Macelignan

Macelignan
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
CAS Number	107534-93-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	8579683 ;
PubChem CID	10404245;
UNII	8PP3614Z43;
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). verify (what is ?) Infobox references

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]

References

^ 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.
^ 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
^ 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
^ ^a ^b 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.
^ 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.
^ says, Tee O. "Best Breast Enlargement Creams Reviewed [UPDATED]". BreastEnlargement.name. Retrieved 2020-08-07.

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[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

[pmid23435944-4] 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. 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.

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v t e Types of lignans
Lignans	Arboreol Arctigenin Chamaecypanone A and B Eudesmin Globoidnan A Gmelanone Gmelinol Gummadiol Isootobanone Lyoniresinol Macelignan Matairesinol Obtulignolide Pinoresinol Pluviatilol Podophyllotoxin Secoisolariciresinol Sesamin Sesamolin Steganacin
Lignan glycosides	Arctiin Aviculin (isolariciresinol-9'-rhamnopyranoside) Secoisolariciresinol diglucoside (SDG)
Mammalian lignans (enterolignans)	Enterodiol Enterolactone Lariciresinol Hydroxymatairesinol Syringaresinol
Neolignans	Balanophonin Eusiderin Honokiol Interiotherin Linderin A Magnolol Megaphone 4-O-Methylhonokiol Rhaphidecursinol A Rhaphidecursinol B
Flavonolignans	Cinchonain-Ib Dehydrosilybin Deoxysilycistin Deoxysilydianin Hydnocarpin Hydnowightin Neosilyhermin Palstatin Rhodiolin Salcolin A Salcolin B Scutellaprostin A, B, C, D, E and F Silandrin Silyamandin Silibinin Silybinome Silicristin Silydianin Silyhermin Tricin 4'-O-(erythro-beta-guaiacylglyceryl) ether Tricin 4'-O-(threo-beta-guaiacylglyceryl) ether