Planta Med 2011; 77(16): 1806-1810
DOI: 10.1055/s-0030-1271138
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Chrysindins A–D, Polyacetylenes from the Flowers of Chrysanthemum indicum

Lei-Lei Liu1 , Rui Wang 2 , Yan-Ping Shi1 , 2
  • 1State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, People's Republic of China
  • 2Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine , of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, People's Republic of China
Further Information

Publication History

received February 22, 2011 revised April 5, 2011

accepted April 26, 2011

Publication Date:
20 May 2011 (online)

Abstract

Four new polyacetylenes, namely chrysindins A–D (14), together with 6 known polyacetylenes, were isolated from the flowers of Chrysanthemum indicum. Their structures were established on the basis of comprehensive spectroscopic analyses. Chrysindins A (1) and B (2) bear a novel carbon skeleton.

Supporting Information

References

  • 1 Editorial Committee for Flora of the Chinese Academy of Science .Flora of China. Vol. 76 (1) Beijing: Science Press; 1983: 28-49
  • 2 Chinese Pharmacopoeia Commission .Chinese Pharmacopoeia. Vol. 1 Beijing: Chemical Industry Press; 2005: 218-219
  • 3 Matsuda H, Morikawa T, Toguchida I, Harima S, Yoshikawa M. Medicinal flowers. II. Inhibitors of nitric ocide production and absolute stereostructures of five new germacrane-type sesquiterpenes, kikkanols D, D monoacetate, E, F, and F monoacetate from the flowers of Chrysanthemum indicum L.  Chem Pharm Bull. 2000;  48 651-656
  • 4 Matsuda H, Morikawa T, Toguchida I, Harima S, Yoshikawa M. Medicinal flowers. VI. Absolute stereostructures of two new flavanone glycosides and a phenylbutanoid glycoside from the flowers of Chrysanthemum indicum L.: their inhibitory activities for rat lens aldose reductase.  Chem Pharm Bull. 2002;  50 972-975
  • 5 Marco J A, Sanz J F. New sesquiterpene lactones and acetylenes from Chrysanthemum lavandulifolium.  Tetrahedron. 1990;  46 6931-6938
  • 6 Pellati F, Calò S, Benvenuti S, Adinolfi B, Nieri P, Melegari M. Isolation and structure elucidation of cytotoxic polyacetylenes and polyenes from Echinacea pallida.  Phytochemistry. 2006;  67 1359-1364
  • 7 Zhu Y, Zhang L X, Zhao Y, Huang G D. Unusual sesquiterpene lactones with a new carbon skeleton and new acetylenes from Ajania przewalskii.  Food Chem. 2010;  118 228-238
  • 8 Robertson J, Sébastien N. Synthesis of spiroacetal enol ethers by oxidative activation of furan derivatives.  Org Lett. 2008;  10 5445-5448
  • 9 Martínez V, Barberá O, Sánchez-Parareda J, Marco J A. Phenolic and acetylenic metabolites from Artemisia assoana.  Phytochemistry. 1987;  26 2619-2624
  • 10 Yano K, Takahashi S, Furukawa T. Polyacetylene compounds from Japanese mugwort.  Phytochemistry. 1972;  11 2577-2579
  • 11 Christensen L P. Acetylenes and related compounds in Anthemideae.  Phytochemistry. 1992;  31 7-49
  • 12 Casu L, Bonsignore L, Pinna M, Casu M, Floris C, Gertsch J, Cottiglia F. Cytotoxic diacetylenic spiroketal enol ethers from Plagius flosculosus.  J Nat Prod. 2006;  69 295-298
  • 13 Nakamura Y, Kawamoto N, Ohto Y, Torikai K, Murakami A, Ohigashi H. A diaacetylenic spiroketal enol ether epoxide, AL-1, from Artemisia lactiflora inhibits 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion possibly by suppression of oxidative stress.  Cancer Lett. 1999;  140 37-45
  • 14 Ahmed A A, Abou Elela M A. Highly oxygenated bisabolenes and an acetylene from Matricaria aurea.  Phytochemistry. 1999;  51 551-554
  • 15 Calzado M A, Schmid Lüdi K, Fiebich B, Ben-Neriah Y, Bacher S, Munoz E, Ballero M, Prosperini S, Appendino G, Schmitz M L. Inhibition of NF-κB activation and expression of inflammatory mediators by polyacetylene spiroketals from Plagius flosculosus.  Biochim Biophys Acta Gene Struct Expr. 2005;  1729 88-93

Prof. Dr. Yan-Ping Shi

Lanzhou Institute of Chemical Physics
Chinese Academy of Sciences

Lanzhou 730000

People's Republic of China

Phone: +86 93 14 96 82 08

Fax: +86 93 18 27 70 88

Email: shiyp@licp.cas.cn

>