光谱学与光谱分析 |
|
|
|
|
|
Study on the Extraction, Geometry Structure and Spectral Characterization of Piperine Alkaloid |
LI Xin1, SHI Jin-ru3, YANG Meng-shi1, LU Yi1, CHEN Liang1, CAO Hua-ru1,2* |
1. School of Engineering, Zhejiang A&F University, Lin’an 311300, China 2. Zhejiang Provincial Key Laboratory of Chemical Utilization of Forestry Biomass, Zhejiang A&F University, Lin’an 311300, China 3. College of Life Sciences, Zhengzhou University, Zhengzhou 450001, China |
|
|
Abstract Using pepper fruit of Hainan as raw material and 95% ethanol as solvent, the alkaloid in pepper is extracted with reflux method in this paper. The piperonylic acid is removed by adjusting the pH; the fat-soluble substance being removed by adding ethyl ether; the piperine alkaloid being purified with acetone by recrystallization anddetected with HPLC, as well as characterized with IR. The characterizations of piperine are discussed. Meanwhile, B3LYP/6-31G (d,p) method of DFT is applied to optimize the structure, calculate frequency and energy of pepper alkaloid, then obtain four kinds of configurations (configuration Ⅰ as Piperine, configuration Ⅱ as Iso Piperine, configuration Ⅲ as Iso Chavicine, configuration Ⅳ as Chavicine) with 64 kinds of stability conformational structure. The distribution of the thermodynamic equilibrium of stable conformations of four kinds of configurations of the molecular is calculated with Gibbs free energy at room temperature (298.15 K). And IR spectra of the experimental were compared with the IR spectra of the theoretical. The results show that the alkaloid extracted from pepper is mainly conformer 1 in configuration Ⅰ, that is, Piperine; after purifying, the content of piperine is 7% with the purity of 99%. With analysis, the methods of extraction, separation and purification of piperine in this paper achieve good results. Established models are in good agreement with the experimental results. This research is of great significance in guiding extracting process, building structural model and the characterization and application of piperine.
|
Received: 2015-04-24
Accepted: 2015-08-16
|
|
Corresponding Authors:
CAO Hua-ru
E-mail: caohuaru@yeah.net
|
|
[1] Pino J,Rodriguez-Feo G,Borges P,et al. Die Nahrung,1990,34(6): 555. [2] Koul I B,Kapil A. Planta Med.,1993,59(5): 413. [3] LONG Yu-zhou(龙宇宙). Processing and Utilizing of Product of Tropical Unique Spice and Beverage Crops(热带特色香辛饮料作物农产品加工与利用). Haikou: Hainan Press(海口: 海南出版社),2007. 63. [4] WEI Kun,DOU De-qiang,PEI Yu-ping,et al(韦 琨,窦德强,裴玉萍,等). Chinese Materia Medica(中国中药杂志),2002,27(5): 328. [5] Govindarajan V S. Crit. Rev. Food Sci. Nutr.,1977,9: 117. [6] Mittal R,Gupta R L. Methods Find Exp. Clin. Pharmacol.,2000,22(5): 271. [7] Vijayakumar R S,Surya D,Nalini N. Redox. Rep.,2004,9(2): 105. [8] Ramasamy S V,Namasivayam N. Cell Biochemicalistry and Function,2006,24(6): 491. [9] Lee C S,Han E S,Kim Y K. Eur. J. Pharmacol.,2006,537(1-3): 37. [10] Bajad S,Bedi K L,Singla A K,et al. Planta Med.,2001,67(3): 284. [11] Bajad S,Bedi K L,Singla A K,et al. Planta Med.,2001,67(2): 176. [12] Capasso R,Izzo A A,Borrelli F,et al. Life Science,2002,71(19): 2311. [13] Lee S A,Hong S S,Han X H,et al. Chem. Pharm. Bull.(Tokyo),2005,53(7): 832. [14] Kong L D,Cheng C H,Tan R X. J. Ethnopharmacol,2004,91(2-3): 351. [15] Pathak N,Khandelwal S. Biochemieal Pharmacol,2006,72(4): 486. [16] Dogra R K,Khalma S,Shanker R. Toxicology,2004,196(3): 229. [17] Pradeep C R,Kuttan G. Clin. Exp. Metastas.,2002,19(8): 703. [18] Menon A N,Padmakumari K. J. Essent Oil Res.,2005,2(17): 153. [19] Bai Y F,Xu H. Acta Pharmacologica Sinica,2000,21(4): 357. [20] Pradeep C R,Kuttan G. Int Immunopharmacol,2004,4(14): 1795. [21] Selvendiran K,Banu S M,Sakthisekaran D. Clin. Chim. Acta,2004,350(1-2): 73. [22] Sunila E S,Kuttan G. J. Ethnopharmacol,2004,90 (2-3): 339. [23] Khajuria A,Thusu N,Zutshi U. Phytomedicine,2002,9(3): 224. [24] Subramanian R,Subbramaniyan P,Noorul Ameen J,et al. Arabian Journal of Chemistry,2011,doi:10.1016/j.arabjc.2011.06.022. [25] MENG Zhao-hui,WANG Zhen-hui,ZHOU Shu-ping(孟召辉,汪振辉,周漱萍). J. Anal. Chem.(分析化学),1994,22(12): 1163. [26] Kanaki N,Dave M,Padh H,et al. J. Nat. Med.,2008,62: 281. [27] FAN Xiu-yu,YIN Ai-qun,SU Wei-guo,et al(范秀玉,尹爱群,苏维国,等). Drug Standards of China(中国药品标准),2004,5(5): 28. [28] Girija R,Vilas G G. Ind. Eng. Chem. Res.,2002,41(10): 2521. [29] CHEN Jian-hua,WENG Shao-wei,LI Zhong,et al(陈建华,翁少伟,李 忠,等). Fine Chemicals(精细化工),2010,27(10): 991. [30] Cao X J,Ye X M,Lu Y B,et al. Anal. Chim. Acta,2009,640: 47. [31] Ternes W,Krause E L. Anal. Bioanal. Chem.,2002,374: 155. [32] Kozukue N,Park M S,Choi S H,et al. J. Agric. Food Chem.,2007,55: 7131. [33] Huang Z J,Yu W B,Lin Z J. J. Mol. Struct. THEOCHEM,2006,81: 7. [34] Zhang M L,Huang Z J,Lin Z J. J. Chem. Phys.,2005,122: 134313. [35] Huang Z J,Yu W B,Lin Z J. J. Mol. Struct. THEOCHEM,2006,758:195. [36] Ling S L,Yu W B,Huang Z J,et al. J. Phys. Chem. A,2006,110: 12282. [37] Huang Z J,Lin Z J. J. Phys. Chem. A,2005,109: 2656. [38] Yu W B,Lin Z J,Huang Z J. Chem. Phys. Chem.,2006,7: 828. [39] Yu W B,Liang L,Lin Z J,et al. J. Comput. Chem.,2009,30: 589. [40] Yu W B,Wu Z Q,Chen H B,et al. J. Comput. Chem.,2009,30: 2105. [41] Yu W B,Xu X E,Li H B,et al. J. Phys. Chem. B,2012,116: 2269. [42] LI Xin,YANG Meng-shi,YE Zhi-peng,et al(李 鑫,羊梦诗,叶志鹏,等). Acta Phys. Sin.(物理学报),2013,15: 156103-1. [43] Li X,Yu S,Yang M S,et al. Physica E,2014,57: 63. [44] LI Xin,ZHANG Liang,YANG Meng-shi,et al(李 鑫,张 梁,羊梦诗,等). Acta Phys. Sin.(物理学报),2014,7: 076102-1. [45] LI Xin,YANG Meng-shi,XU Can,et al(李 鑫,羊梦诗,徐 灿,等). Spectroscopy and Spectal Analysis(光谱学与光谱分析),2014,34(9): 2331. [46] Li X,Yang M S,Shi X,et al,Physica E,2015,69: 273. [47] Von Weizsacker C F,Z. Phys.,1935,96: 431. [48] Becke A D. Phys. Rev. A,1988,38: 3098. [49] Lee C,Yang W,Parr R G. Phys. Rev. B,1998,37: 785. [50] Frisch M J,Trucks G W,Schlegel H B,et al. Gaussian09, Revision C. 01, Gaussian, Inc., Wallingford CT,2009. [51] Stepanian S G,Reva I D,Radchenko E D,et al. J. Phys. Chem. A,1999,103:4404. |
[1] |
CHENG Jia-wei1, 2,LIU Xin-xing1, 2*,ZHANG Juan1, 2. Application of Infrared Spectroscopy in Exploration of Mineral Deposits: A Review[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(01): 15-21. |
[2] |
LI Jie, ZHOU Qu*, JIA Lu-fen, CUI Xiao-sen. Comparative Study on Detection Methods of Furfural in Transformer Oil Based on IR and Raman Spectroscopy[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(01): 125-133. |
[3] |
YANG Cheng-en1, 2, LI Meng3, LU Qiu-yu2, WANG Jin-ling4, LI Yu-ting2*, SU Ling1*. Fast Prediction of Flavone and Polysaccharide Contents in
Aronia Melanocarpa by FTIR and ELM[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(01): 62-68. |
[4] |
GAO Feng1, 2, XING Ya-ge3, 4, LUO Hua-ping1, 2, ZHANG Yuan-hua3, 4, GUO Ling3, 4*. Nondestructive Identification of Apricot Varieties Based on Visible/Near Infrared Spectroscopy and Chemometrics Methods[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(01): 44-51. |
[5] |
LIU Jia, ZHENG Ya-long, WANG Cheng-bo, YIN Zuo-wei*, PAN Shao-kui. Spectra Characterization of Diaspore-Sapphire From Hotan, Xinjiang[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(01): 176-180. |
[6] |
BAO Hao1, 2,ZHANG Yan1, 2*. Research on Spectral Feature Band Selection Model Based on Improved Harris Hawk Optimization Algorithm[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(01): 148-157. |
[7] |
GUO Ya-fei1, CAO Qiang1, YE Lei-lei1, ZHANG Cheng-yuan1, KOU Ren-bo1, WANG Jun-mei1, GUO Mei1, 2*. Double Index Sequence Analysis of FTIR and Anti-Inflammatory Spectrum Effect Relationship of Rheum Tanguticum[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(01): 188-196. |
[8] |
LI Xiao-dian1, TANG Nian1, ZHANG Man-jun1, SUN Dong-wei1, HE Shu-kai2, WANG Xian-zhong2, 3, ZENG Xiao-zhe2*, WANG Xing-hui2, LIU Xi-ya2. Infrared Spectral Characteristics and Mixing Ratio Detection Method of a New Environmentally Friendly Insulating Gas C5-PFK[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(12): 3794-3801. |
[9] |
HU Cai-ping1, HE Cheng-yu2, KONG Li-wei3, ZHU You-you3*, WU Bin4, ZHOU Hao-xiang3, SUN Jun2. Identification of Tea Based on Near-Infrared Spectra and Fuzzy Linear Discriminant QR Analysis[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(12): 3802-3805. |
[10] |
LIU Xin-peng1, SUN Xiang-hong2, QIN Yu-hua1*, ZHANG Min1, GONG Hui-li3. Research on t-SNE Similarity Measurement Method Based on Wasserstein Divergence[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(12): 3806-3812. |
[11] |
SUN Wei-ji1, LIU Lang1, 2*, HOU Dong-zhuang3, QIU Hua-fu1, 2, TU Bing-bing4, XIN Jie1. Experimental Study on Physicochemical Properties and Hydration Activity of Modified Magnesium Slag[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(12): 3877-3884. |
[12] |
BAI Xue-bing1, 2, SONG Chang-ze1, ZHANG Qian-wei1, DAI Bin-xiu1, JIN Guo-jie1, 2, LIU Wen-zheng1, TAO Yong-sheng1, 2*. Rapid and Nndestructive Dagnosis Mthod for Posphate Dficiency in “Cabernet Sauvignon” Gape Laves by Vis/NIR Sectroscopy[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(12): 3719-3725. |
[13] |
WANG Qi-biao1, HE Yu-kai1, LUO Yu-shi1, WANG Shu-jun1, XIE Bo2, DENG Chao2*, LIU Yong3, TUO Xian-guo3. Study on Analysis Method of Distiller's Grains Acidity Based on
Convolutional Neural Network and Near Infrared Spectroscopy[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(12): 3726-3731. |
[14] |
DANG Rui, GAO Zi-ang, ZHANG Tong, WANG Jia-xing. Lighting Damage Model of Silk Cultural Relics in Museum Collections Based on Infrared Spectrum[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(12): 3930-3936. |
[15] |
LUO Li, WANG Jing-yi, XU Zhao-jun, NA Bin*. Geographic Origin Discrimination of Wood Using NIR Spectroscopy
Combined With Machine Learning Techniques[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(11): 3372-3379. |
|
|
|
|