Planta Med 2010; 76(10): 1014-1017
DOI: 10.1055/s-0029-1240840
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

New Cucurbitane-Type Triterpenoids from Bryonia aspera

Shamim Sahranavard1 , 2 , Farzaneh Naghibi1 , 2 , Karsten Siems3 , Kristina Jenett-Siems4
  • 1Pharmacognosy Department, School of Pharmacy, Shaheed Beheshti University of Medical Sciences, Tehran, Iran
  • 2Traditional Medicine & Materia Medica Research Center, Shaheed Beheshti University of Medical Sciences, Tehran, Iran
  • 3Analyticon Discovery GmbH, Potsdam, Germany
  • 4Institut fuer Pharmazie (Pharmazeutische Biologie), Freie Universitaet Berlin, Berlin, Germany
Further Information

Publication History

received September 25, 2009 revised December 16, 2009

accepted January 4, 2010

Publication Date:
27 January 2010 (online)

Abstract

Phytochemical investigation of the chloroform extract of Bryonia aspera roots resulted in the isolation and structure elucidation of two new cucurbitacins (1, 2) together with eight known cucurbitane derivatives (6 – 13), the pentacyclic triterpene bryonolic acid (5) and two hydroxybenzoic acid amides (3, 4). Their structures were elucidated by spectroscopic analysis, including 2D NMR techniques.

References

  • 1 Ghorbani A. Studies on pharmaceutical ethnobotany in the region of Turkmen Sahra, north of Iran.  J Ethnopharmacol. 2005;  102 58-68
  • 2 Hylands P, Kosugi J. Bryonoside and bryoside – new triterpene glycosides – from Bryonia dioica.  Phytochemistry. 1982;  21 1379-1384
  • 3 Pohlmann J. Die Cucurbitacine in Bryonia alba und Bryonia dioica.  Phytochemistry. 1975;  14 1587-1589
  • 4 Oobayashi K, Yoshikawa K, Arihara S. Structure revision of bryonoside and structure elucidation of minor saponins from Bryonia dioica.  Phytochemistry. 1992;  31 943-946
  • 5 Hylands P, Salama A. Cucurbitacin S, a new cucurbitacin from Bryonia dioica.  Phytochemistry. 1976;  15 559-560
  • 6 Kawahara N, Kurata A, Hakamatsuka T, Sekita S, Satake M. Two novel cucurbitacins, neocucurbitacin A and B from the Brazilian folk medicine Buchinh (Luffa operculata) and their effect on PEBP2αA and OCIF gene expression in a human osteoblast-like Saos-2 cell line.  Chem Pharm Bull. 2001;  49 1377-1379
  • 7 Chen C, Qiang S, Lou L, Zhao W. Cucurbitacin-type triterpenoids from the stems of Cucumis melo.  J Nat Prod. 2009;  72 824-829
  • 8 Fiocca L, Po R, Giannotta G, Gleria M, Venzo A, Milani R, Depaoli G. Oxazoline-containing phosphazene derivatives, part III: synthesis and characterization of novel cyclophosphazenes functionalized with chiral 2-oxazoline groups.  Des Monomers Polym. 2008;  11 243-260
  • 9 Claus P, Klein E, Grosch W, Bertl H, Kratzl K. Phenolcarboxylic acid derivatives yielding formaldehyde on cleavage.  Monatsh Chem. 1966;  97 271-280
  • 10 Jaroszewski J W, Staerk D, Holm-Moller S B, Hogh Jensen T, Franzyk H, Somanadhan B. Naravelia zeylanica: occurrence of primary benzamides in flowering plants.  Nat Prod Res. 2005;  19 291-294
  • 11 Akiyama K, Hayashi H. Arbuscular mycorrhizal fungus-promoted accumulation of two new triterpenoids in cucumber roots.  Biosci Biotechnol Biochem. 2002;  66 762-769
  • 12 Wu P, Lin F, Wu T, Kuoh C, Lee K, Lee S. Cytotoxic and anti-HIV priciples from the rhizomes of Begonia nantoensis.  Chem Pharm Bull. 2004;  68 1248-1254
  • 13 Kitajima J, Mukai A, Masuda Y, Tanaka Y. Studies on the constituents of trichosanthes root. III Constiuents of roots of Trichosanthes bracteata Voigt.  Yakugaku Zasshi (J Pharm Soc Jpn). 1989;  109 265-270
  • 14 Galindo A, Villegas N, Mansilla H. Cucurbitacins from Bryonia verrucosa. Isomerization of 2-hydroxy-3-keto-cucurbitacins.  Nat Prod Lett. 1999;  13 285-292
  • 15 Vande Velde V, Lavie D. 13C-NMR spectroscopy of cucurbitacins.  Tetrahedron. 1983;  39 317-321
  • 16 Seger C, Sturm S, Mair M, Ellmerer E, Stuppner H. 1H- and 13C-NMR signal assignment of cucurbitacin derivatives from Citrullus colocynthis (L.) Schrader and Ecballium elaterium L. (Cucurbitaceae).  Magn Reson Chem. 2005;  43 489-491
  • 17 Yamada Y, Hagiwara K, Iguchi K, Takahashi Y. Carbon-13 NMR spectral assignments of cucurbitacin aglycones.  Chem Lett. 1978;  319-322
  • 18 Jacobs H, Singh T. Isolation and 13C-NMR assignments of cucurbitacins from Cayaponia angustiloba, Cayaponia racemosa and Gurania subumbellata.  J Nat Prod. 1990;  53 1600-1605
  • 19 Isaev M. Bryonia isoprenes. II. Cucurbitacin L. and bryoamaride from Bryonia melanocarpa.  Chem Nat Prod. 2000;  36 292-294
  • 20 Hussein H A, Abdel-Halim O B, Marwan E M, El-Gamal A A, Mosana R. Dendrocyin: an isocucurbitacin with novel cyclic side chain from Dendrosicyos socotrana.  Phytochemistry. 2004;  65 2551-2556
  • 21 Panosyan A G, Nikishchenko M N, Mnatsakanyan V A, Sadovskaya V L. New cucurbitacin glucosides from the roots of Bryonia alba L.  Bioorg Khim. 1979;  5 721-729
  • 22 Yamada Y, Hagiwara K, Iguchi K, Suzuki S, Hsu H. Isolation and structure of arvenins from Anagallis arvensis L. (Primulaceae). New cucurbitacin glucosides.  Chem Pharm Bull. 1978;  26 3107-3112
  • 23 Baek N I, Lee D W, Lee Y H, Kim S I, Aprikian G V. Cytotoxic constituents from the roots of Bryonia alba L.  Nat Prod Sci. 1995;  1 43-49
  • 24 Kondo T, Inoue M, Mizukami H, Ogihara Y. Cytotoxic activity of bryonolic acid isolated from transformed hairy roots of Trichosanthes kirilowii var. japonica.  Biol Pharm Bull. 1995;  18 726-729

Shamim Sahranavard

Traditional Medicine & Materia Medica Research Center
Shaheed Beheshti University of Medical Sciences

No. 8 Shams Alley, Valiassr Avenue

P. O. Box 1516745811

Tehran

Iran

Phone: + 98 21 88 77 60 27

Fax: + 98 21 88 77 60 27

Email: ssahranavard@itmrc.org

>