Macelignan

Last updated
Macelignan
Macelignan.svg
Names
IUPAC name
(8S,8′R)-3-Methoxy-3′,4′-[methylenebis(oxy)]lignan-4-ol
Systematic IUPAC name
4-[(2S,3R)-4-(2H-1,3-Benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxyphenol
Other names
Anwulignan
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C20H24O4/c1-13(8-15-4-6-17(21)19(10-15)22-3)14(2)9-16-5-7-18-20(11-16)24-12-23-18/h4-7,10-11,13-14,21H,8-9,12H2,1-3H3/t13-,14+/m0/s1 X mark.svgN
    Key: QDDILOVMGWUNGD-UONOGXRCSA-N X mark.svgN
  • InChI=1/C20H24O4/c1-13(8-15-4-6-17(21)19(10-15)22-3)14(2)9-16-5-7-18-20(11-16)24-12-23-18/h4-7,10-11,13-14,21H,8-9,12H2,1-3H3/t13-,14+/m0/s1
    Key: QDDILOVMGWUNGD-UONOGXRCBH
  • C[C@H](CC1=CC2=C(C=C1)OCO2)[C@@H](C)CC3=CC(=C(C=C3)O)OC
Properties
C20H24O4
Molar mass 328.40 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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Macelignan (Anwulignan) is a lignan. It can be found in Myristica fragrans , the nutmeg.

Medical research

One study has shown that macelignan may exert antimicrobial and anticariogenic activity against Streptococcus mutans , but this is not a currently used treatment. [1] [2]

Macelignan may also act as an antidiabetic molecule via PPAR signaling [3] and upregulate adipocyte gene expression [4]

Macelignan may contain antioxidant and anti-inflammatory properties [5] [4] and is marketed in breast enhancement creams for its anti-aging properties. [6]

Related Research Articles

<i>Streptococcus</i> Genus of bacteria

Streptococcus is a genus of gram-positive coccus or spherical bacteria that belongs to the family Streptococcaceae, within the order Lactobacillales, in the phylum Bacillota. Cell division in streptococci occurs along a single axis, so as they grow, they tend to form pairs or chains that may appear bent or twisted. This differs from staphylococci, which divide along multiple axes, thereby generating irregular, grape-like clusters of cells. Most streptococci are oxidase-negative and catalase-negative, and many are facultative anaerobes.

<span class="mw-page-title-main">Nutmeg</span> Spice from Myristica fragrans

Nutmeg is the seed, or the ground spice derived from that seed, of several tree species of the genus Myristica; fragrant nutmeg or true nutmeg is a dark-leaved evergreen tree cultivated for two spices derived from its fruit: nutmeg, from its seed, and mace, from the seed covering. It is also a commercial source of nutmeg essential oil and nutmeg butter. Indonesia is the main producer of nutmeg and mace, and the true nutmeg tree is native to its islands.

<span class="mw-page-title-main">Xylitol</span> Synthetic sweetener

Xylitol is a chemical compound with the formula C
5
H
12
O
5
, or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular stereoisomer with that structural formula. It is a colorless or white crystalline solid that is freely soluble in water. It can be classified as a polyalcohol and a sugar alcohol, specifically an alditol. The name derives from Ancient Greek: ξύλον, xyl[on] 'wood', with the suffix -itol used to denote sugar alcohols.

<span class="mw-page-title-main">Tooth decay</span> Deformation of teeth due to acids produced by bacteria

Tooth decay, also known as cavities or caries, is the breakdown of teeth due to acids produced by bacteria. The cavities may be a number of different colors from yellow to black. Symptoms may include pain and difficulty with eating. Complications may include inflammation of the tissue around the tooth, tooth loss and infection or abscess formation.

Dental sealants are a dental treatment intended to prevent tooth decay. Teeth have recesses on their biting surfaces; the back teeth have fissures (grooves) and some front teeth have cingulum pits. It is these pits and fissures that are most vulnerable to tooth decay because food and bacteria stick in them and because they are hard-to-clean areas. Dental sealants are materials placed in these pits and fissures to fill them in, creating a smooth surface which is easy to clean. Dental sealants are mainly used in children who are at higher risk of tooth decay, and are usually placed as soon as the adult molar teeth come through.

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

Eugenol is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds. It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove, nutmeg, cinnamon, basil and bay leaf. It is present in concentrations of 80–90% in clove bud oil and at 82–88% in clove leaf oil. Eugenol has a pleasant, spicy, clove-like scent. The name is derived from Eugenia caryophyllata, the former Linnean nomenclature term for cloves. The currently accepted name is Syzygium aromaticum.

Myristic acid is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH. Its salts and esters are commonly referred to as myristates or tetradecanoates. It is named after the binomial name for nutmeg, from which it was first isolated in 1841 by Lyon Playfair.

<i>Streptococcus mutans</i> Species of bacterium

Streptococcus mutans is a facultatively anaerobic, gram-positive coccus commonly found in the human oral cavity and is a significant contributor to tooth decay. It is part of the "streptococci", an informal general name for all species in the genus Streptococcus. The microbe was first described by James Kilian Clarke in 1924.

Dental plaque is a biofilm of microorganisms that grows on surfaces within the mouth. It is a sticky colorless deposit at first, but when it forms tartar, it is often brown or pale yellow. It is commonly found between the teeth, on the front of teeth, behind teeth, on chewing surfaces, along the gumline (supragingival), or below the gumline cervical margins (subgingival). Dental plaque is also known as microbial plaque, oral biofilm, dental biofilm, dental plaque biofilm or bacterial plaque biofilm. Bacterial plaque is one of the major causes for dental decay and gum disease.

<span class="mw-page-title-main">Myristicaceae</span> Family of flowering plants

The Myristicaceae are a family of flowering plants native to Africa, Asia, Pacific islands, and the Americas and has been recognized by most taxonomists. It is sometimes called the "nutmeg family", after its most famous member, Myristica fragrans, the source of the spices nutmeg and mace. The best known genera are Myristica in Asia and Virola in the Neotropics.

<i>Sagittaria sagittifolia</i> Species of flowering plant in the family Alismataceae

Sagittaria sagittifolia is a flowering plant in the family Alismataceae, native to wetlands in most of Europe from Ireland and Portugal to Finland and Bulgaria, and in Russia, Ukraine, Siberia, Japan, Turkey, China, India, Australia, Vietnam and the Caucasus. It is also cultivated as a food crop in some other countries. In Britain it is the only native Sagittaria.

<span class="mw-page-title-main">Oral microbiology</span>

Oral microbiology is the study of the microorganisms (microbiota) of the oral cavity and their interactions between oral microorganisms or with the host. The environment present in the human mouth is suited to the growth of characteristic microorganisms found there. It provides a source of water and nutrients, as well as a moderate temperature. Resident microbes of the mouth adhere to the teeth and gums to resist mechanical flushing from the mouth to stomach where acid-sensitive microbes are destroyed by hydrochloric acid.

<span class="mw-page-title-main">Willoughby D. Miller</span>

Willoughby Dayton Miller (1853–1907) was an American dentist and the first oral microbiologist.

<span class="mw-page-title-main">Oral ecology</span>

Oral ecology is the microbial ecology of the microorganisms found in mouths. Oral ecology, like all forms of ecology, involves the study of the living things found in oral cavities as well as their interactions with each other and with their environment. Oral ecology is frequently investigated from the perspective of oral disease prevention, often focusing on conditions such as dental caries, candidiasis ("thrush"), gingivitis, periodontal disease, and others. However, many of the interactions between the microbiota and oral environment protect from disease and support a healthy oral cavity. Interactions between microbes and their environment can result in the stabilization or destabilization of the oral microbiome, with destabilization believed to result in disease states. Destabilization of the microbiome can be influenced by several factors, including diet changes, drugs or immune system disorders.

<span class="mw-page-title-main">Veillonella parvula</span> Species of bacterium

Veillonella parvula is a strictly anaerobic, Gram-negative, coccus-shaped bacterium in the genus Veillonella. It is a normal part of the oral flora but can be associated with diseases such as periodontitis and dental caries as well as various systemic infections, including meningitis and osteomyelitis. It has also been isolated from women with bacterial vaginosis and has been associated with hypertension together with Campylobacter rectus and Prevotella melaninogenica.

<span class="mw-page-title-main">Lactoperoxidase</span> Mammalian protein found in Homo sapiens

Lactoperoxidase is a peroxidase enzyme secreted from mammary, salivary and other mucosal glands including the lungs, bronchii and nose that functions as a natural and the first line of defense against bacteria and viruses. Lactoperoxidase is a member of the heme peroxidase family of enzymes. In humans, lactoperoxidase is encoded by the LPO gene.

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

Bakuchiol is a meroterpene in the class terpenophenol.

Silver diammine fluoride (SDF), also known as silver diamine fluoride in most of the dental literature, is a topical medication used to treat and prevent dental caries and relieve dentinal hypersensitivity. It is a colorless or blue-tinted, odourless liquid composed of silver, ammonium and fluoride ions at a pH of 10.4 or 13. Ammonia compounds reduce the oxidative potential of SDF, increase its stability and helps to maintain a constant concentration over a period of time, rendering it safe for use in the mouth. Silver and fluoride ions possess antimicrobial properties and are used in the remineralization of enamel and dentin on teeth for preventing and arresting dental caries.

Asad Ullah Khan is an Indian microbiologist, biochemist and a professor at the Interdisciplinary Biotechnology Unit of the Aligarh Muslim University. He is known for his studies on multidrug resistant clinical strains as well as for the first sighting in India of Aligarh super bug (NDM-4), a variant of New Delhi metallo-beta-lactamase 1 (NDM-1). He is an elected fellow of the Royal Society of Chemistry, the Biotech Research Society, India and the Indian Academy of Microbiological Sciences. The Department of Biotechnology of the Government of India awarded him the National Bioscience Award for Career Development, one of the highest Indian science awards, for his contributions to biosciences, in 2012.

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

Trehalulose is a disaccharide made up of a molecule of fructose bound to a molecule of glucose. Like isomaltulose, it is a structural isomer of sucrose that is present in small quantities in honey. It makes up 50% of sugars in the honeydew of silverleaf whiteflies and is synthesised from sucrose by some bacteria, such as Protaminombacter rubrum. Because the anomeric carbon of the fructose moiety is not involved in the glycosidic bond, it is a reducing sugar.

References

  1. Dental Caries and Medicinal Plants –An Overview. B. Parimala Devi and R. Ramasubramaniaraj, Journal of Pharmacy Research 2009, 2(11),1669-1675 "Dental Caries and Medicinal Plants –An Overview - B.Parimala Devi*, R.Ramasubramaniaraja - Journal of Pharmacy Research". Archived from the original on 2011-07-23. Retrieved 2011-08-27.
  2. Anticariogenic activity of macelignan isolated from Myristica fragrans (nutmeg) against Streptococcus mutans. J.Y. Chung, J.H. Choo, M.H. Lee and J.K. Hwang, Phytomedicine, Volume 13, Issue 4, 13 March 2006, Pages 261-266, doi : 10.1016/j.phymed.2004.04.007
  3. Therapeutic Potential of Peroxisome Proliferators–Activated Receptor-α/γ Dual Agonist With Alleviation of Endoplasmic Reticulum Stress for the Treatment of Diabetes http://diabetes.diabetesjournals.org/content/57/3/737.long
  4. 1 2 Paul S, Hwang JK, Kim HY, Jeon WK, Chung C, Han JS (March 2013). "Multiple biological properties of macelignan and its pharmacological implications". Archives of Pharmacal Research . 36 (3): 264–72. doi:10.1007/s12272-013-0048-z. PMID   23435944. S2CID   27489770.
  5. Lee, Kyung-Eun; Mun, Sukyeong; Pyun, Hee-Bong; Kim, Myung-Suk; Hwang, Jae-Kwan (2012). "Effects of macelignan isolated from Myristica fragrans (Nutmeg) on expression of matrix metalloproteinase-1 and type I procollagen in UVB-irradiated human skin fibroblasts". Biological & Pharmaceutical Bulletin. 35 (10): 1669–1675. doi: 10.1248/bpb.b12-00037 . ISSN   1347-5215. PMID   23037157.
  6. says, Tee O. "Best Breast Enlargement Creams Reviewed [UPDATED]". BreastEnlargement.name. Retrieved 2020-08-07.