Isolation and Characterization of Polyphenol Type-A Polymers from Cinnamon with Insulin-like Biological Activity

Department of Molecular, Cellular, and Developmental Biology, University of California, Santa Barbara, Santa Barbara, California, United States
Journal of Agricultural and Food Chemistry (Impact Factor: 2.91). 02/2004; 52(1):65-70. DOI: 10.1021/jf034916b
Source: PubMed


The causes and control of type 2 diabetes mellitus are not clear, but there is strong evidence that dietary factors are involved in its regulation and prevention. We have shown that extracts from cinnamon enhance the activity of insulin. The objective of this study was to isolate and characterize insulin-enhancing complexes from cinnamon that may be involved in the alleviation or possible prevention and control of glucose intolerance and diabetes. Water-soluble polyphenol polymers from cinnamon that increase insulin-dependent in vitro glucose metabolism roughly 20-fold and display antioxidant activity were isolated and characterized by nuclear magnetic resonance and mass spectroscopy. The polymers were composed of monomeric units with a molecular mass of 288. Two trimers with a molecular mass of 864 and a tetramer with a mass of 1152 were isolated. Their protonated molecular masses indicated that they are A type doubly linked procyanidin oligomers of the catechins and/or epicatechins. These polyphenolic polymers found in cinnamon may function as antioxidants, potentiate insulin action, and may be beneficial in the control of glucose intolerance and diabetes.

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    • "Cinnamon is the second most important spice (just behind black pepper) in the USA and Europe (Jayaprakasha, Negi, Jena, & Rao, 2007). Its consumption is related to health benefits, such as: antimicrobial activity, inhibition of cancer cells proliferation, protection against common flu, and glucose control in diabetes (Anderson et al., 2004). Among the compounds related to these effects are polyphenols. "
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    ABSTRACT: The effect of temperature and feed rate on spray dried cinnamon infusions (SDCInf) using maltodextrin as an encapsulating agent was studied (inlet temperature: 140, 160, and 180 °C; feed rate: 8 and 10 mL/min). Total phenolic content (TPC), antioxidant capacity (DPPH*), morphology (SEM), chemical (FTIR) and rheological properties, and releasing profiles were assessed in SDCInf. Cinnamon infusions (CInf) resulted in 29.32 (±0.70) mg of GAE/g of cinnamon. As for DPPH* inhibition, EC50 was 0.291 (±0.09) mg of cinnamon/mL. Microparticles showed a deflated-balloon like shape, encapsulating up to ∼85% of the cinnamon infusion, and a simple shear-thinning behavior (n < 1). Results show that powdered SDCInf obtained at 160 and 180 °C and 10 mL/min yielded the best protection for cinnamon infusions.
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    • "C. cassia as a frequently consumed spice and traditional medicine has attracted great attention in the past. Water-soluble polyphenols have been considered to have anti-diabetic activity (Anderson et al., 2004; Chen et al., 2012). This study revealed that multiple substances including nonpolar sesquiterpenoids in the spice showed reno-protctive effects by inhibiting the expression of fibronectin, MCP-1 and interleukin-6 in high-glucose-induced mesangial cells, which provided partial evidences for the clinic practices of Rou-Gui in diabetic nephropathy prevention and treatment. "
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    ABSTRACT: The bark of Cinnamomum cassia, called 'Rou-Gui', a traditional spice and medicine in China, is used to treat diseases resulted from kidney yang deficiency, including diabetic nephropathy. The aim of this study is to investigate the anti-diabetic nephropathy activity of Rou-Gui and the active compounds in it. The air-dried bark of C. cassia was extracted with 90% EtOH, the obtained residue was successively partitioned by petroleum ether, EtOAc, and n-BuOH followed by concentrating to give petroleum ether (RG-1), EtOAc (RG-2), n-BuOH (RG-3), and water fraction (RG-4), respectively. The anti-diabetic nephropathy activity of fraction (RG-1 to 4) was evaluated in vitro by inhibiting the expression of fibronectin, monocyte chemoattractant protein-1 and interleukin-6 in high-glucose-induced mesangial cells. By bioassay screenings, repeated column chromatography on fractions of RG-1, 2, and 3, led to the isolation of 23 compounds, whose structures were determined by extensive spectroscopic analyses, and the anti-diabetic nephropathy activity of the isolated compounds was also evaluated. Four new sesquiterpenoids, cinnamoids A-D (1-4), a new natural product (5), and eighteen known compounds (6-23) were isolated from the EtOH extract of the bark of C. cassia under the bioassay-guided screenings. The anti-diabetic nephropathy activity assay showed that fractions of RG-1, 2, and 3 could significantly inhibit the production of fibronectin, monocyte chemoattractant protein-1 and interleukin-6 in high-glucose-stimulated mesangial cells at the concentration of 50μg/ml; and sesquiterpenoids 5, 6, 14 and compound 20 could significantly inhibit the expression of fibronectin, monocyte chemoattractant protein-1 and interleukin-6 at the concentration of 50μM. The results revealed that sesquiterpenoids may be the active compounds in C. cassia bark on diabetic nephropathy which provided new evidences for the traditional use of this herb to treat diabetic nephropathy and associated kidney diseases. Copyright © 2015 Elsevier Ireland Ltd. All rights reserved.
    Journal of Ethnopharmacology 02/2015; 165. DOI:10.1016/j.jep.2015.01.049 · 3.00 Impact Factor
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    • "Cinnamon (Cinnamomum cassia) has been used in several cultures for centuries as a spice and traditional medicine and is known as an anti-diabetic agent all over the world. Cinnamon contains volatile oils such as cinnamaldehyde, eugenol, and cinnamic acid; phenolic compounds such as tannin, catechins, and proanthocyandins; monoterpenes, sesquiterpenes; and trace coumarin (Anderson et al. 2004; Barceloux 2009). Among these compounds, proanthocyandins, cinnamic acid and cinnamaldehyde are found to be major components of cinnamon aqueous extract (Jiao et al. 2013). "
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    ABSTRACT: Although the anti-diabetic activity of cinnamic acid, a pure compound from cinnamon, has been reported but its mechanism(s) is not yet clear. The present study was designed to explore the possible mechanism(s) of anti-diabetic activity of cinnamic acid in in vitro and in vivo non-obese type 2 diabetic rats. Non-obese type 2 diabetes was developed by injecting 90 mg/kg streptozotocin in 2-day-old Wistar pups. Cinnamic acid and cinnamaldehyde were administered orally to diabetic rats for assessing acute blood glucose lowering effect and improvement of glucose tolerance. Additionally, insulin secretory activity of cinnamic acid and cinnamaldehyde was evaluated in isolated mice islets. Cinnamic acid, but not cinnamaldehyde, decreased blood glucose levels in diabetic rats in a time- and dose-dependent manner. Oral administration of cinnamic acid with 5 and 10 mg/kg doses to diabetic rats improved glucose tolerance in a dose-dependent manner. The improvement by 10 mg/kg cinnamic acid was comparable to that of standard drug glibenclamide (5 mg/kg). Further in vitro studies showed that cinnamaldehyde has little or no effect on glucose-stimulated insulin secretion; however, cinnamic acid significantly enhanced glucose-stimulated insulin secretion in isolated islets. In conclusion, it can be said that cinnamic acid exerts anti-diabetic activity by improving glucose tolerance in vivo and stimulating insulin secretion in vitro. Copyright © 2015 Elsevier GmbH. All rights reserved.
    Phytomedicine 01/2015; 22(2). DOI:10.1016/j.phymed.2015.01.003 · 3.13 Impact Factor
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