phytosterols and cycloleucalenol

Pseudostem and rhizome are the significant bio-waste generated (43.48%) from the banana plant post fruit harvest, which are usually left in the plantation or incinerated and wasted. Amounts used in production for consumption are negligible. However, the material has an important part to play in indigenous systems of medicine. Based on the huge volume of bio-waste generated and its traditional medicinal use, it is worth exploiting it as a source of natural bioactive compounds. In the current study, sequential extracts from banana pseudostem (BPS) and rhizome (BR), and isolated compounds including chlorogenic acid, 4-epicyclomusalenone and cycloeucalenol acetate, were tested for their antimicrobial activity, antiplatelet aggregation and cytotoxicity.. Isolated compounds and crude extracts exhibited strong antimicrobial activity against a wide range of bacterial and fungal strains, platelet aggregation induced by collagen and cytotoxicity towards human liver cancer (HepG2) cells.. Banana plant bio-waste, pseudostem and rhizome may serve as a potential source of multifunctional bioactive compounds and functional ingredient in food and other allied industries.

Topics: Agriculture; Anti-Infective Agents; Antineoplastic Agents, Phytogenic; Chlorogenic Acid; Hep G2 Cells; Humans; Industrial Waste; Liver Neoplasms; Musa; Phytosterols; Plant Extracts; Plant Stems; Platelet Aggregation Inhibitors; Rhizome

Structures of some bioactive phytochemicals in bran extract of the black rice cv. Riceberry that had demonstrated anti-cancer activity in leukemic cell line were investigated. After saponification with potassium hydroxide, separation of the unsaponified fraction by reversed-phase high performance liquid chromatography (HPLC) resulted in four sub-fractions that had a certain degree of anti-proliferation against a mouse leukemic cell line (WEHI-3 cell), this being IC50 at 24 h ranging between 2.80-467.11 μg/mL. Further purification of the bioactive substances contained in these four sub-fractions was performed by normal-phase HPLC. Structural characterization by gas chromatography-mass spectrometry (GC-MS), liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance spectroscopy (NMR) resulted in, overall, the structures of seven phytosterols and four triterpenoids. Four phytosterols, 24-methylene-ergosta-5-en-3β-ol, 24-methylene-ergosta-7-en-3β-ol, fucosterol, and gramisterol, along with three triterpenoids, cycloeucalenol, lupenone, and lupeol, were found in the two sub-fractions that showed strong anti-leukemic cell proliferation (IC50 = 2.80 and 32.89 μg/mL). The other sterols and triterpenoids were campesterol, stigmasterol, β-sitosterol and 24-methylenecycloartanol. Together with the data from in vitro biological analysis, we suggest that gramisterol is a significant anti-cancer lead compound in Riceberry bran extract.

Topics: Animals; Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Cholesterol; Chromatography, High Pressure Liquid; Gas Chromatography-Mass Spectrometry; Leukemia; Mass Spectrometry; Mice; Molecular Structure; Oryza; Pentacyclic Triterpenes; Phytosterols; Phytotherapy; Plant Extracts; Seeds; Sitosterols; Stigmasterol; Triterpenes

Boophone disticha (Amaryllidaceae) is widely used in traditional medicine in southern Africa. Several alkaloids, volatile oils and fatty acids have been isolated from the plant. However, there has been no literature report of a triterpene from B. disticha. Cycloeucalenol, a cycloartane triterpene, together with its regio-isomer, was isolated from the ethyl acetate extract of the bulbs using column chromatography and preparative thin layer chromatography. Structural elucidation was carried out using 1D and 2D NMR and mass spectroscopy. The MTT and neutral red assays were used to assess the cytotoxicity of the compound in human neuroblastoma (SH-SY5Y) cells. The compound was obtained as a mixture of two regio-isomers, which were separated for the first time by chromatographic optimization. Integration of the 1H NMR spectrum showed that cycloeucalenol and its regio-isomer were present in a ratio of 1.04:1. A dose-dependent decrease in cell viability was observed using both cytotoxicity assays. IC51 values of 173.0 +/- 5.1 microM and 223.0 +/- 6.4 microM were obtained for the MTT and neutral red assays, respectively, indicative of the low toxicity of the compound. This work describes for the first time, the presence of triterpene compounds from the genus Boophone.

Topics: Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Drug Screening Assays, Antitumor; Humans; Isomerism; Liliaceae; Phytosterols; Plants, Medicinal

To isolate and identify the chemical constituents of the root of Chloranthus multistachys Pei.. The compounds were isolated by column chromatography, semi-preparative thin layer chromatography and related techniques, their structures were elucidated through spectroscopic analyses.. Nine compounds were isolated and identified as: lupeol (I), cycloeucalenol (II), isofragidin (III), daphnin (IV), umbelliferone (V), palmitic acid (VI), stigmasterol (VII), beta-sitosterol (VIII), beta-daucosterol (IX).. Except VI, all compounds are isolated from this plant for the first time.

Topics: China; Coumarins; Magnoliopsida; Molecular Structure; Pentacyclic Triterpenes; Phytosterols; Plant Roots; Plants, Medicinal; Stigmasterol; Umbelliferones

To investigate the chemical constituents of the root barks of Periploca sepium.. Column chromatographic techniques were used to isolate the chemical constituents. NMR and MS methods were employed for their structural elucidation.. Eight compounds were isolated and identified as isovanillin (1), vanillin (2), 4-methoxysalicylic acid (3), (24R)-9, 19-cycloart-25-ene-3beta, 24-diol (4), (24S)-9, 19-cycloart-25-ene-3beta, 24-diol (5), cycloeucalenol (6), beta-amyrin acetate (7) and alpha-amyrin (8).. Compounds 1-6 were isolated from this plant for the first time.

Topics: Benzaldehydes; Molecular Structure; Periploca; Phytosterols; Plant Bark; Plant Roots; Plants, Medicinal; Triterpenes

To study the active constituents from Alternanthera philoxeroides.. The constituents were isolated with silica gel and Toyopearl HW-40C gel column chromatography and purified by HPLC. Their structures were elucidated by spectroscopy.. Nine compounds were isolated and identified as phaeophytin a (1), pheophytin a' (2), oleanoic acid (3), beta-sitosterol (4), 3beta-hydroxystigmast-5-en-7-one (5), alpha-spinasterol (6), 24-methylenecycloartanol (7), cycloeucalenol (8), phytol (9).. Compounds 1,2,5,7-9 were isolated from this plant for the first time.

Topics: Amaranthaceae; Chlorophyll; Phytol; Phytosterols; Plant Leaves; Plant Stems; Plants, Medicinal

The smooth muscle relaxant properties of a mixture of the two triterpenoids cycloeuclalenol and cycloartenol (CC) isolated from Herissanthia tiubae (Malvaceae) were studied in several smooth muscle preparations. CC inhibited contractions induced by carbachol, histamine and KCl in the guinea-pig ileum, but no spasmolytic activity was found in guinea-pig trachea or rat aorta. In guinea-pig ileum, concentration-response curves to carbachol and CaCl (2) in high K(+) were shifted to the right by CC in a concentration-dependent manner with slopes of the Schild plot differing from the unity. IC(50) values were 3.4 +/- 0.8 x 10 (-5) M and 8.44 +/- 1.87 x 10 (-5) M for carbachol and CaCl(2), respectively. The phorbol ester TPA, which activates protein kinase C (PKC), potentiated contractions induced by submaximal concentrations of carbachol. This potentiation was inhibited by CC. Desensitization of PKC by TPA completely abolished the inhibition produced by CC on carbachol-induced contractions. Together, our results indicate that inhibition of PKC is involved in the spasmolytic effect of CC in the guinea-pig ileum.

Topics: Animals; Aorta; Carbachol; Drug Combinations; Female; Guinea Pigs; Ileum; In Vitro Techniques; Male; Malvaceae; Muscle Contraction; Parasympatholytics; Phytosterols; Rats; Trachea; Triterpenes

Like most higher plants, leek seedlings (Allium porrum L.) contain a mixture of Delta(5)-sterols in which sitosterol largely predominates. As previously reported (Plant Physiol., 117 (1998) 931), these compounds, which are synthesized at the endoplasmic reticulum level, were shown to be actively transported to the plasma membrane via a membrane-mediated process, together with phosphatidylserine (PS). In the present work, leek seedlings were allowed to germinate for 7 days in the presence of fenpropimorph, a sterol biosynthesis inhibitor. Such a treatment was found to trigger an almost complete replacement of the usual sterols by 9beta,19-cyclopropylsterols (mainly cycloeucalenol and 29-norcycloartenol). Extensive lipid analyses and labeling experiments with sodium [14C]acetate were performed to examine potential changes in the content and the rate of synthesis of the other lipid molecular species. The results indicate that the inhibition of the sterol pathway was accompanied by a severe decrease in PS and glucosylceramide synthesis as well as by a redirection of fatty acids toward the storage triacylglycerol pathway. Triacyglycerols are shown to accumulate concomitantly with a significant increase in intracellular lipid droplets in both aerial parts and roots of leek seedlings. Taken together, the present data emphasize that a coordinated regulation of the biosynthetic pathways of sterols and some specific lipid molecular species could take place during plant membrane biogenesis.

Topics: Allium; Cell Membrane; Enzyme Inhibitors; Fatty Acids; Glucosylceramides; Lipid Metabolism; Lipids; Morpholines; Phosphatidylserines; Phytosterols; Plant Roots; Seeds; Sterols; Triglycerides; Triterpenes

This report describes the isolation of two triterpenes from the stems of Tinospora crispa, namely, cycloeucalenol (1). and cycloeucalenone (2). for the first time. It was found that cycloeucalenol (1). slightly increased the right atrial force of contraction whereas it showed an initial reduction followed by sustained reduction of about 10% on the left atria of the rat in vitro. Cycloeucalenone showed slight change from the control on the right and left atrial force. These results suggest that cycloeucalenol and cycloeucalenone produced mild cardiotonic effects.

Topics: Animals; Heart Atria; Male; Myocardial Contraction; Phytosterols; Phytotherapy; Plant Extracts; Plant Stems; Rats; Rats, Wistar; Tinospora; Triterpenes

The molecular features of 19 synthetic substrates and ground-state analogues of cycloeucalenol, the natural substrate of cycloeucalenol - obtusifoliol isomerase, a membrane-bound enzyme specific to higher plants, and of 9 synthetic carbocationic analogues of the high-energy intermediate occurring during the reaction catalyzed by the isomerase, were related to their ability to be transformed by this enzyme (catalytical competence) and their potency as inhibitors of this enzyme. With substrates and ground-state analogues it has been possible to determine at least two critical domains: significant binding requires the presence of the 3 beta-hydroxyl group on the ring A with the correct stereochemistry together with absence of a 4 beta-methyl group. Moreover initial enzyme-substrate interaction appears to be dependent upon the accessibility of the 3 beta-oxygen. Substitutions on the ring B do not preclude binding whereas they are of great influence on substrate transformation. Modifications of the ring A and other modifications suggest that ground-state and high-energy intermediate analogues bind two different conformations of the isomerase active site.

Topics: Binding Sites; Binding, Competitive; Biotransformation; Catalysis; Isomerases; Methylation; Molecular Structure; Phytosterols; Plants; Polysorbates; Steroid Isomerases; Structure-Activity Relationship; Substrate Specificity