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
PubChem CID
UNII
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).
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Infobox references

Lariciresinol is a lignan, a type of phenylpropanoids. 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

Fir genus of plants in the conifer family Pinaceae

Firs (Abies) are a genus of 48–56 species of evergreen coniferous trees in the family Pinaceae. They are found through much of North and Central America, Europe, Asia, and North Africa, occurring in mountains over most of the range. Firs are most closely related to the genus Cedrus (cedar). Douglas firs are not true firs, being of the genus Pseudotsuga.

<i>Abies balsamea</i> species of plant

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 plant

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 plant

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, Slovenia, Croatia, Bosnia and Herzegovina, Montenegro, Serbia, and south to Italy, Bulgaria, Albania and northern Greece; it is also commonly grown on Christmas tree plantations in the North East region of North America spanning New England in the US to the Maritime provinces of Canada.

<i>Abies grandis</i> species of plant

Abies grandis is a fir native to the Pacific Northwest and Northern California of North America, occurring at altitudes of sea level to 1,800 m. It is a major constituent of the Grand Fir/Douglas Fir Ecoregion of the Cascade Range.

<i>Abies concolor</i> species of fir tree, native to mountains of western North America

Abies concolor, the white fir, is a coniferous tree in the pine family Pinaceae. This tree is native to the mountains of western North America from the southern Cascade range in Oregon, south throughout California and into the Sierra de San Pedro Mártir in northern Baja California; west through parts of southern Idaho, to Wyoming; and south throughout the Colorado Plateau and southern Rocky Mountains in Utah and Colorado, and into the isolated mountain ranges of southern Arizona, New Mexico and northern Mexico. White fir live over 300-years and naturally occur at an elevation between 900–3,400 m (2,950–11,200 ft).

The lignans are a large group of polyphenols found in plants. Some examples of lignans are enterolignans, enterodiol and enterolactone.

<i>Abies magnifica</i> species of plant

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 procera</i> species of plant

Abies procera, the noble fir, also called red fir and Christmastree, is a western North American fir, native to the Cascade Range and Coast Range mountains of extreme northwest California and western Oregon and Washington in the United States. It is a high-altitude tree, typically occurring at 300–1,500 m (980–4,920 ft) altitude, only rarely reaching the tree line.

<i>Abies lasiocarpa</i> Species of plant

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

Secoisolariciresinol chemical compound

Secoisolariciresinol is a lignan, a type of phenylpropanoid. It is present in the water extract of silver fir wood, where its content is more than 5%. It is also present in nettle brew. Its content in flaxseed was found to be 0.3%, which is the highest known content in food.

<i>Abies nephrolepis</i> species of plant

Abies nephrolepis, commonly known as Khingan fir, is a species of fir native to northeastern China, North Korea, South Korea, and southeastern Russia.

<i>Abies sachalinensis</i> species of plant

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(khingan fir) is known to be the closest relative. Which is on the mainland just west of the range of Sakhalin fir.

Matairesinol chemical compound

Matairesinol is a plant lignan. It occurs with secoisolariciresinol in numerous foods such as oil seeds, whole grains, vegetables, and fruits.

Sesamin chemical compound

Sesamin is a lignan isolated from the bark of Fagara plants and from sesame oil. It has been used as a dietary fat-reduction supplement, although no controlled studies on this application have been performed. Its major metabolite is enterolactone, which has an elimination half life of less than 6 hours. Sesamin and sesamolin are minor components of sesame oil, on average comprising only 0.14% of the oil by mass.

Juvabione chemical compound

Juvabione, historically known as the paper factor, is the methyl ester of todomatuic acid, both of which 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.

<i>Cydia duplicana</i> species of insect

Cydia duplicana is a small moth of the family Tortricidae. It is found in all across Europe, extending barely into Asia in the Transcaucasus, Turkestan and Kazakhstan.

Enterolactone chemical compound

Enterolactone is a chemical compound formed by the action of intestinal bacteria on plant lignan precursors present in the diet.

Pinoresinol chemical compound

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

Hydroxymatairesinol chemical compound

Hydroxymatairesinol (HMR) is a lignan found in Norway spruce. It is an enterolactone precursor with anticancer activities. In rats, HMR decreased the volume of induced tumours and stabilised established tumours, as well as preventing the development of new tumours. It has also shown anti-oxidant properties in vitro.

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. 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. doi:10.1016/j.indcrop.2013.10.005.