Arecatannin
Chemical structure of arecatannin A1. | |
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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 | |
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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 |
Chemical compound
Chemical structure of arecatannin A2. | |
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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 | |
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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 |
Chemical compound
Chemical structure of arecatannin A3. | |
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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 |
Chemical compound
Chemical structure of arecatannin B1. | |
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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 | |
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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 |
Chemical compound
Chemical structure of arecatannin B2. | |
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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 | |
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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 |
Chemical compound
Chemical structure of arecatannin C1. | |
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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 | |
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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 |
Chemical compound
Group of chemical compounds
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]
Known molecules
The following six known arecatannins have been detected in A. catechu seeds.[3][4]
- Arecatannin A1
- Arecatannin A2
- Arecatannin A3
- Arecatannin B1
- Arecatannin B2
- Arecatannin C1
References
- ^ 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). 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.
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Types of procyanidins
- Dimers : Procyanidin A1
- A2
- Trimers:Cinnamtannin B1
- Tetramers: Arecatannin A2
- Dimers : Procyanidin B1
- B2
- B3
- B4
- B5
- B6
- B8
- D (ent-Epicatechin(4α→8)catechin)
- Trimers: Arecatannin B1 (epicatechin-(4β→8)-epicatechin-(4β→6)-catechin)
- Procyanidin C1 (epicatechin-(4β→8)-epicatechin-(4β→8)-epicatechin)
- Procyanidin C2 (catechin-(4α→8)-catechin-(4α→8)-catechin)
- Tetramers : Cinnamtannin A2
- Arecatannins
- Arecatannin A1
- Arecatannin A3
- Arecatannin B2
- Arecatannin C1
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