Cinnamtannin B1

Last updated
Cinnamtannin B1
Cinnamtannin B1.png
Names
IUPAC name
[(2S,3R,4R)-Flavan-3,3′,4′,5,7-pentol]-(2-oxy-7,8→4)-[(2R,3R,4S)-flavan-3,3′,4′,5-tetrol]-(4→8)-[(2R,3R)-flavan-3,3′,4′,5,7-pentol]
Systematic IUPAC name
(2R,3R,4S,8S,14R,15R)-2,8-Bis(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H,8H,14H-8,14-methanobenzo[d]pyrano[2,3-h][1,3]benzodioxocine-3,5,11,13,15-pentol
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C45H36O18/c46-18-10-27(54)33-31(11-18)62-45(17-3-6-22(49)26(53)9-17)44(59)38(33)36-32(63-45)14-29(56)35-37(39(58)41(61-43(35)36)16-2-5-21(48)25(52)8-16)34-28(55)13-23(50)19-12-30(57)40(60-42(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,30,37-41,44,46-59H,12H2/t30-,37+,38-,39-,40-,41-,44-,45+/m1/s1 X mark.svgN
    Key: BYSRPHRKESMCPO-LQNPQWRQSA-N X mark.svgN
  • InChI=1/C45H36O18/c46-18-10-27(54)33-31(11-18)62-45(17-3-6-22(49)26(53)9-17)44(59)38(33)36-32(63-45)14-29(56)35-37(39(58)41(61-43(35)36)16-2-5-21(48)25(52)8-16)34-28(55)13-23(50)19-12-30(57)40(60-42(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,30,37-41,44,46-59H,12H2/t30-,37+,38-,39-,40-,41-,44-,45+/m1/s1
    Key: BYSRPHRKESMCPO-LQNPQWRQBE
  • Oc1cc(O)c2c(c1)O[C@@]1([C@@H]([C@H]2c2c(O1)cc(c1c2O[C@H](c2ccc(c(c2)O)O)[C@@H]([C@H]1c1c(O)cc(c2c1O[C@@H]([C@@H](C2)O)c1ccc(c(c1)O)O)O)O)O)O)c1ccc(c(c1)O)O
Properties
C45H36O18
Molar mass 864.75 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cinnamtannin B1 is a condensed tannin found in Cinnamomum verum . It falls under the category of type A proanthocyanidin. [1]

Cinnamon could potentially exhibit pharmacological effects in treating type 2 diabetes mellitus and insulin resistance. The plant material predominantly employed in the study was sourced from Chinese cinnamon (see Chinese cinnamon's medicinal uses). [2] [3] Recent phytochemical research has suggested that cinnamtannin B1, extracted from C. Verum, might have a potential therapeutic impact on type 2 diabetes, [4] with the exception of postmenopausal patients studied using Cinnamomum aromaticum . [5]

Cinnamtannin B1 possesses multiple phenolic hydroxyl groups and is noted for its antioxidant properties, antimicrobial activities, and ability to inhibit platelet aggregation, [6] which could contribute to the protection of damaged tissues in wounds. [7]

Related Research Articles

<span class="mw-page-title-main">Cinnamon</span> Spice from the inner tree bark of several members of genus Cinnamomum

Cinnamon is a spice obtained from the inner bark of several tree species from the genus Cinnamomum. Cinnamon is used mainly as an aromatic condiment and flavouring additive in a wide variety of cuisines, sweet and savoury dishes, breakfast cereals, snack foods, bagels, teas, hot chocolate and traditional foods. The aroma and flavour of cinnamon derive from its essential oil and principal component, cinnamaldehyde, as well as numerous other constituents including eugenol.

Insulin resistance (IR) is a pathological condition in which cells either fail to respond normally to the hormone insulin or downregulate insulin receptors in response to hyperinsulinemia.

Aldose reductase inhibitors are a class of drugs being studied as a way to prevent eye and nerve damage in people with diabetes.

<span class="mw-page-title-main">Type 2 diabetes</span> Type of diabetes mellitus with high blood sugar and insulin resistance

Type 2 diabetes, formerly known as adult-onset diabetes, is a form of diabetes mellitus that is characterized by high blood sugar, insulin resistance, and relative lack of insulin. Common symptoms include increased thirst, frequent urination, and unexplained weight loss. Symptoms may also include increased hunger, feeling tired, and sores (wounds) that do not heal. Often symptoms come on slowly. Long-term complications from high blood sugar include heart disease, strokes, diabetic retinopathy which can result in blindness, kidney failure, and poor blood flow in the limbs which may lead to amputations. The sudden onset of hyperosmolar hyperglycemic state may occur; however, ketoacidosis is uncommon.

Drugs used in diabetes treat diabetes mellitus by altering the glucose level in the blood. With the exception of insulin, most GLP receptor agonists, and pramlintide, all are administered orally and are thus also called oral hypoglycemic agents or oral antihyperglycemic agents. There are different classes of anti-diabetic drugs, and their selection depends on the nature of diabetes, age, and situation of the person, as well as other factors.

<span class="mw-page-title-main">Sulfonylurea</span> Class of organic compounds used in medicine and agriculture

Sulfonylureas or sulphonylureas are a class of organic compounds used in medicine and agriculture. The functional group consists of a sulfonyl group (-S(=O)2) with its sulphur atom bonded to nitrogen atom of a ureylene group (N,N-dehydrourea, a urea derivative). The side chains R1 and R2 distinguish various sulfonylureas.

<span class="mw-page-title-main">Coumarin</span> Aromatic chemical compound

Coumarin or 2H-chromen-2-one is an aromatic organic chemical compound with formula C9H6O2. Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by an unsaturated lactone ring −(CH)=(CH)−(C=O)−O−, forming a second six-membered heterocycle that shares two carbons with the benzene ring. It belongs to the benzopyrone chemical class and considered as a lactone.

<span class="mw-page-title-main">Amylin</span> Peptide hormone that plays a role in glycemic regulation

Amylin, or islet amyloid polypeptide (IAPP), is a 37-residue peptide hormone. It is co-secreted with insulin from the pancreatic β-cells in the ratio of approximately 100:1 (insulin:amylin). Amylin plays a role in glycemic regulation by slowing gastric emptying and promoting satiety, thereby preventing post-prandial spikes in blood glucose levels.

Proanthocyanidins are a class of polyphenols found in many plants, such as cranberry, blueberry, and grape seeds. Chemically, they are oligomeric flavonoids. Many are oligomers of catechin and epicatechin and their gallic acid esters. More complex polyphenols, having the same polymeric building block, form the group of tannins.

<span class="mw-page-title-main">Myricetin</span> Chemical compound

Myricetin is a member of the flavonoid class of polyphenolic compounds, with antioxidant properties. Common dietary sources include vegetables, fruits, nuts, berries, tea, and red wine. Myricetin is structurally similar to fisetin, luteolin, and quercetin and is reported to have many of the same functions as these other members of the flavonol class of flavonoids. Reported average intake of myricetin per day varies depending on diet, but has been shown in the Netherlands to average 23 mg/day.

<span class="mw-page-title-main">Proprotein convertase 2</span> Protein-coding gene in the species Homo sapiens

Proprotein convertase 2 (PC2) also known as prohormone convertase 2 or neuroendocrine convertase 2 (NEC2) is a serine protease and proprotein convertase PC2, like proprotein convertase 1 (PC1), is an enzyme responsible for the first step in the maturation of many neuroendocrine peptides from their precursors, such as the conversion of proinsulin to insulin intermediates. To generate the bioactive form of insulin, a second step involving the removal of C-terminal basic residues is required; this step is mediated by carboxypeptidases E and/or D. PC2 plays only a minor role in the first step of insulin biosynthesis, but a greater role in the first step of glucagon biosynthesis compared to PC1. PC2 binds to the neuroendocrine protein named 7B2, and if this protein is not present, proPC2 cannot become enzymatically active. 7B2 accomplishes this by preventing the aggregation of proPC2 to inactivatable forms. The C-terminal domain of 7B2 also inhibits PC2 activity until it is cleaved into smaller inactive forms that lack carboxy-terminal basic residues. Thus, 7B2 is both an activator and an inhibitor of PC2. PC2 has been identified in a number of animals, including C. elegans.

<span class="mw-page-title-main">Phosphodiesterase 3</span> Class of enzymes

PDE3 is a phosphodiesterase. The PDEs belong to at least eleven related gene families, which are different in their primary structure, substrate affinity, responses to effectors, and regulation mechanism. Most of the PDE families are composed of more than one gene. PDE3 is clinically significant because of its role in regulating heart muscle, vascular smooth muscle and platelet aggregation. PDE3 inhibitors have been developed as pharmaceuticals, but their use is limited by arrhythmic effects and they can increase mortality in some applications.

<span class="mw-page-title-main">Triflusal</span> Antiplatelet drug

Triflusal is a platelet aggregation inhibitor that was discovered and developed in the Uriach Laboratories, and commercialised in Spain since 1981. Currently, it is available in 25 countries in Europe, Asia, Africa and America. It is a derivative of acetylsalicylic acid (ASA)(Aspirin) in which a hydrogen atom on the benzene ring has been replaced by a trifluoromethyl group. Trade names include Disgren, Grendis, Aflen and Triflux.

<span class="mw-page-title-main">Sarpogrelate</span> Chemical compound

Sarpogrelate is a drug which acts as an antagonist at the 5HT2A and 5-HT2B receptors. It blocks serotonin-induced platelet aggregation, and has applications in the treatment of many diseases including diabetes mellitus, Buerger's disease, Raynaud's disease, coronary artery disease, angina pectoris, and atherosclerosis.

<span class="mw-page-title-main">Procyanidin B2</span> Chemical compound

Procyanidin B2 is a B type proanthocyanidin. Its structure is (−)-Epicatechin-(4β→8)-(−)-epicatechin.

A type proanthocyanidins are a specific type of proanthocyanidins, which are a class of flavonoid. Proanthocyanidins fall under a wide range of names in the nutritional and scientific vernacular, including oligomeric proanthocyanidins, flavonoids, polyphenols, condensed tannins, and OPCs. Proanthocyanidins were first popularized by French scientist Jacques Masquelier.

Complications of diabetes mellitus include problems that develop rapidly (acute) or over time (chronic) and may affect many organ systems. The complications of diabetes can dramatically impair quality of life and cause long-lasting disability. Overall, complications are far less common and less severe in people with well-controlled blood sugar levels. Some non-modifiable risk factors such as age at diabetes onset, type of diabetes, gender and genetics may influence risk. Other health problems compound the chronic complications of diabetes such as smoking, obesity, high blood pressure, elevated cholesterol levels, and lack of regular exercise. Complications of diabetes are a strong risk factor for severe COVID-19 illness.

<span class="mw-page-title-main">Procyanidin C1</span> Chemical compound

Procyanidin C1 (PCC1) is a B type proanthocyanidin. It is an epicatechin trimer found in grape, unripe apples, and cinnamon.

<i>Cinnamomum verum</i> Species of tree

Cinnamomum verum, also known as Cinnamomum zeylanicum, colloquially called true cinnamon tree or Ceylon cinnamon tree, is a small evergreen tree belonging to the family Lauraceae, native to Sri Lanka. The inner bark of the tree is historically regarded as the "spice' cinnamon even though this term was later generalized for both C. cassia and C. zeylanicum together.

<span class="mw-page-title-main">Diabetes</span> Medical condition

Diabetes mellitus, often known simply as diabetes, is a group of common endocrine diseases characterized by sustained high blood sugar levels. Diabetes is due to either the pancreas not producing enough insulin, or the cells of the body becoming unresponsive to the hormone's effects. Classic symptoms include thirst, polyuria, weight loss, and blurred vision. If left untreated, the disease can lead to various health complications, including disorders of the cardiovascular system, eye, kidney, and nerves. Untreated or poorly treated diabetes accounts for approximately 1.5 million deaths every year.

References

  1. Anderson; Broadhurst, CL; Polansky, MM; Schmidt, WF; Khan, A; Flanagan, VP; Schoene, NW; Graves, DJ (January 2004). "Isolation and characterization of polyphenol type-A polymers from cinnamon with insulin-like biological activity". J Agric Food Chem. 52 (1): 65–70. doi:10.1021/jf034916b. PMID   14709014.
  2. Khan A, Safdar M, Ali Khan MM, Khattak KN, Anderson RA (December 2003). "Cinnamon improves glucose and lipids of people with type 2 diabetes". Diabetes Care. 26 (12): 3215–8. doi: 10.2337/diacare.26.12.3215 . PMID   14633804.
  3. Verspohl, Eugen J.; Bauer, K; Neddermann, E; et al. (2005). "Antidiabetic effect of Cinnamomum cassia and Cinnamomum zeylanicum In vivo and In vitro". Phytotherapy Research. 19 (3): 203–206. doi:10.1002/ptr.1643. PMID   15934022. S2CID   32335294.
  4. Taher, Muhammad; et al. "A proanthocyanidin from Cinnamomum zeylanicum stimulates phosphorylation of insulin receptor in 3T3-L1 adipocyties" (PDF). Archived from the original (PDF) on 2008-05-28. Retrieved 2008-05-11.
  5. Vanschoonbeek, Kristof; et al. (2006). "Cinnamon Supplementation Does Not Improve Glycemic Control in Postmenopausal Type 2 Diabetes Patients". The Journal of Nutrition. 136 (4): 977–980. doi: 10.1093/jn/136.4.977 . PMID   16549460 . Retrieved 2008-05-11.
  6. López, J. J., Jardín, I., Salido, G. M., & Rosado, J. A. (2008). Cinnamtannin B-1 as an antioxidant and platelet aggregation inhibitor. Life sciences, 82(19), 977-982. doi : 10.1016/j.lfs.2008.03.009
  7. Fujita K, Kuge K, Ozawa N, Sahara S, Zaiki K, Nakaoji K, et al. (2015) Cinnamtannin B-1 Promotes Migration of Mesenchymal Stem Cells and Accelerates Wound Healing in Mice. PLoS ONE 10(12): e0144166. doi : 10.1371/journal.pone.0144166