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NMR based quantitation of cycloartane triterpenes in black cohosh extracts.

ABSTRACT: The cycloartane triterpene content in the roots/rhizomes (RR) and aerial parts (PX) of Actaea racemosa (AR), A. podocarpa (AP), and A. cordifolia (AC) have been investigated by quantitative ¹H NMR (qHNMR). Thereby, it was demonstrated that qHNMR represents a powerful methodology for the analysis of crude plant extracts as it does not rely on the rarely available identical reference triterpenes. Specifically, the presence of the characteristic C-19 cyclopropane (exo/endo) hydrogen signals made it possible to quantify the less common/not ubiquitously present group of cycloartane triterpenes, directly in extracts. As an example, ARPX and ARRR were shown to contain, 3.8-20.8% ± 8.2% and 7.2-19.3% ± 4.0% of cycloartane triterpenes, respectively. The cycloartane concentration in ACPX and ACRR was 7.5-8.7% ± 0.8% and 13.9-28.5% ± 7.3%, respectively, based on the weight of the extract. AP was shown to contain notably lower amounts of the cycloartane triterpenes as compared to AR and AC in the roots/rhizomes. The content for APPX and APRR was only 2.1-3.3% ± 0.7% and 1.1-4.0% ± 1.5%, respectively. In addition, an example is presented for the identification of specific cycloartanes as marker compounds for AR within crude extracts based on the same qHNMR spectra and 2D NMR methods.

SUBMITTER: Imai A

PROVIDER: S-EPMC7066989 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Project description:Previously tested n-hexane extracts of the Scorzonera latifolia showed promising bioactivity in vivo. Because triterpenes could account for this activity, n-hexane extracts were analyzed by HPLC to identify and quantify the triterpenes as the most abundant constituents. Other Scorzonera and Podospermum species, potentially containing triterpenic aglycones, were included in the study. An HPLC method for simultaneous determination of triterpene aglycones was therefore developed for analysis of Podospermum and Scorzonera species. n-Hexane extracts of root and aerial parts of S. latifolia, ten other Scorzonera species and two Podospermum species were studied to compare the content of triterpenes. HPLC was used for the qualitative and quantitative analysis of ?-amyrin, lupeol, lupeol acetate, taraxasteryl acetate, 3-?-hydroxy-fern-7-en-6-one acetate, urs-12-en-11-one-3-acetyl, 3-?-hydroxy-fern-8-en-7-one acetate, and olean-12-en-11-one-3-acetyl. Limits of detection and quantification were determined for each compound. HPLC fingerprinting of n-hexane extracts of Podospermum and Scorzonera species revealed relatively large amounts of triterpenes in a majority of investigated taxa. Lupeol, lupeol acetate, and taraxasteryl acetate were found in a majority of the species, except S. acuminata. The presence of ?-amyrin, 3?-hydroxy-fern-7-en-6-one-acetate, urs-12-en-11-one-3-acetyl, 3?-hydroxy-fern-8-en-7-one-acetate, and olean-12-en-11-one-3-acetyl was detected in varying amounts. The triterpene content could correlate with the analgesic and anti-inflammatory activity of Scorzonera, which was previously observed and Scorzonera species that have been determined to contain triterpenes in large amounts and have not yet been tested for their analgesic activity should be tested for their potential analgesic and anti-inflammatory potential. The presented HPLC method can be used for analysis of triterpene aglycones, for example dedicated to chemosystematic studies of the Scorzonerinae.

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NMR based quantitation of cycloartane triterpenes in black cohosh extracts.

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