Bergenin

Last updated
Bergenin
Bergenin.svg
Bergenin 3D BS.png
Names
Preferred IUPAC name
(2R,3S,4S,4aR,10bS)-3,4,8,10-Tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one
Other names
Cuscutin
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.230.534 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C14H16O9/c1-21-11-5(16)2-4-7(9(11)18)12-13(23-14(4)20)10(19)8(17)6(3-15)22-12/h2,6,8,10,12-13,15-19H,3H2,1H3/t6-,8-,10+,12+,13-/m1/s1 Yes check.svgY
    Key: YWJXCIXBAKGUKZ-HJJNZUOJSA-N Yes check.svgY
  • OC[C@@H](O1)[C@@H](O)[C@H](O)[C@@H]2[C@@H]1c3c(O)c(OC)c(O)cc3C(=O)O2
Properties
C14H16O9
Molar mass 328.27 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Bergenin, alias cuscutin, is trihydroxybenzoic acid glycoside. It is the C-glycoside of 4-O-methyl gallic acid. It possesses an O-demethylated derivative called norbergenin. These are chemical compounds and drugs of Ayurveda, commonly known as Paashaanbhed. It shows a potent immunomodulatory effect. [1]

Bergenin can be isolated from Bergenia species like Bergenia ciliata and Bergenia ligulata , [2] from rhizomes of Bergenia stracheyi . It is also found in the stem bark of Dryobalanops aromatica , [3] in Ardisia elliptica and in Mallotus japonicus . [4]

Related Research Articles

Saponins, also selectively referred to as triterpene glycosides, are bitter-tasting usually toxic plant-derived organic chemicals that have a foamy quality when agitated in water. They are widely distributed but found particularly in soapwort, a flowering plant, the soapbark tree and soybeans. They are used in soaps, medicines, fire extinguishers, speciously as dietary supplements, for synthesis of steroids, and in carbonated beverages. Structurally, they are glycosides, sugars bonded to another organic molecule, usually a steroid or triterpene, a steroid building block. Saponins are both water and fat soluble, which gives them their useful soap properties. Some examples of these chemicals are glycyrrhizin and quillaia, a bark extract used in beverages.

<i>Bergenia</i> Genus of flowering plants in the family Saxifragaceae

Bergenia is a genus of ten species of flowering plants in the family Saxifragaceae, native to central Asia, from Afghanistan to China and the Himalayan region.

<i>Sida cordifolia</i> Species of shrub

Sida cordifolia is a perennial subshrub of the mallow family Malvaceae native to India. It has naturalized throughout the world, and is considered an invasive weed in Africa, Australia, the southern United States, Hawaiian Islands, New Guinea, and French Polynesia. The specific name, cordifolia, refers to the heart-shaped leaf.

<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 India and Nepal east to southwest China (Yunnan), and south to Sri Lanka, Malaysia, and Vietnam.

<i>Dryobalanops aromatica</i> Species of tree

Dryobalanops aromatica, commonly known as Borneo camphor, camphor tree, Malay camphor, or Sumatran camphor, is a species of critically endangered plant in the family Dipterocarpaceae. The species name aromatica is derived from Latin and refers to the smell of the dammar (resin). This species was one of the main sources of camphor and attracted early Arab traders to Borneo, at that time being worth more than gold, and used for incense and perfumes.

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

Afzelechin is a flavan-3-ol, a type of flavonoid. It can be found in Bergenia ligulata. It exists as at least 2 major epimers.

<i>Bergenia ligulata</i> Species of plant

Bergenia ligulata is a plant belonging to the family Saxifragaceae and the genus Bergenia. It is plant is sometimes treated as a form of Bergenia ciliata. It is mostly found in temperate regions of the Himalayas from Kashmir to Bhutan and in Khasia hills at 1,500 m (4,900 ft) altitude.

<i>epsilon</i>-Viniferin Chemical compound

ε-Viniferin is a naturally occurring phenol, belonging to the stilbenoids family. It is a resveratrol dimer.

<i>alpha</i>-Viniferin Chemical compound

α-Viniferin is a stilbene trimer. It can be isolated from Caragana chamlagu and from Caragana sinica and from the stem bark of Dryobalanops aromatica. It is also present in relation to resistance to Botrytis cinerea and Plasmopara viticola in Vitis vinifera and Vitis riparia.It has been shown to inhibit acetylcholinesterase.

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

Diptoindonesin A is a C-glucoside of ε-viniferin isolated from the two Dipterocarpaceae Shorea seminis and Dryobalanops aromatica.

<i>Artemisia herba-alba</i> Species of plant

Artemisia herba-alba, the white wormwood, is a perennial shrub in the genus Artemisia that grows commonly on the dry steppes of the Mediterranean regions in Northern Africa, Western Asia and Southwestern Europe. It is used as an antiseptic and antispasmodic in herbal medicine.

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

Verbascoside is a caffeoyl phenylethanoid glycoside in which the phenylpropanoid caffeic acid and the phenylethanoid hydroxytyrosol form an ester and an ether bond respectively, to the rhamnose part of a disaccharide, namely β-(3′,4′-dihydroxyphenyl)ethyl-O-α-L-rhamnopyranosyl(1→3)-β-D-(4-O-caffeoyl)-glucopyranoside.

<i>Bergenia ciliata</i> Species of flowering plant

Bergenia ciliata is a plant species in the genus Bergenia, deciduous in USDA Zones 5 to 7, but usually remain semi-evergreen south of Zone 7. It is found in Northern India in Uttarakhand and Himachal Pradesh. This flower is related to the famous Phool Dei Festival celebrated in Uttarakhand. It is commonly known in India as Pathar phor buti. Also found in mountain areas of West Bengal, like Kalimpong, and Darjeeling. Afghanistan, south Tibet, Northern Nepal, Bhutan.

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

Norbergenin is a chemical compound. It is the O-demethylated derivative of bergenin. It can be isolated from rhizomes of Bergenia stracheyi.

<i>Bergenia stracheyi</i> Species of flowering plant

Bergenia stracheyi is a plant species in the genus Bergenia found in the Western Himalayas, from 2700 to 4700 m, Afghanistan and Tajikistan.

<i>Mallotus japonicus</i> Species of flowering plant

Mallotus japonicus, also known as East Asian mallotus, the food wrapper plant or "Akamegashiwa" in Japanese, is a plant species in the genus Mallotus native to China. It is also found in Japan and Korea. This species was first described in 1865, its name was verified by AAS Systematic Botanists on October 2, 2015.

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

Mallotusinic acid is a hydrolysable tannin found in the bark of Mallotus japonicus. It is more generally present in Geraniales.

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

Methyl gallate is a phenolic compound. It is the methyl ester of gallic acid.

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

Mallojaponin is a hydrolysable tannin found in the bark of Mallotus japonicus. This compound contains the moiety elaeocarpusinic acid, an oxidized hexahydroxydiphenic acid group which reacted with a dehydroascorbic acid molecule. It also contains a valoneic acid and a gallic acid moieties linked to a glucose molecule.

<i>Styrax japonicus</i> Species of flowering plant

Styrax japonicus, also known as the Japanese snowbell, is a species of flowering plant in the family Styracaceae, native to Korea, Japan, and Southern China. Growing to 12 m (39 ft) tall by 8 m (26 ft) broad, it is a graceful, spreading deciduous tree with oval, upward-facing leaves which occasionally turn yellow or orange before falling in autumn. Masses of slightly fragrant, bell-shaped white flowers hang from the branches in summer, followed by fruits (drupes) which resemble olives in both shape and colour.

References

  1. Nazir, N.; Koul, S.; Qurishi, M. A.; Taneja, S. C.; Ahmad, S. F.; Bani, S.; Qazi, G. N. (2007). "Immunomodulatory effect of bergenin and norbergenin against adjuvant-induced arthritis—A flow cytometric study". Journal of Ethnopharmacology. 112 (2): 401–405. doi:10.1016/j.jep.2007.02.023. PMID   17408893.
  2. Dhalwal, K.; Shinde, V. M.; Biradar, Y. S.; Mahadik, K. R. (2008). "Simultaneous quantification of bergenin, catechin, and gallic acid from Bergenia ciliata and Bergenia ligulata by using thin-layer chromatography". Journal of Food Composition and Analysis. 21 (6): 496–500. doi:10.1016/j.jfca.2008.02.008. INIST:20528090.
  3. Wibowo, A.; Ahmat, N.; Hamzah, A. S.; Sufian, A. S.; Ismail, N. H.; Ahmad, R.; Jaafar, F. M.; Takayama, H. (2011). "Malaysianol A, a new trimer resveratrol oligomer from the stem bark of Dryobalanops aromatica". Fitoterapia. 82 (4): 676–681. doi:10.1016/j.fitote.2011.02.006. PMID   21338657.
  4. Hepatoprotective effects of bergenin, a major constituent of Mallotus japonicus, on carbon tetrachloride-intoxicated rats. Lim HwaKyung, Kim HackSeang, Choi HongSerck, Oh SeiKwan and Choi JongWon, Journal of Ethnopharmacology, 2000, Volume 72 , Number 3, pages 469-474, doi : 10.1016/S0378-8741(00)00260-9