Isovanillin

Res Pharm Sci. 2014 Mar-Apr;9(2):83-9.

Antidiarrheal activities of isovanillin, iso-acetovanillon and Pycnocycla spinosa Decne ex.Boiss extract in mice.[Pubmed: 25657776]

Isovanillin and iso-acetovanillon are two phenolic components isolated from a number of plants including Pycnocycla spinosa. P. spinosa extract has antispasmodic and antidiarrheal activities. However, no comparative study has been done on antidiarrheal action of Isovanillin and iso- acetovanillon, so far. The aim of this study was to investigate antidiarrheal action of Isovanillin and iso-acetovanillon and their effects on small intestinal transit, for comparison with propantheline.
METHODS AND RESULTS:
Male mice (25-30 g), fasted over night with free access to water, were treated with test compounds or control (p.o.). Thirty min later castor oil (0.5 ml) was given orally to the animals. In another groups of animals MgSO4 (0.5 ml of 10% solution) was given first and half an hour later the test drugs were administered. Onset and number of wet defecations were recorded for each animal over 3.5 h after treatment with diarrhoea inducing agents. In another groups, intestinal transit of charcoal meal was determined following administration of the compounds. Isovanillin (2 mg/kg & 5 mg/kg), iso-acetovanillon (2 mg/kg & 5 mg/kg) and P. spinosa extract (5 mg/kg) delayed onset of diarrhoea and significantly reduced wet defecation induced by castor oil and MgSO4. They all had antidiarrheal effect similar to propantheline (5 mg/kg). Isovanillin, iso-acetovanillon and P. spinosa extract compared to control groups, significantly reduced small intestinal transit of charcoal meal.
CONCLUSIONS:
This study shows that antidiarrheal effect of P. spinosa extract is at least partially due to presence of two active compounds Isovanillin and iso-acetovanillon.

Res Pharm Sci. 2014 May-Jun;9(3):187-92.

Antispasmodic activity of isovanillin and isoacetovanillon in comparison with Pycnocycla spinosa Decne.exBoiss extract on rat ileum.[Pubmed: 25657788]

Isovanillin and isoacetovanillon are two components found in P. spinosa Decne.exBoiss extract with no previously reported effect on ileum contractions.
METHODS AND RESULTS:
Spasmolytic effect of Isovanillin and isoacetovanillon were examined on response to electrical field stimulation (EFS), acetylcholine (ACh) and 5-HT in strips of rat ileum. Longitudinal ileum strips were set up in an organ bath containing oxygenated Tyrode's solution. All strips that was contracted in response to EFS, acetylcholine or 5-HT showed relaxation in the presence of Isovanillin (5-320 μg/ml), or isoacetovanillon (5-320 μg/ml). Isovanillin and isoacetovanillon inhibited the response to 5-HT with IC50 values of 356±50μM and 622±110μM respectively. They reduced the response to EFS without significantly affecting the acetylcholine response. P. spinosa extract (5-160 μg/ml) in a concentration dependent manner reduced the response to 5-HT, acetylcholine and EFS.
CONCLUSIONS:
This study demonstrated that Isovanillin and isoacetovanillon are relaxant of ileum contractions induced by 5-HT and EFS and they have contribution to the relaxant effect of P. spinosa extract but other components are responsible for the inhibition of acetylcholine by the extract.

Org Biomol Chem. 2014 Apr 28;12(16):2552-8.

Isovanillin derived N-(un)substituted hydroxylamines possessing an ortho-allylic group: valuable precursors to bioactive N-heterocycles.[Pubmed: 24576957]

METHODS AND RESULTS:
The intramolecular 1,3-dipolar cycloaddition of Isovanillin derived N-aryl hydroxylamines possessing ortho-allylic dipolarophiles affords novel benzo analogues of tricyclic isoxazolidines that can be readily transformed into functionalized lactams, γ-aminoalcohols and oxazepines. The corresponding N-unsubstituted hydroxylamines give rise to tetrahydroisoquinolines.
CONCLUSIONS:
Anxiogenic properties of these compounds are tested in zebra fish.