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Keywords = cholestane glycoside

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17 pages, 2180 KB  
Review
Ethnobotany, Phytochemistry, and Biological Activities of the Genus Cordyline
by Romuald Tematio Fouedjou, Bienvenu Tsakem, Xavier Siwe-Noundou, Hervet P. Dongmo Fogang, Aphalaine Tiombou Donkia, Beaudelaire Kemvoufo Ponou, Madan Poka, Patrick H. Demana, Rémy B. Teponno and Léon Azefack Tapondjou
Biomolecules 2023, 13(12), 1783; https://doi.org/10.3390/biom13121783 - 12 Dec 2023
Cited by 6 | Viewed by 5077
Abstract
Cordyline species have a long history in traditional medicine as a basis of treatment for various ailments such as a bloody cough, dysentery, and a high fever. There are about 26 accepted species names in this genus distributed worldwide, including C. fruticosa, [...] Read more.
Cordyline species have a long history in traditional medicine as a basis of treatment for various ailments such as a bloody cough, dysentery, and a high fever. There are about 26 accepted species names in this genus distributed worldwide, including C. fruticosa, C. autralis, C. stricta, C. cannifolia, and C. dracaenosides. This work presents a comprehensive review of the traditional uses of plants of the genus Cordylie and their chemical constituents and biological activities. A bibliographic search was conducted to identify available information on ethnobotany, ethnopharmacology, chemical composition, and biological activities. A total of 98 isolated compounds potentially responsible for most of the traditional medicinal applications have been reported from eight species of Cordyline and are characterised as flavonoid, spirostane, furostane, and cholestane glycosides. Some of these pure compounds, as well as extracts from some species of Cordyline, have exhibited noteworthy anti-oxidant, antiproliferative, antimicrobial, and hypolipidemic activities. Although many of these species have not yet been investigated phytochemically or pharmacologically, they remain a potential source of new bioactive compounds. Full article
(This article belongs to the Special Issue The Value of Natural Compounds as Therapeutic Agents)
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22 pages, 1602 KB  
Article
Determination of Structure and Cytotoxicity of Ten Undescribed Steroidal Glycosides from Allium cristophii × A. macleanii ‘Globemaster’
by Tamami Shimazaki, Tomoki Iguchi, Yuna Takahashi, Kie Yamamoto, Naoki Takahashi and Yoshihiro Mimaki
Molecules 2023, 28(17), 6248; https://doi.org/10.3390/molecules28176248 - 25 Aug 2023
Cited by 2 | Viewed by 1840
Abstract
‘Globemaster’ is an ornamental hybrid cultivar whose parent plants are Allium cristophii and A. macleanii. The chemical constituents of ‘Globemaster’ bulbs have not yet been examined; thus, a systematic phytochemical investigation was undertaken herein. A series of chromatographic separations of the MeOH [...] Read more.
‘Globemaster’ is an ornamental hybrid cultivar whose parent plants are Allium cristophii and A. macleanii. The chemical constituents of ‘Globemaster’ bulbs have not yet been examined; thus, a systematic phytochemical investigation was undertaken herein. A series of chromatographic separations of the MeOH extract of ‘Globemaster’ bulbs afforded 27 steroidal glycosides (127), which are classified into 23 spirostanol glycosides (18 and 1125), two furostanol glycosides (9 and 26), a pregnane glycoside (10), and a cholestane glycoside (27). The structures of the hitherto undescribed compounds (110) were determined from the two-dimensional NMR spectroscopic data and hydrolysis. The cytotoxicity of the isolated compounds (127) toward HL-60 human promyelocytic leukemia cells, A549 human adenocarcinoma lung cancer cells, and SBC-3 human small-cell lung cancer cells was evaluated. Compounds 8, 22, 23, 24, and 26 exhibited cytotoxicity toward all cell lines in a dose-dependent manner, with IC50 values in the 1.3–49 µM range. Full article
(This article belongs to the Section Natural Products Chemistry)
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14 pages, 1289 KB  
Article
A Total of Eight Novel Steroidal Glycosides Based on Spirostan, Furostan, Pseudofurostan, and Cholestane from the Leaves of Cestrum newellii
by Tomoki Iguchi, Naoki Takahashi and Yoshihiro Mimaki
Molecules 2020, 25(19), 4462; https://doi.org/10.3390/molecules25194462 - 28 Sep 2020
Cited by 2 | Viewed by 2809
Abstract
Previously, various steroidal glycosides were reported from plants of Cestrum species. However, phytochemical investigation has not been conducted on Cestrum newellii. A systematic phytochemical investigation of the leaves of C. newellii resulted in the isolation of eight novel steroidal glycosides (1 [...] Read more.
Previously, various steroidal glycosides were reported from plants of Cestrum species. However, phytochemical investigation has not been conducted on Cestrum newellii. A systematic phytochemical investigation of the leaves of C. newellii resulted in the isolation of eight novel steroidal glycosides (18), which were classified into three spirostanol glycosides (13), two furostanol glycosides (4 and 5), two pseudofurostanol glycosides (6 and 7), and one cholestane glycoside (8). In addition, three known cholestane glycosides (911) were isolated and identified. The structures of the new compounds were determined based on spectroscopic data and chemical transformations. Compounds 1 and 2 are spirostanol glycosides having hydroxy groups at C-2, C-3, C-12, and C-24 of the aglycone moiety. Although C. newellii is known to be a poisonous plant, the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide assay exhibited that none of the isolated compounds were cytotoxic to HL-60 human promyelocytic leukemia cells. Full article
(This article belongs to the Section Natural Products Chemistry)
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21 pages, 4206 KB  
Article
Structural Characterization of Cholestane Rhamnosides from Ornithogalum saundersiae Bulbs and Their Cytotoxic Activity against Cultured Tumor Cells
by Tomoki Iguchi, Minpei Kuroda, Rei Naito, Tomoyuki Watanabe, Yukiko Matsuo, Akihito Yokosuka and Yoshihiro Mimaki
Molecules 2017, 22(8), 1243; https://doi.org/10.3390/molecules22081243 - 25 Jul 2017
Cited by 18 | Viewed by 4987
Abstract
Previous phytochemical studies of the bulbs of Ornithogalum saundersiae, an ornamental perennial plant native to South Africa, resulted in the isolation of 29 new cholestane glycosides, some of which were structurally unique and showed potent cytotoxic activity against cultured tumor cell lines. [...] Read more.
Previous phytochemical studies of the bulbs of Ornithogalum saundersiae, an ornamental perennial plant native to South Africa, resulted in the isolation of 29 new cholestane glycosides, some of which were structurally unique and showed potent cytotoxic activity against cultured tumor cell lines. Therefore, we aimed to perform further phytochemical examinations of methanolic extracts obtained from Ornithogalum saundersiae bulbs, isolating 12 new cholestane rhamnosides (112) and seven known compounds (1319). The structures of the new compounds (112) were identified via NMR-based structural characterization methods, and through a sequence of chemical transformations followed by spectroscopic and chromatographic analysis. The cytotoxic activity of the isolated compounds (119) and the derivatives (1a and 6a) against HL-60 human promyelocytic leukemia cells and A549 human lung adenocarcinoma cells was evaluated. Compounds 1012, 16, and 17 showed cytotoxicity against both HL-60 and A549 cells. Compound 11 showed potent cytotoxicity with an IC50 value of 0.16 µM against HL-60 cells and induced apoptotic cell death via a mitochondrion-independent pathway. Full article
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16 pages, 1137 KB  
Article
Neuritogenic and Neuroprotective Effects of Polar Steroids from the Far East Starfishes Patiria pectinifera and Distolasterias nipon
by Natalia V. Palyanova, Tatyana M. Pankova, Marina V. Starostina, Alla A. Kicha, Natalia V. Ivanchina and Valentin A. Stonik
Mar. Drugs 2013, 11(5), 1440-1455; https://doi.org/10.3390/md11051440 - 3 May 2013
Cited by 23 | Viewed by 8125
Abstract
The neuritogenic and neuroprotective activities of six starfish polar steroids, asterosaponin Р1, (25S)-5α-cholestane-3β,4β,6α,7α,8,15α,16β,26-octaol, and (25S)-5α-cholestane-3β,6α,7α,8,15α,16β,26-heptaol (13) from the starfish Patiria pectinifera and distolasterosides D1–D3 (46) from [...] Read more.
The neuritogenic and neuroprotective activities of six starfish polar steroids, asterosaponin Р1, (25S)-5α-cholestane-3β,4β,6α,7α,8,15α,16β,26-octaol, and (25S)-5α-cholestane-3β,6α,7α,8,15α,16β,26-heptaol (13) from the starfish Patiria pectinifera and distolasterosides D1–D3 (46) from the starfish Distolasterias nipon were analyzed using the mouse neuroblastoma (NB) C-1300 cell line and an organotypic rat hippocampal slice culture (OHSC). All of these compounds enhanced neurite outgrowth in NB cells. Dose-dependent responses to compounds 13 were observed within the concentration range of 10–100 nM, and dose-dependent responses to glycosides 46 were observed at concentrations of 1–50 nM. All the tested substances exhibited notable synergistic effects with trace amounts of nerve growth factor (NGF, 1 ng/mL) or brain-derived neurotrophic factor (BDNF, 0.1 ng/mL). Using NB cells and OHSCs, it was shown for the first time that starfish steroids 16 act as neuroprotectors against oxygen-glucose deprivation (OGD) by increasing the number of surviving cells. Altogether, these results suggest that neurotrophin-like neuritogenic and neuroprotective activities are most likely common properties of starfish polyhydroxysteroids and the related glycosides, although the magnitude of the effect depended on the particular compound structure. Full article
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7 pages, 140 KB  
Article
Carijoside A, a Bioactive Sterol Glycoside from an Octocoral Carijoa sp. (Clavulariidae)
by Chih-Yang Liu, Tsong-Long Hwang, Mei-Ru Lin, Yung-Husan Chen, Yu-Chia Chang, Lee-Shing Fang, Wei-Hsien Wang, Yang-Chang Wu and Ping-Jyun Sung
Mar. Drugs 2010, 8(7), 2014-2020; https://doi.org/10.3390/md8072014 - 29 Jun 2010
Cited by 26 | Viewed by 12630
Abstract
A new bioactive sterol glycoside, 3β-O-(3',4'-di-O-acetyl-β-D-arabinopyranosyl)-25ξ-cholestane-3β,5α,6β,26-tetrol-26-acetate) (carijoside A, 1), was isolated from an octocoral identified as Carijoa sp. The structure of glycoside [...] Read more.
A new bioactive sterol glycoside, 3β-O-(3',4'-di-O-acetyl-β-D-arabinopyranosyl)-25ξ-cholestane-3β,5α,6β,26-tetrol-26-acetate) (carijoside A, 1), was isolated from an octocoral identified as Carijoa sp. The structure of glycoside 1 was established by spectroscopic methods and by comparison with spectral data for the other known glycosides. Carijoside A (1) displayed significant inhibitory effects on superoxide anion generation and elastase release by human neutrophils and this compound exhibited moderate cytotoxicity toward DLD-1, P388D1, HL-60, and CCRF-CEM tumor cells. Full article
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