Hydroxymatairesinol

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Hydroxymatairesinol
Hydroxymatairesinol.svg
Names
IUPAC name
(7′S,8β,8′α)-4,4′,7′-Trihydroxy-3,3′-dimethoxylignano-9,9′-lactone
Systematic IUPAC name
(3R,4R)-4-[(S)-Hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C20H22O7/c1-25-17-8-11(3-5-15(17)21)7-13-14(10-27-20(13)24)19(23)12-4-6-16(22)18(9-12)26-2/h3-6,8-9,13-14,19,21-23H,7,10H2,1-2H3/t13-,14+,19-/m1/s1
    Key: UKHWOLNMBQSCLJ-BIENJYKASA-N
  • InChI=1/C20H22O7/c1-25-17-8-11(3-5-15(17)21)7-13-14(10-27-20(13)24)19(23)12-4-6-16(22)18(9-12)26-2/h3-6,8-9,13-14,19,21-23H,7,10H2,1-2H3/t13-,14+,19-/m1/s1
    Key: UKHWOLNMBQSCLJ-BIENJYKABV
  • COC1=C(C=CC(=C1)C[C@@H]2[C@H](COC2=O)[C@@H](C3=CC(=C(C=C3)O)OC)O)O
Properties
C20H22O7
Molar mass 374.389 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Hydroxymatairesinol (HMR) is a lignan found in Norway spruce (Picea abies). [1] 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. [1] It has also shown anti-oxidant properties in vitro. [1]

HMR's chemical structure is similar to matairesinol. [2] At high concentrations, HMR has estrogenic properties, which are considerably weaker than those of estradiol. [2]

Related Research Articles

<span class="mw-page-title-main">Spruce</span> Genus of evergreen, coniferous tree

A spruce is a tree of the genus Picea, a genus of about 35 species of coniferous evergreen trees in the family Pinaceae, found in the northern temperate and boreal (taiga) regions of the Earth. Picea is the sole genus in the subfamily Piceoideae. Spruces are large trees, from about 20 to 60 m tall when mature, and have whorled branches and conical form. They can be distinguished from other members of the pine family by their needles (leaves), which are four-sided and attached singly to small persistent peg-like structures on the branches, and by their cones, which hang downwards after they are pollinated. The needles are shed when 4–10 years old, leaving the branches rough with the retained pegs. In other similar genera, the branches are fairly smooth.

<span class="mw-page-title-main">Pinaceae</span> Family of conifers

The Pinaceae, or pine family, are conifer trees or shrubs, including many of the well-known conifers of commercial importance such as cedars, firs, hemlocks, larches, pines and spruces. The family is included in the order Pinales, formerly known as Coniferales. Pinaceae are supported as monophyletic by their protein-type sieve cell plastids, pattern of proembryogeny, and lack of bioflavonoids. They are the largest extant conifer family in species diversity, with between 220 and 250 species in 11 genera, and the second-largest in geographical range, found in most of the Northern Hemisphere, with the majority of the species in temperate climates, but ranging from subarctic to tropical. The family often forms the dominant component of boreal, coastal, and montane forests. One species, Pinus merkusii, grows just south of the equator in Southeast Asia. Major centres of diversity are found in the mountains of southwest China, Mexico, central Japan, and California.

<i>Picea abies</i> Species of plant

Picea abies, the Norway spruce or European spruce, is a species of spruce native to Northern, Central and Eastern Europe.

Hot flashes are a form of flushing, often caused by the changing hormone levels that are characteristic of menopause. They are typically experienced as a feeling of intense heat with sweating and rapid heartbeat, and may typically last from two to 30 minutes for each occurrence.

<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, Slovenia, Croatia, Bosnia and Herzegovina, Montenegro, Serbia, and south to Italy, Bulgaria, Kosovo, 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.

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.

4-Hydroxybenzoic acid, also known as p-hydroxybenzoic acid (PHBA), is a monohydroxybenzoic acid, a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. 4-Hydroxybenzoic acid is primarily known as the basis for the preparation of its esters, known as parabens, which are used as preservatives in cosmetics and some ophthalmic solutions. It is isomeric with 2-hydroxybenzoic acid, known as salicylic acid, a precursor to aspirin, and with 3-hydroxybenzoic acid.

<i>Picea obovata</i> Species of conifer

Picea obovata, the Siberian spruce, is a spruce native to Siberia, from the Ural Mountains east to Magadan Oblast, and from the Arctic tree line south to the Altay Mountains in northwestern Mongolia.

<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, e.g. rye, and together with Secoisolariciresinol, has attracted much attention for its beneficial nutritional effects.

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

Piceatannol is the organic compound with the formula ( 2C6H3)2CH)2. Classified as a stilbenoid and a phenol, it is a white solid, although samples often are yellow owing to impurities.

The enzyme abieta-7,13-diene synthase catalyzes the chemical reaction

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

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 to exhibit beneficial medicinal properties.

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

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.

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

Syringetin is an O-methylated flavonol, a type of flavonoid. It is found in red grape, in Lysimachia congestiflora and in Vaccinium uliginosum. It is one of the phenolic compounds present in wine.

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

Astringin is a stilbenoid, the 3-β-D-glucoside of piceatannol. It can be found in the bark of Picea sitchensis or Picea abies.

Cinara pilicornis, the spruce shoot aphid or brown spruce shoot aphid, is an aphid species in the genus Cinara found on Norway spruce and Sitka spruce. It is a quite large aphid species with a plump, dull brown body. It seems to have little effect on the tree. It is a European species but it has also been reported in spruce forests in New Zealand, together with the spruce aphid.

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

Isorhapontigenin is a tetrahydroxylated stilbenoid with a methoxy group. It is an isomer of rhapontigenin and an analog of resveratrol. It is found in the Chinese herb Gnetum cleistostachyum, in Gnetum parvifolium and in the seeds of the palm Aiphanes aculeata.

(+)-Car-3-ene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-car-3-ene-forming]. This enzyme catalyses the following chemical reaction

4-Hydroxybenzoic acid 4-<i>O</i>-glucoside Chemical compound

4-Hydroxybenzoic acid 4-O-glucoside is a glucoside of p-hydroxybenzoic acid. It can be found in mycorrhizal and non-mycorrhizal roots of Norway spruces.

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

Isorhapontin is a stilbenoid. It is the glucoside of isorhapontigenin. It can be found in mycorrhizal and non-mycorrhizal roots of Norway spruces, in the bark of Picea sitchensis or in white spruce.

References

  1. 1 2 3 Saarinen, NM; Warri, A; Makela, SI; et al. (2000). "Hydroxymatairesinol, a novel enterolactone precursor with antitumor properties from coniferous tree (Picea abies)". Nutrition and Cancer. 36 (2): 207–16. doi:10.1207/S15327914NC3602_10. PMID   10890032. S2CID   22124446.
  2. 1 2 Cosentino, M; Marino, F; Ferrari, M; et al. (August 2007). "Estrogenic activity of 7-hydroxymatairesinol potassium acetate (HMR/lignan) from Norway spruce (Picea abies) knots and of its active metabolite enterolactone in MCF-7 cells". Pharmacological Research. 56 (2): 140–7. doi:10.1016/j.phrs.2007.05.001. PMID   17572100.