Discovery of Michael reaction acceptors from the leaves of Ailanthus altissima by a modified tactic.

Ailanthus / chemistry Plant Extracts / chemistry Plant Leaves Quassins / chemistry
Ailanthus altissima (mill.) swingle Cytotoxicity Michael reaction acceptors Simaroubaceae Terpenoids

Journal

Phytochemistry
ISSN: 1873-3700
Titre abrégé: Phytochemistry
Pays: England
ID NLM: 0151434

Informations de publication

Date de publication:
Nov 2023
Historique:
received: 28 05 2023
revised: 09 09 2023
accepted: 09 09 2023
medline: 4 10 2023
pubmed: 15 9 2023
entrez: 14 9 2023
Statut: ppublish

Résumé

Structural characteristics-guided investigation of Ailanthus altissima (Mill.) Swingle resulted in the isolation and identification of seven undescribed potential Michael reaction acceptors (1-7). Ailanlactone A (1) possesses an unusual 1,7-epoxy-11,12-seco quassinoid core. Ailanterpene B (6) was a rare guaianolide-type sesquiterpene with a 5/6/6/6-fused skeleton. Their structures were determined through extensive analysis of physiochemical and spectroscopic data, quantum chemical calculations, and single crystal X-ray crystallographic technology using Cu Kα radiation. The cytotoxic activities of isolates on HepG2 and Hep3B cells were evaluated in vitro. Encouragingly, ailanaltiolide K (4) showed significant cytotoxicity against Hep3B cells with IC

Identifiants

DOI: 10.1016/j.phytochem.2023.113858 PMID: 37709157
pubmed: 37709157
pii: S0031-9422(23)00274-1
doi: 10.1016/j.phytochem.2023.113858
pii:
doi:

Substances chimiques

Plant Extracts 0
Quassins 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

113858

Informations de copyright

Copyright © 2023. Published by Elsevier Ltd.

Déclaration de conflit d'intérêts

Declaration of competing interest No declaration of interest statement exists in the submission of this manuscript.

Auteurs

Zhi-Kang Duan (ZK)

Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province China; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province China; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China.

Shan-Shan Guo (SS)

Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province China; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province China; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China.

Li Ye (L)

Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province China; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province China; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China.

Zhi-Heng Gao (ZH)

Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province China; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province China; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China.

Dai Liu (D)

Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province China; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province China; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China.

Guo-Dong Yao (GD)

Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province China; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province China; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China.

Shao-Jiang Song (SJ)

Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province China; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province China; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China.

Xiao-Xiao Huang (XX)

Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province China; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province China; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China. Electronic address: xiaoxiao270@163.com.

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Classifications MeSH

questionsmedicales.fr › Eucaryotes › Viridiplantae › Streptophyta › Embryophyta › Tracheobionta › Magnoliopsida › Simaroubaceae › Ailanthus › Discovery of Michael reaction acceptors from...
questionsmedicales.fr › Préparations pharmaceutiques › Extraits de plantes › Discovery of Michael reaction acceptors from...
questionsmedicales.fr › Structures de plante › Parties aériennes de plante › Feuilles de plante › Discovery of Michael reaction acceptors from...
questionsmedicales.fr › Composés chimiques organiques › Hydrocarbures › Terpènes › Triterpènes › Quassinoïdes › Discovery of Michael reaction acceptors from...