IUPAC/Chemical Name
Phenol, 4-((2S,3R)-4-(1,3-benzodioxol-5-yl)-2,3-dimethylbutyl)-2-methoxy-
InChi Key
QDDILOVMGWUNGD-UONOGXRCSA-N
InChi Code
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
SMILES Code
C[C@H](Cc1ccc2c(c1)OCO2)[C@@H](C)Cc3ccc(c(c3)OC)O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Biological target:
Macelignan ((+)-Anwulignan; Anwuligan) is an orally active lignan isolated from Myristica fragrans.
In vitro activity:
HaCaT cells were treated with macelignan for the indicated times followed by irradiation with UVB. Macelignan at a concentration of 0.1-1 microM increased the viability of HaCaT cells following UVB irradiation and inhibited MMP-9 secretion and COX-2 expression in a concentration-dependent manner. An inhibitory effect was also seen in the signal transduction network, where macelignan treatment reduced the activation of UVB-induced MAPKs, PI3K/Akt, and their downstream transcription factors.
Reference: J Dermatol Sci. 2010 Feb;57(2):114-22. https://pubmed.ncbi.nlm.nih.gov/19914807/
In vivo activity:
The current study demonstrates that oral administrations of macelignan reduce the hippocampal microglial activation induced by chronic infusions of lipopolysaccharide (LPS) into the fourth ventricle of Fisher-344 rat brains. A Morris water maze was used to evaluate the status of the hippocampal-dependent spatial learning in control rats with an artificial cerebrospinal fluid infusion, rats with chronic LPS infusions, and rats with chronic LPS infusions and oral administrations of macelignan. Daily administration of macelignan reduced the spatial memory impairments induced by the chronic LPS infusions.
Reference: Neurosci Lett. 2008 Dec 19;448(1):110-4. https://pubmed.ncbi.nlm.nih.gov/18940231/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
100.0 |
304.50 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
328.41
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Gu L, Cai N, Li M, Bi D, Yao L, Fang W, Wu Y, Hu Z, Liu Q, Lin Z, Lu J, Xu X. Inhibitory Effects of Macelignan on Tau Phosphorylation and Aβ Aggregation in the Cell Model of Alzheimer's Disease. Front Nutr. 2022 May 18;9:892558. doi: 10.3389/fnut.2022.892558. PMID: 35662922; PMCID: PMC9159362.
2. Anggakusuma, Yanti, Hwang JK. Effects of macelignan isolated from Myristica fragrans Houtt. on UVB-induced matrix metalloproteinase-9 and cyclooxygenase-2 in HaCaT cells. J Dermatol Sci. 2010 Feb;57(2):114-22. doi: 10.1016/j.jdermsci.2009.10.005. Epub 2009 Nov 14. PMID: 19914807.
3. Long J, Qian K, Tan S, Liu J, Li J. Macelignan protects against renal ischemia-reperfusion injury via inhibition of inflammation and apoptosis of renal epithelial cells. Cell Mol Biol (Noisy-le-grand). 2020 Apr 20;66(1):55-59. PMID: 32359384.
4. Cui CA, Jin DQ, Hwang YK, Lee IS, Hwang JK, Ha I, Han JS. Macelignan attenuates LPS-induced inflammation and reduces LPS-induced spatial learning impairments in rats. Neurosci Lett. 2008 Dec 19;448(1):110-4. doi: 10.1016/j.neulet.2008.10.035. Epub 2008 Oct 15. PMID: 18940231.
In vitro protocol:
1. Gu L, Cai N, Li M, Bi D, Yao L, Fang W, Wu Y, Hu Z, Liu Q, Lin Z, Lu J, Xu X. Inhibitory Effects of Macelignan on Tau Phosphorylation and Aβ Aggregation in the Cell Model of Alzheimer's Disease. Front Nutr. 2022 May 18;9:892558. doi: 10.3389/fnut.2022.892558. PMID: 35662922; PMCID: PMC9159362.
2. Anggakusuma, Yanti, Hwang JK. Effects of macelignan isolated from Myristica fragrans Houtt. on UVB-induced matrix metalloproteinase-9 and cyclooxygenase-2 in HaCaT cells. J Dermatol Sci. 2010 Feb;57(2):114-22. doi: 10.1016/j.jdermsci.2009.10.005. Epub 2009 Nov 14. PMID: 19914807.
In vivo protocol:
1. Long J, Qian K, Tan S, Liu J, Li J. Macelignan protects against renal ischemia-reperfusion injury via inhibition of inflammation and apoptosis of renal epithelial cells. Cell Mol Biol (Noisy-le-grand). 2020 Apr 20;66(1):55-59. PMID: 32359384.
2. Cui CA, Jin DQ, Hwang YK, Lee IS, Hwang JK, Ha I, Han JS. Macelignan attenuates LPS-induced inflammation and reduces LPS-induced spatial learning impairments in rats. Neurosci Lett. 2008 Dec 19;448(1):110-4. doi: 10.1016/j.neulet.2008.10.035. Epub 2008 Oct 15. PMID: 18940231.
1: Shin YK, Kim KY. Macelignan inhibits bee pathogenic fungi Ascophaera apis growth through HOG1 pathway. Braz J Med Biol Res. 2016 Jul 4;49(7). pii: S0100-879X2016000700607. doi: 10.1590/1414-431X20165313. PubMed PMID: 27383123; PubMed Central PMCID: PMC4942228.
2: Kiyofuji K, Kurauchi Y, Hisatsune A, Seki T, Mishima S, Katsuki H. A natural compound macelignan protects midbrain dopaminergic neurons from inflammatory degeneration via microglial arginase-1 expression. Eur J Pharmacol. 2015 Aug 5;760:129-35. doi: 10.1016/j.ejphar.2015.04.021. Epub 2015 Apr 25. PubMed PMID: 25917324.
3: Liu H, Wu Z, Ma Z, Wu B. Glucuronidation of macelignan by human liver microsomes and expressed UGT enzymes: identification of UGT1A1 and 2B7 as the main contributing enzymes. Biopharm Drug Dispos. 2014 Dec;35(9):513-24. doi: 10.1002/bdd.1914. Epub 2014 Sep 1. PubMed PMID: 25099990.
4: Shin K, Chung HC, Kim DU, Hwang JK, Lee SH. Macelignan attenuated allergic lung inflammation and airway hyper-responsiveness in murine experimental asthma. Life Sci. 2013 Jun 13;92(22):1093-9. doi: 10.1016/j.lfs.2013.04.010. Epub 2013 Apr 30. PubMed PMID: 23643632.
5: Paul S, Hwang JK, Kim HY, Jeon WK, Chung C, Han JS. Multiple biological properties of macelignan and its pharmacological implications. Arch Pharm Res. 2013 Mar;36(3):264-72. doi: 10.1007/s12272-013-0048-z. Epub 2013 Feb 24. Review. PubMed PMID: 23435944.
6: Han YS, Kim MS, Hwang JK. Macelignan inhibits histamine release and inflammatory mediator production in activated rat basophilic leukemia mast cells. Inflammation. 2012 Oct;35(5):1723-31. doi: 10.1007/s10753-012-9490-1. PubMed PMID: 22729280.
