Tangeretin from <i>Citrus reticulate</i> Inhibits Respiratory Syncytial Virus Replication and Associated Inflammation <i>in Vivo</i>

Xu, Jiaojiao; Liu, Zhong; Tang, Wei; Wang, Guo‐Cai; Chung, Hau Yin; Liu, Qiuying; Zhuang, Ling; Li, Man‐Mei; Li, Yao-Lan

doi:10.1021/acs.jafc.5b03482

Cited by 48 publications

(27 citation statements)

References 29 publications

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“…Interestingly, the two most abundant polymethoxylated flavones identified in the extract of "Guangchenpi", tangeretin and nobiletin, determined a dose-dependent inhibition of the virus, calculated by plaque reduction assay. The same authors have subsequently investigated the activity of tangeretin from C. reticulata in vivo using 3-week-old male BALB/c mice [94]. As previously shown in vitro, the results from this study confirmed an inhibition of the RSV replication exerted by tangeretin in the lung of the mice.…”

Section: Antimicrobial and Antiviral Effect Of Citrus Flavonessupporting

confidence: 81%

Citrus Flavones: An Update on Sources, Biological Functions, and Health Promoting Properties

Barreca

Mandalari

Calderaro

et al. 2020

Plants

101

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Citrus spp. are among the most widespread plants cultivated worldwide and every year millions of tons of fruit, juices, or processed compounds are produced and consumed, representing one of the main sources of nutrients in human diet. Among these, the flavonoids play a key role in providing a wide range of health beneficial effects. Apigenin, diosmetin, luteolin, acacetin, chrysoeriol, and their respective glycosides, that occur in concentrations up to 60 mg/L, are the most common flavones found in Citrus fruits and juices. The unique characteristics of their basic skeleton and the nature and position of the substituents have attracted and stimulated vigorous investigations as a consequence of an enormous biological potential, that manifests itself as (among other properties) antioxidant, anti-inflammatory, antiviral, antimicrobial, and anticancer activities. This review analyzes the biochemical, pharmacological, and biological properties of Citrus flavones, emphasizing their occurrence in Citrus spp. fruits and juices, on their bioavailability, and their ability to modulate signal cascades and key metabolic enzymes both in vitro and in vivo. Electronic databases including PubMed, Scopus, Web of Science, and SciFinder were used to investigate recent published articles on Citrus spp. in terms of components and bioactivity potentials.

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Section: Antimicrobial and Antiviral Effect Of Citrus Flavonessupporting

confidence: 81%

Citrus Flavones: An Update on Sources, Biological Functions, and Health Promoting Properties

Barreca

Mandalari

Calderaro

et al. 2020

Plants

101

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“…Hesperidin was found to be the most predominant flavonoid in tangerine peel, followed by tangeretin and nobiletin (Ho and Kuo, 2014). Even though pharmacological activity such as neuroinflammatory activity, antibacterial, antifungal, antiaging, anti-tyrosinase, anti-acne, antiallergic, anticancer, anti-inflammatory and antiviral activity against the human respiratory syncytial virus (RSV) have been assigned to these compounds, it is known that these compounds individually often do not account for the activity of the extracts, and that these compounds in combination is responsible for the pharmacological activities observed (Kim et al, 2008a;Ho and Kuo, 2014;Rashed et al, 2015;Xu et al, 2015;Vargas et al, 2016;Adhikari et al, 2017;Hagenlocher et al, 2017). Additionally tangeretin and nobiletin also showed the best antibacterial activity against Staphylococcus aureus, Microsporum canis, Escherichia coli, Trichophyton mentagrophytes when tested against bacterial and fungal species when the peel extracts of C. sinensis, C. limon, and C. reticulata were tested, with antimicrobial activity also reported for these compounds in the leaf extract of C. volkameriana (Johann et al, 2007;Rashed et al, 2015).…”

Section: Discussionmentioning

confidence: 99%

1H-NMR Metabolomics and LC-MS Analysis to Determine Seasonal Variation in a Cosmeceutical Plant Leucosidea sericea

2020

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Leucosidea sericea is an evergreen shrub belonging to the Rosaceae family with previous studies that indicated that L. sericea extracts exhibited strong anti-bacterial properties against Propionibacterium acnes, showing potential as a cosmeceutical. The plant is traditionally used as a vermifuge, as an astringent and to treat conjunctivitis. Commercial production is, however, not possible as no information is available on cultivation and the effect of external environmental factors such as seasonal variation on the medicinal properties of the plant. Seasonal variation was investigated and it was found that significant differences were observed between the anti-acne (P. acnes) activity of plant material collected in different seasons. The best activity was found in winter with a mean minimum inhibitory concentration (MIC) of 5.20 µg mL −1 compared to spring at 26.04 µg mL −1. A 1 H NMR-based untargeted metabolomic analysis was used to determine the differences in the chemical profiles of plant samples collected in different seasons. Principal component analysis (PCA) showed clear separation of the seasons and a supervised orthogonal partial least square discriminant analysis (OPLS-DA) was used to determine the compounds that differentiated the spring from the winter samples. The contribution plot indicated a strong positive association with the NMR regions from δ 1.2-1.6, 3.3-4.1, and 6.8-8.0 ppm indicative of a compound with an aromatic ring. Different LC-MS analyses were used in conjunction with a compound database, MAGMa and CSIFingerID, which led to the identification of the compound 2-(4-ethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one and also confirmed the presence of tangeritin, rutin, quercetin glucoside, and kaempferol glucosides as well as several other compounds previously identified from the plant. This compound similar in structure to the anti-microbial flavonoid tangeritin, was only present in the winter samples. It is therefore recommended that seasonal variation be closely monitored during cultivation and commercial harvesting, and that winter is the preferred harvesting season to obtain the best anti-acne activity.

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“…The minimal concentration required to inhibit 50% of plaques (IC 50 ) was calculated by regression analysis of the doseresponse curve generated from the data. The cytotoxicity of the compounds was determined in cultures of HEp-2 cells using the MTT method (25). The assays were carried out in triplicate and the results were from 3 independent experiments.…”

Section: Plaque Assaymentioning

confidence: 99%

Small molecule inhibits respiratory syncytial virus entry and infection by blocking the interaction of the viral fusion protein with the cell membrane

Tang

Liu

et al. 2018

FASEB j.

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Antiviral drug development against respiratory syncytial virus (RSV) is urgently needed due to the public health significance of the viral infection. Here, we report the anti‐RSV activity of a small molecule, (1S,3R,4R,5R)‐3,4‐bis{[(E)‐3‐(3,4‐dihydroxyphenyl)prop‐2‐enoyl]oxy}‐l,5‐dihydroxycyclohexane‐1‐ca methyl ester (3,4‐DCQAME) or 3,4‐O‐Dicaffeoylquinic acid methyl ester, which can be isolated from several plants of traditional Chinese medicine. We showed for the first time that compound 3,4‐DCQAME potently inhibits RSV entry and infection. In vitro, 3,4‐DCQAME can interact with F(ecto), the ectodomain of RSV fusion (F) protein. In cultured cells, the compound can block the interaction of F(ecto) protein with the cellular membrane and inhibit viral fusion during RSV entry, leading to inhibition of viral gene expression and infection. In RSV‐infected mice that were treated with 3,4‐DCQAME, we observed a reduction of RSV‐induced pathologic changes and substantial inhibition of viral infection and growth in the lung tissues. Our results provide the first direct evidence of the anti‐RSV activity of 3,4‐DCQAME. Furthermore, these results suggest that 3,4‐DCQAME represents a promising lead compound for anti‐RSV therapeutic development.—Tang, W., Li, M., Liu, Y., Liang, N., Yang, Z., Zhao, Y., Wu, S., Lu, S., Li, Y., Liu, F. Small molecule inhibits respiratory syncytial virus entry and infection by blocking the interaction of the viral fusion protein with the cell membrane. FASEB J. 33, 4287–4299 (2019). http://www.fasebj.org

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Tangeretin from Citrus reticulate Inhibits Respiratory Syncytial Virus Replication and Associated Inflammation in Vivo

Cited by 48 publications

References 29 publications

Citrus Flavones: An Update on Sources, Biological Functions, and Health Promoting Properties

Citrus Flavones: An Update on Sources, Biological Functions, and Health Promoting Properties

1H-NMR Metabolomics and LC-MS Analysis to Determine Seasonal Variation in a Cosmeceutical Plant Leucosidea sericea

Small molecule inhibits respiratory syncytial virus entry and infection by blocking the interaction of the viral fusion protein with the cell membrane

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