Gummadiol

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Gummadiol
Gummadiol.svg
Names
Preferred IUPAC name
(2R,3R,3aS,6S,6aR)-3,6-Di(2H-1,3-benzodioxol-5-yl)dihydro-1H,3H-furo[3,4-c]furan-1,3a(4H)-diol
Other names
1,4-Dihydroxysesamin
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C20H18O8/c21-19-16-17(10-1-3-12-14(5-10)26-8-24-12)23-7-20(16,22)18(28-19)11-2-4-13-15(6-11)27-9-25-13/h1-6,16-19,21-22H,7-9H2/t16-,17+,18+,19+,20+/m0/s1
    Key: KCQXLVHWDSFFDF-OMQSBVIBSA-N
  • O[C@@H]5O[C@H](c1ccc2OCOc2c1)[C@@]6(O)CO[C@H](c3ccc4OCOc4c3)[C@@H]56
Properties
C20H18O8
Molar mass 386.356 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Gummadiol is a lignan hemiacetal. [1] It can be isolated from the heartwood of Gmelina arborea . [2]

Related Research Articles

The lignans are a large group of low molecular weight polyphenols found in plants, particularly seeds, whole grains, and vegetables. The name derives from the Latin word for "wood". Lignans are precursors to phytoestrogens. They may play a role as antifeedants in the defense of seeds and plants against herbivores.

<i>Gmelina arborea</i> Species of flowering plant

Gmelina arborea,, locally known as gamhar, is a fast-growing deciduous tree in the family Lamiaceae.

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

Gmelina is a genus of plants in the family Lamiaceae. It consists of about 35 species in Australia, New Guinea, New Caledonia, Southeast Asia, India and a few in Africa. Some species such as G. arborea have been planted and/or become naturalised in India, Africa and Australia. It was named by Carl Linnaeus in honour of botanist Johann Georg Gmelin.

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

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Enterolactone is a organic compound classified as an enterolignan. It is formed by the action of intestinal bacteria on plant lignan precursors present in the diet.

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

Arboreol is an epoxylignan. Arboreol can be transformed by acid catalysis into gmelanone.

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Gmelanone is a lignan found in the heartwood of Gmelina arborea. Arboreol can be transformed by acid catalysis into gmelanone.

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

Gmelinol is a lignan. (+)-Gmelinol can be isolated from the heartwood of Gmelina arborea. This compound, along with four other chemicals also found in the same species, (+)-7′-O-ethyl arboreol, (+)-paulownin, (+)-epieudesmin and (−)-β-sitosterol, shows antifungal activity against Trametes versicolor.

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References

  1. Anjaneyulu, A.S.R.; Rao, A.Madhusudhana; Rao, V.Kameswara; Row, L.Ramachandra; Pelter, Andrew; Ward, Robert S. (1975). "The structure of gummadiol - A lignan hemi-acetal". Tetrahedron Letters. 16 (22–23): 1803–1806. doi:10.1016/S0040-4039(00)75261-0.
  2. Anjaneyulu, A.S.R.; Rao, A.Madhusudhana; Rao, V.Kameswara; Row, L.Ramachandra; Pelter, Andrew; Ward, Robert S. (1977). "Novel hydroxy lignans from the heartwood of gmelina arborea". Tetrahedron. 33: 133–143. doi:10.1016/0040-4020(77)80444-4.