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Planta Med 2008; 74(2): 178-181
DOI: 10.1055/s-2008-1034288
Natural Product Chemistry
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Phenylalkanoids and Monoterpene Analogues from the Roots of Rhodiola rosea

Zulfiqar Ali1 , Frank R. Fronczek2 , Ikhlas A. Khan1 , 3
  • 1National Center for Natural Products Research, School of Pharmacy, University of Mississippi, MS, USA
  • 2Department of Chemistry, Louisiana State University, Baton Rouge, LA, USA
  • 3Department of Pharmacognosy, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, MS, USA
Further Information

Publication History

Received: October 16, 2007 Revised: December 11, 2007

Accepted: December 14, 2007

Publication Date:
31 January 2008 (online)

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Abstract

Roots extract of Rhodiola rosea L. is the source of important commercial preparations widely used throughout Europe, Asia, and the USA. Phytochemical investigation of the roots of Rhodiola rosea afforded 17 compounds, belonging to the phenylalkanoids and monoterpene analogues. Their structures were determined by spectroscopic and chemical methods. Rhodioloside F (1) was found to be new. The X-ray crystallographic study on salidroside (7) and the complete NMR data of 5 (mongrhoside) and 1a [(-)-rosiridol] are also described.

Key words

Rhodiola rosea - Crassulaceae - Rhodioloside F - Salidroside - X-ray crystallography

References

  • 1 Ganzera M, Yayla Y, Khan I A. Analysis of the marker compounds of Rhodiola rosea L. (golden root) by reversed phase high performance liquid chromatography.  Chem Pharm Bull. 2001;  49 465-7
    CrossrefPubMedGoogle Scholar
  • 2 Fan W, Tezuka Y, Komatsu K, Namba T, Kadota S. Prolyl endopeptidase inhibitors from the underground part of Rhodiola sacra S. H. Fu.  Biol Pharm Bull. 1999;  22 157-61
    PubMedGoogle Scholar
  • 3 Richard P B, Patricia L G, Zakir P. Rhodiola rosea: a phytomedicinal overview.  Herbal Gram. 2002;  56 40-52
    PubMedGoogle Scholar
  • 4 Yoshikawa M, Shimada H, Shimoda H, Murakami T, Yamahara J, Matsuda H. Bioactive constituents of Chinese natural medicines. II. Rhodiolae Radix. (1). Chemical structures and antiallergic activity of rhodiocyanosides A and B from the underground part of Rhodiola quadrifida (Pall.) Fisch. et Mey. (Crassulaceae).  Chem Pharm Bull. 1996;  44 2086-91
    PubMedGoogle Scholar
  • 5 Maslova L V, Kondratyev B, Maslov L N, Lishmanov I. The cardioprotective and antiadrenergic activity of an extract of Rhodiola rosea in stress.  Eksp Klin Farmakol. 1994;  57 61-3
    PubMedGoogle Scholar
  • 6 Tolonen A, Pakonen M, Hohtola A, Jalonen J. Phenylpropanoid glycosides from Rhodiola rosea. .  Chem Pharm Bull. 2003;  51 467-70
    CrossrefPubMedGoogle Scholar
  • 7 Ma G, Li W, Dou D, Chang X, Bai H, Satou T. et al . Rhodiolosides A - E, monoterpene glycosides from Rhodiola rosea. .  Chem Pharm Bull. 2006;  54 1229-33
    CrossrefPubMedGoogle Scholar
  • 8 Egger P, D'Ambrosio M, Aiello N, Contrini C, Fusani P, Scartezzini F. et al . Active constituents profiling of Rhodiola rosea L.  Planta Med. 2007;  9 907
    PubMedGoogle Scholar
  • 9 Fan W, Tezuka Y, Ni K M, Kadota S. Prolyl endopeptidase inhibitors from the underground part of Rhodiola sachalinensis. .  Chem Pharm Bull. 2001;  49 396-401
    CrossrefPubMedGoogle Scholar
  • 10 Sekiwa Y, Kobayashi A, Kubota K, Takenaka M. First isolation of geranyl disaccharides from ginger and their relations to aroma formation.  Nat Prod Lett. 2001;  15 267-74
    PubMedGoogle Scholar
  • 11 Hara S, Okabe H, Mihashi K. Gas - liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)thiazolidine-4(R)-carboxylates.  Chem Pharm Bull. 1987;  35 501-6
    CrossrefPubMedGoogle Scholar
  • 12 Wiedenfeld H, Dumaa M, Malinowski M, Furmanowa M, Narantuya S. Phytochemical and analytical studies of extracts from Rhodiola rosea and Rhodiola quadrifida. .  Pharmazie. 2007;  62 308-11
    PubMedGoogle Scholar
  • 13 Yousef G G, Grace M H, Cheng D M, Belolipov I V, Raskin I, Lila M A. Comparative phytochemical characterization of three Rhodiola species.  Phytochemistry. 2006;  67 2380-91
    CrossrefPubMedGoogle Scholar
  • 14 Yoshikawa M, Shimada H, Horikawa S, Murakami T, Shimoda H, Yamahara J. et al . Bioactive constituents of Chinese natural medicines. IV. Rhodiolae Radix. (2). on the histamine release inhibitors from the underground part of Rhodiola sacra (Prain ex Hamet) S. H. Fu (Crassulaceae): chemical structures of rhodiocyanoside D and sacranosides A and B.  Chem Pharm Bull. 1997;  45 1498-503
    CrossrefPubMedGoogle Scholar
  • 15 Zapesochnaya G G, Kurkin V A. Glycosides of cinnamyl alcohol from the rhizomes of Rhodiola rosea. .  Chem Nat Comp. 1982;  18 685-8
    PubMedGoogle Scholar
  • 16 Comte G, Chulia A J, Vercauteren J, Allais D P. Phenylpropane glycosides from Juniperus phoenicea. .  Planta Med. 1996;  62 88-9
    Article in Thieme ConnectPubMedGoogle Scholar
  • 17 Chassagne D, Bayonove C L, Brillouet J M, Baumes R L. 6-O-α-L-Arabinopyranosyl-β-D-glucopyranosides as aroma precursors from passion fruit.  Phytochemistry. 1996;  41 1497-500
    CrossrefPubMedGoogle Scholar
  • 18 Baltenweck G R, Trendel J M, Albrecht P, Schaeffer A. Glycosides and phenylpropanoid glycerol in Vitis vinifera Cv. Gewürztraminer wine.  J Agric Food Chem. 2000;  48 6178-82
    CrossrefPubMedGoogle Scholar
  • 19 Hübner G, Wray V, Nahrstedt A. Flavonol oligosaccharides from the seeds of Aesculus hippocastanum. .  Planta Med. 1999;  65 636-42
    Article in Thieme ConnectPubMedGoogle Scholar

Ikhlas A. Khan

National Center for Natural Products Research

University of Mississippi

University

MS 38677

USA

Phone: +1-662-915-7821

Fax: +1-662-915-7989

Email: ikhan@olemiss.edu

    www.thieme-connect.de/ejournals/toc/plantamedica