Limonoids with Diverse Oxidation Patterns of C-12 Indicating a Complete Ring C-seco Biogenetic Pathway from Munronia unifoliolata.
J Nat Prod
; 84(8): 2352-2365, 2021 08 27.
Article
em En
| MEDLINE
| ID: mdl-34357755
ABSTRACT
Munrolins A-Q (1-17), 17 new ring C-seco limonoids with diverse oxidative patterns of C-12, together with nine known analogues (18-26), were isolated from the CH2Cl2 extract of Munronia unifoliolata. The planar structures were elucidated by a combination of 1D and 2D NMR and HR-MS analyses, while the absolute configurations were confirmed by ECD calculations and single-crystal X-ray diffraction. Munrolins A (1) and B (2) were first identified as ring C-seco limonoids with a 12,13-ether bridge moiety. Munrolins C-J (3-10) have a rare reduced primary alcohol fragment, while munrolin Q (17) has an unusual ketal fragment formed by dehydration of C-12/14. These limonoids with diverse alcohol and aldehyde type C11/12 branches may be generated through different degrees of reduction after the Baeyer-Villiger oxidation at the C ring, as key intermediates to supplement the biogenetic pathway of ring C-seco limonoids. Compounds 11, 19, and 26 could reverse the multidrug resistance of MCF-7/doxorubicin cells with reversal fold values of 5.2, 4.5, and 18.3, respectively.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Resistência a Múltiplos Medicamentos
/
Resistencia a Medicamentos Antineoplásicos
/
Meliaceae
/
Limoninas
/
Antineoplásicos Fitogênicos
Limite:
Animals
/
Humans
País/Região como assunto:
Asia
Idioma:
En
Ano de publicação:
2021
Tipo de documento:
Article