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      Crystal Structure Elucidation and Anticancer Studies of (-)-Pseudosemiglabrin: A Flavanone Isolated from the Aerial Parts of Tephrosia apollinea

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          Abstract

          Tephrosia apollinea is a perennial shrublet widely distributed in Africa and is known to have medicinal properties. The current study describes the bio-assay (cytotoxicity) guided isolation of (-)-pseudosemiglabrin from the aerial parts of T. apollinea. The structural and stereochemical features have been described using spectral and x-ray crystallographic techniques. The cytotoxicity of isolated compound was evaluated against nine cancer cell lines. In addition, human fibroblast was used as a model cell line for normal cells. The results showed that (-)-pseudosemiglabrin exhibited dose-dependent antiproliferative effect on most of the tested cancer cell lines. Selectively, the compound showed significant inhibitory effect on the proliferation of leukemia, prostate and breast cancer cell lines. Further studies revealed that, the compound exhibited proapoptotic phenomenon of cytotoxicity. Interestingly, the compound did not display toxicity against the normal human fibroblast. It can be concluded that (-)-pseudosemiglabrin is worthy for further investigation as a potential chemotherapeutic agent.

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          Natural products in drug discovery.

          Alan Harvey (2008)
          Natural products have been the single most productive source of leads for the development of drugs. Over a 100 new products are in clinical development, particularly as anti-cancer agents and anti-infectives. Application of molecular biological techniques is increasing the availability of novel compounds that can be conveniently produced in bacteria or yeasts, and combinatorial chemistry approaches are being based on natural product scaffolds to create screening libraries that closely resemble drug-like compounds. Various screening approaches are being developed to improve the ease with which natural products can be used in drug discovery campaigns, and data mining and virtual screening techniques are also being applied to databases of natural products. It is hoped that the more efficient and effective application of natural products will improve the drug discovery process.
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            Apoptosis as a novel target for cancer chemoprevention.

            Numsen Hail Jr., Reuben Lotan, Shi-yong R Sun (2004)
            Cancer chemopreventive agents are typically natural products or their synthetic analogs that inhibit the transformation of normal cells to premalignant cells or the progression of premalignant cells to malignant cells. These agents are believed to function by modulating processes associated with xenobiotic biotransformation, with the protection of cellular elements from oxidative damage, or with the promotion of a more differentiated phenotype in target cells. However, an increasing number of chemopreventive agents (e.g., certain retinoids, nonsteroidal anti-inflammatory drugs, polyphenols, and vanilloids) have been shown to stimulate apoptosis in premalignant and malignant cells in vitro or in vivo. Apoptosis is arguably the most potent defense against cancer because it is the mechanism used by metazoans to eliminate deleterious cells. Many chemopreventive agents appear to target signaling intermediates in apoptosis-inducing pathways. Inherently, the process of carcinogenesis selects against apoptosis to initiate, promote, and perpetuate the malignant phenotype. Thus, targeting apoptosis pathways in premalignant cells--in which these pathways are still relatively intact--may be an effective method of cancer prevention. In this review, we construct a paradigm supporting apoptosis as a novel target for cancer chemoprevention by highlighting recent studies of several chemopreventive agents that engage apoptosis pathways.
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              Recent advances in chemoprevention of cancer.

              Kwang Hong, M. Sporn (1997)
              Chemoprevention is the use of pharmacologic or natural agents that inhibit the development of invasive cancer either by blocking the DNA damage that initiates carcinogenesis or by arresting or reversing the progression of premalignant cells in which such damage has already occurred. Recent advances in our understanding of the mechanisms of carcinogenesis have led to the synthesis of new drugs that can inhibit tumor development in experimental animals by selective action on specific molecular targets, such as the estrogen, androgen, and retinoid receptors or inducible cyclooxygenase. Several of these agents (including tamoxifen, 13-cis-retinoic acid, retinyl palmitate, and an acyclic retinoid) are clinically effective in preventing the development of cancer, particularly in patients who are at high risk for developing second primary tumors after surgical removal of the initial tumor.
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                Author and article information

                Contributors
                Natasha Kyprianou: Role: Editor
                Journal
                Journal ID (nlm-ta): PLoS One
                Journal ID (iso-abbrev): PLoS ONE
                Journal ID (publisher-id): plos
                Journal ID (pmc): plosone
                Title: PLoS ONE
                Publisher: Public Library of Science (San Francisco, USA )
                ISSN (Electronic): 1932-6203
                Publication date Collection: 2014
                Publication date (Electronic): 7 March 2014
                Volume: 9
                Issue: 3
                Electronic Location Identifier: e90806
                Affiliations
                [1 ]EMAN Research and Testing Laboratory, School of Pharmaceutical Sciences, Universiti Sains Malaysia, Penang, Malaysia
                [2 ]Advanced Medical and Dental Institute (IPPT), Universiti Sains Malaysia, Penang, Malaysia
                [3 ]School of Chemical Sciences, Universiti Sains Malaysia, Penang, Malaysia
                [4 ]Institute for Research in Molecular Medicine (INFORMM), Universiti Sains Malaysia, Penang, Malaysia
                University of Kentucky College of Medicine, United States of America
                Author notes

                Competing Interests: The authors have declared that no competing interests exist.

                Conceived and designed the experiments: AMSAM MBKA RAH ZI LEAH MAI FSRS. Performed the experiments: LEAH MAI FSRS. Analyzed the data: LEAH MAI AMSAM MBKA. Contributed reagents/materials/analysis tools: RAH ZI. Wrote the paper: LEAH MBKA MAI ASAM. Manuscript reviewed: ASAM OCE.

                Article
                Publisher ID: PONE-D-13-29039
                DOI: 10.1371/journal.pone.0090806
                PMC ID: 3946547
                SO-VID: 868d66ce-3fc3-4d7c-b9a6-34151b7a3088
                Copyright statement: Copyright @ 2014
                License:

                This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

                History
                Date received : 10 July 2013
                Date accepted : 4 February 2014
                Page count
                Pages: 12
                Funding
                The authors wish to acknowledge TWAS-USM (FR number: 3240240313) for the fellowship to LEAH and financial support for this research. RAH is thankful to USM for the research grant No 304/PKIMIA/6311123. The authors state that the funders had no role in the study design, data collection and analysis, decision to publish, or preparation of the manuscript.
                Categories
                Subject: Research Article
                Subject: Biology
                Subject: Biochemistry
                Subject: Drug Discovery
                Subject: Biotechnology
                Subject: Drug Discovery
                Subject: Chemistry
                Subject: Medicinal Chemistry
                Subject: Phytochemistry
                Subject: Stereochemistry
                Subject: Medicine
                Subject: Drugs and Devices
                Subject: Drug Research and Development
                Subject: Drug Discovery
                Subject: Environmental Pharmacology
                Subject: Oncology
                Subject: Basic Cancer Research
                Subject: Cancer Prevention

                ScienceOpen disciplines: Uncategorized
                Data availability:
                ScienceOpen disciplines: Uncategorized

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