| Identification | Back Directory | [Name]
pluviatolide | [CAS]
28115-68-6 | [Synonyms]
pluviatolide
trans-Pluviatolide
3α-(4-Hydroxy-3-methoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one
4,5-Dihydro-4β-[(1,3-benzodioxole-5-yl)methyl]-3α-(4-hydroxy-3-methoxybenzyl)furan-2(3H)-one
2(3H)-Furanone, 4-(1,3-benzodioxol-5-ylmethyl)dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R,4R)-
(3R,4R)-4-[(1,3-Benzodioxol-5-yl)methyl]-4,5-dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]furan-2(3H)-one | [Molecular Formula]
C20H20O6 | [MDL Number]
MFCD32004287 | [MOL File]
28115-68-6.mol | [Molecular Weight]
356.37 |
| Chemical Properties | Back Directory | [storage temp. ]
Store at -20°C | [solubility ]
DMF: Soluble; DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble | [form ]
A solid | [color ]
White to off-white | [LogP]
2.590 (est) |
| Hazard Information | Back Directory | [Description]
Pluviatolide is a lignan that has been found in B. chinense and has diverse biological activities, including antioxidant, enzyme inhibitory, and antispasmodic properties. It scavenges ABTS and 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals in cell-free assays (IC50s = 23.2 and 88.5 μM, respectively). Pluviatolide inhibits matrix metalloproteinase-7 (MMP-7) with an IC50 value of 260 μM. It decreases contractions induced by acetylcholine in isolated guinea pig ileum when used at concentrations of 30 and 100 μM. | [Uses]
Pluviatolide ((-)-Pluviatolide) is a lignan that can be found in the bark of Zanthoxylum pluviatile Hartley. Pluviatolide can be used as (-)-Podophyllotoxin precursor[1][2]. | [Definition]
ChEBI: A butan-4-olide that is dihydrofuran-2(3H)-one which is substituted by a vanillyl group at position 3 and by a 3,4-methylenedioxybenzyl group at position 4 (the R,R stereoisomer). | [References]
[1] Corrie JET, et, al. The chemical constituents of Australian Zanthoxylum species. V. The constituents of Z. pluviatile Hartley; the structures of two new lignans. Australian Journal of Chemistry 23(1) 133-145.
[2] Decembrino D, et, al. Assembly of Plant Enzymes in E. coli for the Production of the Valuable (-)-Podophyllotoxin Precursor (-)-Pluviatolide. ACS Synth Biol. 2020 Nov 20;9(11):3091-3103. DOI:10.1021/acssynbio.0c00354 |
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