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Planta Med 2007; 73(2): 157-162
DOI: 10.1055/s-2007-967106
Original Paper
Analytical Methods
© Georg Thieme Verlag KG Stuttgart · New York

Solubility Studies of Oleanolic Acid and Betulinic Acid in Aqueous Solutions and Plant Extracts of Viscum album L.

Sebastian Jäger1 , Karin Winkler1 , Uwe Pfüller2 , Armin Scheffler1
  • 1Carl Gustav Carus-Institut, Niefern-Öschelbronn, Germany
  • 2Institute of Phytochemistry, Witten/Herdecke University, Witten, Germany
Further Information

Publication History

Received: January 10, 2006

Accepted: December 18, 2006

Publication Date:
18 January 2007 (online)

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Abstract

Mistletoe (Viscum album L.) contains the triterpene acids oleanolic acid (OA) and betulinic acid (BA), which were found to have anti-tumour properties. In this study, the solubilities of OA and BA were studied in water (up to 0.02 μg/mL in each case) and in alkaline solutions of 10 mM trisodium phosphate (pH 11.5; OA: 77.2 μg/mL; BA: 40.1 μg/mL). Furthermore, triterpene acids were quantified in aqueous mistletoe extracts (pH 7.3; drug to extract ratio 1 : 25). OA (1.1 μg/mL) and BA (0.9 μg/mL) were extracted with a yield of less than 5 %. Preparing plant extracts with basic pH values resulted in a triterpene acid content of 9.3 μg/mL OA and 5.2 μg/mL BA (pH 12.1), reaching neither the solubility limits nor a complete extraction of the plant material. The triterpene acid content of neutral plant extracts above the solubility limit could be due to interactions with biocolloids. Interaction studies were performed by gel permeation chromatography. Different mechanisms of the dissolution at pH 7.3 and pH 10.2 are discussed.

Abbreviations

BA:betulinic acid

CI:confidence interval (α = 0.05)

CV:coefficient of variation [%]

DER:drug-to-extract ratio

FID:flame ionisation detection

GC:gas chromatography

GPC:gel permeation chromatography

LOD:limit of detection

LOQ:limit of quantification

OA:oleanolic acid

Key words

Oleanolic acid - betulinic acid - solubility - synergy - Loranthaceae - Viscum album L. - aqueous mistletoe extracts

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Dr. Armin Scheffler

Carl Gustav Carus-Institut

Am Eichhof 30

75223 Niefern-Öschelbronn

Germany

Phone: +49-7233-68410

Fax: +49-7233-68413

Email: info@carus-institut.de

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