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[Studies on chemical constituents of Caesalpinia decapetala (Roth) Alston].

OBJECTIVE: To study the chemical constituents from Caesalpinia decapetala (Roth) Alston. METHODS: Chromatography and spectroscopic analysis were employed to isolate and elucidate the chemical constituents in the plant. RESULTS: Seven compounds were isolated and elucidated as lupeol acetate(I), lupeol(II), oleanoic acid(III), pentacosanoic acid 2,3-dihydroxypropyl ester(IV), 1-(26-hydroxyhexacosanoyl)-glycerol(V), stigmasterol(VI), beta-sitosterol(VI). CONCLUSION: I approximattely VII were isolated from this plant for the first time.

Caesalpinia↗

[Studies on chemical constituents in herb of Chondrilla piptocoma].

OBJECTIVE: To study the chemical constituents of Chondrilla piptocoma. METHOD: The chemical constituents were isolated and repeatedly purified on silica gel column and the structures were elucidated by the NMR spectra and physico-chemical properties. RESULT: Seven compounds were obtained and they are identified as luteolin, 5,7,4'-trihydroxy-3'-methoxy flavone, luteolin-7-O-beta-D-glucoside, apigenin, beta-sitosterol, stigmasterol, ursolic acid. CONCLUSION: All the compounds were obtained from C. piptocoma for the first time.

Apigenin↗

[Research on chemical ingredients of the root from cultivar Aralia cordata Thunb].

Eight components were isolated and purified from the ethereal extract from cultivar Aralia cordata Thumb. By means of UV, IR, 1H-NMR, 13CNMR, they were identified as (I) kaur-16-en-19-oic acid, (II) docosanoic, (III) hexadecanoic acid, (V) stigmasterol, (V) 16-formyl-kaur-15-en-19-oic acid, (VI) 7-oxo-ent-pimara-8 (14), 15-dien-19-oic acid, (VII) 17-Hydroxy-ent-kaur-15-en-19-oic acid, (VlII) sitosterol. Among them, components II, III, V were isolated from the gunus of Aralia for the first time.

Aralia↗

[Chemical constituents from roots of Ficus hirta].

OBJECTIVE: To study the chemical constituents from the roots of Ficus hirta. METHOD: Compounds were isolated by chromatographic techniques on silica gel and HP-20 resin columns. Their structures were elucidated by chemical and spectroscopic methods. RESULT: Ten compounds were identified as beta-sitosterol (1), stigmasterol (2), psoralene (3), 3beta-hydroxy-stigmast-5-en-7-one (4), 5-hydroxy-4', 6, 7, 8-tetramethoxy flavone (5), 4', 5, 6, 7, 8-pentamethoxy flavone (6), 4', 5, 7-trihydroxy-flavone (7), 3beta-acetoxy-beta-amyrin (8), 3beta-acetoxy-alpha-amyrin (9) and hesperidin (10). CONCLUSION: The compounds 4, 5, 6 were obtained from this genus for the first time, and all the compounds were obtained from this plant for the first time.

Ficus↗

[Studies on chemical constituents in roots of Heracleum rapula].

OBJECTIVE: To study the chemical constituents in roots of Heracleum rapula. METHOD: The constituents were isolated by column chromatography on silica gel and ODS, and identified by spectroscopic methods. RESULT: Eight compounds, xanthotoxol (I), 8-geranyloxypsoralen (II), (+)-marmesin (III), beta-sitosterol (IV), stigmasterol (V), oleanolic acid (VI), ferulic (VII), scopoletin (VIII) were isolated and identified. CONCLUSION: Compounds IV, V, VI, VII, VIII were isolated from this plant for the first time.

Coumaric Acids↗

[Chemical constituents of mangrove plant Barringtonia racemosa].

OBJECTIVE: To study the chemical constituents of mangrove plant Barringtonia racemosa. METHODS: Chemical constituents from the ethyl acetate extract of the stem bark of this plant were isolated by silica, Sephadex LH-20 column chromatography and identified by NMR analysis. RESULTS: Five compounds were isolated and identified. They are 3,3'-dimethoxy ellagic acid (1), dihydromyticetin (2), gallic acid (3), bartogenic acid (4) and stigmasterol (5). CONCLUSION: Compounds 1-3 were isolated from this plant for the first time.

Barringtonia↗

Studies on steroidal plant-growth regulators (XVII)--a new synthesis of homobrassinolide and (22S, 23S)-22, 23-epi-homobrassinolide.

Homobrassinolide (2) and (22S, 23S)-22,23-epi-homobrassinolide (4) were synthesized from stigmasterol in seven steps respectively in 4.7% and 24.1% overall yields. The ratio of 2 to 4 is 1:5. The key step is the highly regioselective formation of the B-homo-7-oxa-lactone ring by oxidation of an enol silyl ether with 3-chloro-peroxybenzoic acid.

Cholestanones↗

Inhaled tobacco sterols: uptake by the lungs and disposition to selected organs of rats.

Tobacco sterols (cholesterol, beta-sitosterol, campesterol, and stigmasterol) are present in tobacco smoke and appear in plasma of mammals exposed to cigarette smoke. Because tobacco sterols may be important in the pathogenesis of smoking-induced lung and vascular diseases, we studied the pattern of deposition of cigarette sterols in the lungs and appearance of cigarette sterols in plasma and body organs of rats. After exposure to twenty 5 ml "puffs" of smoke from tobacco labeled with [4-14C]cholesterol or beta-[4-14C]sitosterol, rats were killed just after exposure (day 0) and on days 2, 5, 8, 11, 15, and 30, and the lungs and selected body organs analyzed for activity. We found that cigarette sterols are associated with particulates in cigarette smoke, deposited mostly in distal airspaces and parenchyma of the lungs, and appear in plasma and several body organs for more than 30 days after this single exposure to cigarette smoke. Bronchoalveolar lavage fluid contained relatively small amounts of radiolabel for only the first few days, suggesting that most of the sterols were rapidly incorporated in lung parenchyma. Because disorders of sterol metabolism have been implicated in a variety of diseases including atherosclerosis and cancer, the significance of tobacco sterols to human smoking-induced diseases deserves further study.

Animals↗

Hypercalcemia and neoplasia. Biologic, biochemical, and ultrastructural studies of a hypercalcemia-producing Leydig cell tumor of the rat.

A localized, transplantable testicular tumor of the Fischer rat regularly produces hypercalcemia and increased phosphorus clearance in host animals. Light and electron microscopic examinations of the tumor indicate that it is of Leydig origin. There is no evidence that the tumor secretes any biologically active sex steroids, judges by weights of target tissues, when the tumor is grown in castrated or spayed rats. No radioactive steroid hormone formation in vitro was detected using 1-14C-acetate as a precursor although 14C was incorporated into the "C27" sterol fraction. Mass (micrograms) amounts of sex steroids were not detected after purifying large amounts of tumor extracts. The phytosterols, beta-sitosterol, stigmasterol, campesterol, were tentatively identified in tumor extracts but were also found in other tissues and in tumors not associated with hypercalcemia. Administered in vivo, human chorionic gonadotropin caused an acute rise in serum calcium in 3 to 5 hours in tumor-bearing hypercalcemic rats. Only trophic hormones with luteinizing hormone activity were found to compete with 125I-human chorionic gonadotropin for binding to the tumor homogenate in vitro indicating the tumor possessed luteinizing hormone receptors. When the tumor was transplanted intrasplenically, hypercalcemia did not occur unless adhesions formed, suggesting that the tumor hormone was rapidly metabolized by the liver and was probably of small molecular weight. Secretory granules, usually thought to be associated with peptide hormone secretion, were not detected at the ultrastructure level. Cortisol, conjugated estrogen, and an inhibitor of sterol biosynthesis (AY-9944) were effective in lowering the elevated serum calcium. Definitive identification of the agent causing lethal hypercalcemia has not been accomplished. The available data suggest it is not parathyroid hormone or vitamin D. The Leydig cell origin of the tumor, its response to human chorionic gonadotropin in vivo, the lack of secretory granules at the ultrastructural level, and biologic characteristics, all lead to the speculation that the secretory product of the tumor is a new hormonal substance, possibly a steroid precursor or related substance not previously described or is a known substance of small molecular weight whose calcium-mobilizing properties have not been fully characterized. This transplantable tumor may represent a model for one form of neoplastic hypercalcemia occurring in man and may have important implications in the general area of calcium and phosphorus homeostasis.

Animals↗

[Sterols in Stevia rebaudiana Bertoni].

The sterol fraction of Stevia rebaudiana Bertoni contains, essentially, the following sterols: stigmasterol (45,8%), beta-sitosterol (39,4%) and campesterol (13,1%). The individual components were separated, after acetylation, by HPLC with absolute methanol as eluant. The identification of the compounds has been carried out through NMR and MS, while the corresponding percentages have been desumed from the GLC data.

Cholesterol↗

Smith-Lemli-Opitz syndrome diagnosed by using time-of-flight secondary-ion mass spectrometry.

We describe a rapid and sensitive method involving time-of-flight secondary-ion mass spectrometry (TOF-SIMS) for specific laboratory diagnosis of the Smith-Lemli-Opitz syndrome, which is characterized by massive (approximately 1000-fold) accumulation of the biosynthetic cholesterol precursor 7-dehydrocholesterol. Minute amounts of blood (1-50 microL) were extracted with n-hexane, and aliquots were analyzed by TOF-SIMS. 7-Dehydrocholesterol and its isomers were detected at 491.3 mass units ([M + 107Ag]+) and cholesterol at 495.3 mass units ([M + 109Ag]+). Quantitation of 7-dehydrocholesterol and cholesterol was achieved after saponification and addition of stigmasterol as internal standard. Whereas 7-dehydrocholesterol and isomeric dehydrocholesterol were not detectable in controls, the patients revealed concentrations ranging between 0.84 and 1.25 mmol/L. Comparison with results obtained by gas chromatography indicated that quantitation by TOF-SIMS yielded the sum of 7-dehydrocholesterol, isomeric dehydrocholesterol II, and sterol III, the latter two also being increased in the patients. Consistent with quantitation by gas chromatography, the cholesterol concentrations in the patients ranged between 1.54 and 2.12 mmol/L (controls: 6.10 +/- 1.37 mmol/L).

Cholesterol↗

[Chemical constituents of flower of David lily].

Three compounds were isolated from the flower of Lilium devidii. On the basis of chemical reaction, UV, MS, 1HNMR and 13CNMR spectral data, they were identified as beta-sitosterol, stigmasterol and emodin. These compounds are obtained from the plant for the first time.

Drugs, Chinese Herbal↗

[Chemical constituents of Emilia sonchifolia L. DC].

Five known compounds were obtained from the whole plant of Emilia sonchifolia. By means of chemical and spectral methods, they were identified to be simiral, beta-sitosterol, stigmasterol, palmitic acid and honey acid.

Drugs, Chinese Herbal↗

[Chemical components of Lindernia ciliata (Colsm) Pennell].

Three known compounds were isolated from the petroleum ether extract of the whole plant of Lindernia ciliata. They are beta-sitosterol, stigmasterol and lup-20(29)-en-3 beta-ol. Their structures were established by IR, MS, 1HNMR and 13CNMR spectroscopy.

Drugs, Chinese Herbal↗

Plasma and dietary phytosterols in children.

Plasma phytosterol (plant sterol) levels were studied in 26 infants on various commercial formulas, in 36 infants on breast or cow's milk formulas, in 101 normal and 22 hypercholesterolemic children on a free diet, and in 32 hypercholesterolemic children on a low-cholesterol diet. Commercial formulas, poor in animal fats and enriched with vegetable oils, and low-cholesterol, phytosterol-rich diets generally elevated total plasma phytosterol levels in infants and hypercholesterolemic children from normal mean levels of 2 mg/100 ml to about 9 mg/100 ml. The implications of long-term three- to five-fold elevations of the plasma phytosterols (campesterol, stigmasterol, beta-sitosterol) in infancy and childhood are unknown. Watchful prospective analysis of plasma phytosterol levels may be useful, particularly in regards to otherwise unanticipated long-term effects of cholesterol-poor, phytosterol rich diets.

Adolescent↗

[Chemical constituents of Eclipta alba (L.) Hassk].

Ecliptasaponin C (1), a new triterpenoid glucoside, was isolated together with daucosterol (2) and stigmasterol-3-O-glucoside (3) from Eclipta alba. Based on spectral analysis, chemical evidence and hydrolytic results, it's structure was deduced as 3-beta-O-beta-D-glucopyranosyl-19beta-hydroxy olean-12-ene-28-oic acid 28-O-beta-D-glucopyranoside, Compounds 2 and 3 were obtained from Eclipta for the fist time.

Asteraceae↗

[Chemical constituents of Aster albscens Hand.-Mazz].

Four compounds, stigmasterol, D-hurulon-14-en-3-ol, stigma-delta7.22-dien-3beta-palmitate and friedelin were isolated from the root of Aster albscens for the first time. Their structures were elucidated by spectral methods.

Asteraceae↗

Determination of cholesterol at the low picomole level by nano-electrospray ionization tandem mass spectrometry.

A mass spectrometric method for the quantification of free cholesterol in cells and subcellular membranes is presented. The method is based on a simple one-step chemical derivatization of cholesterol to cholesterol-3-sulfate by a sulfur trioxide-pyridine complex. Quantification is performed by nano-electrospray ionization tandem mass spectrometry (nanoESI-MS/MS) using a stable isotope labeled internal standard. The determination of free cholesterol is demonstrated in about 250 cells of a Chinese hamster ovary (CHO) cell line. With this method a molar ratio of free cholesterol to total phospholipids of 0.34 mol/mol in CHO cells was determined. In a subcellular membrane fraction enriched in Golgi membranes, a molar ratio of free cholesterol to total phospholipids of 0.57 mol/mol was determined. The method should be of value for quantification of other sterols as demonstrated for ergosterol and stigmasterol.

Animals↗