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GAO Xing, ZHAO Fengping, WANG Wentao, TIAN Wei, ZHENG Canhui, CHEN Xin. Research on the chemical compositions and their biological activities of Piper nigrum L.[J]. Journal of Pharmaceutical Practice and Service. doi: 10.12206/j.issn.2097-2024.202308065
Citation: GAO Xing, ZHAO Fengping, WANG Wentao, TIAN Wei, ZHENG Canhui, CHEN Xin. Research on the chemical compositions and their biological activities of Piper nigrum L.[J]. Journal of Pharmaceutical Practice and Service. doi: 10.12206/j.issn.2097-2024.202308065

Research on the chemical compositions and their biological activities of Piper nigrum L.

doi: 10.12206/j.issn.2097-2024.202308065
  • Received Date: 2023-08-29
  • Rev Recd Date: 2024-01-11
  • Piper nigrum L. is an evergreen climbing vine, which belongs to the genus Piperia in the Piperaceae family. Piper nigrum L., which known as the “king of spices”, is used as both food and medicine. The main active substances in Piper nigrum L. are alkaloids mainly composed of amides, and essential oil, as well as phenolic compounds. In this paper, the chemical compositions, especially amide alkaloids, and their biological activities of Piper nigrum L. were summarized. These studies showed that Piper nigrum L., as a medicinal and food plant, had a wide range of biological activities and was deserved further research and in-depth utilization.
  • [1] 严永清. 中药辞海. 第二卷 [M]. 中药辞海. 第二卷, 1996.
    [2] 郑维全, 杨建峰, 鱼欢, 等. 我国胡椒产业现状与创新发展探析[J]. 热带农业科学, 2017, 37(12):102-8.
    [3] TAKOOREE H, AUMEERUDDY M Z, RENGASAMY K R R, et al. A systematic review on black pepper (Piper nigrum L.): from folk uses to pharmacological applications[J]. Critical Reviews in Food Science and Nutrition, 2019, 59(sup1):S210-S43. doi:  10.1080/10408398.2019.1565489
    [4] 于岚, 郝正一, 胡晓璐, 等. 胡椒的化学成分与药理作用研究进展[J]. 中国实验方剂学杂志, 2020, 26(6):9.
    [5] GORGANI L, MOHAMMADI M, NAJAFPOUR G D, et al. Piperine—The Bioactive Compound of Black Pepper: From Isolation to Medicinal Formulations[J]. Comprehensive Reviews in Food Science and Food Safety, 2017, 16(1):124-40. doi:  10.1111/1541-4337.12246
    [6] YUN Y S, SACHIETAKAHASHI, SHIGERUTAKAHASHI, YUJIINOUE, HIDESHI. Piperine-like alkamides from Piper nigrum induce BDNF promoter and promote neurite outgrowth in Neuro-2a cells[J]. Journal of natural medicines, 2018, 72(1):238-45. doi:  10.1007/s11418-017-1140-3
    [7] LIU H L, LUO R, CHEN X Q, et al. Identification and simultaneous quantification of five alkaloids in Piper longum L. by HPLC-ESI-MS(n) and UFLC-ESI-MS/MS and their application to Piper nigrum L[J]. Food Chemistry, 2015, 177(jun.15):191-6.
    [8] TU Y, ZHONG Y, DU H, et al. Anticholinesterases and antioxidant alkamides from Piper nigrum fruits[J]. Natural Product Research, 2016, 30(17):1945-9. doi:  10.1080/14786419.2015.1089243
    [9] PEI H, XUE L, TANG M, et al. Alkaloids from Black Pepper (Piper nigrum L.) Exhibit Anti-Inflammatory Activity in Murine Macrophages by Inhibiting Activation of NF-κB Pathway[J]. Journal of Agricultural and Food Chemistry, 2020, 68(8):2406-17. doi:  10.1021/acs.jafc.9b07754
    [10] SUN C, PEI S, PAN Y, et al. Rapid structural determination of amides in Piper longum by high-performance liquid chromatography combined with ion trap mass spectrometry[J]. Rapid Communications in Mass Spectrometry, 2007, 21(9):1497-503. doi:  10.1002/rcm.2986
    [11] R. B L, CORINNA D, MADELINE B, et al. The Effect of Pungent and Tingling Compounds from Piper nigrum L. on Background K+ Currents [J]. Frontiers in Pharmacology, 2017, 8: 408.
    [12] NGO Q M T, TRAN P T, TRAN M H, et al. Alkaloids from Piper nigrum Exhibit Antiinflammatory Activity via Activating the Nrf2/HO1 Pathway[J]. Phytotherapy Research, 2017, 31(4):663-70. doi:  10.1002/ptr.5780
    [13] SRIWIRIYAJAN S, SUKPONDMA Y, SRISAWAT T, et al. (−)-Kusunokinin and piperloguminine from Piper nigrum: An alternative option to treat breast cancer[J]. Biomedicine & Pharmacotherapy, 2017, 92:732-43.
    [14] NICOLUSSI S, VIVEROS-PAREDES J M, GACHET M S, et al. Guineensine is a novel inhibitor of endocannabinoid uptake showing cannabimimetic behavioral effects in BALB/c mice[J]. Pharmacological Research, 2014, 80:52-65. doi:  10.1016/j.phrs.2013.12.010
    [15] YU L, HU X, XU R, et al. Amide alkaloids characterization and neuroprotective properties of Piper nigrum L.: A comparative study with fruits, pericarp, stalks and leaves[J]. Food Chemistry, 2022, 368:130832. doi:  10.1016/j.foodchem.2021.130832
    [16] 王勇, 魏娜, 李洪福, 等. 海南黑胡椒超临界萃取物中化学成分的GC-MS分析[J]. 中国实验方剂学杂志, 2013, 19(12):121-3.
    [17] FUJIWARA Y, NAITHOU K, MIYAZAKI T, et al. Two new alkaloids, pipercyclobutanamides A and B, from Piper nigrum[J]. Tetrahedron Letters, 2001, 42(13):2497-9. doi:  10.1016/S0040-4039(01)00209-X
    [18] HUU D M N, DANG P H, HUYNH N V, et al. Pipercyclobutanamide D, a new member of the cyclobutanamide-type alkaloid, from the roots of Piper nigrum[J]. Journal of Asian Natural Products Research, 2021, 23(9):906-12. doi:  10.1080/10286020.2020.1794858
    [19] 段梦雅, 王福清, 吴桂苹, 等. 4种胡椒精油风味特征分析[J]. 食品科学, 2022(008):043.
    [20] BUTT M S, PASHA I, SULTAN M T, et al. Black Pepper and Health Claims: A Comprehensive Treatise[J]. Critical Reviews in Food Science and Nutrition, 2013, 53(9):875-86. doi:  10.1080/10408398.2011.571799
    [21] AZIZ N S, SOFIAN-SENG N-S, MOHD RAZALI N S, et al. A review on conventional and biotechnological approaches in white pepper production[J]. Journal of the Science of Food and Agriculture, 2019, 99(6):2665-76. doi:  10.1002/jsfa.9481
    [22] 姜太玲, 沈绍斌, 张林辉, 等. 胡椒的化学成分 生理功能及应用研究进展[J]. 农产品加工:下, 2018(1):4.
    [23] RENJIE L, SHIDI S, YONGJUN M. Analysis of volatile oil composition of the peppers from different production areas[J]. Medicinal Chemistry Research, 2010, 19(2):157-65. doi:  10.1007/s00044-009-9180-1
    [24] CHUNG H Y, JUNG H J, KIM D H, et al. Anti-inflammatory and antioxidant activities of piperine on t-BHP-induced in Ac2F cells [J]. 2019.
    [25] VIJAYAKUMAR R S, NALINI N. Piperine, an Active Principle from Piper Nigrum, Modulates Hormonal and Apolipoprotein Profiles in Hyperlipidemic Rats[J]. Journal of Basic and Clinical Physiology and Pharmacology, 2006, 17(2):71-86. doi:  10.1515/JBCPP.2006.17.2.71
    [26] BRAHMANAIDU P, NEMANI H, MERIGA B, et al. Mitigating efficacy of piperine in the physiological derangements of high fat diet induced obesity in Sprague Dawley rats[J]. Chemico-Biological Interactions, 2014, 221:42-51. doi:  10.1016/j.cbi.2014.07.008
    [27] REYNOSO MORENO I, NAJAR-GUERRERO I, ESCARENO N, et al. An Endocannabinoid Uptake Inhibitor from Black Pepper Exerts Pronounced Anti-Inflammatory Effects in Mice [J]. Journal of Agricultural & Food Chemistry, 2017: 9435.
    [28] RATHER R A, BHAGAT M. Cancer Chemoprevention and Piperine: Molecular Mechanisms and Therapeutic Opportunities [J]. Frontiers in Cell and Developmental Biology, 2018, 6.
    [29] YAFFE P B, POWER COOMBS M R, DOUCETTE C D, et al. Piperine, an alkaloid from black pepper, inhibits growth of human colon cancer cells via G1 arrest and apoptosis triggered by endoplasmic reticulum stress[J]. Molecular Carcinogenesis, 2015, 54(10):1070-85. doi:  10.1002/mc.22176
    [30] HAN S Z, LIU H X, YANG L Q, et al. Piperine (PP) enhanced mitomycin-C (MMC) therapy of human cervical cancer through suppressing Bcl-2 signaling pathway via inactivating STAT3/NF-κB[J]. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 2017, 96:1403-10.
    [31] GUNASEKARAN V, ELANGOVAN K, NIRANJALI DEVARAJ S. Targeting hepatocellular carcinoma with piperine by radical-mediated mitochondrial pathway of apoptosis: An invitro and invivo study[J]. Food and Chemical Toxicology, 2017, 105:106-18. doi:  10.1016/j.fct.2017.03.029
    [32] TURRINI E, SESTILI P, FIMOGNARI C. Overview of the anticancer potential of the “king of spices” piper nigrum and its main constituent piperine[J]. Toxins, 2020, 12(12):747. doi:  10.3390/toxins12120747
    [33] MATSUDA H, NINOMIYA K, MORIKAWA T, et al. Protective effects of amide constituents from the fruit of Piper chaba on d-galactosamine/TNF-α-induced cell death in mouse hepatocytes[J]. Bioorganic & Medicinal Chemistry Letters, 2008, 18(6):2038-42.
    [34] SABINA E P, SOURIYAN A D H, JACKLINE D, et al. Piperine, an active ingredient of black pepper attenuates acetaminophen–induced hepatotoxicity in mice[J]. Asian Pacific Journal of Tropical Medicine, 2010, 3(12):971-6. doi:  10.1016/S1995-7645(11)60011-4
    [35] CHOI S, CHOI Y, CHOI Y, et al. Piperine reverses high fat diet-induced hepatic steatosis and insulin resistance in mice[J]. Food Chemistry, 2013, 141(4):3627-35. doi:  10.1016/j.foodchem.2013.06.028
    [36] YOUNIS N. Protective mechanisms of piperine against acetaminophen-induced hepatotoxicity may be mediated through TGFBRAP1[J]. European review for medical and pharmacological sciences, 2020, 24:10169-80.
    [37] SAMRA Y A, SAID H S, ELSHERBINY N M, et al. Cepharanthine and Piperine ameliorate diabetic nephropathy in rats: role of NF-κB and NLRP3 inflammasome [J]. Life Sciences, 2016: S0024320516303484.
    [38] BOORANASUBKAJORN S, HUABPRASERT S, WATTANARANGSAN J, et al. Vasculoprotective and vasodilatation effects of herbal formula (Sahatsatara) and piperine in spontaneously hypertensive rats[J]. Phytomedicine, 2017, 24:148-56. doi:  10.1016/j.phymed.2016.11.013
    [39] MURTAZA A, REHMAN T, ZAFAR Z, et al. Synthesis and Characterization of Herbal Nano-suspensions and Evaluation of their In-vivo Antihypertensive Potential with Especial Focus on Piperine [J]. Journal of Pharmaceutical Research International, 2020.
    [40] CHAUDHARY, KUMAR S, MUKHERJEE P K, et al. Evaluation of angiotensin converting enzyme inhibition and anti-oxidant activity of Piper longum L; proceedings of the Lattice Gauge Theories Supersymmetry & Grand Unification Johns Hopkins Workshop on Current Problems in Particle Theory, F, 2013 [C
    [41] MAO Q-Q, HUANG Z, ZHONG X-M, et al. Brain-derived neurotrophic factor signalling mediates the antidepressant-like effect of piperine in chronically stressed mice[J]. Behavioural Brain Research, 2014, 261:140-5. doi:  10.1016/j.bbr.2013.12.020
    [42] LUCIAN, HRITCU, A J, et al. Anxiolytic and antidepressant profile of the methanolic extract of Piper nigrum fruits in beta-amyloid (1-42) rat model of Alzheimer's disease [J]. Behavioral and brain functions : BBF, 2015.
    [43] KHOM S, STROMMER B, SCHöFFMANN A, et al. GABAA receptor modulation by piperine and a non-TRPV1 activating derivative[J]. Biochemical Pharmacology, 2013, 85(12):1827-36. doi:  10.1016/j.bcp.2013.04.017
    [44] MAO K, LEI D, ZHANG H, et al. Anticonvulsant effect of piperine ameliorates memory impairment, inflammation and oxidative stress in a rat model of pilocarpine-induced epilepsy[J]. Exp Ther Med, 2017, 13(2):695-700. doi:  10.3892/etm.2016.4001
    [45] SUBEDEE L, SURESH R N, JAYANTHI M K, et al. Preventive role of Indian black pepper in animal models of Alzheimer's disease[J]. Journal of Clinical & Diagnostic Research Jcdr, 2015, 9(4):FF01.
    [46] CHONPATHOMPIKUNLERT P, WATTANATHORN J, MUCHIMAPURA S. Piperine, the main alkaloid of Thai black pepper, protects against neurodegeneration and cognitive impairment in animal model of cognitive deficit like condition of Alzheimer's disease [J]. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 2010, 48: 798-802.
    [47] 赵贤武, 黄丽平, 邓敏贞, 等. 高良姜、胡椒和槟榔有效成分对岗田酸诱导p-tau细胞模型的作用研究[J]. 中医学报, 2017, 32(11):5.
    [48] 邹兰, 胡月英, 陈文学. 黑胡椒提取物对枯草芽孢杆菌生理代谢的影响[J]. 食品工业科技, 2015, 36(23):4.
    [49] 邹兰, 胡月英, 陈文学. 黑胡椒石油醚相提取物对大肠杆菌和金黄色葡萄球菌的抑菌机制研究[J]. 食品科技, 2018, 43(6):5.
    [50] FREIRE-DE-LIMA L, RIBEIRO T, ROCHA G, et al. The toxic effects of piperine against Trypanosoma cruzi: Ultrastructural alterations and reversible blockage of cytokinesis in epimastigote forms[J]. Parasitology research, 2008, 102:1059-67. doi:  10.1007/s00436-008-0876-9
    [51] CHOUHAN G, ISLAMUDDIN M, WANT M Y, et al. Leishmanicidal Activity of Piper nigrum Bioactive Fractions is Interceded via Apoptosis In Vitro and Substantiated by Th1 Immunostimulatory Potential In Vivo [J]. Frontiers in Microbiology, 2015, 6.
    [52] SAMUEL M, OLIVER S V, COETZEE M, et al. The larvicidal effects of black pepper (Piper nigrum L.) and piperine against insecticide resistant and susceptible strains of Anopheles malaria vector mosquitoes[J]. Parasites & Vectors, 2016, 9(1):238.
    [53] TAQVI S I H, SHAH A J, GILANI A H. Insight into the possible mechanism of antidiarrheal and antispasmodic activities of piperine [J]. Pharmaceutical Biology.
    [54] SMILKOV K, ACKOVA D G, CVETKOVSKI A, et al. Piperine: Old Spice and New Nutraceutical?[J]. Curr Pharm Des, 2019, 25(15):1729-39. doi:  10.2174/1381612825666190701150803
    [55] CHATTERJEE S, NIAZ Z, GAUTAM S, et al. Antioxidant activity of some phenolic constituents from green pepper (Piper nigrum L.) and fresh nutmeg mace (Myristica fragrans)[J]. Food Chemistry, 2007, 101(2):515-23. doi:  10.1016/j.foodchem.2006.02.008
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Research on the chemical compositions and their biological activities of Piper nigrum L.

doi: 10.12206/j.issn.2097-2024.202308065

Abstract: Piper nigrum L. is an evergreen climbing vine, which belongs to the genus Piperia in the Piperaceae family. Piper nigrum L., which known as the “king of spices”, is used as both food and medicine. The main active substances in Piper nigrum L. are alkaloids mainly composed of amides, and essential oil, as well as phenolic compounds. In this paper, the chemical compositions, especially amide alkaloids, and their biological activities of Piper nigrum L. were summarized. These studies showed that Piper nigrum L., as a medicinal and food plant, had a wide range of biological activities and was deserved further research and in-depth utilization.

GAO Xing, ZHAO Fengping, WANG Wentao, TIAN Wei, ZHENG Canhui, CHEN Xin. Research on the chemical compositions and their biological activities of Piper nigrum L.[J]. Journal of Pharmaceutical Practice and Service. doi: 10.12206/j.issn.2097-2024.202308065
Citation: GAO Xing, ZHAO Fengping, WANG Wentao, TIAN Wei, ZHENG Canhui, CHEN Xin. Research on the chemical compositions and their biological activities of Piper nigrum L.[J]. Journal of Pharmaceutical Practice and Service. doi: 10.12206/j.issn.2097-2024.202308065
    • 胡椒(Piper nigrum L.)在植物分类上属于胡椒科(Piperaceae)胡椒属(Piper)是一种原产于印度的多年生常绿攀援藤本植物。胡椒在我国始载于唐代的《新修本草》又名古月、黑川(黑胡椒)、白川(白胡椒)[1],其中黑胡椒被誉为“香料之王”,是一种被全世界广泛使用的香料,可为菜肴增添独特的风味,并增强其他食材的味道,目前对胡椒的研究大部分是聚焦于黑胡椒。我国从1947年开始引种胡椒, 目前我国胡椒种植面积和产量在世界的排名分别是第6位和第5位[2]。但是我国胡椒加工产品多为初级产品, 导致胡椒产品附加值低, 这也限制了胡椒产业的发展。为了让胡椒得到更好的发展,近年来, 国内外学者对胡椒的化学成分和生物活性进行了较多研究,为胡椒的开发利用提供理论参考[3, 4]。本文通过查阅近些年的文献,针对胡椒的化学成分和生物活性进行了综述,为其进一步研究与开发提供参考。

    • 近年来的研究发现胡椒果实、根、茎、叶和花中含有多种成分,主要包括酰胺类生物碱、挥发性精油、酚类、有机酸、木脂素及微量元素等,其中生物碱是其最主要的活性成分。

    • 生物碱类是胡椒中重要的一类活性成分,其中以胡椒碱为代表的酰胺类化合物含量最高、活性最广,胡椒碱在胡椒中含量大致为2%~7.4%[5]。目前从胡椒中分离得到的酰胺类化合物见表1图1

      化合物 中英文名称
      1 胡椒碱 [6]
      2 胡椒新碱[7]
      3 胡椒亭碱[6]
      4 胡椒油碱A[8]
      5 荜茇壬二烯哌啶[6]
      6 荜茇壬三烯哌啶[6]
      7 胡椒油碱B[6]
      8 N-哌啶-11-(3,4亚甲二氧基苯基)-2E,10E-十一碳二烯酰胺[8]
      9 N-哌啶-13-(3,4亚甲二氧基苯基)-2E,4E,12E-十三碳三烯酰胺[6]
      10 N-哌啶-13-(3,4亚甲二氧基苯基)-2E,12E-十三碳二烯酰胺[8]
      11 1-[(2E,4E,10E)-11-(3,4-亚甲基二氧苯基)-2,4,10-十一碳三烯酰基]吡咯烷[9]
      12 (2E,4E,10E)-N-11-(3,4-亚甲基二氧苯基癸三烯酰基)哌啶[10]
      13 胡椒林碱[6]
      14 胡椒内酰胺-C5:1(2E)[4]
      15 胡椒内酰胺-C7:3(2E,4E,6E)[8]
      16 胡椒内酰胺-C7:2(2E,6E)[4]
      17 胡椒内酰胺-C7:1(6E)[4]
      18 胡椒内酰胺-C9:3(2E,4E,8E)[6]
      19 胡椒内酰胺-C9:2(2E,8E)[4]
      20 胡椒内酰胺-C9:1(8E)[8]
      21 胡椒内酰胺-C13:3(2E,4E,12E)[11]
      22 胡椒内酰胺-C10:1(9E)[12]
      23 荜茇明宁碱[13]
      24 二氢荜茇明宁碱[7]
      25 N-异丁基-9-(3,4-亚甲二氧基苯基)-2E,4E,8E-壬三烯酰胺[6]
      26 N-异丁基-11-(3,4-亚甲二氧基苯基)2E,4E,10E-十一碳三烯酰胺[8]
      27 N-异丁基-11-(3,4-亚甲二氧基苯基)-2E,4E-十一碳二烯酰胺[14]
      28 (2E,4E)-9-(1,3-苯并二恶茂-5-基)-N-(2-甲基丙基)壬-2,4-二酰胺[15]
      29 几内亚胡椒酰胺[6]
      30 N-异丁基15-(3,4-亚甲二氧基苯基)2E,4E,14E-十一碳三烯酰胺[8]
      31 N-反式阿魏酰基哌啶[4]
      32 阿魏波因[4]
      33 去氢阿魏波因[4]
      34 1-桂皮酰基哌啶[16]
      35 N-5-(4-羟基苯)-2E,4E-戊二烯酰基吡咯烷[4]
      36 N-反式阿魏酰基酪胺[8]
      37 N-反式阿魏酰-3-甲氧基酪胺[8]
      38 1-[(2E,4E,13Z)十八烷三烯酰基]哌啶[11]
      39 1-[(2E,4E,13Z)十八烷三烯酰基]吡咯[11]
      40 1-[(2E,4E,12Z)十八烷三烯酰基]哌啶[11]
      41 1-[(2E,4E,12Z)十八烷三烯酰基]吡咯[11]
      42 1-[(2E,4E)葵二烯酰基]吡咯[14]
      43 1-[(2E,4E)十二烷二烯酰基]吡咯[4]
      44 1-[(2E,4E,12Z)十四烷三烯酰基]哌啶[10]
      45 1-(十四烷基-2E-烯酰基)哌啶[10]
      46 1-[(2E,4E)十四烷二烯酰基]哌啶[10]
      47 1-[(2E,4E,10E)十六烷三烯酰基]哌啶[10]
      48 1-[(2E,4E)十六烷二烯酰基]哌啶[10]
      49 1-[(2E,4E)十八烷二烯酰基]哌啶[10]
      50 1-[(2E,4E,14E)二十烷三烯酰基]哌啶[10]
      51 1-[(2E,4E)二十烷二烯酰基]哌啶[10]
      52 N-异丁基-2E,4E,13Z三烯十八酰胺[11]
      53 N-异丁基-2E,4E,15Z三烯二十酰胺[11]
      54 N-异丁基-2E,4E,14Z三烯二十酰胺[11]
      55 墙草碱[7]
      56 N-异丁基-2E,4E-二烯十二酰胺[6]
      57 N-异丁基-2E,4E-二烯十六酰胺[4]
      58 N-异丁基-2E,4E,10Z-三烯十六酰胺[8]
      59 N-异丁基-2E,4E-二烯十八酰胺[11]
      60 N-异丁基-2E,4E,12Z-三烯十八酰胺[6]
      61 N-异丁基-2E,4E,10E-三烯二十二酰胺[4]
      62 N-异丁基-2E,4E,8E-三烯十四酰胺[10]
      63 N-异丁基-2E,4E-二烯十四酰胺[10]
      64 N-异丁基-2E,4E,8E-二烯二十酰胺[10]
      65 哌啶环丁酰胺A[17]
      66 哌啶环丁酰胺B[17]
      67 哌啶环丁酰胺D[18]
      68 Chabamide[12]
    • 胡椒的价值很大一部分在于它的辛辣和风味,这归因于一种自然存在的生物碱,即胡椒碱,以及挥发性精油的存在。挥发油约占胡椒的0.4%~7%,是胡椒香气的主要来源[5]。胡椒精油以单萜、倍半萜烯类化合物为主,目前为止胡椒精油已经发现了48种化合物[19-22],其中主要成分包括β-石竹烯、3-蒈烯、D-柠檬烯、β-蒎烯、δ-榄香烯、β-月桂烯、E-β-石竹烯、柠檬烯、β-蒎烯、β-水芹烯、δ-3-蒈烯、桧烯、β-红没药烯、α-蒎烯、丁子香酚、萜品烯-4-醇、耳草蒈烷醇、β-桉叶醇、石竹烯氧化物等。

    • 胡椒的酚类成分是黄酮醇糖苷和酚酸糖苷的混合物[23],其中主要成分有异槲皮素、槲皮素、3-β-D-芸香苷异鼠李素、山奈酚-3-ο-β-半乳糖苷、山奈酚-3-阿拉伯糖苷和槲皮素-3-ο-β-D-芸香苷等[20]

    • 胡椒中主要的生物活性物质为胡椒碱、挥发性精油以及酚类化合物(如图2所示),生物碱中尤其对胡椒碱的研究十分广泛,它们具有广泛的生物活性,胡椒中的化合物有助于改善各种疾病。

    • 胡椒碱对叔丁基过氧化氢(t-BHP)诱导的Ac2F细胞氧化应激有预防作用。根据Chung等人的研究表明,胡椒碱通过清除自由基和活性氧(ROS)来防止氧化损伤,并且发现通过胡椒碱预处理Donryu大鼠肝细胞(Ac2F细胞)可调节凝血酶和锰依赖性超氧化物歧化酶(MnSOD)的蛋白表达,这是降低线粒体氧化应激所必需的重要抗氧化酶,表明胡椒碱存在抗氧化方面的作用[24]

    • 胡椒碱通过调节脂代谢相关酶,如卵磷脂-胆固醇酰基转移酶(LCAT)和脂蛋白脂酶(LPL),降低高脂血症大鼠血脂和脂蛋白水平,从而起到减肥作用[25]。根据Brahmanaidu等人的研究,胡椒碱可改善高脂饮食(HFD)引起的生化指标的水平升高,增强了胰岛素和瘦素的敏感性,表明胡椒碱可以作为治疗肥胖的潜在药物[26]

    • 胡椒碱可以通过抑制细胞内反应性物种激活的NF-κB和丝裂原活化蛋白激酶(MAPK)来预防t-BHP诱导的Ac2F细胞炎症[24]。Pei等人研究发现,胡椒碱在脂多糖刺激的原始264.7细胞中可以抑制白细胞介素-6(IL-6),白细胞介素-1β(IL-1β),肿瘤坏死因子-α(TNF-α),前列腺素E2(PGE2)和诱导型一氧化氮合酶(iNOS)介导的NO的释放,可以通过靶向IκB激酶 β(IKK-β)抑制NF-κb的活化和p65亚基的细胞核易位,这些结果表明胡椒碱可能是炎症治疗的有效药物[9]

      胡椒中的另一个化合物几内亚胡椒酰胺也具有较好的抗炎作用。Reynoso等人构建了急性炎性疼痛和内毒素血症小鼠模型,通过几内亚胡椒酰胺治疗后,发现小鼠的炎性疼痛有所改善,同时抑制了水肿的形成,研究结果表明几内亚胡椒酰胺能够抑制内毒素血症中促炎细胞因子的产生,并且其抗炎和急性镇痛作用呈现显著的剂量依赖性[27]

    • 胡椒碱可以通过影响凋亡信号的激活和抑制细胞周期的进程,抑制多种类型癌细胞的增殖和存活[28]。Yaffe等人研究发现胡椒碱可以抑制HT-29结肠癌细胞的生长并诱导细胞凋亡,此研究表明胡椒碱通过调节参与癌细胞增殖,细胞周期阻滞,凋亡和转移的酶的表达水平而表现出显著的抗肿瘤活性[29]。胡椒碱和丝裂霉素共同处理导致细胞增殖的剂量依赖性抑制,同时磷酸化信号转导和转录激活因子(p-STAT3)的减少与它们对p65的抑制有关[30]。还有研究确定了胡椒碱对Hep G2细胞具有剂量和时间依赖性细胞毒性,进一步研究表明胡椒碱的促氧化特性,通过抑制过氧化物解毒酶过氧化氢酶,驱动线粒体介导的 Hep G2细胞凋亡,同时胡椒碱还可抑制酪氨酸激酶受体并减轻肝细胞癌的进展[31]

      墙草碱是从胡椒中分离出的另一种具有抗癌活性的生物活性化合物,对乳腺(MCF-7)和人早幼粒细胞白血病(HL60)细胞有细胞毒作用,其IC50值分别为1.8和13 μg/ml[32]。另外,Sriwiriyajan等人发现荜茇明宁碱也具有强大的抗癌活性,他们利用流式细胞仪检测细胞周期和凋亡,发现荜茇明宁碱能诱导细胞G2/M期停滞和发生凋亡,且诱导的细胞凋亡只和外源性途径有关[13]

    • 胡椒碱可以以剂量依赖的方式抑制肝损伤小鼠肝细胞的凋亡。根据Matsuda等人的研究表明,胡椒碱保肝作用可能取决于肝细胞对肿瘤坏死因子(TNF-α)的敏感性降低[33]。Sabina等人进行的另一项动物研究声称,胡椒碱通过增加抗氧化剂来减轻对乙酰氨基酚诱导的小鼠肝毒性肿瘤坏死因子(TNF-α)的表达和肝脏标志物酶活性的抑制,包括天冬氨酸转氨酶(AST)、丙氨酸转氨酶(ALT)和碱性磷酸酶(ALP)[34]。Choi等人发现胡椒碱可以通过激活脂联素-腺苷5′-单磷酸活化蛋白激酶(AMPK)信号途径来减少高脂饮食(HFD)喂养小鼠的肝脂质积累[35]。Morsy等人发现胡椒碱可通过增强肝转化生长因子-β 受体相关结合蛋白1(TGFBRAP1)的表达,改善小鼠对乙酰氨基酚导致的肝损伤[36]

    • 胡椒碱还能对降血糖有作用。Samra等人研究发现胡椒碱能够显著降低大鼠糖尿病模型中肾脏的TXNIP和NLRP3表达,而大鼠糖尿病模型中肾脏的TXNIP和NLRP3表达是显著增加的。同时高血糖会诱导NF-κB激活,导致IL-1β和TNF-α水平升高。而胡椒碱在大鼠糖尿病模型中展示出NF-κB的显著抑制以及IL-1β和TNF-α水平的降低。此外,大鼠糖尿病模型中的肌酐清除率显著降低,血糖、血清肌酐、血尿素氮、丙二醛、蛋白尿和肾脏重量与体重比增加,而胡椒碱对上述指标均有改善作用[37]

    • 胡椒碱对高血压有改善作用。在Booranasubkajorn等人的研究中,用胡椒碱治疗自发性高血压大鼠28 d。结果表明,胡椒碱的补充部分恢复了内皮介导的主动脉血管舒张,并降低了N(G)硝基-L-精氨酸甲酯(L-NAME)给药引起的血压升高,表明胡椒碱对高血压和一氧化氮受损大鼠的血管保护作用[38]。Chaudhary等人发现胡椒碱能抑制血管紧张素转换酶的活性,清除2,2-二苯基-1-苦参酰肼(DPPH)自由基,表明胡椒碱作为降压药的潜力[39, 40]

    • ① 抗抑郁与抗焦虑

      胡椒中有多种生物碱对抑郁和焦虑有缓解作用。Mao等人研究发现胡椒中的胡椒林碱和胡椒亭碱可以增加小鼠神经瘤母细胞Neuro-2a中脑源性神经营养因子(BDNF)的表达,并且胡椒林碱能促进维甲酸诱导的神经突生长,表明其对BDNF表达失调导致的抑郁症具有一定的治疗作用[41]。Hritcu等人研究发现,胡椒碱通过减轻大鼠杏仁核氧化应激,改善β-淀粉样蛋白(1-42)诱导的焦虑和抑郁[42]。Khom等人研究发现,胡椒碱的抗焦虑作用与成年小鼠大脑中GABA水平的增加有关[43]

      ② 抗惊厥与抗癫痫

      胡椒碱治疗能够降低大鼠诱发癫痫后的癫痫持续状态,并预防记忆障碍。Mao等人研究发现胡椒碱的抗惊厥作用降低了毛果芸香碱诱导的大鼠癫痫后的炎症和氧化应激。在匹罗卡品诱导的癫痫大鼠中,经胡椒碱治疗后,半胱天冬酶-3的上调活性和Bax/Bcl-2的表达水平受到抑制[44]

      ③ 神经保护作用

      胡椒碱可以显著改善氯化铝诱导的阿尔茨海默症所导致的学习和记忆缺陷,这与抑制胆碱酯酶活性有关[45]。Chonpathompikunlert等人研究了阿尔茨海默症模型中口服胡椒碱后的记忆性能和神经退行性变,研究发现,在不同实验剂量下,胡椒碱均能改善认知功能,减少神经退化,这可能是与脂质过氧化和乙酰胆碱酯酶的降低有关[46]。胡椒碱能显著减少岗田酸诱导磷酸化Tau(p-Tau)过度表达的PC12痴呆细胞模型中的p-Tau水平,减少细胞外乳酸脱氢酶(LDH)的水平,缓解细胞损伤[47]

    • ① 抗菌

      胡椒提取物可以抑制细菌生长。邹兰等人对胡椒的不同溶剂萃取物进行了抑菌机制研究,结果表明采用胡椒提取物的石油醚萃取部位处理大肠埃希氏菌和金黄色葡萄球菌、乙酸乙酯萃取部位处理枯草芽孢杆菌后,胞外丙酮酸含量增高,转氨酶活性显著增强,推测其可能通过影响菌株的正常生理代谢过程中能量供给和关键物质的合成导致菌体衰亡,从而抑制细菌生长[48, 49]

      ② 抗寄生

      胡椒碱在抗寄生虫方面也有不错的效果。胡椒碱的抗寄生虫活性取决于它产生一氧化氮的能力,从而产生各种作用,如免疫调节效应和细胞周期检测(克氏锥虫的表向散光形式),并在生化和细胞内水平影响寄生虫的线粒体[50]。Chouhan等人在针对利什曼病的研究中,发现了胡椒碱可以增加Th1细胞因子(INF-γ、TNF-α和IL-2)的分泌,降低IL-4和IL-10,并增加了IgG2a的产生和共刺激分子CD80和CD86的表达,同时胡椒碱还能增加脾脏CD4+、CD8+T细胞的数量,这些发现均体现出胡椒碱对利什曼病有治疗效果[51]

      ③ 抗虫

      胡椒碱是一种潜在的杀虫剂和杀幼虫剂,因其具有神经毒素作用,使昆虫瘫痪。胡椒碱作为杀虫剂的优点是对哺乳动物毒性低、在环境中不持久、且在阳光下可迅速降解。 Samuel等人研究了胡椒碱对几个抗性和敏感品系的阿拉伯按蚊幼虫的杀灭效果,通过比较胡椒碱在对幼虫使用后24 h和48 h两个阶段的死亡率,发现胡椒碱对不同品系的幼虫均有明显毒性,说明胡椒碱具有作为杀幼虫剂的潜力[52]

    • 胡椒碱具有止泻和解痉活性。Taqvi等人研究了胡椒碱的抗痉挛和止泻作用机制。其作用机制是通过高钾(80 mmol)引起的持续收缩而阻断钙通道,而胡椒碱对这种收缩有抑制作用,研究发现当胡椒碱浓度为80.86 μmol时有钙通道阻断作用[53]

    • 众所周知,胡椒碱可以影响药物和营养素的生物利用度,增加其肠道吸收,调节其代谢和转运,是一种生物增强剂[54]。胡椒碱的生物增强作用主要有三个机制。首先胡椒碱增加肠血管的血供;其次增强药物通过肠道屏障的主动转运;最后胡椒碱能够抑制药物转运体和药物代谢酶,从而可能影响作为这些酶底物的药物的血药浓度[32]

    • 关于胡椒挥发性精油的生物活性研究相对生物碱较少。有研究表明其可以抑制96%微小牛蜱的产卵,并显示出剂量依赖性,从而推测其能降低微小牛蜱的繁殖力[4]。研究表明经胡椒精油也具有一定的抗菌作用,经胡椒精油处理后的细菌,其转氨酶均发生泄漏,胞外的ALT和AST活性增强,细菌内的丙酮酸也出现不同程度的积累。这表明细菌的细胞壁和细胞膜被胡椒精油破坏,致使胞内物质外泄,同时由于丙酮酸代谢受阻,影响了菌体内多肽和蛋白质的合成,使细菌的能量代谢和物质代谢受到影响,致使细菌死亡。

    • 胡椒中酚类化合物3,4-二羟基苯基乙醇糖苷、3,4-二羟-6-(N-乙基氨基)苯甲酰胺和酚酸糖苷的EC50值分别为0.076、0.27和0.12 mg/ml,EC50值是将初始DPPH浓度降低50%所需的抗氧化剂的浓度,这表明这些酚类化合物具有较高的自由基清除活性[55]。另外其也能作为生物利用度增强剂[32]

    • 胡椒不仅是一种调味品,也是一种作用广泛的药材。胡椒含有丰富的酰胺类生物碱,其中含量最多的是胡椒碱,这也是胡椒中最重要的生物活性物质之一。胡椒中的生物活性物质还有以胡椒精油为主的挥发性成分以及酚类化合物。这些物质给胡椒带来了许多生物活性,例如:抗氧化、抗炎、保肝、降血糖、降血压、抗菌等作用。胡椒作为药食同源的传统中药,具有应用历史悠久和安全性好的特点,是开发药物和功能食品很好的潜在资源。为了更好的促进我国胡椒产业的发展,需要进一步加强胡椒的深入研究,阐明其发挥功效的物质基础及作用机制,为合理开发和利用胡椒资源提供科学依据。该研究也能为提高中药资源的综合利用价值,延伸资源经济产业链,促进中药资源优势转化为经济优势和生态优势提供引导和借鉴。

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