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. 2013 Oct 16;3(5):250–255. doi: 10.1007/s13659-013-0053-4

Isoprenylated flavonoids and clerodane diterpenoids from Dodonaea viscosa

Yuan Gao 1,2,3, Yin-Dong Fang 2, Ping Hai 2, Fei Wang 1,2, Ji-Kai Liu 1,
PMCID: PMC4131623

Abstract

Phytochemical investigation of the aerial parts of Dodonaea viscosa led to the isolation of six new compounds including four isoprenylated flavonoids, dodovisones A-D (14), and two clerodane diterpenoids, dodovislactones A and B (5 and 6). Their structures were established by extensive spectroscopic analysis. graphic file with name 13659_2013_53_Article_Fig1_HTML.jpg

Electronic Supplementary Material

Supplementary material is available for this article at 10.1007/s13659-013-0053-4 and is accessible for authorized users.

Keywords: Dodonaea viscosa, isoprenylated flavonoid, clerodane diterpenoid, dodovisone, dodovislactone

Electronic supplementary material

13659_2013_53_MOESM1_ESM.pdf (1.8MB, pdf)

Supplementary material, approximately 1.79 MB.

Footnotes

This article is published with open access at Springerlink.com

References

  • [1].Editorial Committee of Flora Reipublicae Popularis Sinicae. Flora Reipublicae Popularis Sinicae. Beijing: Academic Press; 1985. pp. 58–59. [Google Scholar]
  • [2].Zhang L B, Ji J, Lei C, Wang H Y, Zhao Q S, Hou A J. J. Nat. Prod. 2012;75:699–706. doi: 10.1021/np2009797. [DOI] [PubMed] [Google Scholar]
  • [3].Niu H M, Zeng D Q, Long C L, Peng Y H, Wang Y H, Luo J F, Wang H S, Shi Y N, Tang G H, Zhao F W. J. Asian Nat. Prod. Res. 2010;11:7–14. doi: 10.1080/10286020903407379. [DOI] [PubMed] [Google Scholar]
  • [4].Ortega A, García P E, Cárdenas J, Mancera C, Marquina S, Garduño M L C, Maldonado E. Tetrahedron. 2001;57:2981–2989. doi: 10.1016/S0040-4020(01)00161-2. [DOI] [Google Scholar]
  • [5].Cao S G, Brodie P, Callmander M, Randrianaivo R, Razafitsalama J, Rakotobe E, Rasamison V E, TenDyke K, Shen Y C, Suh E M, Kingston D G I. J. Nat. Prod. 2009;72:1705–1707. doi: 10.1021/np900293x. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • [6].Wagner H, Ludwig C, Grotjahn L, Khan M S Y. Phytochemistry. 1987;26:697–701. doi: 10.1016/S0031-9422(00)84767-6. [DOI] [Google Scholar]
  • [7].Mata R, Contreras J L, Crisanto D, Pereda-Miranda R, Castañeda P, Rio F D. J. Nat. Prod. 1991;54:913–917. doi: 10.1021/np50075a033. [DOI] [Google Scholar]
  • [8].Teffo L S, Aderogba M A, Eloff J N. South Afric. J. Bot. 2010;76:25–29. doi: 10.1016/j.sajb.2009.06.010. [DOI] [Google Scholar]
  • [9].Muhammad A, Anis I, Khan A, Marasini B P, Choudhary M I, Shah M R. Arch. Pharm. Res. 2012;35:431–436. doi: 10.1007/s12272-012-0305-6. [DOI] [PubMed] [Google Scholar]
  • [10].Muhammada A, Anis I, Ali Z, Awadelkarim S, Khan A, Khalid A, Shah M R, Galal M, Khan I A, Choudhary M I. Bioorg. Med. Chem. Lett. 2012;22:610–612. doi: 10.1016/j.bmcl.2011.10.072. [DOI] [PubMed] [Google Scholar]
  • [11].Shalaby N M M, Abd-Alla H I, Hamed M A, Al-Ghamdi S N, Jambi S M S. Int. J. Phytomed. 2012;4:27–39. [Google Scholar]
  • [12].Salinas-Sánchez D O, Herrera-Ruiz M, Pérez S, Jiménez-Ferrer E, Zamilpa A. Molecules. 2012;17:4292–4299. doi: 10.3390/molecules17044292. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • [13] (a).Wang F, Gao Y, Zhang L, Bai B, Hu Y N, Dong Z J, Zhai Q W, Zhu H J, Liu J K. Org. Lett. 2010;12:3196–3199. doi: 10.1021/ol1011289. [DOI] [PubMed] [Google Scholar]
  • [13] (b).Gao Y, Zhou D S, Kong L M, Hai P, Li Y, Wang F, Liu J K. Nat. Prod. Bioprospect. 2012;2:65–69. doi: 10.1007/s13659-012-0012-5. [DOI] [Google Scholar]
  • [13] (c).Gao Y, Wang G Q, Wei K, Hai P, Wang F, Liu J K. Org. Lett. 2012;14:5936–5939. doi: 10.1021/ol302849v. [DOI] [PubMed] [Google Scholar]
  • [13] (d).Gao Y, Li G T, Li Y, Hai P, Wang F, Liu J K. Nat. Prod. Bioprospect. 2013;3:14–19. doi: 10.1007/s13659-012-0102-4. [DOI] [Google Scholar]
  • [14].Sachdev K, Kulshreshtha D K. Phytochemistry. 1983;22:1253–1256. doi: 10.1016/0031-9422(83)80234-9. [DOI] [Google Scholar]
  • [15].Wollenweber E, Roitman J N. Nat. Prod. Comm. 2007;2:385–389. [Google Scholar]
  • [16].Heerden F R V, Viljoen A M, Wyk B-E V. Fitoterapia. 2000;71:602–604. doi: 10.1016/S0367-326X(00)00201-X. [DOI] [PubMed] [Google Scholar]
  • [17].Vasconcelos J M J, Silva A M S, Cavaleiro J A S. Phytochemistry. 1998;49:1421–1424. doi: 10.1016/S0031-9422(98)00180-0. [DOI] [Google Scholar]
  • [18].Singh P, Jain S, Jakupovic J. Phytochemistry. 1988;27:1537–1539. doi: 10.1016/0031-9422(88)80235-8. [DOI] [Google Scholar]
  • [19].Iqbal K, Malik A, Mukhtare N, Anis I, Khan S N, Choudhary M I. Chem. Pharm. Bull. 2004;52:785–789. doi: 10.1248/cpb.52.785. [DOI] [PubMed] [Google Scholar]
  • [20].Jolad S D, Hoffmann J J, Schram K H, Cole J R, Tempesta M S, Bates R B. J. Org. Chem. 1982;47:1356–1358. doi: 10.1021/jo00346a042. [DOI] [Google Scholar]
  • [21].Hatano T, Takagi M, Ito H, Yoshida T. Chem. Pharm. Bull. 1997;45:1485–1492. doi: 10.1248/cpb.45.1485. [DOI] [Google Scholar]
  • [22] (a).Ferracin R J, Silva M F D G F D, Fernandes J B, Vieira P C. Phytochemisty. 1998;47:393–396. doi: 10.1016/S0031-9422(97)00598-0. [DOI] [Google Scholar]
  • [22] (b).Ikeya Y, Taguchi H, Sasaki H, Nakajima K, Yosioka I. Chem. Pharm. Bull. 1980;28:2414–2421. doi: 10.1248/cpb.28.2414. [DOI] [Google Scholar]
  • [22] (c).Wu Y B, Zheng C J, Qiu L P, Sun L N, Han T, Jiao L, Zhang Q Y, Wu J Z. Molecules. 2009;14:573–583. doi: 10.3390/molecules14010573. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • [22] (d).Sasaki H, Taguchi H, Endo T, Yosioka I. Chem. Pharm. Bull. 1982;30:3555–3562. doi: 10.1248/cpb.30.3555. [DOI] [Google Scholar]
  • [22] (e).Sinha A, Taylor W H, Khan I H, McDaniel S T, Esko J D. J. Nat. Prod. 1999;62:1036–1038. doi: 10.1021/np980543a. [DOI] [PubMed] [Google Scholar]
  • [23].Omosa L K, Midiwo J O, Derese S, Yenesew A, Peter M G, Heydenreich M. Phytochemistry Lett. 2010;3:217–220. doi: 10.1016/j.phytol.2010.08.001. [DOI] [Google Scholar]
  • [24].Costa M, Tanakac C M A, Imamuraa P M, Marsaioli A J. Phytochemistry. 1999;50:117–122. doi: 10.1016/S0031-9422(98)00464-6. [DOI] [Google Scholar]
  • [25].Heymann H, Tezuka Y, Kikuchi T, Supriyatna S. Chem. Pharm. Bull. 1994;42:1204–1207. [Google Scholar]

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Supplementary Materials

13659_2013_53_MOESM1_ESM.pdf (1.8MB, pdf)

Supplementary material, approximately 1.79 MB.


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