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Arecatannin

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Arecatannin A1
Chemical structure of arecatannin A1.
Chemical structure of arecatannin A1.
Names
IUPAC name (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4--8--3,4-dihydro-2H-chromene-3,5,7-triol
Other names
  • Procyanidin T2
  • (-)-Epicatechin-(4β→8)-(-)-epicatechin-(4β→8)-(+)-catechin
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
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/s1Key: MOJZMWJRUKIQGL-POEQRLLMSA-N
SMILES
  • OC1=C2C(=C(C(O)=C1)3C=4C(O(3O)C5=CC(O)=C(O)C=C5)=CC(O)=CC4O)O((O)2C6=C7C(C(O)(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 , 100 kPa). Infobox references
Chemical compound
Arecatannin A2
Chemical structure of arecatannin A2.
Chemical structure of arecatannin A2.
Names
IUPAC name (2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4--3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-8--3,4-dihydro-2H-chromene-3,5,7-triol
Other names
  • (-)-Epicatechin-(4β→8)-(-)-epicatechin-(4β→8)-(-)epicatechin-(4β→8)-(+)-catechin
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
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/s1Key: QFLMUASKTWGRQE-MPCJJEQZSA-N
SMILES
  • O1(C=2C(=C(C(O)=CC2O)3C=4C(O(3O)C5=CC(O)=C(O)C=C5)=CC(O)=CC4O)O1C6=CC(O)=C(O)C=C6)C7=C8C(((O)(O8)C9=CC(O)=C(O)C=C9)C%10=C%11C(C(O)(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 , 100 kPa). Infobox references
Chemical compound
Arecatannin A3
Chemical structure of 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--3,3′,3′′,3′′′,3′′′′,5,5′,5′′,5′′′,5′′′′,7,7′,7′′,7′′′,7′′′′-pentadecol
  • (-)-Epicatechin-(4β→8)-(-)epicatechin-(4β→8)-(-)epicatechin-(4β→8)-(-)epicatechin-(4β→8)-(+)-catechin
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
KEGG
PubChem CID
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/s1Key: QRFZGLTZLZZHCM-QSFSAXMJSA-N
SMILES
  • OC1=C2C(=C(C(O)=C1)3C=4C(=C(C(O)=CC4O)5C=6C(O(5O)C7=CC(O)=C(O)C=C7)=CC(O)=CC6O)O(3O)C8=CC(O)=C(O)C=C8)O((O)2C9=C%10C(((O)(O%10)C%11=CC(O)=C(O)C=C%11)C%12=C%13C(C(O)(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 , 100 kPa). Infobox references
Chemical compound
Arecatannin B1
Chemical structure of arecatannin B1.
Chemical structure of arecatannin B1.
Names
IUPAC name (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4--8--3,4-dihydro-2H-chromene-3,5,7-triol
Other names
  • (-)-Epicatechin-(4β→8)-(-)-epicatechin-(4β→6)-(+)-catechin
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
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/s1Key: PBYRKMXDROOXMU-XKDUFCMJSA-N
SMILES
  • OC=1C(=C2C(((O)(O2)C3=CC(O)=C(O)C=C3)C=4C(O)=C5C(=CC4O)O((O)C5)C6=CC(O)=C(O)C=C6)=C(O)C1)7C=8C(O(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 , 100 kPa). Infobox references
Chemical compound
Arecatannin B2
Chemical structure of arecatannin B2.
Chemical structure of arecatannin B2.
Names
IUPAC name (2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4--3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-8--3,4-dihydro-2H-chromene-3,5,7-triol
Other names
  • (-)-Epicatechin-(4β→8)-(-)-epicatechin-(4β→8)-(-)-epicatechin-(4β→8)-(-)-epicatechin-(4β→6)-(+)-catechin
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
KEGG
PubChem CID
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/s1Key: OPJKXOWSIGSXPM-BFRGWOJKSA-N
SMILES
  • OC=1C(=C2C(((O)(O2)C3=CC(O)=C(O)C=C3)C4=C5C(((O)(O5)C6=CC(O)=C(O)C=C6)C=7C(O)=C8C(=CC7O)O((O)C8)C9=CC(O)=C(O)C=C9)=C(O)C=C4O)=C(O)C1)%10C=%11C(=C(C(O)=CC%11O)%12C=%13C(O(%12O)C%14=CC(O)=C(O)C=C%14)=CC(O)=CC%13O)O(%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 , 100 kPa). Infobox references
Chemical compound
Arecatannin C1
Chemical structure of arecatannin C1.
Chemical structure of arecatannin C1.
Names
IUPAC name (2R,3S,4R)-2-(3,4-dihydroxyphenyl)-4--8--3,4-dihydro-2H-chromene-3,5,7-triol
Other names
  • Procyanidin C4
  • (-)-Epicatechin-(4β→8)-(+)-catechin-(4α→8)-(+)-catechin
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
KEGG
PubChem CID
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/s1Key: MOJZMWJRUKIQGL-LKMJJRCWSA-N
SMILES
  • OC1=C2C(=C(C(O)=C1)3C=4C(O(3O)C5=CC(O)=C(O)C=C5)=CC(O)=CC4O)O((O)2C6=C7C(C(O)(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 , 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. 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.

Known molecules

The following six known arecatannins have been detected in A. catechu seeds.

References

  1. 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
  2. "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.
  3. "KEGG DRUG: Areca". www.genome.jp. Archived from the original on 2017-03-25. Retrieved 2023-01-20.
  4. 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. PMID 25681543.
Types of procyanidins
A-type proanthocyanidins
B type proanthocyanidins
Types
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