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An investigation was undertaken to evaluate the comparative efficacy of single dose treatment with santonin and piperazine against naturally acquired Neoascaris vitulorum in sixty-two buffalo calves of 20-60 days of age. Santonin was administered orally in doses of 5 mg, 10 mg and 15 mg/kg body weight to thirteen, eighteen, and sixteen buffalo calves, respectively. As a control, piperazine (88 mg/kg) was given by drench to a group of fifteen infected buffalo calves. Pretreatment and post treatment faecal eggs per gram (EPG) counts were determined by the Stoll's technique. The percentage reductions in EPG counts on the third and seventh days after administration of the two drugs were calculated. The percentage reduction in EPG counts in the piperazine treated group on the third day was 82 +/- 15, 90.2 +/- 3 and 91.3 +/- 2.3% while on the seventh day these values were 88 +/- 16, 97 +/- 3, and 98 +/- 2% in high, moderate and heavy infection calves, respectively. Treatment with santonin at 5, 10 and 15 mg/kg body weight also reduced the EPG counts. The percentage reduction in EPG counts in the calves treated with 15 mg/kg of santonin on the third day was 92.3 +/- 18, 95.8 +/- 7 and 93.5 +/- 4% while on the seventh day these values were 100 +/- 0, 100 +/- 0 and 99.7 +/- 2% in high, moderate and heavily infected calves, respectively. Both piperazine and santonin were associated with some side effects like diarrhoea, restlessness, etc. but their percentage incidence was not significantly different from each other. These findings suggest that santonin in a 15 mg/kg dose has an efficacy similar to piperazine given at the 88 mg/kg dose level for the treatment of ascariasis in buffalo calves.
The microbial transformation of a sesquiterpene lactone, 1-alpha-santonin was carried out by Streptomyces roseochromogenes NRRL-B-1233. The product obtained from 1-alpha-santonin was purified using silica gel column chromatography with 1% acetone-benzene as the eluant. The molecular weight of the product was 248, estimated by mass spectroanalysis. The product was assigned the chemical structure of 1,2-dihydro-1-alpha santonin on the bases of 1H and 13C-NMR and mass spectroanalyses. Similar products were also obtained from other actinomycetes. The conversion of 1-alpha-santonin to 1,2-dihydro-1-alpha-santonin was 28% for Streptomyces roseochromogenes NRRL-B-1233, 14% for S. roseochromogenes ATCC 13400, 30.9% for S. aureofaciens KCC-S-0008, and 43.0% for S. aureofaciens KCC-S-0624, respectively.
Berberine and santonin were isolated from rhizomes of Berberis aristata and unexpanded flower buds of Artemisia maritima, respectively. Efficacy of these two chemicals individually as well as of their mixtures, was tested against spore germination of some saprophytic and obligate fungi. While berberine individually was effective against most of the fungi, Helminthosporium spp. were least affected even at the highest dose (1500 ppm). Santonin was equally effective against several fungi. Mixture of both alkaloids found to be more effective than individual ones. Keeping the dose of berberine constant and santonin at two different concentrations (viz. 250 and 500 ppm) the spore germination of Helminthosporium oryzae was stimulated. Increasing concentration of santonin inhibited the spore germination of all other fungi tested, Colletotrichum capsici being affected only by 20 and 5% (at berberine concentration of 250 and 500 ppm, respectively). On the other hand, santonin being constant and berberine at different concentrations, the mixture was effective against all the fungi.
The antipyretic activity of two sesquiterpene lactones, beta-santonin and arsubin, isolated from the lipid fraction of Artemisia coerulescens subsp. gallica was determined in rats along with the activity of alpha-santonin. In its alpha- and beta-forms, santonin caused a decrease in the body temperature of rats made febrile by the subcutaneous injection of beer yeast. This decrease, more pronounced in the case of beta-santonin, was dose-dependent and antagonized by pretreatment with haloperidol, an agent that also opposes the antipyretic activity of dopamine. These findings seem to show that the alpha- and beta-forms of santonin act on rectal temperature in a way similar to dopamine.
Fungal biotransformations of alpha-santonin (1) were conducted with Mucor plumbeus (ATCC 4740), Cunninghamella bainieri (ATCC 9244), Cunninghamella echinulata (ATCC 9245), Curvularia lunata (ATCC 12017) and Rhizopus stolonifer (ATCC 10404). Rhizopus stolonifer (ATCC 10404) metabolized compound 1 to afford 3,4-epoxy-alpha-santonin (2) and 4,5-dihydro-alpha-santonin (3) while Cunninghamella bainieri (ATCC 9244), Cunninghamella echinulata (ATCC 9245) and Mucor plumbeus (ATCC 4740) were capable of metabolizing compound 1 to give a reported metabolite, 1,2-dihydro-alpha-santonin (4). The structures of these transformed metabolites were established with the aid of extensive spectroscopic studies. These fungi regiospecifically reduced the carbon-carbon double bond in ring A of alpha-santonin.
Santonin, a sesquiterpene lactone, commonly found in the plants of the family Compositae was found to show significant antiinflammatory activity on acute inflammatory processes. The activity profile of santonin closely resembled that of a standard non-steroidal antiinflammatory drug, diclofenac sodium. It also showed a significant inhibitory effect on granuloma formation; however, this effect of santonin was less pronounced as compared to diclofenac sodium. Santonin caused a significant antipyretic effect in mice, which was found to be independent of the route of administration of the drug. It also increased the hot plate reaction time of treated mice, similar to morphine.
Santonin gives a characteristic alkaline vs acidic difference spectrum. This was used for its estimation in pharmaceuticals and in the crude drug. Santonin was first extracted and purified through a specific partition procedure; then the difference absorbance was measured either at the maximum, 285 nm, or the minimum, 242 nm. The percentage of santonin can be calculated either by reference to the difference absorbance of a reference santonin sample, treated similarly, or by making use of the determined absorptivity. Measurement at the maximum is advisable, especially when the crude drug is assayed, because natural contaminants may interfere with the difference absorbance at the minimum.
The synthesis of two new santonin derivatives namely 3-oxo-6 beta-H-11 beta-phenylselenoeudesm-1,4-dien-6,13-olide and 3-oxo-6 beta H-eudesm-1,4,11-trien-6,13-olide is reported along with the results of a series of santonins tested for activity against the growth of KB cells in vitro, a human epidermoid nasopharynx carcinoma. Select compounds were found to be active at concentrations lower than 5 X 10(-5) M. In particular, the compound 2 alpha-bromo-3 beta-hydroxy-6 beta H-eudesm-11-en-6,13-olide exhibits an extremely low ID50 value at 0.33 X 10(-6) M. Some relationships between chemical structure and cytotoxic activity are suggested, i.e. the alpha-methylene-gamma-lactone moiety appears to be necessary for cytotoxic activity toward KB cells growth in vitro by santonin derivatives.
Santonin-related compounds (SRCs) were synthesized from the starting material L-alpha-santonin and tested for the biological activity on the expression of intercellular adhesion molecule-1 (ICAM-1) in response to IL-1 stimulation on human adenocarcinoma cells. One of the bromoketone derivatives termed SRC2 [11S-2 alpha-bromo-3-oxoeudesmanno-13,6 alpha-lactone] strongly inhibited the ICAM-1 expression at an IC(50) value of 5.9 microM, whereas L-alpha-santonin itself was totally inactive up to 100 microM. The blockage of ICAM-1 expression by SRC2 was not due to the direct inhibition of de novo RNA and protein synthesis. The nuclear translocation of NF-kappaB subunit p65 was markedly prevented by SRC2. Moreover, I kappa B alpha degradation upon IL-1 stimulation was strongly inhibited by SRC2. These observations suggest that SRC2 blocks the IL-1 signaling pathway upstream of I kappa B degradation.
1,2-Dihydrosantonin is the first stable product in the degradative pathway of alpha-santonin by Pseudomonas cichorii S. Its formation is catalyzed by an oxidoreductase, which is NADH or NADPH dependent and has an apparent Km value of 66.66 microM for santonin and 44.33 microM for NADH. The enzyme activity is stable at pH 6.0, 7.0, and 8.0, and is not affected by EDTA and divalent metal ions. It is postulated that the enzymic reduction of santonin occurs via formation of a transient zwitterionic intermediate, which undergoes nonenzymatic 1,4-sigmatropic rearrangement to yield lumisantonin during the solvent extraction process. Lumisantonin is, thus, not a true metabolic intermediate but an artifact.
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. 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.