Cytotoxic activities of five compounds with high polarity in BT-474 ...
Galangin, Curcumin, Pycnogenol (PYC), Puerarin (isoflavone) và Axit Ursolic kháng BT-474
Galangin
From Wikipedia, the free encyclopedia
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| Names | |
|---|---|
| IUPAC name
3,5,7-Trihydroxy-2-phenylchromen-4-one
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| Other names
Norizalpinin
3,5,7-Trihydroxyflavone 3,5,7-triOH-Flavone | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.008.147 |
| KEGG | |
PubChem CID
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| UNII | |
| Properties | |
| C15H10O5 | |
| Molar mass | 270.24 g·mol−1 |
| Density | 1.579 g/mL |
| Melting point | 214 to 215 °C (417 to 419 °F; 487 to 488 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Occurrence[edit]
Galangin is found in high concentrations in Alpinia officinarum (lesser galangal)[1] and Helichrysum aureonitens.[2] It is also found in the rhizome of Alpinia galanga[3] and in propolis.[4]
Biological activities[edit]
Galangin has been shown to have in vitro antibacterial[5][6] and antiviral activity.[7] It also inhibits the growth of breast tumor cells in vitro.[8][9]
Curcumin
From Wikipedia, the free encyclopedia
Enol form
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Keto form
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| Names | |
|---|---|
| Pronunciation | /ˈkɜːrkjᵿmɪn/ |
| Preferred IUPAC name
(1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
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| Other names
(1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
Diferuloylmethane Curcumin I C.I. 75300 Natural Yellow 3 | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| E number | E100 (colours) |
PubChem CID
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| UNII | |
| Properties | |
| C21H20O6 | |
| Molar mass | 368.39 g·mol−1 |
| Appearance | Bright yellow-orange powder |
| Melting point | 183 °C (361 °F; 456 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Curcumin is a bright yellow chemical produced by some plants. It is the principal curcuminoid of turmeric (Curcuma longa), a member of the ginger family (Zingiberaceae). It is sold as an herbal supplement, cosmetics ingredient, food flavoring, and food coloring.[1] As a food additive, its E number is E100.[2]
It was first isolated in 1815 when Vogel and Pierre Joseph Pelletier reported the isolation of a "yellow coloring-matter" from the rhizomes of turmeric and named it curcumin.[3] Although curcumin has been used historically in Ayurvedic medicine,[4] its potential for medicinal properties remains unproven and is questionable as a therapy when used orally.[5][6][7]
Chemically, curcumin is a diarylheptanoid, belonging to the group of curcuminoids, which are natural phenols responsible for turmeric's yellow color. It is a tautomeric compound existing in enolic form in organic solvents and as a keto form in water.[8]
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[hide]Applications[edit]
The most common applications are as a dietary supplement, in cosmetics, as a food coloring, and as flavoring for foods such as turmeric-flavored beverages (Japan).[1]
Annual sales of curcumin have increased since 2012, largely due to an increase in its popularity as a dietary supplement.[1] It is increasingly popular in skincare products that are marketed as containing natural ingredients or dyes, especially in Asia.[1] The largest market is in North America, where sales exceeded US$20 million in 2014.[1]
Chemistry[edit]
Curcumin incorporates several functional groups whose structure was first identified in 1910.[9] The aromatic ring systems, which are phenols, are connected by two α,β-unsaturated carbonyl groups. The diketones form stable enols and are readily deprotonated to form enolates; the α,β-unsaturated carbonyl group is a good Michael acceptor and undergoes nucleophilic addition.
Curcumin is used as a complexometric indicator for boron.[10] It reacts with boric acid to form a red-colored compound, rosocyanine.
Biosynthesis[edit]
The biosynthetic route of curcumin is uncertain. In 1973, Roughly and Whiting proposed two mechanisms for curcumin biosynthesis. The first mechanism involves a chain extension reaction by cinnamic acid and 5 malonyl-CoA molecules that eventually arylized into a curcuminoid. The second mechanism involves two cinnamate units coupled together by malonyl-CoA. Both use cinnamic acid as their starting point, which is derived from the amino acid phenylalanine.[11]
Plant biosyntheses starting with cinnamic acid is rare compared to the more common p-coumaric acid.[11] Only a few identified compounds, such as anigorufone and pinosylvin, build from cinnamic acid.[12][13]
Research[edit]
In vitro, curcumin exhibits numerous interference properties which may lead to misinterpretation of results.[5][6][14]
Although curcumin has been assessed in numerous laboratory and clinical studies, it has no medical uses established by well-designed clinical research.[15] According to a 2017 review of over 120 studies, curcumin has not been successful in any clinical trial, leading the authors to conclude that "curcumin is an unstable, reactive, non-bioavailable compound and, therefore, a highly improbable lead".[5]
Cancer studies using curcumin conducted by Bharat Aggarwal, formerly a researcher at the MD Anderson Cancer Center, were deemed fraudulent and subsequently retracted by the publisher.[16]
Pharmacology[edit]
Curcumin, which shows positive results in most drug discovery assays, is regarded as a false lead that medicinal chemists include among "pan-assay interference compounds" attracting undue experimental attention while failing to advance as viable therapeutic or drug leads.[5][6][17] In vitro, curcumin inhibits certain epigeneticenzymes (the histone deacetylases: HDAC1, HDAC3, HDAC8), transcriptional co-activator proteins (the p300 histone acetyltransferase)[18][19][20] and the arachidonate 5-lipoxygenase enzyme.[21]
In Phase I clinical trials, curcumin had poor bioavailability, was rapidly metabolized, retained low levels in plasma and tissues, and was extensively and rapidly excreted, factors that make its in vivo bioactivity unlikely and difficult to accurately assess.[5][22] Curcumin appears to reduce circulating C-reactive protein in human subjects, although no dose-response relationship was established.[23] Factors that limit the bioactivity of curcumin or its analogs include chemical instability, water insolubility, absence of potent and selective target activity, low bioavailability, limited tissue distribution, extensive metabolism, and potential for toxicity.[5]
Toxicity[edit]
Two preliminary clinical studies in cancer patients consuming high doses of curcumin (up to 8 grams per day for 3–4 months) showed no toxicity, though some subjects reported mild nausea or diarrhea.[24]
Alternative medicine[edit]
Despite concerns about safety or efficacy and the absence of reliable clinical research,[5][6] some alternative medicine practitioners give turmeric intravenously, supposedly as a treatment for numerous diseases, in one case causing a death in 2017.[25]
Condensed tannin
From Wikipedia, the free encyclopedia
(Redirected from Pycnogenol)
Condensed tannins (proanthocyanidins, polyflavonoid tannins, catechol-type tannins, pyrocatecollic type tannins, non-hydrolyzable tannins or flavolans) are polymers formed by the condensation of flavans. They do not contain sugar residues.[1]
They are called proanthocyanidins as they yield anthocyanidins when depolymerized under oxidative conditions. Different types of condensed tannins exist, such as the procyanidins, propelargonidins, prodelphinidins, profisetinidins, proteracacinidins (from mesquitol), proguibourtinidins or prorobinetidins. All of the above are formed from flavan-3-ols, but flavan-3,4-diols, called (leucoanthocyanidin) also form condensed tannin oligomers, e.g. leuco-fisetinidin form profisetinidin, and flavan-4-ols form condensed tannins, e.g. 3',4',5,7-flavan-4-ol form proluteolinidin (luteoforolor).[2] One particular type of condensed tannin, found in grape, are procyanidins, which are polymers of 2 to 50 (or more) Catechin units joined by carbon-carbon bonds. These are not susceptible to being cleaved by hydrolysis.
While many hydrolyzable tannins and most condensed tannins are water-soluble, several tannins are also highly octanol-soluble.[3][4] Some large condensed tannins are insoluble. Differences in solubilities are likely to affect their biological functions.
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[hide]Natural occurrences[edit]
Tannins of tropical woods tend to be of a catechin nature rather than of the gallic type present in temperate woods.[5]
Condensed tannins can be recovered from Lithocarpus glaber[6] or can be found in Prunus sp.[7] The bark of Commiphora angolensis contains condensed tannins.[8]
Commercial sources of condensed tannins are plants such as quebracho wood (Schinopsis lorentzii), mimosa bark (Acacia mollissima), grape seeds (Vitis vinifera), pine barks and spruce barks.[9][10]
Condensed tannins are formed in tannosomes, specialized organelles, in Tracheophytes, i.e. vascular plants.[11]
Dietary supplement[edit]
Pycnogenol is a dietary supplement derived from extracts from maritime pine bark, is standardised to contain 70% procyanidin and is marketed with claims it can treat many conditions; however, according to a 2012 Cochrane review, the evidence is insufficient to support its use for the treatment of any chronic disorder.[12]
Analysis[edit]
Condensed tannins can be characterised by a number of modern techniques including depolymerisation, asymmetric flow field flow fractionation, small-angle X-ray scattering[13] and MALDI-TOF mass spectrometry.[14] Their interactions with proteins can be studied by isothermal titration calorimetry [15] and this provides information on the affinity constant, enthalpy and stoichiometry in the tannin-protein complex.
Depolymerisation[edit]
Depolymerisation reactions are mainly analytical techniques but it is envisaged to use them as means to produce molecules for the chemical industry derived from waste products, such as bark from the wood industry[16] or pomaces from the wine industry.
Depolymerisation is an indirect method of analysis allowing to gain informations such as average degree of polymerisation, percentage of galloylation, etc. The depolymerised sample can be injected on a mass spectrometer with an electrospray ionization source, only able to form ions with smaller molecules.
Oxidative depolymerisation[edit]
The butanol–hydrochloric acid–iron assay[17] (Porter assay) is a colorimetric assay. It is based on acid catalysed oxidative depolymerization of condensed tannins into corresponding anthocyanidins.[18] The method has also been used for determination of bound condensed tannins, but has limitations.[19] This reagent has recently been improved considerably by inclusion of acetone.[20]
Non-oxidative chemical depolymerisation[edit]
The condensed tannins can nevertheless undergo acid-catalyzed cleavage in the presence of (an excess of) a nucleophile[21] like phloroglucinol (reaction called phloroglucinolysis), benzyl mercaptan (reaction called thiolysis), thioglycolic acid (reaction called thioglycolysis) or cysteamine. These techniques are generally called depolymerisation and give informations such as average degree of polymerisation or percentage of galloylation. These are SN1 reactions, a type of substitution reaction in organic chemistry, involving a carbocation intermediate under strongly acidic conditions in polar protic solvents like methanol. The reaction leads to the formation of free and derived monomers that can be further analyzed. The free monomers correspond to the terminal units of the condensed tannins chains. If thiolysis is done directly on plant material (rather than on purified tannins), it is, however, important to subtract naturally occurring free flavanol monomers from the concentration of terminal units that are released during depolymerisation.
Reactions are generally made in methanol, especially thiolysis, as benzyl mercaptan has a low solubility in water. They involve a moderate (40 to 90 °C) heating for a few minutes. Epimerisation may happen.[22]
Phloroglucinolysis can be used for instance for proanthocyanidins characterisation in wine[23] or in the grape seed and skin tissues.[24]
Thioglycolysis can be used to study proanthocyanidins[25] or the oxidation of condensed tannins.[13] It is also used for lignin quantitation.[26] Reaction on condensed tannins from Douglas fir bark produces epicatechin and catechin thioglycolates.[16]
Condensed tannins from Lithocarpus glaber leaves have been analysed through acid-catalyzed degradation in the presence of cysteamine.[6]
Puerarin
From Wikipedia, the free encyclopedia
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| Names | |
|---|---|
| IUPAC name
7-Hydroxy-3-(4-hydroxyphenyl)-8-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
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| Other names
Daidzein-8-C-glucoside
7,4'-Dihydroxy-8-C-glucosylisoflavone | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.130.674 |
PubChem CID
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| Properties | |
| C21H20O9 | |
| Molar mass | 416.38 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Puerarin, one of several known isoflavones, is found in a number of plants and herbs, such as the root of Pueraria (Radix puerariae)[1] notably of the kudzu plant.
List of plants that contain the chemical[edit]
Ursolic acid
From Wikipedia, the free encyclopedia
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| Names | |
|---|---|
| IUPAC name
(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-Hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid[1]
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| Other names
Prunol, Malol, beta-Ursolic acid, NSC4060, CCRIS 7123, TOS-BB-0966, 3-beta-hydroxyurs-12-en-28-oic acid[1]
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.000.941 |
PubChem CID
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| Properties | |
| C30H48O3 | |
| Molar mass | 456.71 g·mol−1 |
| Melting point | 285 to 288 °C (545 to 550 °F; 558 to 561 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Ursolic acid (sometimes referred to as urson, prunol, malol, or 3-beta-3-hydroxy-urs-12-ene-28-oic-acid), is a pentacyclic triterpenoid identified in the epicuticular waxes of apples as early as 1920 and widely found in the peels of fruits, as well as in herbs and spices like rosemary and thyme.[citation needed]
Natural occurrence[edit]
Ursolic acid is present in many plants, such as Mirabilis jalapa,[2] as well as in many fruits and herbs used in daily life (e.g. apples, basil, bilberries, cranberries, elder flower, peppermint, rosemary, lavender, oregano, thyme, hawthorn, and prunes). Apple peels contain large quantities of ursolic acid and related compounds.[citation needed]
Potential biochemical effects[edit]
A number of potential biochemical effects of ursolic acid have been investigated, but there has been no clinical study demonstrating benefits to human health. In vitro, ursolic acid inhibits the proliferation of various cancer cell types by inhibiting the STAT3 activation pathway,[3][4] and may also decrease proliferation of cancer cells and induce apoptosis.[5] Ursolic acid has also been shown to inhibit JNK expression and IL-2 activation of JURKAT leukemic T Cells leading to the reduction in proliferation and T cell activation.[6] Ursolic acid is a weak aromatase inhibitor (IC50 = 32 μM),[7] and has been shown to increase the amount of muscle and brown fat and decrease white fat obesity and associated conditions when added to diets fed to mice.[8] Under physiological concentrations, ursolic acid also induces eryptosis (the apoptosis-like suicidal cell death in defective red blood cells).[9] It has been found to reduce muscle atrophy and to stimulate muscular growth in mice,[10] also shows a potential cardioprotection.[11]
In mice, ursolic acid induces neural regeneration after sciatic nerve injury.[12] Ursolic acid improves domoic acid-induced cognitive deficits in mice.[13] Ursolic acid improves high fat diet-induced cognitive impairments by blocking endoplasmic reticulum stress and IκB kinase β/nuclear factor-κB-mediated inflammatory pathways in mice.[14] Ursolic acid attenuates lipopolysaccharide-induced cognitive deficits in mouse brain through suppressing p38/NF-κB mediated inflammatory pathways.[15] Ursolic acid ameliorates cognition deficits and attenuates oxidative damage in the brain of senescent mice induced by D-galactose.[16] Ursolic acid enhances mouse liver regeneration after partial hepatectomy.[17] Ursolic acid enhances the cellular immune system and pancreatic beta-cell function in streptozotocin-induced diabetic mice fed a high-fat diet.[18] UA increased skeletal muscle mass, as well as grip strength and exercise capacity. Improved endurance, reduced the expression of the genes involved in the development of muscle atrophy, and decreased indicators of accumulated fatigue and exercise-induced stress.[19] Ursolic acid ameliorates aging-metabolic phenotype through promoting of skeletal muscle rejuvenation.[20]
In rats, ursolic acid ameliorated high-fat diet-induced hepatic steatosis and improved metabolic disorders in high-fat diet-induced non-alcoholic fatty liver disease.[21]
Uses[edit]
Ursolic acid is used as a cosmetics additive.[citation needed] Ursolic acid can serve as a starting material for synthesis of more potent bioactive derivatives, such as experimental antitumor agents.[22]
