(1) Hâ
NMR-Guided Isolation of Formyl-Phloroglucinol Meroterpenoids from the Leaves of Eucalyptus robusta.
Chemistry
; 22(33): 11778-84, 2016 Aug 08.
Article
em En
| MEDLINE
| ID: mdl-27412352
ABSTRACT
Nine formyl-phloroglucinolmeroterpenoids (FPMs), namely, eucalrobusonesâ
A-I (1-9), were isolated from the leaves of Eucalyptus robusta by tracking the phenolic hydroxyl (1) Hâ
NMR peaks. The Snatzke helicity rules for the Cotton effects of twisted benzene rings were applied to elucidate the absolute configurations of the FPMs. These findings, along with NMR spectroscopy, the circular dichroism (CD) exciton chirality method, and CD calculations, allowed complete structures for the FPMs to be assigned. Eucalrobusonesâ
A-F (1-6) are novel adducts formed between a formyl-derived carbon atom on the phloroglucinol ring and monoterpene and sesquiterpene components. Eucalrobusonesâ
G-I (7-9) are the first examples of FPMs with cubebane part structures connected by an unusual 1-oxaspiro[5.5]undecane subunit. Among these isolates, eucalrobusoneâ
C (3) showed significant cytotoxicity against HepG2, MCF-7, and U2OS cancer cell lines, with IC50 values less than 10â
µm. Compound 3 significantly blocks cell proliferation in MCF-7 cells and induces MCF-7 cell death through apoptosis.
Palavras-chave
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Floroglucinol
/
Sesquiterpenos
/
Terpenos
/
Apoptose
/
Folhas de Planta
/
Proliferação de Células
/
Eucalyptus
Limite:
Humans
Idioma:
En
Ano de publicação:
2016
Tipo de documento:
Article