Total Synthesis of Taspine

and, T. Ross Kelly; Xie, Roger L.

doi:10.1021/jo981099j

Cited by 31 publications

(11 citation statements)

References 20 publications

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“…18 Reductive amination of 2 with dimethylamine and sodium triacetoxyborohydride gave taspine (1) in 77% yield. 8 Synthetic 1 was identical to taspine isolated from plant in all aspects: TLC, 1 H NMR, 13 C NMR, MS, IR, and melting point.…”

Section: Methodsmentioning

confidence: 82%

“…This makes taspine synthesis very difficult. Kelly and Xie reported the first total synthesis of taspine in 1998, 8 but the synthetic scheme had complicated reaction conditions, expensive reagents, and lower overall yield (9.6%). We report the facile and efficient total synthesis of taspine under mild reaction conditions using inexpensive reagents to produce higher overall yield (16.5%).…”

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confidence: 99%

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Facile and Efficient Total Synthesis of Taspine

Cheng¹,

Zhang²,

Zhu³

et al. 2009

Synthesis

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The facile and efficient total synthesis of taspine was achieved in 10 steps in high yield (16.5% overall) from commercially available isovanillin. Key steps in the synthesis are preparation of a symmetrical homodimer employing a classical Ullmann coupling reaction, and introduction of an allyl substituent by the Claisen rearrangement reaction. Significantly, the facile synthetic scheme proposed in this work has the characteristics of mild reaction conditions, inexpensive reagents, higher yield, and simple operation.

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Section: Methodsmentioning

confidence: 82%

mentioning

confidence: 99%

Facile and Efficient Total Synthesis of Taspine

Cheng¹,

Zhang²,

Zhu³

et al. 2009

Synthesis

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“…Taspine (Fig. 1), which was first isolated from HMQ, has many pharmacological actions, for example bacteriostasis, anti-inflammatory, cytotoxicity, and antiviral properties [8,9]. In previous studies we found that taspine has an anti-tumor effect [10] and inhibits angiogenesis in chicken chorioallantoic membrane (CAM).…”

Section: Introductionmentioning

confidence: 99%

Determination of Taspine Using HPLC–MS, and Its Effect on EGFR in A431 and HEK293/EGFR Cells

et al. 2011

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Taspine was isolated for the first time from Radix et Rhizoma Leonticis. Epidermal growth factor receptor (EGFR) is important in cell growth and differentiation and has become an important target in anti-cancer drug design. In this study, we found taspine could inhibit proliferation of A431 and HEK293/EGFR cells. To investigate whether it could enter the cell or acted on the cell membrane receptor, a cell-based assay was established to determine the concentration of taspine in A431 and HEK293/EGFR cells using high-performance liquid chromatography-mass spectrometry (HPLC-MS). The inhibitory effects of taspine on EGFR expression and mRNA expression were also investigated. The HPLC-MS results showed that taspine decreased in the supernatant liquid, and increased in the cell lysate, which indicated that taspine could enter the cell or act on the cell membrane receptor. Subsequent analysis using a cell-membrane chromatography (CMC) assay showed that taspine could act on EGFR at the cell membrane. In addition, ELISA and reverse transcriptase polymerase chain reaction (RT-PCR) assays showed that taspine inhibited proliferation, EGFR protein, and EGFR mRNA expression in A431 and HEK293/EGFR cells. These results indicated that taspine, with antitumor activity, could interact with the cell, act on EGFR at the cell membrane, and inhibit cell proliferation by down-regulating EGFR protein and mRNA expression.

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“…Taspine was isolated for the first time from HMQ. Taspine has many pharmacological actions: bacteriostasis, antiinflammatory, cytotoxicity and antivirus (Kelly and Xie, 1998; Perdue et al ., 1979). Studies have shown that taspine has an antitumour effect and inhibits angiogenesis of chicken chorioallantoic membrane (CAM) (Zhang et al ., 2007, 2008).…”

Section: Introductionmentioning

confidence: 99%

Effects of taspine on proliferation and apoptosis by regulating caspase‐3 expression and the ratio of Bax/Bcl‐2 in A431 cells

Zhang

Jiang

Wang

et al. 2011

Phytotherapy Research

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Taspine is an active component isolated from Radix et Rhizoma Leonticis. It has been shown that taspine can inhibit tumour angiogenesis. However, how it inhibits the proliferation of, and induces apoptosis in, A431 cells is unknown. The study investigated the effects of taspine on the proliferation and apoptosis in the A431 cell line using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), flow cytometry, transmission electron microscopy (TEM), western blotting (WB) and real-time reverse transcription-polymerase chain reaction (PCR). Changes in microstructure, cell cycle and protein expressions of caspase-3, cleaved caspase-3, cyclindependent kinase 2 (CDK2), cyclin-dependent kinase 4 (CDK4), Bcl-2 and Bax were observed after treatment of A431 cells with taspine. Taspine could inhibit the growth of, and induce apoptosis in, A431 cells in a dose-dependent manner. The cell cycle was significantly stopped at S phase. Nuclear karyopyknosis, chromatin agglutination and typical apoptotic bodies were found in A431 cells. There was a decrease in the expression of Bcl-2, whereas the expression of caspase-3, cleaved caspase-3, CDK2, CDK4 and Bax increased. These data demonstrated that taspine can inhibit the proliferation of, and induce apoptosis in, A431 cells by activating caspase-3 expression and up-regulating the ratio of Bax/Bcl-2 in A431 cells.

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Total Synthesis of Taspine

Cited by 31 publications

References 20 publications

Facile and Efficient Total Synthesis of Taspine

Facile and Efficient Total Synthesis of Taspine

Determination of Taspine Using HPLC–MS, and Its Effect on EGFR in A431 and HEK293/EGFR Cells

Effects of taspine on proliferation and apoptosis by regulating caspase‐3 expression and the ratio of Bax/Bcl‐2 in A431 cells

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