:Macelignan
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 449564799
| Name = Macelignan
| ImageFile = Macelignan.svg
| ImageSize =
| ImageName = Chemical structure of macelignan
| ImageAlt = Chemical structure of macelignan
| IUPACName = (8S,8′R)-3-Methoxy-3′,4′-[methylenebis(oxy)]lignan-4-ol
| SystematicName = 4-[(2S,3R)-4-(2H-1,3-Benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxyphenol
| OtherNames = Anwulignan
|Section1={{Chembox Identifiers
| CASNo = 107534-93-0
| CASNo_Ref = {{Cascite|changed|CAS}}
| PubChem = 10404245
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8579683
| UNII = 8PP3614Z43
| SMILES = C[C@H](CC1=CC2=C(C=C1)OCO2)[C@@H](C)CC3=CC(=C(C=C3)O)OC
| 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
| InChIKey = QDDILOVMGWUNGD-UONOGXRCBH
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = QDDILOVMGWUNGD-UONOGXRCSA-N
}}
|Section2={{Chembox Properties
| Formula = C20H24O4
| MolarMass = 328.40 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
| GHS_ref =
}}
}}
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.Dental Caries and Medicinal Plants –An Overview. B. Parimala Devi and R. Ramasubramaniaraj, Journal of Pharmacy Research 2009, 2(11),1669-1675 {{cite web |url=http://jpronline.info/article/view/906/708 |title=Dental Caries and Medicinal Plants –An Overview - B.Parimala Devi*, R.Ramasubramaniaraja - Journal of Pharmacy Research |access-date=2011-08-27 |url-status=dead |archive-url=https://web.archive.org/web/20110723075209/http://jpronline.info/article/view/906/708 |archive-date=2011-07-23 }}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}}
Macelignan may also act as an antidiabetic molecule via PPAR signalingTherapeutic 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 and upregulate adipocyte gene expression{{cite journal |vauthors=Paul S, Hwang JK, Kim HY, Jeon WK, Chung C, Han JS |title=Multiple biological properties of macelignan and its pharmacological implications |journal=Archives of Pharmacal Research |volume=36 |issue=3 |pages=264–72 |date=March 2013 |pmid=23435944 |doi=10.1007/s12272-013-0048-z |s2cid=27489770 }}
Macelignan may contain antioxidant and anti-inflammatory properties{{Cite journal|last1=Lee|first1=Kyung-Eun|last2=Mun|first2=Sukyeong|last3=Pyun|first3=Hee-Bong|last4=Kim|first4=Myung-Suk|last5=Hwang|first5=Jae-Kwan|date=2012|title=Effects of macelignan isolated from Myristica fragrans (Nutmeg) on expression of matrix metalloproteinase-1 and type I procollagen in UVB-irradiated human skin fibroblasts|journal=Biological & Pharmaceutical Bulletin|volume=35|issue=10|pages=1669–1675|doi=10.1248/bpb.b12-00037|issn=1347-5215|pmid=23037157|doi-access=free}} and is marketed in breast enhancement creams for its anti-aging properties.{{Cite web|last=says|first=Tee O.|title=Best Breast Enlargement Creams Reviewed [UPDATED]|url=https://www.breastenlargement.name/cream/|access-date=2020-08-07|website=BreastEnlargement.name|language=en-US}}