Arecatannin

Last updated
Arecatannin A1
Arecatannin A1.svg
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
PubChem CID
  • 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
  • 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
Arecatannin A2.svg
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
KEGG
PubChem CID
  • 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
  • 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
Arecatannin A3.svg
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)
KEGG
PubChem CID
  • 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
  • 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
Arecatannin B1 v2.svg
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
PubChem CID
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
  • 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
Arecatannin B2.svg
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)
KEGG
PubChem CID
  • 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
  • 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
Arecatannin C1.svg
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)
KEGG
PubChem CID
  • 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
  • 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).

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]

Related Research Articles

<i>Acacia sensu lato</i> Genus of legumes

Acacia s.l., known commonly as mimosa, acacia, thorntree or wattle, is a polyphyletic genus of shrubs and trees belonging to the subfamily Mimosoideae of the family Fabaceae. It was described by the Swedish botanist Carl Linnaeus in 1773 based on the African species Acacia nilotica. Many non-Australian species tend to be thorny, whereas the majority of Australian acacias are not. All species are pod-bearing, with sap and leaves often bearing large amounts of tannins and condensed tannins that historically found use as pharmaceuticals and preservatives.

<span class="mw-page-title-main">Areca nut</span> Fruit of the areca palm chewed as a stimulant

The areca nut is the fruit of the areca palm, which grows in much of the tropical Pacific, South Asia, Southeast Asia, and parts of east Africa. It is commonly referred to as betel nut, not to be confused with betel leaves that are often used to wrap it. Consumption has many harmful effects on health and is carcinogenic to humans. Various compounds present in the nut, including arecoline, contribute to histologic changes in the oral mucosa. It is known to be a major risk factor for cancers of the mouth and esophagus. As with chewing tobacco, its use is discouraged by preventive efforts. Consumption by hundreds of millions of people worldwide – mainly of South Asian or Southeast Asian origins – has been described as a "neglected global public health emergency".

<span class="mw-page-title-main">Tannin</span> Class of astringent, bitter plant polyphenolic chemical compounds

Tannins are a class of astringent, polyphenolic biomolecules that bind to and precipitate proteins and various other organic compounds including amino acids and alkaloids.

<i>Areca</i> Genus of palms

Areca is a genus of 51 species of palms in the family Arecaceae, found in humid tropical forests from the islands of the Philippines, Malaysia and India, across Southeast Asia to Melanesia. The generic name Areca is derived from a name used locally on the Malabar Coast of India.

<span class="mw-page-title-main">Ruminant</span> Hoofed herbivorous grazing or browsing mammals

Ruminants are hoofed herbivorous grazing or browsing mammals that are able to acquire nutrients from plant-based food by fermenting it in a specialized stomach prior to digestion, principally through microbial actions. The process, which takes place in the front part of the digestive system and therefore is called foregut fermentation, typically requires the fermented ingesta to be regurgitated and chewed again. The process of rechewing the cud to further break down plant matter and stimulate digestion is called rumination. The word "ruminant" comes from the Latin ruminare, which means "to chew over again".

<span class="mw-page-title-main">Betel</span> Species of plant

The betel is a vine of the family Piperaceae, which includes pepper and kava. The betel plant is native to Southeast Asia. It is an evergreen, dioecious perennial, with glossy heart-shaped leaves and white catkins. Betel plants are cultivated for their leaves which is most commonly used as flavoring in chewing areca nut.

<span class="mw-page-title-main">Catechu</span> Extract of acacia trees

Catechu is an extract of acacia trees used variously as a food additive, astringent, tannin, and dye. It is extracted from several species of Acacia, but especially Senegalia catechu, by boiling the wood in water and evaporating the resulting brew. It is also known as cutch, black cutch, cachou, cashoo, terra Japonica, or Japan earth, and also katha in Hindi, kaath in Marathi, khaira in Odia, khoyer in Assamese and Bengali, and kachu in Malay.

<span class="mw-page-title-main">Betel nut chewing</span> Preparation of betel leaf and areca nut

Betel nut chewing, also called betel quid chewing or areca nut chewing, is a practice in which areca nuts are chewed together with slaked lime and betel leaves for their stimulant and narcotic effects. The practice is widespread in Southeast Asia, Micronesia, Island Melanesia, and South Asia. It is also found among the indigenous peoples of Taiwan, Madagascar and parts of southern China. It has also been introduced to the Caribbean in colonial times.

<i>Areca catechu</i> Species of palm

Areca catechu is a species of palm which grows in much of the tropical Pacific, Asia, and parts of east Africa. The palm is believed to have originated in the Philippines, but is widespread in cultivation and is considered naturalized in southern China, Taiwan, India, Bangladesh, the Maldives, Sri Lanka, Cambodia, Laos, Thailand, Vietnam, Malaysia, Indonesia, New Guinea, many of the islands in the Pacific Ocean, and also in the West Indies.

<i>Nuphar</i> Genus of aquatic plants

Nuphar is a genus of aquatic plants in the family Nymphaeaceae, with a temperate to subarctic Northern Hemisphere distribution. Common names include water-lily, pond-lily, alligator-bonnet or bonnet lily, and spatterdock.

<i>Acacia</i> Genus of plants

Acacia, commonly known as the wattles or acacias, is a large genus of shrubs and trees in the subfamily Mimosoideae of the pea family Fabaceae. Initially, it comprised a group of plant species native to Africa and Australasia. The genus name is New Latin, borrowed from the Greek ἀκακία, a term used by Dioscorides for a preparation extracted from the leaves and fruit pods of Vachellia nilotica, the original type of the genus. In his Pinax (1623), Gaspard Bauhin mentioned the Greek ἀκακία from Dioscorides as the origin of the Latin name.

<span class="mw-page-title-main">Arecoline</span> Mild stimulant

Arecoline is a nicotinic acid-based mild parasympathomimetic stimulant alkaloid found in the areca nut, the fruit of the areca palm. It is an odourless oily liquid. It can bring a sense of enhanced alertness and energy, euphoria and relaxation. Its psychoactive effects are comparable to that of nicotine.

<span class="mw-page-title-main">Procyanidin</span>

Procyanidins are members of the proanthocyanidin class of flavonoids. They are oligomeric compounds, formed from catechin and epicatechin molecules. They yield cyanidin when depolymerized under oxidative conditions.

<i>Senegalia catechu</i> Species of legume

Senegalia catechu is a deciduous, thorny tree which grows up to 15 m (50 ft) in height. The plant is called khair in Hindi, and kachu in Malay, hence the name was Latinized to "catechu" in Linnaean taxonomy, as the type-species from which the extracts cutch and catechu are derived. Common names for it include kher, catechu, cachou, cutchtree, black cutch, and black catechu.

<span class="mw-page-title-main">Euphoria</span> Intense feelings of well-being

Euphoria is the experience of pleasure or excitement and intense feelings of well-being and happiness. Certain natural rewards and social activities, such as aerobic exercise, laughter, listening to or making music and dancing, can induce a state of euphoria. Euphoria is also a symptom of certain neurological or neuropsychiatric disorders, such as mania. Romantic love and components of the human sexual response cycle are also associated with the induction of euphoria. Certain drugs, many of which are addictive, can cause euphoria, which at least partially motivates their recreational use.

<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

<span class="mw-page-title-main">Leucocyanidin</span> Chemical compound

Leucocyanidin is a colorless chemical compound that is a member of the class of natural products known as leucoanthocyanidins.

<span class="mw-page-title-main">Phlobaphene</span>

Phlobaphenes are reddish, alcohol-soluble and water-insoluble phenolic substances. They can be extracted from plants, or be the result from treatment of tannin extracts with mineral acids. The name phlobaphen come from the Greek roots φλoιὀς (phloios) meaning bark and βαφή (baphe) meaning dye.

<span class="mw-page-title-main">Gambier (extract)</span>

Gambier or gambir is an extract derived from the leaves of Uncaria gambir, a climbing shrub native to tropical Southeast Asia. Gambier is produced in Indonesia and Malaysia where it was an important trade item into the late nineteenth century. It can be used as a tanning agent, a brown dye, a food additive and as herbal medicine. Also known as pale catechu, white catechu or Japan Earth, it is often confused with other forms of catechu.

<span class="mw-page-title-main">Areca nut production in India</span>

Areca nut production in India is dominant in the coastal region within 400 kilometres (250 mi) from the coast line, and also in some other non-coastal states of India. Areca nut, a tropical crop, is popularly known as betel nut, as its common usage in the country is for mastication with betel leaves. It is a palm tree species under the family of Arecaceae. It has commercial and economic importance not only in India but also in China and Southeast Asia.

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.