Patuletin

Last updated
Patuletin
Patuletin.svg
Names
IUPAC name
3,3′,4′,5,7-Pentahydroxy-6-methoxyflavone
Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4H-1-benzopyran-4-one
Other names
6-Methoxyquercetin
Quercetagetin 6-methyl ether
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4-benzopyrone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.529 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-280-8
PubChem CID
UNII
  • InChI=1S/C16H12O8/c1-23-16-9(19)5-10-11(13(16)21)12(20)14(22)15(24-10)6-2-3-7(17)8(18)4-6/h2-5,17-19,21-22H,1H3 X mark.svgN
    Key: JMIFIYIEXODVTO-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C16H12O8/c1-23-16-9(19)5-10-11(13(16)21)12(20)14(22)15(24-10)6-2-3-7(17)8(18)4-6/h2-5,17-19,21-22H,1H3
    Key: JMIFIYIEXODVTO-UHFFFAOYAR
  • COC1=C(C=C2C(=C1O)C(=O)C(=C(O2)C3=CC(=C(C=C3)O)O)O)O
Properties
C16H12O8
Molar mass 332.264 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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Patuletin is an O-methylated flavonol. It can be found in the genus Eriocaulon . [1]

Glycosides

Patuletin glycosides can be found in Ipomopsis aggregata . [2]

Patuletin-3-O-rutinoside can be isolated from the aerial parts of Echinacea angustifolia . [3]

Patuletin acetylrhamnosides can be isolated from Kalanchoe brasiliensis . [4]

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<i>Ipomopsis aggregata</i> Species of flowering plant

Ipomopsis aggregata is a species of biennial flowering plant in the phlox family (Polemoniaceae), commonly known as scarlet trumpet, scarlet gilia, or skyrocket because of its scarlet red flowers with lobes curving back as if blown back by rocketing through the air.

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

Phenanthrenoids are chemical compounds formed with a phenanthrene backbone. These compounds occur naturally in plants, although they can also be synthesized.

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

Malvin is a naturally occurring chemical of the anthocyanin family.

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

Malvidin is an O-methylated anthocyanidin, the 3',5'-methoxy derivative of delphinidin. As a primary plant pigment, its glycosides are highly abundant in nature.

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

Catalpol is an iridoid glucoside. This natural product falls in the class of iridoid glycosides, which are simply monoterpenes with a glucose molecule attached.

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

Antirrhinin is an anthocyanin. It is the 3-rutinoside of cyanidin.

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

Iridin is an isoflavone, a type of flavonoid. It is the 7-glucoside of irigenin and can be isolated from several species of irises like orris root, Iris florentina or Iris versicolor, also commonly known as the larger blue flag. It can also be found in Iris kemaonensis.

<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.

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

Eupatolitin is a chemical compound. It is an O-methylated flavonol, a type of flavonoid. Eupatolitin can be found in Brickellia veronicaefolia and in Ipomopsis aggregata.

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

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

Ombuin is an O-methylated flavonol, a type of flavonoid. It is the 4',7-O-methyl derivative of quercetin.

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

Syringetin is an O-methylated flavonol, a type of flavonoid. It is found in red grape, in Lysimachia congestiflora and in Vaccinium uliginosum. It is one of the phenolic compounds present in wine.

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

Quercetagetin is a flavonol, a type of flavonoid. It can be found in the genus Eriocaulon.

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

Eupalitin is an O-methylated flavonol. It can be found in Ipomopsis aggregata.

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

Axillarin is an O-methylated flavonol. It can be found in Pulicaria crispa, Filifolium sibiricum, Inula britannica, Wyethia bolanderi in Balsamorhiza macrophylla and in Tanacetum vulgare. It can also be synthesized.

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

Rotenoids are naturally occurring substances containing a cis-fused tetrahydrochromeno[3,4-b]chromene nucleus. Many have insecticidal activity, such as the prototypical member of the family, rotenone. Rotenoids are related to the isoflavones.

<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 pomegranates.

Kaempferol 3-<i>O</i>-rutinoside Chemical compound

Kaempferol-3-O-rutinoside is a bitter-tasting flavonol glycoside. It can be isolated from the rhizomes of the fern Selliguea feei.

References

  1. ↑ Bate-Smith, E. C.; Harborne, J. B. (1969). "Quercetagetin and patuletin in Eriocaulon". Phytochemistry. 8 (6): 1035. doi:10.1016/S0031-9422(00)86351-7.
  2. ↑ Smith, D. M.; Glennie, C. W.; Harborne, J. B. (1971). "Identification of eupalitin, eupatolitin and patuletin glycosides in Ipomopsis aggregata". Phytochemistry. 10 (12): 3115. doi:10.1016/S0031-9422(00)97361-8.
  3. ↑ Lin, L.; Qiu, S.; Lindenmaier, M.; He, X.; Featherstone, T.; Cordell, G. A. (2002). "Patuletin-3-O-Rutinoside from the Aerial Parts of Echinacea angustifolia". Pharmaceutical Biology. 40 (2): 92. doi:10.1076/phbi.40.2.92.5839. S2CID   84855629.
  4. ↑ Costa, S. S.; Jossang, A.; Bodo, B.; Souza, M. L. M.; Moraes, V. L. G. (1994). "Patuletin Acetylrhamnosides from Kalanchoe brasiliensis as Inhibitors of Human Lymphocyte Proliferative Activity". Journal of Natural Products. 57 (11): 1503–1510. doi:10.1021/np50113a005. PMID   7853000.
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