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Monodemethylated polymethoxyflavones from sweet orange (Citrus sinensis) peel Inhibit growth of human lung cancer cells by apoptosis

Identifieur interne : 001E63 ( Main/Exploration ); précédent : 001E62; suivant : 001E64

Monodemethylated polymethoxyflavones from sweet orange (Citrus sinensis) peel Inhibit growth of human lung cancer cells by apoptosis

Auteurs : Hang Xiao [États-Unis] ; Chung S. Yang ; Shiming Li [États-Unis] ; Huanyu Jin ; Chi-Tang Ho [États-Unis] ; Trusha Patel

Source :

Molecular Nutrition & Food Research [ 1613-4125 ] ; 2009-03.

RBID : ISTEX:5E37EAC5D532F43769C2AF33CC67187FC8929216

English descriptors

KwdEn :
- Anticarcinogenic Agents (pharmacology), Antioxidants (pharmacology), Apoptosis, Apoptosis (drug effects), Cell Division (drug effects), Cell Line, Tumor, Citrus sinensis (chemistry), Flavones (chemistry), Flavones (isolation & purification), Flavones (pharmacology), Flavonoids (pharmacology), Fruit (chemistry), Humans, Hydroxylation, Lung Neoplasms (pathology), Lung cancer, Monodemethylated polymethoxyflavone, Structure-Activity Relationship.
MESH :
- chemical , chemistry : Flavones.
- chemical , isolation & purification : Flavones.
- chemical , pharmacology : Anticarcinogenic Agents, Antioxidants, Flavones, Flavonoids.
- chemistry : Citrus sinensis, Fruit.
- drug effects : Apoptosis, Cell Division.
- pathology : Lung Neoplasms.
- Cell Line, Tumor, Humans, Hydroxylation, Structure-Activity Relationship.

Abstract

Polymethoxyflavones (PMFs) are almost exclusively found in the Citrus genus, particularly in the peels of sweet orange (Citrus sinensis L. Osbeck) and mandarin (C. reticulate Blanco). We studied the effects of two major PMFs, namely, nobiletin and 3,5,6,7,8,3′,4′‐heptamethoxyflavone (HMF), and two major monodemethylated PMFs, namely 5‐hydroxy‐3,7,8,3′,4′‐pentamethoxyflavone (5HPMF), and 5‐hydroxy‐3,6,7,8,3′,4′‐hexamethoxyflavone (5HHMF), on the growth of human lung cancer H1299, H441, and H460 cells. Monodemethylated PMFs were much more potent in growth inhibition of lung cancer cells than their permethoxylated counterpart PMFs. In H1299 cells, cell cycle analyses further revealed that monodemethylated PMFs caused significant increase in sub‐G0/G1 phase, suggesting possible role of apoptosis in the growth inhibition observed, whereas the permethoxylated counterpart PMFs did not affect cell cycle distribution at same concentrations tested. These results strongly suggested that the phenolic group is essential for the growth inhibitory activity of monodemethylated PMFs. Further studies in H1299 cells demonstrated that monodemethylated PMFs downregulated oncogenic proteins, such as iNOS, COX‐2, Mcl‐1, and K‐ras, as well as induced apoptosis evidenced by activation of caspase‐3 and cleavage of PARP. Our results provide rationale to develop orange peel extract enriched with monodemethylated PMFs into value‐added nutraceutical products for cancer prevention.

Url:

https://api.istex.fr/document/5E37EAC5D532F43769C2AF33CC67187FC8929216/fulltext/pdf

DOI: 10.1002/mnfr.200800057

Affiliations:

Le document en format XML

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<front><div type="abstract" xml:lang="en">Polymethoxyflavones (PMFs) are almost exclusively found in the Citrus genus, particularly in the peels of sweet orange (Citrus sinensis L. Osbeck) and mandarin (C. reticulate Blanco). We studied the effects of two major PMFs, namely, nobiletin and 3,5,6,7,8,3′,4′‐heptamethoxyflavone (HMF), and two major monodemethylated PMFs, namely 5‐hydroxy‐3,7,8,3′,4′‐pentamethoxyflavone (5HPMF), and 5‐hydroxy‐3,6,7,8,3′,4′‐hexamethoxyflavone (5HHMF), on the growth of human lung cancer H1299, H441, and H460 cells. Monodemethylated PMFs were much more potent in growth inhibition of lung cancer cells than their permethoxylated counterpart PMFs. In H1299 cells, cell cycle analyses further revealed that monodemethylated PMFs caused significant increase in sub‐G0/G1 phase, suggesting possible role of apoptosis in the growth inhibition observed, whereas the permethoxylated counterpart PMFs did not affect cell cycle distribution at same concentrations tested. These results strongly suggested that the phenolic group is essential for the growth inhibitory activity of monodemethylated PMFs. Further studies in H1299 cells demonstrated that monodemethylated PMFs downregulated oncogenic proteins, such as iNOS, COX‐2, Mcl‐1, and K‐ras, as well as induced apoptosis evidenced by activation of caspase‐3 and cleavage of PARP. Our results provide rationale to develop orange peel extract enriched with monodemethylated PMFs into value‐added nutraceutical products for cancer prevention.</div>
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Monodemethylated polymethoxyflavones from sweet orange (Citrus sinensis) peel Inhibit growth of human lung cancer cells by apoptosis

Monodemethylated polymethoxyflavones from sweet orange (Citrus sinensis) peel Inhibit growth of human lung cancer cells by apoptosis

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Abstract

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