Coumarin-monoterpenes from Gerbera anandria (Linn.) Sch.-Bip and their neuroprotective activity.

Animals Antioxidants Asteraceae / chemistry Coumarins / pharmacology Monoterpenes Neuroprotective Agents / pharmacology PC12 Cells Rats Scopolamine Derivatives
Coumarin-monoterpenes Gerbera anandria (Linn.) Sch.-Bip Neuroprotective activity

Journal

Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703

Informations de publication

Date de publication:
07 2022
Historique:
received: 15 03 2022
revised: 12 04 2022
accepted: 19 04 2022
pubmed: 30 4 2022
medline: 7 6 2022
entrez: 29 4 2022
Statut: ppublish

Résumé

Thirty-two undescribed coumarin-monoterpenes, including the first report of six pairs of enantiomeric and twenty congeners, were isolated from the petroleum ether extract of the stems of Gerbera anandria (Linn.) Sch.-Bip. Structurally, these compounds represented C3-substituted 5-methyl-4-hydroxycoumarin-monoterpenes. Among them, 1-7 and 10-24 were rare 5-methylcoumarin-monoterpenes formed through a furan ring. Their chemical structures and absolute configurations were determined by comprehensive analysis of spectroscopic data, including HRESIMS, 1D and 2D NMR spectroscopic data, Mosher's method, ECD calculations and single crystal X-ray diffraction. Furthermore, biological studies revealed that compounds 1-3, 3a, 5, 5a, 11-12, 21-22 and 26 had the neuroprotective effects on scopolamine-induced injury in PC12 cells. Notably, 3 exhibited the strongest neuroprotective activity with the cell viability values of 77.24%. Meanwhile, pretreatment with 3 significantly downregulate apoptosis and reactive oxygen species (ROS) production, as well as strengthen antioxidant enzyme activities (MDA and SOD). Moreover, pretreatment with 3 also could attenuate the down-regulation of HO-1 and Nrf2 induced by scopolamine. In conclusion, these results demonstrated that these compounds possessed the protective effects on scopolamine-injured PC12 cells through anti-apoptotic and anti-oxidant activities.

Identifiants

DOI: 10.1016/j.bioorg.2022.105826 PMID: 35487072
pubmed: 35487072
pii: S0045-2068(22)00231-0
doi: 10.1016/j.bioorg.2022.105826
pii:
doi:

Substances chimiques

Antioxidants 0
Coumarins 0
Monoterpenes 0
Neuroprotective Agents 0
Scopolamine Derivatives 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

105826

Informations de copyright

Copyright © 2022 Elsevier Inc. All rights reserved.

Auteurs

Zhi-Li Wu (ZL)

School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, Jiangsu 211198, PR China; School of Pharmacy, Second Military Medical University, Shanghai 200433, PR China.

Peng-Li Huang (PL)

School of Pharmacy, Second Military Medical University, Shanghai 200433, PR China; The Research Center for Traditional Chinese Medicine, Shanghai Institute of Infectious Diseases and Biosafety, Institute of Interdisciplinary Integrative Medicine Research, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, PR China.

Qun Wang (Q)

The Research Center for Traditional Chinese Medicine, Shanghai Institute of Infectious Diseases and Biosafety, Institute of Interdisciplinary Integrative Medicine Research, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, PR China.

Jia-Yu Li (JY)

School of Pharmacy, Second Military Medical University, Shanghai 200433, PR China.

Ze-Shi Sun (ZS)

School of Pharmacy, Second Military Medical University, Shanghai 200433, PR China.

Hui-Liang Li (HL)

School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, Jiangsu 211198, PR China; School of Pharmacy, Second Military Medical University, Shanghai 200433, PR China. Electronic address: faranli@hotmail.com.

Wei-Dong Zhang (WD)

School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, Jiangsu 211198, PR China; School of Pharmacy, Second Military Medical University, Shanghai 200433, PR China; The Research Center for Traditional Chinese Medicine, Shanghai Institute of Infectious Diseases and Biosafety, Institute of Interdisciplinary Integrative Medicine Research, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, PR China. Electronic address: wdzhangy@hotmail.com.

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Classifications MeSH

questionsmedicales.fr › Eucaryotes › Animaux › Coumarin-monoterpenes from Gerbera anandria...
questionsmedicales.fr › Actions chimiques et utilisations › Utilisations spécialisées de produits chimiques › Agents protecteurs › Antioxydants › Coumarin-monoterpenes from Gerbera anandria...
questionsmedicales.fr › Eucaryotes › Viridiplantae › Streptophyta › Embryophyta › Tracheobionta › Magnoliopsida › Asteraceae › Coumarin-monoterpenes from Gerbera anandria...
questionsmedicales.fr › Composés hétérocycliques › Composés hétérocycliques à cycles fusionnés › Composés hétérobicycliques › Benzopyranes › Coumarines › Coumarin-monoterpenes from Gerbera anandria...
questionsmedicales.fr › Composés chimiques organiques › Hydrocarbures › Terpènes › Monoterpènes › Coumarin-monoterpenes from Gerbera anandria...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Utilisations thérapeutiques › Agents du système nerveux central › Neuroprotecteurs › Coumarin-monoterpenes from Gerbera anandria...
questionsmedicales.fr › Cellules › Cellules chromaffines › Cellules PC12 › Coumarin-monoterpenes from Gerbera anandria...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Rodentia › Muridae › Murinae › Rats › Coumarin-monoterpenes from Gerbera anandria...
questionsmedicales.fr › Composés hétérocycliques › Composés hétérocycliques, cycle ponté › Tropanes › Dérivés de la scopolamine › Coumarin-monoterpenes from Gerbera anandria...