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PubMed1995

Antinociceptive properties of steroids isolated from Phyllanthus corcovadensis in mice.

The antinociceptive actions of the steroid compounds isolated from the leaves, stems, and roots of P. corcovadensis have been investigated in mice. Stigmasterol, stigmasterol acetate, beta-sitosterol, and aspirin (3-100 mk/kg, i.p.) inhibited, in a dose-related manner, acetic acid-induced abdominal constriction in mice with ID50s of 16, 11, 9, and 24 mg/kg, respectively. In the formalin test, stigmasterol and stigmasterol acetate (10-100 mg/kg, i.p.) caused graded inhibition of both the neurogenic (first phase) and inflammatory phases (second phase) of formalin-induced pain. However, both compounds were more effective in relation of the second phase of the formalin test with ID50 values of 26 and 41 mg/kg, respectively. Furthermore, both steroids failed to affect the edematogenic response of the formalin test. Given orally, stigmasterol and stigmasterol acetate (50-200 mg/kg) also exhibited significant though less potent analgesic action against both acetic acid- and formalin-induced nociception in mice. In addition, stigmasterol (up to 100 mg/kg, i.p.), in contrast to morphine (10 mg/kg, s.c.), had no analgesic effect in either tail-flick or hot-plate models. These findings suggest that stigmasterol and beta-sitosterol may account, at least in part, for the antinociceptive actions reported previously for the hydroalcoholic extract of Phyllanthus corcovadensis.

Analgesics↗
PubMed1976

Phytosterols in aortic tissue in adults and infants.

Relationships between aortic tissue phytosterols and cholesterol in five adults, five infants, two neonates, and one 30 week abortus were studied. In the normal aortic tissue of the abortus and two neonates, tissue cholesterol levels were 0.67, 0.08, and 0.89 mg. per gram of wet weight, respectively; tissue phytosterol levels were as follows: compesterol (0.94, 0.62. 1.8), stigmasterol (0.18, 0.54, 0.80) and beta-sitosterol (0.78, 1.84, 2.80) mug per gram of wet weight. In 11 aortic tissue samples from five infants studied at 3, 4, 6, 6, and 36 months of age, all having been on phytosterol-rich formulas, mean aortic cholesterol was 0.66 mg. per gram, campesterol 3.57, stigmasterol 9.22, and beta-sitosterol 8.93 mug per gram. In the 11 aortic samples from five infants, mean (+/-S.E.) tissue stigmasterol (9.2+/-2.7) and beta-sitosterol ((8.9+/-1.3) were greater than mean levels (0.51+/-0.18 and 1.8+/-0.6) in the four aortic sections from the abortus and two neonates. Mean (+/-S.E.) cholesterol in the 11 aortic sections from five infants (0.66+/-0.11) was not significantly higher than cholesterol (0.55+/-0.24 mg. per gram) in the four aortic sections from the abortus and two neonates, but was considerably higher than the tissue cholesterol level of 0.08 mg. per gram in one of the two neonates. Mean (+/-S.E.) cholesterol in 11 normal aortic tissue sections from five adults (3.4+/-0.7 mg. per gram) was higher than in the five infants, whereas mean compesterol, stigmasterol, and beta sitosterol, respectively 14, 13, and 16 mug per gram, were somewhat higher but generally comparable to infant levels. In five aortic tissue samples from mature atheromatous plaques in two adults, cholesterol was 54 mg. per gram and mean campesterol, stigmasterol, and beta-sitosterol were, respectively, 112, 167, and 236 mug per gram. In 15 aortic tissue samples from five adults, cholesterol correlated closely with stigmasterol, r=0.865, beta-sitosterol, r=0.918, and with total phytosterols, r=0.938, p less than 0.01, but not with campesterol, r=0.448. In 11 aortic tissue samples from five infants, cholesterol did not correlate with campesterol, r=0.005, stigmasterol, r=0.006, beta-sitosterol, r=-0.099, or total phytosterols, r=-0.045. Prior to birth some phystosterols apparently cross the placenta. In the first several months of life, vegetable-oil formula-fed infants accrue plant sterols in their aortic tissues. Moderate amounts of phytosterols are present in mature atheromatous lesions in adults. The implications of these findings are unknown and their relationship to deposition of cholesterol in atheromatous and in normal aortic tissues remains to be elucidated.

Adult↗
PubMed1981

Uptake and esterification of plant sterols by rat small intestine.

The commonly found plant sterols, beta-sitosterol, campesterol, and stigmasterol, differ structurally from cholesterol only in side chains but are absorbed in much smaller amounts than cholesterol. Because intestinal mucosal cell uptake and esterification are important steps in absorption, these were studied in vivo after feeding the sterols and in vitro using everted sacs of rat small intestine. The studies showed that campesterol uptake was significantly higher than that of beta-sitosterol, whereas stigmasterol uptake was extremely low throughout the intestine. The total intestinal content of campesterol was 2.223 mg/g or about 14% of the dose fed as compared with 1.496 mg/g or 7.4% for beta-sitosterol and only 0.392 mg/g or 2.3% for stigmasterol. Intestinal tissue concentration of esterified campesterol was higher than that of beta-sitosterol, whereas that of esterified stigmasterol was extremely low. The results suggest that campesterol absorption would be higher than that of beta-sitosterol; stigmasterol probably would not be absorbed in any significant amount because of its negligible uptake due to its inability to partition out of the mixed micelles. It appears that the structure of the side chain of a sterol is an important determinant for uptake and esterification, and probably absorption, in the small intestine.

Animals↗
PubMed1999

Study of the topical anti-inflammatory activity of Achillea ageratum on chronic and acute inflammation models.

We have produced a chloroform extract from Achillea which includes stigmasterol and sitosterol. By comparing it with the pure compounds an anti-inflammatory effect (with mouse ears) is assumed. The topical anti-inflammatory effect of the chloroform extract from Achillea ageratum (Asteraceae) and of stigmasterol and beta-sitosterol, isolated of this extract has been evaluated, against to 12-0-tetradecanoylphorbol acetate (TPA)-induced mouse ear edema, using simple (acute model) and multiple applications (chronic model) of the phlogistic agent. Myeloperoxydase activity also was studied in the inflamed ears. In the acute model the extract exerted a dose-dependent effect. All the doses assayed (1, 3 and 5 mg/ear) significantly reduced the edema (50%, 66% and 82%, respectively). The isolated sterols stigmasterol and beta-sitosterol (with doses of 0.5 mg/ear) had similar effect as the extract with doses of 1 and 3 mg (59% and 65% respectively). In the chronic model the anti-inflammatory effect generally was a more moderate one. The highest dose of the extract decreased the edema reduction to 26% with the highest dose of the extract applied. With the compounds the effect decreased to 36% with stigmasterol, and 40.6% with beta-sitosterol. Myeloperoxydase activity (MPO) was reduced by the extract and the compounds in the acute model, however, in the chronic edema, the enzyme inhibition was very weak with all treatments even with the standard substance. These results indicate that the chloroform extract of Achillea ageratum and some of the its components stigmasterol and beta-sitosterol are more effective as topical anti-inflammatory agents in acute than in the chronic process and their action is markedly influenced by the inhibition of neutrophil migration into inflamed tissue.

Acute Disease↗
PubMed1996

Synthesis of Deuterium-Labeled Plant Sterols and Analysis of Their Side-Chain Mobility by Solid State Deuterium NMR.

The plant sterols sitosterol and stigmasterol exert very different effects on plant model membranes, the first one being a "reinforcer" like cholesterol, the second one not. 25-(2)H-Stigmasterol has been synthesized by coupling of the 22-aldehyde derived from stigmasterol by ozonolysis, with the proper sulfone labeled in position 25. The configuration of the ethyl side chain at C-24 was controlled by separation of the diastereomers introduced via a chiral sulfoxide. This synthetic scheme allowed the introduction of a labeled side chain in plant sterols in eight steps for stigmasterol and nine for sitosterol (overall yield ca. 15%). Using both diastereomers, the 24-epimers of sitosterol (clionasterol) and stigmasterol (poriferasterol) have also been synthesized. Deuterium NMR on oriented lipid bilayers made of soybean phosphatidylcholine and containing these four labeled plant sterols clearly reveals the difference of orientation and mobility of the four side chains.

Journal Article↗