Arecatannins are a class of condensed tannins in the sub-class procyanidins contained in the seeds of Areca catechu also called betel nut.[1] The arecatannin-type natural products from Ceylonese cassia bark and Areca seed are examples of polyphenols by both current definitions, and fit the distinct definition of a polymeric phenol as well.[2]
^Screening of various plant extracts used in ayurvedic medicine for inhibitory effects on human immunodeficiency virus type 1 (HIV-1) protease. Ines Tomoco Kusumoto, Takeshi Nakabayashi1, Hiroaki Kida, Hirotsugu Miyashiro, Masao Hattori, Tsuneo Namba and Kunitada Shimotohno, Phytotherapy Research, Volume 9, Issue 3, May 1995, pp. 180–184, doi:10.1002/ptr.2650090305
^"Isolation and structure elucidation of tannins. G. Nonaka, Pure & Appl. Chem.,Vol. 61, No. 3, pp. 357–360, 1989" (PDF). (PDF) from the original on 2012-11-28. Retrieved 2011-05-27.
^"KEGG DRUG: Areca". www.genome.jp. from the original on 2017-03-25. Retrieved 2023-01-20.
^Peng, Wei; Liu, Yu-Jie; Wu, Na; Sun, Tao; He, Xiao-Yan; Gao, Yong-Xiang; Wu, Chun-Jie (April 2015). "Areca catechu L. (Arecaceae): A review of its traditional uses, botany, phytochemistry, pharmacology and toxicology". Journal of Ethnopharmacology. 164: 340–356. doi:10.1016/j.jep.2015.02.010.
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arecatannin, class, condensed, tannins, class, procyanidins, contained, seeds, areca, catechu, also, called, betel, arecatannin, type, natural, products, from, ceylonese, cassia, bark, areca, seed, examples, polyphenols, both, current, definitions, distinct, d. Arecatannins are a class of condensed tannins in the sub class procyanidins contained in the seeds of Areca catechu also called betel nut 1 The arecatannin type natural products from Ceylonese cassia bark and Areca seed are examples of polyphenols by both current definitions and fit the distinct definition of a polymeric phenol as well 2 Arecatannin A1 Chemical structure of arecatannin A1 Names IUPAC name 2R 3R 4S 2 3 4 dihydroxyphenyl 4 2R 3S 2 3 4 dihydroxyphenyl 3 5 7 trihydroxy 3 4 dihydro 2H chromen 8 yl 8 2R 3R 4R 2 3 4 dihydroxyphenyl 3 5 7 trihydroxy 3 4 dihydro 2H chromen 4 yl 3 4 dihydro 2H chromene 3 5 7 triol Other names Procyanidin T2 Epicatechin 4b 8 epicatechin 4b 8 catechin Identifiers CAS Number 79813 67 5 3D model JSmol Interactive image ChEMBL ChEMBL4476324 ChemSpider 10290129 KEGG C17894 PubChem CID 13752000 InChI InChI 1S C45H38O18 c46 18 10 27 54 33 32 11 18 61 42 16 2 5 21 48 25 52 8 16 39 59 37 33 35 29 56 14 30 57 36 38 40 60 43 63 45 35 36 17 3 6 22 49 26 53 9 17 34 28 55 13 23 50 19 12 31 58 41 62 44 19 34 15 1 4 20 47 24 51 7 15 h1 11 13 14 31 37 43 46 60H 12H2 t31 37 38 39 40 41 42 43 m0 s1 SMILES OC1 C2C C C O C1 C H 3C 4C O C H C H 3O C5 CC O C O C C5 CC O CC4O O C H C H O C H 2C6 C7C C C H O C H O7 C8 CC O C O C C8 C O C C6O C9 CC O C O C C9 Properties Chemical formula C45H38O18 Molar mass 866 77 g mol Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Arecatannin A2 Chemical structure of arecatannin A2 Names IUPAC name 2R 3R 4R 2 3 4 dihydroxyphenyl 4 2R 3R 4S 2 3 4 dihydroxyphenyl 4 2R 3S 2 3 4 dihydroxyphenyl 3 5 7 trihydroxy 3 4 dihydro 2H chromen 8 yl 3 5 7 trihydroxy 3 4 dihydro 2H chromen 8 yl 8 2R 3R 4R 2 3 4 dihydroxyphenyl 3 5 7 trihydroxy 3 4 dihydro 2H chromen 4 yl 3 4 dihydro 2H chromene 3 5 7 triol Other names Epicatechin 4b 8 epicatechin 4b 8 epicatechin 4b 8 catechin Identifiers CAS Number 79763 29 4 3D model JSmol Interactive image ChEBI CHEBI 192503 KEGG C17893 PubChem CID 16142155 InChI InChI 1S C60H50O24 c61 23 13 34 71 42 41 14 23 81 55 20 2 6 26 63 31 68 10 20 51 78 48 42 44 36 73 17 38 75 46 50 53 80 57 83 59 44 46 22 4 8 28 65 33 70 12 22 47 39 76 18 37 74 45 49 52 79 56 84 60 45 47 21 3 7 27 64 32 69 11 21 43 35 72 16 29 66 24 15 40 77 54 82 58 24 43 19 1 5 25 62 30 67 9 19 h1 14 16 18 40 48 57 61 80H 15H2 t40 48 49 50 51 52 53 54 55 56 57 m0 s1 SMILES O C H 1 C H C 2C C C O CC2O C H 3C 4C O C H C H 3O C5 CC O C O C C5 CC O CC4O O C H 1C6 CC O C O C C6 C7 C8C C H C H O C H O8 C9 CC O C O C C9 C 10 C 11C C C H O C H O 11 C 12 CC O C O C C 12 C O C C 10O C O C C7O Properties Chemical formula C60H50O24 Molar mass 1155 03 g mol Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Arecatannin A3 Chemical structure of arecatannin A3 Names Other names 2R 2 R 2 R 2 R 2 R 3R 3 R 3 R 3 R 3 S 4R 4 R 4 R 4 S 2 2 2 2 2 pentakis 3 4 dihydroxyphenyl 3 3 3 3 3 4 4 4 4 4 decahydro 4 8 4 8 4 8 4 8 quinque 2H 1 benzopyran 3 3 3 3 3 5 5 5 5 5 7 7 7 7 7 pentadecol Epicatechin 4b 8 epicatechin 4b 8 epicatechin 4b 8 epicatechin 4b 8 catechin Identifiers CAS Number 86588 85 4 3D model JSmol Interactive image KEGG C17895 PubChem CID 16162334 InChI InChI 1S C75H62O30 c76 28 16 41 88 51 50 17 28 101 68 24 2 7 31 78 37 84 12 24 63 97 59 51 53 43 90 20 45 92 55 61 65 99 70 103 73 53 55 26 4 9 33 80 39 86 14 26 57 47 94 22 48 95 58 62 66 100 71 105 75 57 58 27 5 10 34 81 40 87 15 27 56 46 93 21 44 91 54 60 64 98 69 104 74 54 56 25 3 8 32 79 38 85 13 25 52 42 89 19 35 82 29 18 49 96 67 102 72 29 52 23 1 6 30 77 36 83 11 23 h1 17 19 22 49 59 71 76 100H 18H2 t49 59 60 61 62 63 64 65 66 67 68 69 70 71 m0 s1 SMILES OC1 C2C C C O C1 C H 3C 4C C C O CC4O C H 5C 6C O C H C H 5O C7 CC O C O C C7 CC O CC6O O C H C H 3O C8 CC O C O C C8 O C H C H O C H 2C9 C 10C C H C H O C H O 10 C 11 CC O C O C C 11 C 12 C 13C C C H O C H O 13 C 14 CC O C O C C 14 C O C C 12O C O C C9O C 15 CC O C O C C 15 Properties Chemical formula C75H62O30 Molar mass 1443 28 g mol Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Arecatannin B1 Chemical structure of arecatannin B1 Names IUPAC name 2R 3R 4S 2 3 4 dihydroxyphenyl 4 2R 3S 2 3 4 dihydroxyphenyl 3 5 7 trihydroxy 3 4 dihydro 2H chromen 6 yl 8 2R 3R 4R 2 3 4 dihydroxyphenyl 3 5 7 trihydroxy 3 4 dihydro 2H chromen 4 yl 3 4 dihydro 2H chromene 3 5 7 triol Other names Epicatechin 4b 8 epicatechin 4b 6 catechin Identifiers CAS Number 79763 28 3 3D model JSmol Interactive image ChEBI CHEBI 75642 ChemSpider 10290128 KEGG C17892 PubChem CID 14237657 UNII 3S8S4BYC2M InChI InChI 1S C45H38O18 c46 18 10 26 53 33 32 11 18 62 43 16 2 5 21 48 24 51 8 16 40 59 37 33 35 27 54 13 28 55 36 38 41 60 44 63 45 35 36 17 3 6 22 49 25 52 9 17 34 29 56 14 31 19 39 34 58 12 30 57 42 61 31 15 1 4 20 47 23 50 7 15 h1 11 13 14 30 37 38 40 44 46 60H 12H2 t30 37 38 40 41 42 43 44 m0 s1 SMILES OC 1C C2C C H C H O C H O2 C3 CC O C O C C3 C 4C O C5C CC4O O C H C H O C5 C6 CC O C O C C6 C O C1 C H 7C 8C O C H C H 7O C9 CC O C O C C9 CC O CC8O Properties Chemical formula C45H38O18 Molar mass 866 77 g mol Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Arecatannin B2 Chemical structure of arecatannin B2 Names IUPAC name 2R 3R 4R 2 3 4 dihydroxyphenyl 4 2R 3R 4R 2 3 4 dihydroxyphenyl 4 2R 3R 4S 2 3 4 dihydroxyphenyl 4 2R 3S 2 3 4 dihydroxyphenyl 3 5 7 trihydroxy 3 4 dihydro 2H chromen 6 yl 3 5 7 trihydroxy 3 4 dihydro 2H chromen 8 yl 3 5 7 trihydroxy 3 4 dihydro 2H chromen 8 yl 8 2R 3R 4R 2 3 4 dihydroxyphenyl 3 5 7 trihydroxy 3 4 dihydro 2H chromen 4 yl 3 4 dihydro 2H chromene 3 5 7 triol Other names Epicatechin 4b 8 epicatechin 4b 8 epicatechin 4b 8 epicatechin 4b 6 catechin Identifiers CAS Number 86588 86 5 3D model JSmol Interactive image KEGG C17896 PubChem CID 71448962 InChI InChI 1S C75H62O30 c76 28 16 40 87 51 50 17 28 102 69 24 2 7 31 78 36 83 12 24 64 97 59 51 53 41 88 19 43 90 55 61 66 99 71 104 73 53 55 26 4 9 33 80 38 85 14 26 57 45 92 21 46 93 58 62 67 100 72 105 75 57 58 27 5 10 34 81 39 86 15 27 56 44 91 20 42 89 54 60 65 98 70 103 74 54 56 25 3 8 32 79 37 84 13 25 52 47 94 22 49 29 63 52 96 18 48 95 68 101 49 23 1 6 30 77 35 82 11 23 h1 17 19 22 48 59 62 64 72 76 100H 18H2 t48 59 60 61 62 64 65 66 67 68 69 70 71 72 m0 s1 SMILES OC 1C C2C C H C H O C H O2 C3 CC O C O C C3 C4 C5C C H C H O C H O5 C6 CC O C O C C6 C 7C O C8C CC7O O C H C H O C8 C9 CC O C O C C9 C O C C4O C O C1 C H 10C 11C C C O CC 11O C H 12C 13C O C H C H 12O C 14 CC O C O C C 14 CC O CC 13O O C H C H 10O C 15 CC O C O C C 15 Properties Chemical formula C75H62O30 Molar mass 1443 28 g mol Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Arecatannin C1 Chemical structure of arecatannin C1 Names IUPAC name 2R 3S 4R 2 3 4 dihydroxyphenyl 4 2R 3S 2 3 4 dihydroxyphenyl 3 5 7 trihydroxy 3 4 dihydro 2H chromen 8 yl 8 2R 3R 4R 2 3 4 dihydroxyphenyl 3 5 7 trihydroxy 3 4 dihydro 2H chromen 4 yl 3 4 dihydro 2H chromene 3 5 7 triol Other names Procyanidin C4 Epicatechin 4b 8 catechin 4a 8 catechin Identifiers CAS Number 87727 69 3 3D model JSmol Interactive image KEGG C17897 PubChem CID 9876038 InChI InChI 1S C45H38O18 c46 18 10 27 54 33 32 11 18 61 42 16 2 5 21 48 25 52 8 16 39 59 37 33 35 29 56 14 30 57 36 38 40 60 43 63 45 35 36 17 3 6 22 49 26 53 9 17 34 28 55 13 23 50 19 12 31 58 41 62 44 19 34 15 1 4 20 47 24 51 7 15 h1 11 13 14 31 37 43 46 60H 12H2 t31 37 38 39 40 41 42 43 m0 s1 SMILES OC1 C2C C C O C1 C H 3C 4C O C H C H 3O C5 CC O C O C C5 CC O CC4O O C H C H O C H 2C6 C7C C C H O C H O7 C8 CC O C O C C8 C O C C6O C9 CC O C O C C9 Properties Chemical formula C45H38O18 Molar mass 866 77 g mol Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesKnown molecules editThe following six known arecatannins have been detected in A catechu seeds 3 4 Arecatannin A1 Arecatannin A2 Arecatannin A3 Arecatannin B1 Arecatannin B2 Arecatannin C1References edit Screening of various plant extracts used in ayurvedic medicine for inhibitory effects on human immunodeficiency virus type 1 HIV 1 protease Ines Tomoco Kusumoto Takeshi Nakabayashi1 Hiroaki Kida Hirotsugu Miyashiro Masao Hattori Tsuneo Namba and Kunitada Shimotohno Phytotherapy Research Volume 9 Issue 3 May 1995 pp 180 184 doi 10 1002 ptr 2650090305 Isolation and structure elucidation of tannins G Nonaka Pure amp Appl Chem Vol 61 No 3 pp 357 360 1989 PDF Archived PDF from the original on 2012 11 28 Retrieved 2011 05 27 KEGG DRUG Areca www genome jp Archived from the original on 2017 03 25 Retrieved 2023 01 20 Peng Wei Liu Yu Jie Wu Na Sun Tao He Xiao Yan Gao Yong Xiang Wu Chun Jie April 2015 Areca catechu L Arecaceae A review of its traditional uses botany phytochemistry pharmacology and toxicology Journal of Ethnopharmacology 164 340 356 doi 10 1016 j jep 2015 02 010 nbsp This article about an aromatic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Arecatannin amp oldid 1135060161, wikipedia, wiki, book, books, library,
