4H-1-Benzopyran-4-one, 2-(4-methoxyphenyl)-5,6,7,8-tetramethoxy-/Ponkanetin/4',5,6,7,8-pentamethoxyflavone/4H-1-Benzopyran-4-one, 5,6,7,8-tetra-methoxy-2-(4-methoxyphenyl)-/Flavone, 5,6,7,8,4'-pentamethoxy/Flavone, 4',5,6,7,8-pentamethoxy-/TANGERETIN,NATURAL/4H-1-Benzopyran-4-one, 5,6,7,8-tetramethoxy-2-(p-methoxyphenyl)-/5,6,7,8,4'-Pentamethoxyflavone/4H-1-Benzopyran-4-one, 5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-/5-18-05-00491/5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one/TANGARETIN/Tangeritin/Tangeritine/Tangeretin/5-18-05-00491 (Beilstein Handbook Reference)
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Polymethoxyflavones (PMFs) are found almost exclusively in citrus peel and have attracted much attention due to their potential health benefits. Dried citrus peel is an important ingredient for applications in food and traditional Chinese medicine. However, the structural changes of PMFs during drying processes of citrus peel remain unknown. In this study, for the first time we discovered that four major permethoxylated PMFs, i.e. sinensetin, nobiletin, heptamethoxyflavone and tangeretin, underwent demethylation at the 5-position on the A ring of their flavonoid structures to yield corresponding 5-demethylated PMFs during the drying process of citrus peel. Our results further demonstrated that the aforementioned PMF demethylation was through two mechanisms: acid hydrolysis and enzyme-mediated catalysis. PMF demethylation in citrus peels was systematically characterized during hot-air drying (HAD), vacuum-freeze drying (VFD) and sun drying (SD). The highest PMF demethylation was obtained in SD followed by HAD and VFD. This study provided a solid scientific basis for rational control of PMF demethylation in citrus peels, which could facilitate the production of high-quality citrus peel and related products.
Characterization of polymethoxyflavone demethylation during drying processes of citrus peels.
Zhang H1, Tian G1, Zhao C1, Han Y2, DiMarco-Crook C2, Lu C1, Bao Y1, Li C1, Xiao H2, Zheng J1.
2019 Sep 1
Tangeretin (TAN), a major phytochemical in tangerine peels and an important Chinese herb, has multiple biological properties, especially antioxidative and anti-inflammatory effects. However, the mechanisms remain unclear. Based on these findings, the aim of the present study was to assess the antioxidant and anti-inflammatory properties of TAN in bovine type II collagen-induced arthritis rats.
TAN (50 mg/kg) was given orally once daily for 14 days. The effects of treatment were evaluated by biochemical assay (articular elastase, myeloperoxidase, end products of lipid peroxidation [MDA], antioxidant enzyme, such as superoxide dismutase, catalase, glutathione), nitric oxide, and inflammatory cytokines (interleukin-1β [IL-1β], -IL-10, tumor necrosis factor-alpha [TNF-α], interferon-γ [IFN-γ], and prostaglandin E2 [PGE2]). The protective effects of TAN against rheumatoid arthritis (RA) were evident from the decrease in arthritis scoring. Furthermore, the Nrf-2 signaling pathway was assessed to illustrate the molecular mechanism.
TAN had therapeutic effects on RA by decreasing the oxidative stress damage and regulating inflammatory cytokine expression, including suppression of the accumulation of MDA products, decreasing the IL-1β, TNF-α, IFN-γ, and PGE2 levels, enhancing the IL-10 and the activity of antioxidant enzymes, which was through upregulating Nrf-2 signaling pathway.
TAN might have potential as a therapeutic agent for the treatment of RA.
© 2019 S. Karger AG, Basel.
Collagen-induced arthritis; Cytokines; Nrf-2; Oxidative stress; Tangeretin
Tangeretin Inhibits Oxidative Stress and Inflammation via Upregulating Nrf-2 Signaling Pathway in Collagen-Induced Arthritic Rats.
Li X1,2,3, Xie P4, Hou Y1,2,3, Chen S1,2,3, He P5, Xiao Z1,2,3, Zhan J1,2,3, Luo D1,2,3, Gu M5, Lin D6,7,8.
Glioblastoma multiforme (GBM) is the most aggressive primary brain tumor with poor prognosis, largely due to resistance to current radiotherapy and Temozolomide chemotherapy. The constitutive activation of Signal Transducer and Activator of Transcription 3 (STAT3) is evidenced as a pivotal driver of GBM pathogenesis and therapy resistance, and hence, is a promising GBM drug target. 5-acetyloxy-6,7,8,4′-tetramethoxyflavone (5-AcTMF) is an acetylated derivative of Tangeretin which is known to exert anticancer effects on breast, colon, lung, and multiple myeloma; however, its effect on GBM remains elusive. Herein, we reported that 5-AcTMF suppressed the viability and clonogenicity along with inducing apoptosis in multiple human GBM cell lines. Mechanistic analyses further revealed that 5-AcTMF lowered the levels of Tyrosine 705-phosphorylated STAT3 (p-STAT3), a canonical marker of STAT3 activation, but also dampened p-STAT3 upregulation elicited by Interleukin-6. Notably, ectopic expression of dominant-active STAT3 impeded 5-AcTMF-induced suppression of viability and clonogenicity plus apoptosis induction in GBM cells, confirming the prerequisite of STAT3 blockage for the inhibitory action of 5-AcTMF on GBM cell survival and growth. Additionally, 5-AcTMF impaired the activation of STAT3 upstream kinase JAK2 but also downregulated antiapoptotic BCL-2 and BCL-xL in a STAT3-dependent manner. Moreover, the overexpression of either BCL-2 or BCL-xL abrogated 5-AcTMF-mediated viability reduction and apoptosis induction in GBM cells. Collectively, we, for the first time, revealed the anticancer effect of 5-AcTMF on GBM cells, which was executed via thwarting the JAK2-STAT3-BCL-2/BCL-xL signaling axis. Our findings further implicate the therapeutic potential of 5-AcTMF for GBM treatment.
5-acetyloxy-6,7,8,4′-tetramethoxyflavone; BCL-2; BCL-xL; STAT3; apoptosis; glioblastoma multiforme; polymethoxyflavone; tangeretin
Blockade of STAT3 Signaling Contributes to Anticancer Effect of 5-Acetyloxy-6,7,8,4'-Tetra-Methoxyflavone, a Tangeretin Derivative, on Human Glioblastoma Multiforme Cells.
Cheng YP1,2, Li S3,4, Chuang WL5, Li CH2, Chen GJ2, Chang CC2, Or CR6, Lin PY7,8, Chang CC9,10,11,12.
2019 Jul 9;
Tangeretin, a flavonoid from citrus fruit peels, has been proven to play an important role in anti-inflammatory responses and neuroprotective effects in several disease models, and was also selected as a Notch-1 inhibitor.IC50 value:Target: Notch-1In vitro: Tangeretin enhanced the radiosensitivity of GC cells as demonstrated by MTT and colony formation assays. Tangeretin also attenuated radiation-induced EMT, invasion and migration in GC cells, accompanied by a decrease in Notch-1, Jagged1/2, Hey-1 and Hes-1 expressions. Tangeretin triggered the upregulation of miR-410, a tumor-suppressive microRNA. Furthermore, re-expression of miR-410 prevented radiation-induced EMT and cell invasion . In vivo: In this study, we investigated the in vivo anti-RSV activity of tangeretin in 3-week-old male BALB/c mice. A plaque reduction assay and fluorescence quantitative polymerase chain reaction (FQ-PCR) showed that tangeretin inhibited RSV replication in the lung of mice .