Lariciresinol

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Lariciresinol
Lariciresinol.svg
Names
IUPAC name
4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.222.965 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m0/s1 X mark.svgN
    Key: MHXCIKYXNYCMHY-AUSJPIAWSA-N X mark.svgN
  • InChI=1/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m0/s1
    Key: MHXCIKYXNYCMHY-AUSJPIAWBV
  • COc1cc(ccc1O)C[C@H]2CO[C@@H]([C@H]2CO)c3ccc(c(c3)OC)O
Properties
C20H24O6
Molar mass 360.40 g/mol
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 ?)

Lariciresinol is a lignan, i.e., a type of phenylpropanoids. It is the precursor to enterolignans by the action of gut microflora. Enterolignans are of interest because they are speculated[ by whom? ] to exhibit beneficial medicinal properties.[ which? ][ citation needed ]

Contents

Occurrence

In food, it is found in sesame seeds and in Brassica vegetables. [1] It is also found in the bark and wood of white fir ( Abies alba ). [2]

See also

Related Research Articles

<span class="mw-page-title-main">Fir</span> Genus of plants in the conifer family cedar

Firs are evergreen coniferous trees belonging to the genus Abies in the family Pinaceae. There are approximately 48–65 extant species, found on mountains throughout much of North and Central America, Eurasia, and North Africa. The genus is most closely related to Keteleeria, a small genus confined to eastern Asia.

<i>Abies balsamea</i> Species of conifer tree

Abies balsamea or balsam fir is a North American fir, native to most of eastern and central Canada and the northeastern United States.

<i>Abies nordmanniana</i> Species of conifer tree

Abies nordmanniana, the Nordmann fir or Caucasian fir, is a fir indigenous to the mountains south and east of the Black Sea, in Turkey, Georgia and the Russian Caucasus. It occurs at altitudes of 900–2,200 m on mountains with precipitation of over 1,000 mm.

<i>Abies alba</i> Species of conifer tree

Abies alba, the European silver fir or silver fir, is a fir native to the mountains of Europe, from the Pyrenees north to Normandy, east to the Alps and the Carpathians, Slovakia, Slovenia, Croatia, Bosnia and Herzegovina, Montenegro, Serbia, and south to Italy, Bulgaria, Kosovo, Albania and northern Greece.

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

Nordihydroguaiaretic acid (NDGA) is a classic lignan, a phenylpropane dimer linked by a bond between positions C8 and C8′, as opposed to a neolignan. It is a natural compound found in the creosote bush.

<i>Abies bracteata</i> Species of conifer

Abies bracteata, the Santa Lucia fir or bristlecone fir, is the rarest fir in North America, and according to some, the world. It is confined to steep-sided slopes and the bottoms of rocky canyons in the Santa Lucia Mountains, in the Big Sur region on the central coast of California, United States.

<i>Abies grandis</i> Species of conifer tree

Abies grandis is a fir native to northwestern North America, occurring at altitudes of sea level to 1,700 metres (5,600 ft). It is a major constituent of the Grand Fir/Douglas Fir Ecoregion of the Cascade Range.

<i>Abies concolor</i> Species of conifer tree

Abies concolor, the white fir, concolor fir, or Colorado fir, is a coniferous tree in the pine family Pinaceae. This tree is native to the mountains of western North America, including the Sierra Nevada and southern Rocky Mountains, and into the isolated mountain ranges of southern Arizona, New Mexico, and Northern Mexico. It naturally occurs at elevations between 900 and 3,400 metres.

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>Abies magnifica</i> Species of tree found in North America

Abies magnifica, the red fir or silvertip fir, is a western North American fir, native to the mountains of southwest Oregon and California in the United States. It is a high-elevation tree, typically occurring at 1,400–2,700 metres (4,600–8,900 ft) elevation, though only rarely reaching tree line. The name red fir derives from the bark color of old trees.

<i>Abies lasiocarpa</i> North American fir tree species

Abies lasiocarpa, the subalpine fir or Rocky Mountain fir, is a western North American fir tree.

<i>Abies amabilis</i> Species of conifer

Abies amabilis, commonly known as the Pacific silver fir, is a fir native to the Pacific Northwest of North America, occurring in the Pacific Coast Ranges and the Cascade Range. It is also commonly referred to in English as the white fir, red fir, lovely fir, amabilis fir, Cascades fir, or silver fir. The species name is Latin for 'lovely'.

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

Secoisolariciresinol is an organic compound. It is classified as a lignan, i.e., a type of phenylpropanoid. It is present in some cereals, such as rye, and together with matairesinol has attracted much attention for its beneficial nutritional effects.

<i>Abies sachalinensis</i> Species of conifer

Abies sachalinensis, the Sakhalin fir, is a species of conifer in the family Pinaceae. It is found in Sakhalin island and southern Kurils (Russia), and also in northern Hokkaido (Japan). The first discovery by a European was by Carl Friedrich Schmidt (1832-1908), the Baltic German botanist, on the Russian island of Sakhalin in 1866, but he did not introduce it to Europe. The plant was re-discovered by the English plant-collector, Charles Maries in 1877 near Aomori on the main Japanese island of Honshū, who initially thought it to be a variety of Abies veitchii. Abies nephrolepis is known to be the closest relative, which exists on the mainland just west of the range of Sakhalin fir.

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

Matairesinol is an organic compound. It is classified as a lignan, i.e., a type of phenylpropanoid. It is present in some cereals, such as rye, and together with secoisolariciresinol has attracted much attention for its beneficial nutritional effects.

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

Juvabione, historically known as the paper factor, is the methyl ester of todomatuic acid. Both are sesquiterpenes (C15) found in the wood of true firs of the genus Abies. They occur naturally as part of a mixture of sesquiterpenes based upon the bisabolane scaffold. Sesquiterpenes of this family are known as insect juvenile hormone analogues (IJHA) because of their ability to mimic juvenile activity in order to stifle insect reproduction and growth. These compounds play important roles in conifers as the second line of defense against insect induced trauma and fungal pathogens.

<span class="mw-page-title-main">Enterolignan</span> Class of chemical compounds

Enterolignans are organic compounds formed by the action of gut microflora on lignans. They are thus the products of the combined action of both plants and of the animal gut. Prominent enterolignans are enterodiol and enterolactone. Enterolignans are also called "mammalian lignans", although that term is self-contradictory since mammals do not produce lignans.

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

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

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

Pinoresinol is a tetrahydrofuran lignan found in Styrax sp., Forsythia suspensa, and in Forsythia koreana. It is also found in the caterpillar of the cabbage butterfly, Pieris rapae where it serves as a defence against ants.

<i>Cryphalus piceae</i> Species of beetle

Cryphalus piceae, the small fir bark beetle, is a tiny bark beetle, about 1.7 mm long that is found in central and southern Europe. It infests mainly fir (Abies) and spruce trees (Picea) and occasionally can cause damage to branches and young trees, including tree death.

References

  1. Milder, Ivon E. J; Arts, Ilja C. W; Putte, Betty van de; Venema, Dini P; Hollman, Peter C. H (2007). "Lignan contents of Dutch plant foods: A database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol". British Journal of Nutrition. 93 (3): 393–402. doi: 10.1079/BJN20051371 . PMID   15877880.
  2. Benković, Eva Tavčar; Grohar, Tina; Žigon, Dušan; Švajger, Urban; Janeš, Damjan; Kreft, Samo; Štrukelj, Borut (2014). "Chemical composition of the silver fir (Abies alba) bark extract Abigenol® and its antioxidant activity". Industrial Crops and Products. 52: 23–28. doi:10.1016/j.indcrop.2013.10.005.