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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
1   Organic-analytical Chemistry, Weihenstephan-Triesdorf University of Applied Sciences, Straubing, Germany
2   Campus Straubing for Biotechnology and Sustainability, Technical University of Munich, Straubing, Germany
,
Corinna Urmann
1   Organic-analytical Chemistry, Weihenstephan-Triesdorf University of Applied Sciences, Straubing, Germany
2   Campus Straubing for Biotechnology and Sustainability, Technical University of Munich, Straubing, Germany
,
Rainer Herzog
1   Organic-analytical Chemistry, Weihenstephan-Triesdorf University of Applied Sciences, Straubing, Germany
2   Campus Straubing for Biotechnology and Sustainability, Technical University of Munich, Straubing, Germany
,
Jan Glaser
3   PhytoLab GmbH & Co. KG, Vestenbergsgreuth, Germany
,
Sebastian Bieringer
1   Organic-analytical Chemistry, Weihenstephan-Triesdorf University of Applied Sciences, Straubing, Germany
2   Campus Straubing for Biotechnology and Sustainability, Technical University of Munich, Straubing, Germany
,
Thomas Geisberger
4   Department of Chemistry, Technical University of Munich, Garching, Germany
,
Wolfgang Eisenreich
4   Department of Chemistry, Technical University of Munich, Garching, Germany
,
Herbert Riepl
1   Organic-analytical Chemistry, Weihenstephan-Triesdorf University of Applied Sciences, Straubing, Germany
2   Campus Straubing for Biotechnology and Sustainability, Technical University of Munich, Straubing, Germany
› Author AffiliationsSupported by: Hans Fischer Gesellschaft
Supported by: Bundesministerium für Bildung und Forschung 031B0823D
Further Information

Publication History

received 16 January 2020
revised 10 March 2020

accepted 12 March 2020

Publication Date:
23 April 2020 (online)

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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

Supporting Information

    The supporting information includes GC-MS data of the reference substances as well as 1H NMR spectra, 13C NMR spectra, 1H,1H COSY, 1H,13C HMBC, 1H,13C HSQC, and 1H,1H NOESY NMR spectra of the extract of B. monnieri, a reference substance bought as bacosine, and a reference substance bought as betulinic acid. A table of the constituents of all investigated supplements, a table of the predicted 1H NMR and 13C NMR data in comparison to our obtained data, and a table of the 1H,1H COSY, 1H,13C HMBC, 1H,13C HSQC correlations are also included. A table comparing all 1H NMR and 13C NMR data of the pure substance extracted from B. monnieri, the reference substance bought as bacosine, the reference substance bought as betulinic acid, the bacosine extracted from B. monnieri reported by Ahmed and Rahman [14], bacosine extracted from B. monnieri reported by Kishore et al. [7], and betulinic acid reported by Khaliq et al. [23] are also available.

  • Supporting Information
 

  • References

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