Where Is Bacosine in Commercially Available Bacopa monnieri?

Stefanie Ritter; Corinna Urmann; Rainer Herzog; Jan Glaser; Sebastian Bieringer; Thomas Geisberger; Wolfgang Eisenreich; Herbert Riepl

doi:10.1055/a-1137-4289

Planta Medica, Table of Contents

Planta Med 2020; 86(08): 565-570
DOI: 10.1055/a-1137-4289

Biological and Pharmacological Activity

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Where Is Bacosine in Commercially Available Bacopa monnieri?

Stefanie Ritter

¹Organic-analytical Chemistry, Weihenstephan-Triesdorf University of Applied Sciences, Straubing, Germany

²Campus Straubing for Biotechnology and Sustainability, Technical University of Munich, Straubing, Germany

,

Corinna Urmann

¹Organic-analytical Chemistry, Weihenstephan-Triesdorf University of Applied Sciences, Straubing, Germany

²Campus Straubing for Biotechnology and Sustainability, Technical University of Munich, Straubing, Germany

,

Rainer Herzog

¹Organic-analytical Chemistry, Weihenstephan-Triesdorf University of Applied Sciences, Straubing, Germany

²Campus Straubing for Biotechnology and Sustainability, Technical University of Munich, Straubing, Germany

,

Jan Glaser

³PhytoLab GmbH & Co. KG, Vestenbergsgreuth, Germany

,

Sebastian Bieringer

¹Organic-analytical Chemistry, Weihenstephan-Triesdorf University of Applied Sciences, Straubing, Germany

²Campus Straubing for Biotechnology and Sustainability, Technical University of Munich, Straubing, Germany

,

Thomas Geisberger

⁴Department of Chemistry, Technical University of Munich, Garching, Germany

,

Wolfgang Eisenreich

⁴Department of Chemistry, Technical University of Munich, Garching, Germany

,

Herbert Riepl

¹Organic-analytical Chemistry, Weihenstephan-Triesdorf University of Applied Sciences, Straubing, Germany

²Campus Straubing for Biotechnology and Sustainability, Technical University of Munich, Straubing, Germany

› Author Affiliations

Abstract

Bacopa monnieri is an Ayurvedic plant with rising interest in the pharmacological effects of its extract and constituents, including flavonoids, saponins, and triterpenes such as cucurbitacins, betulinic acid, and bacosine. The latter two compounds are isomeric 3-hydroxy lupenoic acids, which vary only in the arrangement of the carboxylic acid group and the methyl group at C-27 and C-28 and the orientation of the hydroxy group at C-3. In this study, we have reinvestigated the contents of betulinic acid and bacosine, respectively, in extracts from various commercially available B. monnieri powders and food supplements. To our surprise, HPLC-ion trap time-of-flight analyses identified only betulinic acid, but not bacosine, in all extracts under study, which was verified by GC-MS, HPLC-ELSD, 1D NMR (¹H,¹³C), and 2D NMR (¹H,¹H COSY, ¹H,¹³C HMBC, ¹H,¹³C HSQC, ¹H,¹H NOESY) experiments. Moreover, it turned out that commercially available reference samples of bacosine were structurally identical with betulinic acid.

Key words

Bacopa monnieri - Plantaginaceae - Brahmi - bacosine - betulinic acid - triterpene - constitutional isomers

Full Text

References

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