Stigmast-7-en-3-ol

Identification of Antidiabetic Metabolites from Paederia foetida L. Twigs by Gas Chromatography-Mass Spectrometry-Based Metabolomics and Molecular Docking Study.[Pubmed:31275982]

Biomed Res Int. 2019 May 29;2019:7603125.

Paederia foetida L. (Rubiaceae) is a climber which is widely distributed in Asian countries including Malaysia. The plant is traditionally used to treat various diseases including diabetes. This study is to evaluate the enzymatic inhibition activity of Paederia foetida twigs extracts and to identify the metabolites responsible for the bioactivity by gas chromatography-mass spectrometry (GC-MS) metabolomics profiling. Three different twig extracts, namely, hexane (PFH), chloroform (PFC), and methanol (PFM), were submerged for their alpha-amylase and alpha-glucosidase inhibition potential in 5 replicates for each. Results obtained from the loading column scatter plot of orthogonal partial least square (OPLS) model revealed the presence of 12 bioactive compounds, namely, dl-alpha-tocopherol, n-hexadecanoic acid, 2-hexyl-1-decanol, stigmastanol, 2-nonadecanone, cholest-8(14)-en-3-ol, 4,4-dimethyl-, (3beta,5alpha)-, stigmast-4-en-3-one, stigmasterol, 1-ethyl-1-tetradecyloxy-1-silacyclohexane, -sitosterol, Stigmast-7-en-3-ol, (3beta,5alpha,24S)-, and alpha-monostearin. In silico molecular docking was carried out using the crystal structure alpha-amylase (PDB ID: 4W93) and alpha-glucosidase (PDB ID: 3WY1). alpha-Amylase-n-hexadecanoic acid exhibited the lowest binding energy of -2.28 kcal/mol with two hydrogen bonds residue, namely, LYS178 and TYR174, along with hydrophobic interactions involving PRO140, TRP134, SER132, ASP135, and LYS172. The binding interactions of alpha-glucosidase-n-hexadecanoic acid complex ligand also showed the lowest binding energy among 5 major compounds with the energy value of -4.04 kcal/mol. The complex consists of one hydrogen bond interacting residue, ARG437, and hydrophobic interactions with ALA444, ASP141, GLN438, GLU432, GLY374, LEU373, LEU433, LYS352, PRO347, THR445, HIS348, and PRO351. The study provides informative data on the potential antidiabetic inhibitors identified in Paederia foetida twigs, indicating the plant has the therapeutic effect properties to manage diabetes.

CHEMICAL CHARACTERIZATION OF A HYPOGLYCEMIC EXTRACT FROM CUCURBITA FICIFOLIA BOUCHE THAT INDUCES LIVER GLYCOGEN ACCUMULATION IN DIABETIC MICE.[Pubmed:28480434]

Afr J Tradit Complement Altern Med. 2017 Mar 1;14(3):218-230.

BACKGROUND: The aqueous extract of Cucurbita ficifolia (C. ficifolia) fruit has demonstrated hypoglycemic effect, which may be attributed to some components in the extract. However, the major secondary metabolites in this fruit have not yet been identified and little is known about its extra-pancreatic action, in particular, on liver carbohydrate metabolism. Therefore, in addition to the isolation and structural elucidation of the principal components in the aqueous extract of C. ficifolia, the aim of this study was to determine whether or not the hypoglycemic effect of the aqueous extract of Cucurbita ficifolia (C. ficifolia) fruit is due to accumulation of liver glycogen in diabetic mice. MATERIALS AND METHODS: The aqueous extract from fruit of C. ficifolia was fractionated and its main secondary metabolites were purified and chemically characterized (NMR and GC-MS). Alloxan-induced diabetic mice received daily by gavage the aqueous extract (30 days). The liver glycogen content was quantified by spectroscopic method and by PAS stain; ALT and AST by spectrometric method; glycogen synthase, glycogen phosphorylase and GLUT2 by Western blot; the mRNA expression of GLUT2 and glucagon-receptor by RT-PCR; while serum insulin was quantified by ELISA method. A liver histological analysis was also performed by H&E stain. RESULTS: Chemical fingerprint showed five majoritarian compounds in the aqueous extract of C. ficifolia: p-coumaric acid, p-hydroxybenzoic acid, salicin, stigmast-7,2,2-dien-3-ol and Stigmast-7-en-3-ol. The histological analysis showed accumulation of liver glycogen. Also, increased glycogen synthase and decreased glycogen phosphorylase were observed. Interestingly, the histological architecture evidenced a liver-protective effect due the extract. CONCLUSION: Five compounds were identified in C. ficifolia aqueous extract. The hypoglycemic effect of this extract may be partially explained by liver glycogen accumulation. The bioactive compound responsible for the hypoglycemic effect of this extract will be elucidated in subsequent studies.

[Study on chemical constituents from leaf of Bombax ceiba (II)].[Pubmed:25095343]

Zhong Yao Cai. 2014 Feb;37(2):240-2.

OBJECTIVE: To study the chemical constituents from the leaf of Bombax ceiba. METHODS: The compounds were isolated and purified with silica gel and Sephadex LH-20 column chromatography. Their structures were determined on the basis of physicochemical properties and spectroscopic analysis. RESULTS: Eleven compounds were isolated and identified as taraxeryl acetate (1), squalene (2), taraxerone (3), beta-sitosterol palmitate (4), taraxerol (5), 4-methyl Stigmast-7-en-3-ol (6), 1H-indole-3-carboxylic acid (7), 6-O-palmitoylsitosteryl-D-glucoside (8), 12beta-hydroxyl-pregnane-4, 16-diene-3, 20-dione (9), loliolide (10) and 5-(hydroxymethyl) furfural (11). CONCLUSION: All the compounds are isolated from this genus for the first time.

Extraction optimization by response surface methodology: Purification and characterization of phytosterol from sugarcane (Saccharum officinarum L.) rind.[Pubmed:24648272]

J Sep Sci. 2014 Jun;37(11):1308-14.

A green, simple, and effective method for the extraction of sugarcane lipids from sugarcane rind was investigated by response surface methodology. The optimum conditions of technological progress obtained through response surface methodology were as follows: liquid-to-solid ratio 7.94: 1 mL/g, extraction temperature 50 degrees C and extraction time 5.98 h. The practical sugarcane lipids extraction yield was 6.55 +/- 0.28%, which was in good consistence with the predicted extraction yield of 6.47%. The results showed that the sugarcane lipids extraction yield obtained in optimum conditions increased by 1.16 approximately 7.28-fold compared to the yields obtained in single-factor experiments. After saponification and SPE steps, the nonsaponifiable fraction of sugarcane lipids was analyzed by gas chromatography with mass spectrometry and high-performance liquid chromatography. beta-Sitosterol, stigmasterol, and campesterol were the prevailing phytosterols in the sample, while fucosterol, gramisterol, Stigmast-7-en-3-ol, (3beta,5alpha,24S)-, stigmasta-4,6,22-trien-3alpha-ol, and cholest-8(14)-en-3beta-ol acetate were also identified as minor steroids. Furthermore, the content of beta-sitosterol and a mixture of campesterol and stigmasterol (quantified by high-performance liquid chromatography) was 44.18 mg/100 g dry weight and 43.20 mg stigmasterol/100 g dry weight, respectively. Our results indicate that sugarcane rind is a good source of phytosterol.

[Study on chemical constituents of Myricaria paniculata I].[Pubmed:17511145]

Zhongguo Zhong Yao Za Zhi. 2007 Mar;32(5):403-6.

OBJECTIVE: To study the chemical constituents of Myricaria paniculata. METHOD: Silica gel column chromatography was used to separate and purify the chemical constituents, and the structures were elucidated by spectral analysis. RESULT: Four compounds were isolated from the petroleum ether soluble portion, identified as 28-aldehyde-taraxerenone (1), 28-hydroxy-taraxerenone (2), epi-friedelanol (3), 4-methyl Stigmast-7-en-3-ol (4). Three compounds were isolated from the EtOAc soluble portion, identified as morelloflavone (5), methyl 3, 5-dihydroxy-4-methoxybenzoate (6), 3-hydroxy-4-methoxy cinnamic acid (7). CONCLUSION: All of these compounds were isolated from the genus for the first time.

Flavonoid aglycones and phytosterols from the Erigeron acris L. herb.[Pubmed:17203871]

Acta Pol Pharm. 2006 Jul-Aug;63(4):317-9.

Four flavonoid aglycones (apigenin, kaempferol, luteolin, quercetin) were isolated from methanolic extract from the herb of Erigemn acris L. (Asteraceae). In this extract five phytosterols (campesterol, chondrillasterol, Stigmast-7-en-3-ol(5alpha,3alpha), stigmasterol and spinasterone) were also identified.

Triterpenoids from the stems of Myricaria paniculata.[Pubmed:15621634]

J Asian Nat Prod Res. 2005 Jun;7(3):253-7.

Two new pentacyclic triterpenoids myricarin A and B (1 and 2) have been isolated from the stems of Myricaria paniculata, together with seven known compounds, myriconal, 28-hydroxy-14-taraxeren-3-one, epi-friedelanol, beta-sitosterol, 4-methyl Stigmast-7-en-3-ol, 12-hentriacontanol and 1-triacontanol. Their structures have been established by chemical and spectroscopic methods. Cytotoxic activities of 1 and 2 have been evaluated against several different cell lines.

Evidence for the presence of "metabolic sterols" in Pneumocystis: identification and initial characterization of Pneumocystis carinii sterols.[Pubmed:8124270]

J Eukaryot Microbiol. 1994 Jan-Feb;41(1):78-85.

Mixed life cycle stages of rat-derived Pneumocystis carinii were isolated from host lungs and their sterols were compared with those present in lungs from normal and immunosuppressed uninfected rats. Gas-liquid chromatography consistently detected, resolved, and quantified 9, 10, and 20 sterol components in the total nonsaponifiable neutral lipid fraction of lungs from normal rats, lungs from immunosuppressed uninfected rats, and P. carinii preparations, respectively. In all samples, cholesterol was the most abundant sterol present, comprising 97%, 93%, and 78% of total sterols in lungs from normal rats, lungs from immunosuppressed uninfected rats, and P. carinii, respectively. Tentative identifications of several rat lung and P. carinii minor sterols were made based on gas-liquid chromatogram retention times and fragmentation patterns from mass spectral analyses. Campesterol (ergost-5-en-3-ol), cholest-5-en-3-one, and beta-sitosterol (stigmast-5-en-3-ol) were among the minor components present in both types of lung controls, and were also components of P. carinii sterols. In contrast to lung controls, the sterols of P. carinii were enriched in C28 and C29 sterols with one or two double bonds, and a hydroxyl group at C-3 (ergost-5-en-3-ol, ergost-7-en-3-ol, ergosta-dien-3-ol, stigmast-5-en-3-ol, Stigmast-7-en-3-ol and stigmasta-dien-3-ol). Steryl esters of P. carinii, probably stored in cytoplasmic lipid droplets, were dominated by those present in the host lung.(ABSTRACT TRUNCATED AT 250 WORDS)

[Steroidal constituents from Saussurea gossypiphora D. Don].[Pubmed:1786098]

Zhongguo Zhong Yao Za Zhi. 1991 Jun;16(6):356-8, 383.

Four steroids were isolated from the Saussurea gossypiphora for the fist time. They were determined as 3-stigmastanol, beta-sitosterol, Stigmast-7-en-3-ol and ergostan-3,24-diol by spectral and chemical methods.