WordNet
- any of various complex phenolic substances of plant origin; used in tanning and in medicine (同)tannic_acid
- capable of undergoing hydrolysis
PrepTutorEJDIC
- タンニン(皮なめし・インク製造などに用いられる植物成分)
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/03/25 21:15:11」(JST)
[Wiki en表示]
A hydrolyzable tannin or pyrogallol-type tannin is a type of tannin that, on heating with hydrochloric or sulfuric acids, yields gallic or ellagic acids.[1]
At the center of a hydrolyzable tannin molecule, there is a carbohydrate (usually D-glucose but also cyclitols like quinic or shikimic acids). The hydroxyl groups of the carbohydrate are partially or totally esterified with phenolic groups such as gallic acid in gallotannins or ellagic acid in ellagitannins. Hydrolysable tannins are mixtures of polygalloyl glucoses and/or poly-galloyl quinic acid derivatives containing in between 3 up to 12 gallic acid residues per molecule.[2]
Hydrolyzable tannins are hydrolyzed by weak acids or weak bases to produce carbohydrate and phenolic acids.
Examples of gallotannins are the gallic acid esters of glucose in tannic acid (C76H52O46), found in the leaves and bark of many plant species.
Uses
Tannins, including gallo and ellagic acid (epigallitannins), are inhibitors of HIV replication. 1,3,4-Tri-O-galloylquinic acid, 3,5-di-O-galloyl-shikimic acid, 3,4,5-tri-O-galloylshikimic acid, punicalin, punicalagin inhibited HIV replication in infected H9 lymphocytes with little cytotoxicity. Two compounds, punicalin and punicacortein C, inhibited purified HIV reverse transcriptase.[3]
Hydrolysable tannins have shown also potential antibacterial effects against Helicobacter pylori.[4]
In the past few years, hydrolysable tannins have also been studied for their potential effects against cancer through different mechanisms[5] .[6]
References
- ^ Notes on Tannins from PharmaXChange.info
- ^ Pentagalloyl glucose on www.natural-specialities.com
- ^ Nonaka G, Nishioka I, Nishizawa M, et al. (1990). "Anti-AIDS agents, 2: Inhibitory effects of tannins on HIV reverse transcriptase and HIV replication in H9 lymphocyte cells". J. Nat. Prod. 53 (3): 587–95. doi:10.1021/np50069a008. PMID 1698933.
- ^ Funatogawa K, Hayashi S, Shimomura H, et al. (2004). "Antibacterial activity of hydrolyzable tannins derived from medicinal plants against Helicobacter pylori" (pdf). Microbiol. Immunol. 48 (4): 251–61. PMID 15107535.
- ^ Yang LL, Lee CY, Yen KY (August 2000). "Induction of apoptosis by hydrolyzable tannins from Eugenia jambos L. on human leukemia cells". Cancer Lett. 157 (1): 65–75. doi:10.1016/S0304-3835(00)00477-8. PMID 10893444.
- ^ Tanimura S, Kadomoto R, Tanaka T, Zhang YJ, Kouno I, Kohno M (May 2005). "Suppression of tumor cell invasiveness by hydrolyzable tannins (plant polyphenols) via the inhibition of matrix metalloproteinase-2/-9 activity". Biochem. Biophys. Res. Commun. 330 (4): 1306–13. doi:10.1016/j.bbrc.2005.03.116. PMID 15823585.
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Types of tannins
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| Types |
- Hydrolysable
- Condensed
- Phlorotannins
- Flavono-ellagitannins (complex tannins)
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| Tannin uses |
- Enological
- Drilling
- Ink
- Tanning
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| Other |
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| Miscellaneous |
- Pseudo tannins
- Synthetic tannins
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Types of hydrolysable tannins
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| Carbohydrates |
- Glucose
- Quinic acid
- Shikimic acid
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| Types |
- Ellagitannins
- Gallotannins
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| unclassified |
- 1,2-di-O-galloyl-3-O-digalloyl-4,6-O-(S)-hexa- hydroxydiphenoy-β-D-glucose
- 2,3-(S)-Hexahydroxydiphenoyl-D-glucose
- Alienanin B
- Alunusnin A
- Aromatinin A
- Castavaloninic acid
- Chebulagic acid
- Cinchotannic acid
- Cocciferin D2
- Emblicanins (Emblicanin A and Emblicanin B)
- Euprostin A
- Flavogallonic acid
- Flavogallonic acid dilactone
- Heterophylliin D
- Helioscopin A (1,6-(S)-hexahydroxydiphenoyl-2,4-(R)-elaeocarpusinoyl-3-O-galloyl-β-D-glucose)
- Helioscopin B (1,3,6-tri-O-galloyl-2,4-(R)-elaeocarpusinoyl-β-D-glucose)
- Helioscopinin A (1,6-(S)-hexahydroxydiphenoyl-2,4-(S)-dehydrohexahydroxydiphenoyl-3-O-galloyl-β-D-glucose)
- Helioscopinin B (1,6-(S)-hexahydroxydiphenoyl-3-O-galloyl-β-D-glucose)
- Hipophaenin D
- Isostrictinin
- Kinotannic acid
- Platycaryanin A
- Rugosin C, D and F
- Squarrosanin A
- Strictinin
- Syzyginin A
- Tannic acid
- Tellimagrandin I
- Tercatin
- Tergallagin
- Theograndins I and II
- Vescalin
- Valoneic acid
- Valoneic acid dilactone
- Vescavaloneic acid/Castavaloneic acid
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| Other |
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UpToDate Contents
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English Journal
- Polysaccharides from by-products of the Wonderful and Laffan pomegranate varieties: New insight into extraction and characterization.
- Khatib M1, Giuliani C1, Rossi F2, Adessi A2, Al-Tamimi A3, Mazzola G4, Di Gioia D4, Innocenti M1, Mulinacci N5.
- Food chemistry.Food Chem.2017 Nov 15;235:58-66. doi: 10.1016/j.foodchem.2017.05.041. Epub 2017 May 10.
- PMID 28554647
- Oxygen consumption rates by different oenological tannins in a model wine solution.
- Pascual O1, Vignault A2, Gombau J1, Navarro M1, Gómez-Alonso S3, García-Romero E4, Canals JM1, Hermosín-Gutíerrez I5, Teissedre PL6, Zamora F7.
- Food chemistry.Food Chem.2017 Nov 1;234:26-32. doi: 10.1016/j.foodchem.2017.04.148. Epub 2017 Apr 29.
- PMID 28551234
- Structures and Antibacterial Properties of Isorugosins H-J, Oligomeric Ellagitannins from Liquidambar formosana with Characteristic Bridging Groups between Sugar Moieties.
- Shimozu Y1, Kuroda T2, Tsuchiya T3, Hatano T1.
- Journal of natural products.J Nat Prod.2017 Oct 11. doi: 10.1021/acs.jnatprod.7b00496. [Epub ahead of print]
- PMID 29019685
Japanese Journal
- Castalagin Exerts Inhibitory Effects on Osteoclastogenesis Through Blocking a Broad Range of Signaling Pathways with Low Cytotoxicity
- Iwatake Mayumi,Okamoto Kuniaki,Tanaka Takashi,Tsukuba Takayuki
- Phytotherapy Research 29(6), 917-924, 2015-06
- … Castalagin is a rare plant polyphenol that is classified as a hydrolyzable tannin. …
- NAID 120005621903
- 抗酸化性ポリフェノールの探索及び機能開発に関する研究
- 抗酸化性ポリフェノールの探索及び機能開発に関する研究
- 好村 守生
- 薬学雑誌. 乙号 134(9), 957-964, 2014
- … In an exploratory study of natural antioxidants with biological effects, we investigated the tannin constituents of myrtaceous plants reported to be rich in polyphenols. …
- NAID 130004684827
Related Links
- Tannase (tannin acylhydrolase, EC 3.1.1.20) catalyzes the hydrolysis of bonds present in hydrolyzable tannins and gallic acid esters (Lekha & Lonsane, 1997). It is an extracellular, inducible enzyme produced by bacteria, fungi
- Hydrolyzable tannins are derivatives of gallic acid (3, 4, 5‐trihydroxyl benzoic acid). Gallic acid is esterified to a core polyol, and the galloyl groups may be further esterified or oxidatively crosslinked to yield more complex
- Key words: high molecular weight polyphenols, tannin, proanthocyanidin , hydrolyzable tannin oligomer, intermolecular C-O oxidative coupling, dendrimer, biological activity, corn-plexation between tannin and protein 近年,ナ ノ ...
★リンクテーブル★
[★]
- 関
- hydrolysable、hydrolytic
[★]
タンニン
- 関
- tannic acid