| RRC ID |
67441
|
| Author |
Tanabe G, Sugano Y, Shirato M, Sonoda N, Tsutsui N, Morikawa T, Ninomiya K, Yoshikawa M, Muraoka O.
|
| Title |
Total Synthesis of 4,5-Didehydroguadiscine: A Potent Melanogenesis Inhibitor from the Brazilian Medicinal Herb, Hornschuchia obliqua.
|
| Journal |
J Nat Prod
|
| Abstract |
The first total synthesis of the 7,7-dimethylaporphinoid, 4,5-didehydroguadiscine (6), originally isolated from the stems and roots of Hornschuchia oblique (Annonaceae), was achieved by the condensation of homopiperonylamine (7) with an α,α-dimethylphenylacetic acid derivative (8) and subsequent Pschorr reaction of the resulting benzylisoquinoline intermediate (22). The reported (13)C NMR data were partially revised on the basis of the analysis of HMBC spectra measured under different conditions. The melanogenesis inhibitory activity (IC50 = 4.7 μM) of 6 was 40 times stronger than that of arbutin (174 μM), which was used as reference standard. Furthermore, 6 was the most potent natural melanogenesis inhibitor within this class of compounds.
|
| Volume |
78(7)
|
| Pages |
1536-42
|
| Published |
2015-7-24
|
| DOI |
10.1021/np500995z
|
| PMID |
26135746
|
| MeSH |
Annonaceae / chemistry*
Aporphines / chemical synthesis*
Aporphines / chemistry
Aporphines / pharmacology*
Arbutin / pharmacology
Brazil
Esters
Melanins / antagonists & inhibitors*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Roots / chemistry
Plants, Medicinal / chemistry*
|
| IF |
3.782
|
| Resource |
| Human and Animal Cells |
B16 melanoma 4A5(RCB0557) |
