Stenophyllanin A

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Stenophyllanin A
Stenophyllanin A.PNG
Names
IUPAC name
[(10R,11R)-10-[(15S,19S)-19-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-2,3,4,7,8,9-hexahydroxy-12,17-dioxo-13,16-dioxatetracyclo[13.3.1.05,18.06,11]nonadeca-1,3,5(18),6,8,10-hexaen-14-yl]-3,4,5,17,18,19-hexahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.4.0.02,7]nonadeca-1(19),2,4,6,15,17-hexaen-11-yl] 3,4,5-trihydroxybenzoate
Identifiers
3D model (JSmol)
PubChem CID
  • InChI=1S/C56H40O31/c57-18-2-1-12(3-20(18)59)47-27(66)6-14-19(58)10-21(60)32(48(14)84-47)35-34-36-33(44(74)46(76)45(34)75)31-17(9-26(65)40(70)43(31)73)55(80)87-51(50(35)86-56(36)81)49-28(83-52(77)13-4-22(61)37(67)23(62)5-13)11-82-53(78)15-7-24(63)38(68)41(71)29(15)30-16(54(79)85-49)8-25(64)39(69)42(30)72/h1-5,7-10,27-28,35,47,49-51,57-76H,6,11H2/t27?,28-,35-,47?,49-,50+,51?/m1/s1
    Key: MRRHAYNXHYEUOD-KJJOKTLFSA-N
  • C1C(C(OC2=C1C(=CC(=C2C3C4C(OC(=O)C5=CC(=C(C(=C5C6=C(C3=C(C(=C6O)O)O)C(=O)O4)O)O)O)C7C(COC(=O)C8=CC(=C(C(=C8C9=C(C(=C(C=C9C(=O)O7)O)O)O)O)O)O)OC(=O)C1=CC(=C(C(=C1)O)O)O)O)O)C1=CC(=C(C=C1)O)O)O
Properties
C42H30O25
Molar mass 934,64 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Stenophyllanin A is an ellagitannin. It can be found in Cowania mexicana , Coleogyne ramosissima [1] and Quercus stenophylla . [2]

Related Research Articles

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<i>Quercus rubra</i> Species of flowering plant in the beech and oak family Fagaceae

Quercus rubra, the northern red oak, is an oak tree in the red oak group. It is a native of North America, in the eastern and central United States and southeast and south-central Canada. It has been introduced to small areas in Western Europe, where it can frequently be seen cultivated in gardens and parks. It prefers good soil that is slightly acidic. Often simply called red oak, northern red oak is so named to distinguish it from southern red oak (Q. falcata), also known as the Spanish oak. Northern Red Oak is sometimes called champion oak.

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

Tannic acid is a specific form of tannin, a type of polyphenol. Its weak acidity (pKa around 6) is due to the numerous phenol groups in the structure. The chemical formula for commercial tannic acid is often given as C76H52O46, which corresponds with decagalloyl glucose, but in fact it is a mixture of polygalloyl glucoses or polygalloyl quinic acid esters with the number of galloyl moieties per molecule ranging from 2 up to 12 depending on the plant source used to extract the tannic acid. Commercial tannic acid is usually extracted from any of the following plant parts: Tara pods (Caesalpinia spinosa), gallnuts from Rhus semialata or Quercus infectoria or Sicilian sumac leaves (Rhus coriaria).

Ellagic acid Natural phenol antioxidant

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

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Tanbark Tree bark

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<i>Coleogyne</i> Genus of flowering plants

Coleogyne ramosissima or blackbrush, is a low lying, dark grayish-green, aromatic, spiny, perennial, soft wooded shrub, native to the deserts of the southwestern United States. It is called blackbrush because the gray branches darken when wet by rains. It is in the rose family (Rosaceae), and is the only species in the monotypic genus Coleogyne.

<i>Quercus mongolica</i> Species of oak tree

Quercus mongolica, commonly known as Mongolian oak, is a species of oak native to Japan, China, Korea, Mongolia, and Siberia. The species can grow to be 30 metres tall.

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

Grandinin Chemical compound

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Roburin A Chemical compound

Roburin A is a tannin found in oak wood or oak cork.

<i>Purshia mexicana</i> Species of plant in Mexico

Purshia mexicana is a species of perennial flowering small tree in the rose family known by the common name Mexican cliffrose. It is native to western-northern Mexico, the region of the Sierra Madre Occidental cordillera.

<i>Quercus infectoria</i> Species of oak tree

Quercus infectoria or the Aleppo oak is a species of oak well known for producing galls that have been traditionally used for centuries in Asia medicinally while also used in softening leather and in making black dye and ink.

<i>Quercus salicina</i> Species of oak tree

Quercus salicina is an oak species found in Japan, South Korea and Taiwan.

The Flavono-ellagitannins or complex tannins are a class of tannins formed from the complexation of an ellagitannin with a flavonoid. Flavono-ellagitannins can be found in Quercus mongolica var. grosseserrata.

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Valoneic acid dilactone is a hydrolysable tannin that can be isolated from the heartwood of Shorea laeviforia and in oaks species like the North American white oak and European red oak.

Valoneic acid Chemical compound

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Friedelin Chemical compound

Friedelin is a triterpenoid chemical compound found in Azima tetracantha, Orostachys japonica, and Quercus stenophylla. Friedelin is also found in the roots of the Cannabis plant.

The flora of the Colorado Plateau and Canyonlands region of the Western United States.

References

  1. Anti-tumor promoting activity of polyphenols from Cowania mexicana and Coleogyne ramosissima. Hideyuki Ito, Masateru Miyake, Eisei Nishitani, Kazuko Mori, Tsutomu Hatano, Takuo Okuda, Takao Konoshima, Midori Takasaki, Mutsuo Kozuka, Teruo Mukainaka, Harukuni Tokuda, Hoyoku Nishino and Takashi Yoshida, Cancer Letters, Volume 143, Issue 1, 23 August 1999, Pages 5–13, doi : 10.1016/S0304-3835(99)00160-3
  2. Tannins and related compounds part 26: isolation and structures of stenophyllanins A, B, and C, novel tannins from Quercus stenophylla, G. Nonaka, H. Nishimura, I. Nishioka, J. Chem. Soc. Perkin Trans. 1, 1985, pp. 163–172, doi : 10.1039/P19850000163