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Arecatannin

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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.
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-(4β→8)-(-)-epicatechin-(4β→8)-(+)-catechin
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
  • 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
    Key: MOJZMWJRUKIQGL-POEQRLLMSA-N
  • 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
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).
Arecatannin A2
Chemical structure of 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-(4β→8)-(-)-epicatechin-(4β→8)-(-)epicatechin-(4β→8)-(+)-catechin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • 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
    Key: QFLMUASKTWGRQE-MPCJJEQZSA-N
  • 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
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).
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-[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-(4β→8)-(-)epicatechin-(4β→8)-(-)epicatechin-(4β→8)-(-)epicatechin-(4β→8)-(+)-catechin
Identifiers
3D model (JSmol)
ChemSpider
KEGG
  • 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
    Key: QRFZGLTZLZZHCM-QSFSAXMJSA-N
  • 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
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).
Arecatannin B1
Chemical structure of 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-(4β→8)-(-)-epicatechin-(4β→6)-(+)-catechin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • 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
    Key: PBYRKMXDROOXMU-XKDUFCMJSA-N
  • 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
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).
Arecatannin B2
Chemical structure of 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-(4β→8)-(-)-epicatechin-(4β→8)-(-)-epicatechin-(4β→8)-(-)-epicatechin-(4β→6)-(+)-catechin
Identifiers
3D model (JSmol)
ChemSpider
KEGG
  • 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
    Key: OPJKXOWSIGSXPM-BFRGWOJKSA-N
  • 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
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).
Arecatannin C1
Chemical structure of 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-(4β→8)-(+)-catechin-(4α→8)-(+)-catechin
Identifiers
3D model (JSmol)
ChemSpider
KEGG
  • 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
    Key: MOJZMWJRUKIQGL-LKMJJRCWSA-N
  • 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
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).

Known molecules

edit

The following six known arecatannins have been detected in A. catechu seeds.[3][4]

References

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  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.
 

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