Amurensin A

Last updated
Amurensin A
Amurensin A.svg
Names
IUPAC name
5,5'-((3S,4S,Z)-4-hydroxy-1,4-bis(4-hydroxyphenyl)but-1-ene-2,3-diyl)bis(benzene-1,3-diol)
Identifiers
3D model (JSmol)
PubChem CID
UNII
  • InChI=1S/C28H24O7/c29-20-5-1-16(2-6-20)9-26(18-10-22(31)14-23(32)11-18)27(19-12-24(33)15-25(34)13-19)28(35)17-3-7-21(30)8-4-17/h1-15,27-35H/b26-9+/t27-,28+/m0/s1
    Key: GCORPFHXPBERCR-WFRBMYQMSA-N
  • OC1=CC(/C([C@@H]([C@H](O)C2=CC=C(O)C=C2)C3=CC(O)=CC(O)=C3)=C\C4=CC=C(O)C=C4)=CC(O)=C1
Properties
C28H24O7
Molar mass 472.48 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Amurensin A is an oligostilbene isolated from the roots of Vitis amurensis . [1] It is a partially oxidized resveratrol dimer with a C8-C8' connection. [2]

Related Research Articles

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<i>Vitis rupestris</i> Species of grapevine

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<i>Vitis amurensis</i> Species of grapevine

Vitis amurensis, the Amur grape, is a species of grape native to the Asian continent. Its name comes from the Amur Valley in Russia and China.

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Hybrid grapes are grape varieties that are the product of a crossing of two or more Vitis species. This is in contrast to crossings between grape varieties of the same species, typically Vitis vinifera, the European grapevine. Hybrid grapes are also referred to as inter-specific crossings or "Modern Varieties." Due to their often excellent tolerance to powdery mildew, other fungal diseases, nematodes, and phylloxera, hybrid varieties have, to some extent, become a renewed focus for European breeding programs. The recently developed varieties, Rondo, and Regent are examples of newer hybrid grape varieties for European viticulturalists. Several North American breeding programs, such as those at Cornell and the University of Minnesota, focus exclusively on hybrid grapes, with active and successful programs, having created hundreds if not thousands of new varieties.

Rondo (grape) Variety of grape

Rondo is a dark-skinned grape variety, used for making red wine. It is a hybrid grape or inter-specific crossing. It was created in 1964 by Professor Vilém Kraus in then-Czechoslovakia by crossing the varieties Zarya Severa and St. Laurent. He offered it to Dr. Helmut Becker (1927-1990) of the Geisenheim Grape Breeding Institute who conducted further work on it, which explains why the grape is known under a Geisenheim designation. The variety was first planted for research and later in bigger scale in the mid 1980s by Thomas Walk Vineyard in Ireland under the name Amurensis Walk; it was named Rondo in 1997.

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Vitis (grapevine) is a genus of 79 accepted species of vining plants in the flowering plant family Vitaceae. The genus is made up of species predominantly from the Northern Hemisphere. It is economically important as the source of grapes, both for direct consumption of the fruit and for fermentation to produce wine. The study and cultivation of grapevines is called viticulture.

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Pterocarpan

Pterocarpans are derivatives of isoflavonoids found in the family Fabaceae. It is a group of compounds which can be described as benzo-pyrano-furano-benzenes which can be formed by coupling of the B ring to the 4-one position.

Amurensin may refer to:

Amurensin K Chemical compound

Amurensin K is an oligostilbene. It is a resveratrol tetramer found in Vitis amurensis. Preliminary tests have shown it to be an effective neuraminidase inhibitor against the influenza A virus subtype H1N1.

Quadrangularin A Chemical compound

Quadrangularin A is an oligostilbene found in Cissus quadrangularis and in Parthenocissus laetevirens. It is a resveratrol dimer.

Amurensin E Chemical compound

Amurensin E is an oligostilbene found in Vitis amurensis. It is a pentamer of resveratrol.

Zarya severa is a red grape variety. It is a descendant of the Asiatic wild grape Vitis amurensis and the grape Malingre Précoce and is thus a hybrid vine. The crossing took place at the Potapenko Viticulture Research Institute in Rostov Oblast, Russia in 1936. Because of its high winter frost resistance as well as its resistance to downy mildew, this variety, often mentioned by breeders in Eastern Europe, became a major breeding stock in the search for new varieties.

References

  1. Huang, K. S.; Lin, M. (1999). "Oligostilbenes from the Roots of Vitis amurensis". Journal of Asian Natural Products Research. 2 (1): 21–28. doi:10.1080/10286029908039886. PMID   11261202.
  2. Natural stilbenes: an overview. Tao Shen, Xiao-Ning Wang and Hong-Xiang Lou, Nat. Prod. Rep.,2009, 26, pages 916-935, doi : 10.1039/B905960A