Cynaroside

Last updated
Cynaroside
Cynaroside.svg
Names
IUPAC name
7-(β-D-Glucopyranosyloxy)-3′,4′,5-trihydroxyflavone
Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one
Other names
Glucoluteolin
Luteoloside
Cinaroside
7-Glucoluteolin
7-Glucosylluteolin
Luteolin 7-glucoside
Luteolin-7-glucoside
Luteolin 7-O-glucoside
Luteolin-7-O-glucoside
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.023.968 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1 X mark.svgN
    Key: PEFNSGRTCBGNAN-QNDFHXLGSA-N X mark.svgN
  • InChI=1/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1
    Key: PEFNSGRTCBGNAN-QNDFHXLGBE
  • C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
Properties
C21H20O11
Molar mass 448.37 g/mol
AppearanceYellow amorphous powder
Melting point 266 to 268 °C (511 to 514 °F; 539 to 541 K)
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 ?)

Cynaroside (also known as luteoloside) is a flavone, a flavonoid-like chemical compound. It is a 7-O-glucoside of luteolin.

Contents

Natural occurrences

It can be found in Ferula varia and F. foetida [1] in Campanula persicifolia and C. rotundifolia , [2] in the bamboo Phyllostachys nigra , [3] and in Teucrium gnaphalodes . [4]

In food

It can be found in dandelion (the highest concentration in the flowers, [5] but also in the roots) and in Cynara scolymus (artichoke). [6]

Metabolism

Flavone 7-O-beta-glucosyltransferase adds a glucose to luteolin.

A cynaroside 7-O-glucosidase has been identified in the artichoke. [6]

Spectral data

UV-Vis [7]
Lambda-max UV : 348, 260 nm
Extinction coefficient (log ε): 4.11, 4.23
IR
Major absorption bands ? cm−1
NMR
Proton NMR 1H-NMR (500 MHz, CD3COCD3 + D2O):

δ 3.42 (1H, t, J = 9.0 Hz, H-4′), 3.49
(1H, t, J = 9.0 Hz, H-2″), 3.56
(1H, t, J = 9.0 Hz, H-3″), 3.60 (1H, m, H-5″)
, 3.68 (1H, dd, J = 12.2, 5.6 Hz, H-6a″),
3.85 (1H, dd, J = 12.2, 1.8 Hz, H-6b″),
5.10 (1H, d, J = 7.8 Hz, H-1″), 6.44
(1H, d, J = 1.8 Hz, H-6), 6.63 (1H, s, H-3),
6.83 (1H, d, J = 1.8 Hz, H-8), 6.95
(1H, d, J = 8.0 Hz, H-5′), 7.41
(1H, d, J = 8.0 Hz, H-6′), 7.43 (1H, bs, H-2′)

Carbon-13 NMR 13C-NMR (125 MHz, CD3COCD3 + D2O):

δ 61.7 (C-6″), 70.3 (C-4″), 73.8 (C-2″),
76.8 (C-3″), 77.4 (C-5″), 95.8 (C-8), 100.5
(C-6), 100.7 (C-1″), 103.7 (C-3), 106.3 (C-10),
113.8 (C-2″), 116.5 (C-5′), 120.3 (C-6′),
122.6 (C-1′), 146.3(C-3′), 150.4 (C-4′),
158.0 (C-9), 161.8 (C-5), 163.9 (C-7),
165.8(C-2), 183.1 (C-4)

Other NMR data
MS
Masses of
main fragments		ESI-MS [M+H]+ m/z 449.1

Related Research Articles

<span class="mw-page-title-main">Flavonoid</span> Class of plant and fungus secondary metabolites

Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.

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

Flavone is an organic compound with the formula C6H4OC3H(Ph)O. A white solid, flavone is a derivative of chromone with a phenyl (Ph) substituent adjacent to the ether group. The compound is of little direct practical importance, but susbstituted derivatives, the flavones and flavonoids are a large class of nutritionally important natural products. Flavone can be prepared in the laboratory by cyclization of 2-hydroxacetophenone. Isomeric with flavone is isoflavone, where the phenyl group is adjacent to the ketone.

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

Luteolin is a flavone, a type of flavonoid, with a yellow crystalline appearance.

<i>Phyllostachys nigra</i> Species of grass

Phyllostachys nigra, commonly known as black bamboo or purple bamboo, is a species of bamboo, native to Hunan Province of China, and is widely cultivated elsewhere.

<span class="mw-page-title-main">Alpha-glucosidase</span> Enzyme

α-Glucosidase is a glucosidase located in the brush border of the small intestine that acts upon α(1→4) bonds:

<i>Scutellaria lateriflora</i> Species of flowering plant

Scutellaria lateriflora, is a hardy perennial herb of the mint family, Lamiaceae, native to North America.

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

Flavonoids are synthesized by the phenylpropanoid metabolic pathway in which the amino acid phenylalanine is used to produce 4-coumaroyl-CoA. This can be combined with malonyl-CoA to yield the true backbone of flavonoids, a group of compounds called chalcones, which contain two phenyl rings. Conjugate ring-closure of chalcones results in the familiar form of flavonoids, the three-ringed structure of a flavone. The metabolic pathway continues through a series of enzymatic modifications to yield flavanones → dihydroflavonols → anthocyanins. Along this pathway, many products can be formed, including the flavonols, flavan-3-ols, proanthocyanidins (tannins) and a host of other various polyphenolics.

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

Orientin is a flavone, a chemical flavonoid-like compound. It is the 8-C glucoside of luteolin.

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

Tricetin is a flavone, a type of flavonoid. It is a rare aglycone found in the pollen of members of the Myrtaceae, subfamily Leptospermoideae, such as Eucalyptus globulus. This compound shows anticancer effects on human breast adenocarcinoma MCF-7 cells. Moreover. a potent anti-inflammatory effect of tricetin has also been demonstrated in a model of acute pancreatitis. This observation was explained by the compound's radical scavenging effects, its inhibitory effect on the DNA damage sensor enzyme poly (ADP-ribose) polymerase-1 (PARP1) and PARP1-mediated cell death and suppression of inflammatory gene expression.

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

Vitexin is an apigenin flavone glucoside, a chemical compound found in the passion flower, Vitex agnus-castus, in the Phyllostachys nigra bamboo leaves, in the pearl millet, and in Hawthorn.

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

Isoorientin is a flavone, a chemical flavonoid-like compound. It is the luteolin-6-C-glucoside. Bioassay-directed fractionation techniques led to isolation of isoorientin as the main hypoglycaemic component in Gentiana olivieri. Studies also showed that isoorientin is a potential neuroprotective compound against Alzheimer's disease.

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

Apigetrin is a chemical compound that can be found in dandelion coffee and in Teucrium gnaphalodes.

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

Isoquercetin, isoquercitrin or isotrifoliin is a flavonoid, a type of chemical compound. It is the 3-O-glucoside of quercetin. Isoquercitrin can be isolated from various plant species including Mangifera indica (mango) and Rheum nobile. It is also present in the leaves of Annona squamosa, Camellia sinensis (tea). and Vestia foetida

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

Hyperoside is a chemical compound. It is the 3-O-galactoside of quercetin.

<i>Phyllostachys edulis</i> Species of grass

Phyllostachys edulis, the mōsō bamboo, or tortoise-shell bamboo, or mao zhu, , is a temperate species of giant timber bamboo native to China and Taiwan and naturalised elsewhere, including Japan where it is widely distributed from south of Hokkaido to Kagoshima. The edulis part of the Latin name refers to its edible shoots. This bamboo can reach heights of up to 28 m (92 ft). This particular species of bamboo is the most common species used in the bamboo textile industry of China and other countries, for the production of rayon. Moso is less cold-hardy than many phyllostachys, surviving at a reduced height down to 5 degrees Fahrenheit (-15°C).

Flavonolignans are natural phenols composed of a part flavonoid and a part phenylpropane.

<span class="mw-page-title-main">Flora of Lebanon</span>

The flora of Lebanon includes approximately 2,600 plant species. Situated on the eastern coast of the Mediterranean Basin, Lebanon is a reservoir of plant diversity and one of the world's biodiversity hotspots for conservation priorities. Endemic species constitute 12% of the Lebanese flora; 221 plant species are broad endemics and 90 are narrow endemics. Important Plant Areas (IPAs) featuring the country exceptional botanical richness were defined in 2018.

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

Cirsilineol is a bioactive flavone isolated from Artemisia and from Teucrium gnaphalodes.

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

Veronicastroside is a flavone, a type of flavonoid. It is the 7-O-neohesperidoside of luteolin. It can be found in Veronicastrum sibiricum var. japonicum and in Teucrium gnaphalodes.

<i>Teucrium gnaphalodes</i> Species of flowering plant

Teucrium gnaphalodes is a plant species in the genus Teucrium. It is endemic to the Iberian Peninsula and grows at altitudes between 200 and 1500 m. It flowers from March to July.

References

  1. ↑ Yuldashev, M. P. (1997). "Cynaroside content of the plants Ferula varia and F. Foetida". Chemistry of Natural Compounds. 33 (5): 597–8. doi:10.1007/BF02254816. S2CID   45802688.
  2. ↑ Teslov, L. S.; Teslov, S. V. (1972). "Cynaroside and luteolin from Campanula persicifolia and C. Rotundifolia". Chemistry of Natural Compounds. 8: 117. doi: 10.1007/BF00564462 .
  3. ↑ Hu, Chun; Zhang, Ying; Kitts, David D. (2000). "Evaluation of Antioxidant and Prooxidant Activities of Bamboo Phyllostachys nigra Var. Henonis Leaf Extract in Vitro". Journal of Agricultural and Food Chemistry. 48 (8): 3170–6. doi:10.1021/jf0001637. PMID   10956087.
  4. ↑ Flavonoid Aglycones and Glycosides from Teucrium gnaphalodes. F. A. T. Barberán, M. I. Gil, F. Tomás, F. Ferreres and A. Arques, J. Nat. Prod., 1985, 48 (5), pages 859–860, doi : 10.1021/np50041a040
  5. ↑ "Is the Healthiest Part of Dandelion Its Flower?". 17 April 2014.
  6. 1 2 Nüβlein, B; Kreis, W (2005). "Purification and Characterization of a Cynaroside 7-O-β-D-Glucosidase from Cynarae scolymi folium". Acta Horticulturae. 681 (681): 413–20. doi:10.17660/ActaHortic.2005.681.58.
  7. ↑ Lin, Yi-Pei; Chen, Tai-Yuan; Tseng, Hsiang-Wen; Lee, Mei-Hsien; Chen, Shui-Tein (2009). "Neural cell protective compounds isolated from Phoenix hanceana var. Formosana". Phytochemistry. 70 (9): 1173–81. doi:10.1016/j.phytochem.2009.06.006. PMID   19628235.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.