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Pure Appl. Chem., 1989, Vol. 61, No. 3, pp. 443-448

http://dx.doi.org/10.1351/pac198961030443

Chemical and pharmacological studies on sedative cyclopeptide alkaloids in some Rhamnaceae plants

B. H. Han, M. H. Park and J. H. Park

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  • Lin Rong-Jyh, Wu Mei-Hsuan, Ma Yi-Hsuan, Chung Li-Yu, Chen Chung-Yi, Yen Chuan-Min: Anthelmintic Activities of Aporphine from Nelumbo nucifera Gaertn. cv. Rosa-plena against Hymenolepis nana. IJMS 2014, 15, 3624. <http://dx.doi.org/10.3390/ijms15033624>
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  • Zhao Simeng, Kuang Bin, Peng Wenwen, He Wenjun, Xu Huimin, Ji Changjiu, Han Jing, Zheng Yuqing, Song Weiwu, Tan Ninghua: Chemical Progress in Cyclopeptide-containing Traditional Medicines Cited in Chinese Pharmacopoeia. Chin. J. Chem. 2012, 30, 1213. <http://dx.doi.org/10.1002/cjoc.201200508>
  • Liao Lijuan, Won Tae Hyung, Kang Sam Sik, Shin Jongheon: Simultaneous analysis of bioactive metabolites from Ziziphus jujuba by HPLC–DAD–ELSD–MS/MS. Journal of Pharmaceutical Investigation 2012, 42, 21. <http://dx.doi.org/10.1007/s40005-012-0004-9>
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  • Shanmugavasan A., Vaitheeswaran K.S.R., Ramachandran T.: Design and development of pyrolyser to extract medicinal oil from the stem of Ziziphus jujuba. APPL PYROLYSIS 2011, 92, 176. <http://dx.doi.org/10.1016/j.jaap.2011.05.016>
  • Maldaner Graciela, Marangon Patricia, Ilha Vinicius, Balparda Caro Miguel S., Burrow Robert A., Dalcol Ionara Irion, Morel Ademir F.: Cyclopeptide alkaloids from Scutia buxifolia Reiss. Phytochemistry 2011, 72, 804. <http://dx.doi.org/10.1016/j.phytochem.2011.02.019>
  • Panseeta Panomwan, Lomchoey Kanlaya, Prabpai Samran, Kongsaeree Palangpon, Suksamrarn Apichart, Ruchirawat Somsak, Suksamrarn Sunit: Antiplasmodial and antimycobacterial cyclopeptide alkaloids from the root of Ziziphus mauritiana. Phytochem 2011, 72, 909. <http://dx.doi.org/10.1016/j.phytochem.2011.03.003>
  • Xu Chu-Pei, Xiao Zhen-Hua, Zhuo Bi-Qin, Wang Yu-Huang, Huang Pei-Qiang: Efficient and chemoselective alkylation of amines/amino acids using alcohols as alkylating reagents under mild conditions. Chem Commun 2010, 46, 7834. <http://dx.doi.org/10.1039/c0cc01487g>
  • DU Liang-Cheng, TAN Ning-Hua, XU Wen-Yan, LOU Li-Li: : Plant Cyclopeptides and Possible Biosynthetic Mechanisms. Acta Botanica Yunnanica 2010, 31, 374. <http://dx.doi.org/10.3724/SP.J.1143.2009.09093>
  • Toumi Mathieu, Rincheval Vincent, Young Ashley, Gergeres Danielle, Turos Edward, Couty François, Mignotte Bernard, Evano Gwilherm: A General Route to Cyclopeptide Alkaloids: Total Syntheses and Biological Evaluation of Paliurines E and F, Ziziphines N and Q, Abyssenine A, Mucronine E, and Analogues. Eur J Org Chem 2009, 2009, 3368. <http://dx.doi.org/10.1002/ejoc.200900122>
  • Ma Yuan, Han Huishan, Nam Sang-Yoon, Kim Yun-Bae, Hong Jin-Tae, Yun Yeo-Pyo, Oh Ki-Wan: Cyclopeptide alkaloid fraction from Zizyphi Spinosi Semen enhances pentobarbital-induced sleeping behaviors. J Ethopharmacol 2008, 117, 318. <http://dx.doi.org/10.1016/j.jep.2008.02.006>
  • Ma Yuan, Han Huishan, Eun Jae Soon, Kim Hyung-Chun, Hong Jin-Tae, Oh Ki-Wan: Sanjoinine A Isolated from Zizyphi Spinosi Semen Augments Pentobarbital-Induced Sleeping Behaviors through the Modification of GABA-ergic Systems. Biol Pharm Bull 2007, 30, 1748. <http://dx.doi.org/10.1248/bpb.30.1748>
  • Cristau Pierre, Temal-Laïb Taoues, Bois-Choussy Michèle, Martin Marie-Thérèse, Vors Jean-Pierre, Zhu Jieping: Total Synthesis of Mauritines A, B, C, and F: Cyclopeptide Alkaloids with a 14-Membered Paracyclophane Unit. Chem Eur J 2005, 11, 2668. <http://dx.doi.org/10.1002/chem.200401070>
  • Han Yong Nam, Hwang Keum Hee, Han Byung Hoon: Inhibition of calmodulin-dependent protein kinase II by cyclic and linear peptide alkaloids fromZizyphus species. Arch Pharm Res 2005, 28, 159. <http://dx.doi.org/10.1007/BF02977707>
  • Raghavan Sadagopan, Tony K.A.: Stereoselective synthesis of (2R,3R) and (2R,3S)-3-hydroxyleucines. Tetrahetron Lett 2004, 45, 2639. <http://dx.doi.org/10.1016/j.tetlet.2004.01.117>
  • Kim Young-Ah, Shin Hyo-Nim, Park Myoung-Soon, Cho So-Hye, Han So-Yeop: Studies toward a synthesis of C3-epimauritine D: construction of the macrocycle. Tetrahetron Lett 2003, 44, 2557. <http://dx.doi.org/10.1016/S0040-4039(03)00278-8>
  • Morel Ademir F, Araujo Carla A, da Silva Ubiratan F, Hoelzel Solange C.S.M, Záchia Renato, Bastos Nelci R: Antibacterial cyclopeptide alkaloids from the bark of Condalia buxifolia. Phytochemisry 2002, 61, 561. <http://dx.doi.org/10.1016/S0031-9422(02)00287-X>
  • Hwang Keum Hee, Han Yong Nam, Han Byung Hoon: Inhibition of calmodulin-dependent Calcium-ATPase and phosphodiesterase by various cyclopeptides and peptide alkaloids from the zizyphus species. Arch Pharm Res 2001, 24, 202. <http://dx.doi.org/10.1007/BF02978257>
  • Laı̈b Taoues, Bois-Choussy Michèle, Zhu Jieping: The first total synthesis of mauritine-A. Tetrahetron Lett 2000, 41, 7645. <http://dx.doi.org/10.1016/S0040-4039(00)01335-6>
  • Laïb Taoues, Zhu Jieping: An asymmetric total synthesis of sanjoinine G1. Tetrahetron Lett 1999, 40, 83. <http://dx.doi.org/10.1016/S0040-4039(98)80025-7>
  • East Stephen P., Shao Feng, Williams Lorenzo, Joullié Madeleine M.: Total synthesis of the cyclopeptide alkaloid sanjoinine G1 and its C-11 epimer. Tetrahedron 1998, 54, 13371. <http://dx.doi.org/10.1016/S0040-4020(98)00808-4>
  • Xiao Dong, East Stephen P., Joullié Madeleine M.: Total synthesis of sanjoinine A (frangufoline). Tetrahetron Lett 1998, 39, 9631. <http://dx.doi.org/10.1016/S0040-4039(98)02278-3>
  • Gournelis Dimitris C., Laskaris Gregory G., Verpoorte Robert: Cyclopeptide alkaloids. Nat Prod Rep 1997, 14, 75. <http://dx.doi.org/10.1039/np9971400075>
  • Park Myung Hwan, Suh Dae-Yeon, Han Byung Hoon: Absolute configuration of a cyclopeptide alkaloid, sanjoinine-G1, from Zizyphus vulgaris var. spinosus. Phytochemisry 1996, 43, 701. <http://dx.doi.org/10.1016/0031-9422(96)00292-0>
  • Lee Shoei-Sheng, Lin Buh-Fang, Liu Karin C.: Three triterpene esters from Zizyphus jujuba. Phytochemisry 1996, 43, 847. <http://dx.doi.org/10.1016/0031-9422(96)00379-2>
  • Couladouros Elias A., Soufli Ioanna C.: Synthesis of combretastatin D-2. An efficient route to caffrane macrolactones. Tetrahetron Lett 1994, 35, 4409. <http://dx.doi.org/10.1016/S0040-4039(00)73369-7>
  • Han Yong Nam, Kim Geum -Yi, Hwang Keum Hee, Han Byung Hoon: Binding of sanjoinine-A (frangufoline) to calmodulin. Arch Pharm Res 1993, 16, 289. <http://dx.doi.org/10.1007/BF02977518>
  • Park Man Ki, Park Jeong Hill, Shin Young Geun, Cho Kyung Hee, Han Byung Hoon, Park Myung Hwan: Analysis of alkaloids in the seeds ofZizyphus jujuba by high performance liquid chromatography. Arch Pharm Res 1991, 14, 99. <http://dx.doi.org/10.1007/BF02892010>
  • Han Byung Hoon, Park Myung Hwan, Han Yong Nam: Cyclic peptide and peptide alkaloids from seeds ofZizyphus vulgaris. Phytochemisry 1990, 29, 3315. <http://dx.doi.org/10.1016/0031-9422(90)80207-W>