Alkaloids from the Traditional Chinese Medicine ChanSu: synthesis-enabled structural reassignment of bufopyramide to bufoserotonin C.

A synthesis of putative bufopyramide has shown the structure assigned to the natural product to be incorrect. The spectroscopic data for the natural product bufopyramide matches that obtained from a synthetic sample of bufoserotonin C, confirming that the two natural products are not distinct, but instead the same compound.

[1]  J. Sperry,et al.  Bioinspired total synthesis and structural revision of yuremamine, an alkaloid from the entheogenic plant Mimosa tenuiflora. , 2015, Chemical communications.

[2]  J. S. Clark,et al.  Synthesis of four diastereomers of sclerophytin F and structural reassignment of several sclerophytin natural products. , 2015, Chemistry.

[3]  Fengying Zhang,et al.  Palladium-catalyzed synthesis of benzofurans via C-H activation/oxidation tandem reaction and its application to the synthesis of decursivine and serotobenine. , 2014, Chemical communications.

[4]  Chun Xing Li,et al.  The Mechanisms of Chansu in Inducing Efficient Apoptosis in Colon Cancer Cells , 2013, Evidence-based complementary and alternative medicine : eCAM.

[5]  W. Marsden I and J , 2012 .

[6]  Zhang Weidong,et al.  N-containing compounds from the traditional Chinese medicine ChanSu , 2009, Chemistry of Natural Compounds.

[7]  W. Lewis,et al.  Biomimetic synthesis and structural reassignment of the tridachiahydropyrones. , 2009, Journal of the American Chemical Society.

[8]  B. Pan,et al.  Efficacy and safety of gemcitabine-oxaliplatin combined with huachansu in patients with advanced gallbladder carcinoma. , 2008, World journal of gastroenterology.

[9]  Y. Hayashizaki,et al.  Synthesis of 5-acetyl-2-aminopyrrole C-deoxyribonucleoside , 2007 .

[10]  Juan Su,et al.  Three New Alkaloids from the Traditional Chinese Medicine ChanSu , 2007 .

[11]  M. Cascio,et al.  New N-arachidonoylserotonin analogues with potential "dual" mechanism of action against pain. , 2007, Journal of medicinal chemistry.

[12]  Zheng Cui,et al.  Quality evaluation of traditional Chinese drug toad venom from different origins through a simultaneous determination of bufogenins and indole alkaloids by HPLC. , 2005, Chemical & pharmaceutical bulletin.

[13]  Yung-Hyun Choi,et al.  Induction of apoptosis by Chan Su, a traditional Chinese medicine, in human bladder carcinoma T24 cells. , 2005, Oncology reports.

[14]  M. Hayashi,et al.  Inhibitory effects of bufadienolides on interleukin-6 in MH-60 cells. , 2004, Journal of natural products.

[15]  H. Morita,et al.  Bufobutanoic acid and bufopyramide, two new indole alkaloids from the Chinese traditional drug Ch'an Su , 1999 .

[16]  H. Yeung,et al.  Simultaneous Determination of Bufadienolides in the Traditional Chinese Medicine Preparation, Liu‐Shen‐Wan, by Liquid Chromatography * , 1992, The Journal of pharmacy and pharmacology.

[17]  H. Skovronek,et al.  The Acylation of Amides , 1958 .