Abstract
The pterocarpan fraction from aerial parts of Bituminaria bituminosa was investigated for both chemical characterization and biological evaluation. Chemical studies were in accordance with the literature data on Bituminaria genus resulting in the identification of typical 4,8-prenyl pterocarpans. Three new members, bituminarins A-C (1-3), were isolated along with main bitucarpin A (4), erybraedin C (5) and erybraedin D (6) already reported from this plant. Further, biological studies evidenced antiproliferative properties of the most abundant pterocarpans 4 and 5 on neuroblastoma SH-SY5Y cell line, in agreement with previously described antiproliferative activity of these compounds against cancer cell lines other than neuroblastoma. The structure and the stereochemistry of the new molecules was determined by extensive spectroscopic analysis and chemical derivatization methods. The biological investigation was carried out by using an assay platform based on a live-cell imaging system revealing an apoptotic cell death induction.
Keywords:
Bituminaria bituminosa; biological activity; natural products chemistry; neuroblastoma; pterocarpans.
MeSH terms
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Antineoplastic Agents, Phytogenic* / chemistry
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Antineoplastic Agents, Phytogenic* / isolation & purification
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Antineoplastic Agents, Phytogenic* / pharmacology
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Apoptosis / drug effects
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Cell Line, Tumor
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Cell Proliferation / drug effects
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Humans
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Molecular Structure
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Neuroblastoma* / drug therapy
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Neuroblastoma* / pathology
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Plant Extracts / chemistry
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Plant Extracts / pharmacology
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Pterocarpans* / chemistry
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Pterocarpans* / isolation & purification
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Pterocarpans* / pharmacology
Substances
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Pterocarpans
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Antineoplastic Agents, Phytogenic
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Plant Extracts
Grants and funding
This work was partly funded under the National Recovery and Resilience Plan (NRRP), Mission 4 Component 2 Investment 1.4—Call for tender No. 3138 of 16 December 2021, rectified by Decree n.3175 of 18 December 2021 of Italian Ministry of University and Research funded by the European Union—NextGenerationEU, Project code CN_00000033, Concession Decree No. 1034 of 17 June 2022 adopted by the Italian Ministry of University and Research, CUP B83C22002930006, Project title “National Biodiversity Future Center—NBFC”. H.B. is deeply grateful to the Algerian Ministry of Higher Education and Scientific Research for training program and mobility support.