Alpha-Santonin

Eur J Med Chem. 2013 Feb;60:365-75.

Diminutive effect on T and B-cell proliferation of non-cytotoxic α-santonin derived 1,2,3-triazoles: a report.[Pubmed: 23314050 ]

METHODS AND RESULTS:
Alpha-Santonin derived new series of 1,2,3-triazoles synthesized through Azide-Alkyne Huisgen 1,3-dipolar cycloaddition reaction between substituted aryl azide and a propargylated α-desmotrosantonin were bio-evaluated for their diminutive effect on ConA induced T-cell and LPS induced B-cell proliferation. Interestingly, most of the synthesized compounds showed better immunosuppressant activity than Alpha-Santonin. Triazole derivatives 9, 10, 17, 18, 29, and 30 displayed significant diminutive effect on cell proliferation. Compounds 12 and 13 were found selective against ConA T-cell proliferation exhibiting >90% inhibition at 1 × 10(-6) M concentration.
CONCLUSIONS:
The present study resulted in identification of several triazole derivatives as effective immunosuppressive agents.

Acta Crystallogr Sect E Struct Rep Online. 2012 Jul 1;68(Pt 7):o2112.

3,5a,9-Trimethyl-8-(2-phenylhydrazin-1-ylidene)-4,5,5a,9b-tetrahydro-3aH,8H-naphtho[1,2-b]furan-2(3H)-one.[Pubmed: 22798789 ]

The title compound, C(21)H(24)N(2)O(2), is a phenyl hydrazine derivative of the well known anthelminthic agent Alpha-Santonin, which is composed of three fused rings (benzodieneone, cyclo-hexane and γ-lactone). The cyclo-hexa-dienone ring adopts a boat conformation, the cyclo-hexane ring is in a chair conformation and the trans-fused γ-lactone ring adopts a C-envelope conformation. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds, forming chains along the a axis.

Z Naturforsch C. 2000 Sep-Oct;55(9-10):713-7.

Biotransformation of two cytotoxic terpenes, alpha-santonin and sclareol by Botrytis cinerea.[Pubmed: 11098821]

Two cytotoxic terpenes, Alpha-Santonin (1) and sclareol (3) were biotransformed by a plant pathogenic fungus Botrytis cinerea to produce oxidized metabolites in high yields.
METHODS AND RESULTS:
Alpha-Santonin (1) on fermentation with the fungus for ten days afforded a hydroxylated metabolite identified as 11beta-hydroxy-Alpha-Santonin (2) in a high yield (83%), while sclareol (3) was metabolized to epoxysclareol (4) (64%) and a new compound 8-deoxy-14,15-dihydro-15-chloro-14-hydroxy-8,9-dehydrosclareol (5) (7%), representing a rare example of microbial halogenation.

J Chromatogr. 1992 Feb 28;593(1-2):209-15.

Use of high-performance liquid chromatographic peak deconvolution and peak labelling to identify antiparasitic components in plant extracts.[Pubmed: 1639905]

Artemisia absynthium L. is a commonly used medicinal plant for parasitic diseases all over the world.
METHODS AND RESULTS:
By means of high-performance liquid chromatography with diode-array detection and the PU6100 solvent optimization system, two sesquiterpene lactones, Alpha-Santonin and ketopelenolid-A, were tentatively identified in methanolic extracts of this plant. Alpha-Santonin is a well known antiparasitic compound and could be one of the active principles of this plant species.
CONCLUSIONS:
Reconstructed spectra are potentially useful in scanning a complex chromatogram for pharmacologically active compounds.