Macelignan

Macelignan (Anwulignan) is a lignan. It can be found in Myristica fragrans, the nutmeg.

Macelignan

Names
IUPAC name (8R, 8′S)-7-(3,4-methylenedioxyphenyl)-7′-(4-hydroxy-3-methoxyphenyl)-8,8′-dimethybutane
Identifiers
3D model (JSmol)	Interactive image
ChemSpider	8579683
PubChem CID	10404245
CompTox Dashboard (EPA)	DTXSID00148077
InChI 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 Key: QDDILOVMGWUNGD-UONOGXRCSA-N 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
SMILES C[C@H](CC1=CC2=C(C=C1)OCO2)[C@@H](C)CC3=CC(=C(C=C3)O)OC
Properties
Chemical formula	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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Infobox references

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]

References

1. Dental Caries and Medicinal Plants –An Overview. B. Parimala Devi and R. Ramasubramaniaraj, Journal of Pharmacy Research 2009, 2(11),1669-1675 "Archived copy". Archived from the original on 2011-07-23. Retrieved 2011-08-27.CS1 maint: archived copy as title (link)
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. 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.
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.