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  • A New Cytotoxic Steroidal Glycoalkaloid from the Methanol Extract of Blumea lacera Leaves

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    Author(s)
    Akter, Raushanara
    Uddin, Shaikh J
    Tiralongo, Joe
    Grice, I Darren
    Tiralongo, Evelin
    Griffith University Author(s)
    Grice, Darren D.
    Tiralongo, Joe
    Tiralongo, Evelin
    Year published
    2015
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    Abstract
    PURPOSE: Blumea lacera (B. lacera) (Asteraceae) is a well-known Bangladeshi medicinal plant. This study aimed to identify and characterize constituents associated with the significant cytotoxic activity of this plant that we reported previously. Here, we describe the isolation and characterization of a new steroidal glycoalkaloid (SGA) 1, the evaluation of its cytotoxic activity, apoptotic potential, and effect on cell cycle in comparison to analogous steroidal glycoalkaloids (SGAs). METHODS: SGA 1 was isolated using C18 SPE and HPLC, and subsequently structurally characterized using 1D and 2D NMR, MS and other spectroscopic ...
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    PURPOSE: Blumea lacera (B. lacera) (Asteraceae) is a well-known Bangladeshi medicinal plant. This study aimed to identify and characterize constituents associated with the significant cytotoxic activity of this plant that we reported previously. Here, we describe the isolation and characterization of a new steroidal glycoalkaloid (SGA) 1, the evaluation of its cytotoxic activity, apoptotic potential, and effect on cell cycle in comparison to analogous steroidal glycoalkaloids (SGAs). METHODS: SGA 1 was isolated using C18 SPE and HPLC, and subsequently structurally characterized using 1D and 2D NMR, MS and other spectroscopic methods, along with a comparative inspection of the literature. Cytotoxic activity of 1 and seven SGA analogues and steroidal alkaloids (SAs), (β-solamarine, α-solanine, β-solamargine, α-solasonine, khasianine, solasodine, tomatidine HCl) were evaluated for their cytotoxicity against two healthy (NIH3T3 and VERO) and four human cancer (AGS, HT-29, MCF-7 and MDA-MB-231) cell lines using the MTT assay. Cytotoxic SGAs were further evaluated for apoptosis-inducing potential and cell cycle arresting ability against breast cancer cells (MCF-7) using the FITC Annexin V and propidium iodide (PI) assay. RESULTS: Bioactivity guided fractionation of the methanol extract of B. lacera led to isolation of compound 1: (25R)-3β-{O-β-D-glucopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→4)-[O-α-L-rhamnopyranosyl-(1→2)]-α-L-rhamnopyranosyl}-22αN-spirosol-5-ene. SGA 1 was the most cytotoxic compound against a number of human cancer cell lines with an IC50 of 2.62 µM against MCF-7 cells. It displayed the highest apoptotic potential (32% AV+/PI-) on MCF-7 cells compared to other cytotoxic SGA analogues and a slight, but significant cell cycle arresting effect. CONCLUSIONS: A new SGA 1 was isolated from B. lacera and its cytotoxic activity, as well as that of other SAGs, was evaluated. SAR investigations on SGA 1, in relation to SGA analogues, show that the number and nature of sugar moieties along with the linkages of the sugar to the aglycone are crucial for cytotoxic and apoptotic activity.
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    Journal Title
    Journal of Pharmacy & Pharmaceutical Sciences
    Volume
    18
    Issue
    4
    DOI
    https://doi.org/10.18433/J3161Q
    Copyright Statement
    © The Author(s) 2015. This is an Open Access article distributed under the terms of the Creative Commons Attribution-ShareAlike 3.0 (CC BY-SA 3.0) License (http://creativecommons.org/licenses/by-sa/3.0/) which permits unrestricted, distribution and reproduction in any medium, providing that the work is properly cited. If you alter, transform, or build upon this work, you may distribute the resulting work only under a licence identical to this one.
    Subject
    Pharmacology and pharmaceutical sciences
    Pharmaceutical sciences
    Publication URI
    http://hdl.handle.net/10072/123487
    Collection
    • Journal articles

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