmad VU, Sultana A (1991) Demethylacrovestone from Acronychia pedunculata fruits. Phytochemistry 30:1709–1710
Sy LK, Brown GD (1999) 1-[2′,4′-Dihydroxy-3′-(3″-methylbut-2″-enyl)- 5′-(1″′-ethoxy-3″′-methylbutyl)-6′-methoxy]phenylethanone from Acronychia pedunculata. Phytochemistry 52:681–683
Su CR, Kuo PC, Wang ML, Liou MJ, Damu AG, Wu TS (2003) Acetophenone derivatives from Acronychia pedunculata. J Nat Prod 66:990–993
Wu TS, Wang ML, Jong TT, McPhail AT, McPhail DR, Lee KH (1989) X-ray crystal structure of acrovestone, a cytotoxic principle from Acronychia pedunculata. J Nat Prod 52:1284–1289
Han X, Pathmasiri W, Bohlin L, Janson JC (2004) 1-[2′,4′-Dihydroxy-3′,5′-di-(3″-methyl-2″-butenyl)-6′-methoxy]phenylethanone from Acronychia pedunculata (L.) Miq. by high-speed counter-current chromatography. J Chromatogr A 1022:213–216
Pathmasiri W, El-Seedi HR, Han X, Janson JC, Huss U, Bohlin L (2005) Aryl ketones from Acronychia pedunculata with cyclooxygenase-2 inhibitory effects. Chem Biodivers 2:463–469
Jayasinghea L, Kumarihamya BMM, Jayarathnab NKHR, Udishanib NWMG, Bandara BMR, Hara N, Fujimoto Y (2003) Antifungal constituents of the stem bark of Bridelia retusa. Phytochemistry 62:637–641
Mizushina Y (2009) Specific inhibitors of mammalian DNA polymerase species. Biosci Biotechnol Biochem 73:1239–1251
Tamai K, Kojima K, Hanaichi T, Masaki S, Suzuki M, Umekawa H, Yoshida S (1988) Structural study of immunoaffinity-purified DNA polymerase α-DNA primase complex from calf thymus. Biochim Biophys Acta 950:263–273
Date T, Yamaguchi M, Hirose F, Nishimoto Y, Tanihara K, Matsukage A (1988) Expression of active rat DNA polymerase β in Escherichia coli. Biochemistry 27:2983–2990
Mizushina Y, Tanaka N, Yagi H, Kurosawa T, Onoue M, Seto H, Horie T, Aoyagi N, Yamaoka M, Matsukage A, Yoshida S, Sakaguchi K (1996) Fatty acids selectively inhibit eukaryotic DNA polymerase activities in vitro. Biochim Biophys Acta 1308:256–262
Mizushina Y, Yoshida S, Matsukage A, Sakaguchi K (1997) The inhibitory action of fatty acids on DNA polymerase β. Biochim Biophys Acta 1336:509–521
Ishiyama M, Tominaga H, Shiga M, Sasamoto K, Ohkura Y, Ueno K (1996) A combined assay of cell viability and in vitro cytotoxicity with a highly water-soluble tetrazolium salt, neutral red and crystal violet. Biol Pharm Bull 19:1518–1520
Acknowledgments
This research was financially supported by the Kobe Pharmaceutical University Collaboration Fund. Thanks are also due to Dr. C. Tode (Kobe Pharmaceutical University) for 1H- and 13C-NMR spectra, and to Dr. A. Takeuchi (Kobe Pharmaceutical University) for mass spectrum measurements.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kozaki, S., Takenaka, Y., Mizushina, Y. et al. Three acetophenones from Acronychia pedunculata . J Nat Med 68, 421–426 (2014). https://doi.org/10.1007/s11418-013-0803-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11418-013-0803-y