Secondary Metabolites from Otanthus maritimus, Stachys glutinosa and Withania somnifera: Isolation, Structure Elucidation and Interactions with Cannabinoid and Opioid Systems
type: CreativeWork
description: In our continuous search for plant secondary metabolites that bind to CB and/or opioid receptors, we selected four extracts that showed interesting affinity versus the above mentioned receptors . In particular: the DCM extract obtained from the aerial parts of Stachys glutinosa (SGE) was able to bind with a good affinity both MOR and DOR with a Ki of 10.3 and 9 μg/mL, respectively while the DCM extract from the leaves of Otanthus maritimus (OME) showed good binding affinity to CB1 (Ki = 2.2 μg/mL) and CB2 (Ki = 1.3 μg/mL) and moderate affinity to MOR and DOR. The third was an alkaloid fraction obtained from the MeOH extract of the roots of Withania somnifera (WSAE) that displayed appreciable affinity versus DOR (Ki = 25.5 μg/mL), CB1 (Ki = 23.5 μg/mL), CB2 (Ki = 20.3 μg/mL) and GABAA (Ki = 14 μg/mL). The in toto MeOH extract (WSE) bound with very low affinity to CB and opioid receptors but displayed interesting affinity to GABAA receptors (Ki = 14 μg/mL) Based on this results this study, carried out in collaboration with the group of Dr. Stefania Ruiu of CNR-­‐Institute of Translational Pharmacology of Cagliari, aimed to: 1. Isolate the secondary metabolites that were responsible of the observed binding affinity 2. Identify the compounds by spectrometric and spectroscopic methods 3. Evaluate the binding affinity of the isolated metabolites to opioid and cannabinoid receptors. 4. Evaluate the most potent and abundant compounds in antinociceptive experiments in mice. A total of 30 secondary metabolites were isolated from the extracts. Two semisynthetic derivatives were also prepared. The OME yielded two new alkylamides and one new neo-­‐lignan , along with thirteen known compounds. Among the constituents identified, 1-­‐[(2E,4E,8Z)-­‐tetradecatrienoyl]piperidine was the most potent binder to both CB1 and CB2 receptors with a Ki value of 0.8 M and 0.16 M, respectively. The molecular modeling approaches applied in this study put in evidence, important requirements for…
abstract: In our continuous search for plant secondary metabolites that bind to CB and/or opioid receptors, we selected four extracts that showed interesting affinity versus the above mentioned receptors . In particular: the DCM extract obtained from the aerial parts of Stachys glutinosa (SGE) was able to bind with a good affinity both MOR and DOR with a Ki of 10.3 and 9 μg/mL, respectively while the DCM extract from the leaves of Otanthus maritimus (OME) showed good binding affinity to CB1 (Ki = 2.2 μg/mL) and CB2 (Ki = 1.3 μg/mL) and moderate affinity to MOR and DOR. The third was an alkaloid fraction obtained from the MeOH extract of the roots of Withania somnifera (WSAE) that displayed appreciable affinity versus DOR (Ki = 25.5 μg/mL), CB1 (Ki = 23.5 μg/mL), CB2 (Ki = 20.3 μg/mL) and GABAA (Ki = 14 μg/mL). The in toto MeOH extract (WSE) bound with very low affinity to CB and opioid receptors but displayed interesting affinity to GABAA receptors (Ki = 14 μg/mL) Based on this results this study, carried out in collaboration with the group of Dr. Stefania Ruiu of CNR-­‐Institute of Translational Pharmacology of Cagliari, aimed to: 1. Isolate the secondary metabolites that were responsible of the observed binding affinity 2. Identify the compounds by spectrometric and spectroscopic methods 3. Evaluate the binding affinity of the isolated metabolites to opioid and cannabinoid receptors. 4. Evaluate the most potent and abundant compounds in antinociceptive experiments in mice. A total of 30 secondary metabolites were isolated from the extracts. Two semisynthetic derivatives were also prepared. The OME yielded two new alkylamides and one new neo-­‐lignan , along with thirteen known compounds. Among the constituents identified, 1-­‐[(2E,4E,8Z)-­‐tetradecatrienoyl]piperidine was the most potent binder to both CB1 and CB2 receptors with a Ki value of 0.8 M and 0.16 M, respectively. The molecular modeling approaches applied in this study put in evidence, important requirements for…
author: ANZANI, NICOLA
language: eng
keywords: Otanthus maritimus, Stachys glutinosa, analgesia immunomodulatory, cannabinoid receptors, opiod receptors, withania somnifera, Settore CHIM/08 - Chimica Farmaceutica
date published: 2014-04-14
date modified: 2026-07-24T01:30:09Z
provider: Università di Cagliari
publisher: Networked Digital Library of Theses and Dissertations
type: WebPage
source organization: Università degli Studi di Cagliari

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property ID: Handle
value: http://hdl.handle.net/11584/266436