Chebulinic acid

Last updated
Chebulinic acid
Chebulinic acid.svg
Names
Other names
1,3,6-Tri-O-galloyl-2,4-chebuloyl-β-D-glucopyranoside [1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49, 50)/t14-,22+,24-,30-,31+,33-,34+,41-/m0/s1
    Key: YGVHOSGNOYKRIH-FJPMMHPYSA-N
  • C1=C(C=C(C(=C1O)O)O)C(=O)OCC2C3C(C(C(O2)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C6=C5C(C(C(=O)O3)CC(=O)O)C(C(=O)O6)O)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O
Properties
C41H32O27
Molar mass 956.680 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chebulinic acid is an ellagitannin found in the seeds of Euphoria longana , in the fruits of Terminalia chebula [2] or in the leaves of T. macroptera .

Related Research Articles

<i>Terminalia</i> (plant) Genus of flowering plants

Terminalia is a genus of large trees of the flowering plant family Combretaceae, comprising nearly 300 species distributed in tropical regions of the world. The genus name derives from the Latin word terminus, referring to the fact that the leaves appear at the very tips of the shoots.

The common name myrobalan can refer to several unrelated fruit-bearing plant species:

<i>Terminalia chebula</i> Species of flowering plant

Terminalia chebula, commonly known as black- or chebulic myrobalan, is a species of Terminalia, native to South Asia from Pakistan, India and Nepal east to southwest China (Yunnan), and south to Sri Lanka, Malaysia, and Vietnam.

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

Chebulagic acid is a benzopyran tannin and an antioxidant that has many potential uses in medicine.

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

Ethyl gallate is a food additive with E number E313. It is the ethyl ester of gallic acid. Ethyl gallate is added to food as an antioxidant.

A hydrolysable tannin or pyrogallol-type tannin is a type of tannin that, on heating with hydrochloric or sulfuric acids, yields gallic or ellagic acids.

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

Terflavin B is an ellagitannin, a type of hydrolysable tannin. It can be found in Myrobalanus chebula, the black chebulic, and in Terminalia catappa, the Indian almond.

Ketapangia leucochorda is a moth of the family Gracillariidae. It is known from India, Japan and Kiribati.

Acrocercops niphocremna is a moth of the family Gracillariidae, known from Maharashtra, India. It was described by Edward Meyrick in 1932. The hostplant for the species is Terminalia chebula.

Tergallic acids are trimers of gallic acid, often found naturally in the form of glycosides. Tergallic acid O- or C-glucosides that can be found in acorns of several Quercus (oak) species. The dehydrated tergallic acid C-glucoside and tergallic acid O-glucoside can be characterised in the acorns of Quercus macrocarpa. Dehydrated tergallic-C-glucoside can be found in the cork from Quercus suber.

<span class="mw-page-title-main">1,3,6-Trigalloyl glucose</span> Chemical compound

1,3,6-Trigalloyl glucose is a gallotannin. It can be found in Paeonia lactiflora and Terminalia chebula.

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

Chebulic acid is a phenolic compound isolated from the ripe fruits of Terminalia chebula.

Chebulic may refer to:

<span class="mw-page-title-main">Pomegranate ellagitannin</span> Ellagitannins found in the pomegranate fruit

The pomegranate ellagitannins, which include punicalagin isomers, are ellagitannins found in the sarcotestas, rind (peel), bark or heartwood of the pomegranate fruit.

Maximilian Nierenstein was a professor of biochemistry at the University of Bristol.

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

Luteic acid is a natural phenol found in numerous fruits. It is a monolactonized tergalloyl group. Maximilian Nierenstein showed in 1945 that luteic acid was a molecule present in the myrobalanitannin, a tannin found in the fruit of Terminalia chebula and is an intermediary compound in the synthesis of ellagic acid. It can form from hexahydroxydiphenic acid. It is also present in the structure of the tannins alnusiin and bicornin.

<i>Terminalia macroptera</i> Species of flowering plant

Terminalia macroptera is a species of flowering plant in the Combretaceae known by the Hausa common name kwandari. It is native to Africa, where it can be found in Benin, Burkina Faso, Ghana, Senegal, Sudan, Uganda, and Nigeria.

Churna is a mixture of powdered herbs and or minerals used in Ayurvedic medicine. Triphala is an example of a classic Ayurvedic formula, used for thousands of years that is made from the powders of three fruits Amalaki, Haritaki and Bibhitaki.

<span class="mw-page-title-main">Mesir macunu</span> Traditional Turkish sweet

Mesir Macunu is a traditional Turkish sweet associated with the city of Manisa. Earlier versions of Mesir macunu were not sweet, but rather spicy in flavor.

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

Tellimagrandin I is an ellagitannin found in plants, such as Cornus canadensis, Eucalyptus globulus, Melaleuca styphelioides, Rosa rugosa, and walnut. It is composed of two galloyl and one hexahydroxydiphenyl groups bound to a glucose residue. It differs from Tellimagrandin II only by a hydroxyl group instead of a third galloyl group. It is also structurally similar to punigluconin and pedunculagin, two more ellagitannin monomers.

References

  1. Karel D. Klika, Ammar Saleem, Jari Sinkkonen, Marja Kähkönen, Jyrki Loponen, Petri Tähtinen and Kalevi Pihlaja (2004). "The structural and conformational analyses and antioxidant activities of chebulinic acid and its thrice-hydrolyzed derivative, 2,4-chebuloyl-β-D-glucopyranoside, isolated from the fruit of Terminalia chebula". Arkivoc. vii: 83–105.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. Han, Quanbin; Song, Jingzheng; Qiao, Chunfeng; Wong, Lina; Xu, Hongxi (2006). "Preparative isolation of hydrolysable tannins chebulagic acid and chebulinic acid from Terminalia chebula by high-speed counter-current chromatography". Journal of Separation Science. 29 (11): 1653–1657. doi:10.1002/jssc.200600089. PMID   16922284.