Pyranoflavanones and Pyranochalcones from the Fruits of Amomum tsao-ko.

Eight new geranylated and farnesylated pyranoflavanones (1-8) and two new farnesylated pyranochalcones (9 and 10) were isolated from the methanolic extract of the fruits of Amomum tsao-ko. Their structures were elucidated by extensive analysis of the 1D and 2D NMR spectra and from the HRESIMS, combined with experimental ECD data. All compounds were evaluated for their inhibitory effects on the nitric oxide production against lipopolysaccharide-induced RAW 264.7 macrophages and exhibited IC50 values ranging from 10.6 to 41.5 μM.

[1]  Jun Gu Kim,et al.  Nitric Oxide Inhibitory Constituents from the Fruits of Amomum tsao-ko , 2019, Natural Product Sciences.

[2]  Xiaochi Ma,et al.  Identification and bioactivity evaluation of ingredients from the fruits of Amomum tsaoko Crevost et Lemaire , 2018, Phytochemistry Letters.

[3]  Vivek Asati,et al.  Chalcone Derivatives: Anti-inflammatory Potential and Molecular Targets Perspectives. , 2017, Current topics in medicinal chemistry.

[4]  B. Hwang,et al.  Potential Anti-inflammatory Effects of the Fruits of Paulownia tomentosa. , 2017, Journal of natural products.

[5]  Yu-jie Fu,et al.  Rapid extraction of Amomum tsao-ko essential oil and determination of its chemical composition, antioxidant and antimicrobial activities. , 2017, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[6]  Jian-Guo Jiang,et al.  Neuroprotective and Anti-Inflammatory Effects of Diphenylheptanes from the Fruits of Amomum tsaoko, a Chinese Spice , 2016, Plant Foods for Human Nutrition.

[7]  Eun-Kyung Ahn,et al.  Amotsaokonal A–C, benzaldehyde and cycloterpenal from Amomum tsao-ko , 2015 .

[8]  Kyung-Tae Lee,et al.  Amomum tsao‐ko fruit extract suppresses lipopolysaccharide‐induced inducible nitric oxide synthase by inducing heme oxygenase‐1 in macrophages and in septic mice , 2015, International journal of experimental pathology.

[9]  S. Dall’Acqua,et al.  C-Geranylated Flavanones from Paulownia tomentosa Fruits as Potential Anti-inflammatory Compounds Acting via Inhibition of TNF-α Production. , 2015, Journal of natural products.

[10]  Jian-Guo Jiang,et al.  Bioactivity evaluation of ingredients identified from the fruits of Amomum tsaoko Crevost et Lemaire, a Chinese spice. , 2014, Food & function.

[11]  E. Foss,et al.  Antimicrobial and Antiinsectan Phenolic Metabolites of Dalea searlsiae , 2014, Journal of natural products.

[12]  X. Chen,et al.  A systematic review on biological activities of prenylated flavonoids , 2014, Pharmaceutical biology.

[13]  M. Yasuda,et al.  Inhibitory effects of 4-hydroxyderricin and xanthoangelol on lipopolysaccharide-induced inflammatory responses in RAW264 macrophages. , 2014, Journal of agricultural and food chemistry.

[14]  J. Hošek,et al.  Prenylated and geranylated flavonoids increase production of reactive oxygen species in mouse macrophages but inhibit the inflammatory response. , 2013, Journal of natural products.

[15]  Chin-Lin Hsu,et al.  Geranyl Flavonoid Derivatives from the Fresh Leaves of Artocarpus communis and Their Anti-inflammatory Activity , 2012, Planta Medica.

[16]  O. Potterat,et al.  Bicyclononane aldehydes and antiproliferative constituents from Amomum tsao-ko. , 2009, Planta medica.

[17]  Dongho Lee,et al.  Prenylated and benzylated flavonoids from the fruits of Cudrania tricuspidata. , 2009, Journal of natural products.

[18]  Ki Yong Lee,et al.  Inhibitory Constituents of Lipopolysaccharide-Induced Nitric Oxide Production in BV2 Microglia isolated from Amomum tsao-ko , 2008, Planta medica.

[19]  Ah-Reum Han,et al.  Prenylated flavonoids from the heartwood of Artocarpus communis with inhibitory activity on lipopolysaccharide-induced nitric oxide production. , 2006, Journal of natural products.

[20]  D. Ferreira,et al.  Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids. , 2005, Phytochemistry.

[21]  A. Vitali,et al.  Prenylated flavonoids: pharmacology and biotechnology. , 2005, Current medicinal chemistry.

[22]  Ji-Young Lee,et al.  Isotsaokoin, an antifungal agent from Amomum tsao-ko. , 2004, Journal of natural products.