题名

Anticancer Principles from Medicinal Piper (胡椒 Hú Jiāo) Plants

DOI

10.4103/2225-4110.124811

作者

Yue-Hu Wang;Susan L. Morris-Natschke;Jun Yang;Hong-Mei Niu;Chun-Lin Long;Kuo-Hsiung Lee

关键词

Amide alkaloids ; Anticancer ; Cytotoxicity ; Piper ; Piperaceae

期刊名称

Journal of Traditional and Complementary Medicine

卷期/出版年月

4卷1期(2014 / 01 / 01)

页次

8 - 16

内容语文

英文

中文摘要

The ethnomedical uses of Piper (胡椒 Hú Jiāo) plants as anticancer agents, in vitro cytotoxic activity of both extracts and compounds from Piper plants, and in vivo antitumor activity and mechanism of action of selected compounds are reviewed in the present paper. The genus Piper (Piperaceae) contains approximately 2000 species, of which 10 species have been used in traditional medicines to treat cancer or cancer-like symptoms. Studies have shown that 35 extracts from 24 Piper species and 32 compounds from Piper plants possess cytotoxic activity. Amide alkaloids account for 53% of the major active principles. Among them, piplartine (piperlongumine) shows the most promise, being toxic to dozens of cancer cell lines and having excellent in vivo activity. It is worthwhile to conduct further anticancer studies both in vitro and in vivo on Piper plants and their active principles.

主题分类 醫藥衛生 > 中醫藥學
参考文献
  1. Adams, DJ,Boskovic, ZV,Theriault, JR,Wang, AJ,Stern, AM,Wagner, BK(2013).Discovery of small‑molecule enhancers of reactive oxygen species that are nontoxic or cause genotype‑selective cell death.ACS Chem Biol,8,923-929.
  2. Adams, DJ,Dai, MJ,Pellegrino, G,Wagner, BK,Stern, AM,Shamji, AF(2012).Synthesis, cellular evaluation, and mechanism of action of piperlongumine analogs.Proc Natl Acad Sci USA,109,15115-15120.
  3. Alonso‑Castro, AJ,Villarreal, ML,Salazar‑Olivo, LA,Gomez‑Sanchez, M,Dominguez, F,Garcia‑Carranca, A(2011).Mexican medicinal plants used for cancer treatment: Pharmacological, phytochemical and ethnobotanical studies.J Ethnopharmacol,133,945-972.
  4. An, J,Gao, Y,Wang, J,Zhu, Q,Ma, Y,Wu, J(2012).Flavokawain B induces apoptosis of non‑small cell lung cancer H460 cells via Bax‑initiated mitochondrial and JNK pathway.Biotechnol Lett,34,1781-1788.
  5. Bezerra, DP,Militão, GC,De Castro, FO,Pessoa, C,de Moraes, MO,Silveira, ER(2007).Piplartine induces inhibition of leukemia cell proliferation triggering both apoptosis and necrosis pathways.Toxicol In Vitro,21,1-8.
  6. Bezerra, DP,Pessoa, C,de Moraes, MO,Saker‑Neto, N,Silveira, ER,Costa‑Lotufo, LV(2013).Overview of the therapeutic potential of piplartine (piperlongumine).Eur J Pharm Sci,48,453-463.
  7. Bezerra, DP,Pessoa, C,de Moraes, MO,Silveira, ER,Lima, MS,Elmiro, FM(2005).Antiproliferative effects of two amides, piperine and piplartine, from Piper species.Z Naturforsch C,60,539-543.
  8. Bhardwaj, RK,Glaeser, H,Becquemont, L,Klotz, U,Gupta, SK,Fromm, MF(2002).Piperine, a major constituent of black pepper, inhibits human P‑glycoprotein and CYP3A4.J Pharmacol Exp Ther,302,645-650.
  9. Bi, Y,Liu, JH,Luo, R,Wang, QS,Wu, X(2012).Simultaneous determination of piperine and piperlongumine in Piper longum by HPLC.Chin J Exper Tradit Med Formulae,18,47-50.
  10. Bourdy, G,DeWalt, SJ,de Michel, LR,Roca, A,Deharo, E,Munoz, V(2000).Medicinal plants uses of the Tacana, an Amazonian Bolivian ethnic group.J Ethnopharmacol,70,87-109.
  11. Calderón, ÁI,Vázquez, Y,Solís, PN,Caballero‑George, C,Zacchino, S,Gimenez, A(2006).Screening of Latin American plants for cytotoxic activity.Pharm Biol,44,130-140.
  12. Chaveerach, A,Mokkamul, P,Sudmoon, R,Tanee, T(2006).Ethnobotany of the genus Piper(Piperaceae) in Thailand.Ethnobot Res Appl,4,223-231.
  13. Chavez, P,Sanchez, I,González, F,Rodríguez, J,Axelrod, F(1997).Cytotoxicity correlations of Puerto Rican plants using a simplified brine shrimp lethality screening procedure.Pharm Biol,35,222-226.
  14. Chen, GG,Lai, PB(2012).Novel apoptotic regulators in carcinogenesis.Berlin:Springer.
  15. Chen, JJ,Duh, CY,Huang, HY,Chen, IS(2003).Cytotoxic constituents of Piper sintenense.HeIv Chim Acta,86,2058-2064.
  16. Chen, JJ,Huang, YC,Chen, YC,Huang, YT,Want, SW,Peng, CY(2002).Cytotoxic amides from Piper sintenense.Planta Med,68,980-985.
  17. Chen, TC(2008).Observation of the medicine made by oneself in treating with 97 cases with gastric diseases.J Pract Med Technol,15,593-594.
  18. Daoudi, A,El Youbl, AE,Bagrel, D,Aarab, L(2013).In vitro anticancer activity of some plants used in Moroccan traditional medicine.J Med Plants Res,7,1182-1189.
  19. Desai, SJ,Prabhu, BR,Mulchandani, NB(1988).Aristolactams and 4,5‑dioxoaporphines from Piper longum.Phytochemistry,27,1511-1515.
  20. Dharmaratne, RW,Nanayakkara, NP,Khan, IA(2002).Kavalactones from Piper methysticum, and their 13C NMR spectroscopic analyses.Phytochemistry,59,429-433.
  21. Diaz, LE,Munoz, DR,Prieto, RE,Cuervo, SA,Gonzalez, DL,Guzman, JD(2012).Antioxidant, antitubercular and cytotoxic activities of Piper imperiale.Molecules,17,4142-4157.
  22. Do, MT,Kim, HG,Choi, JH,Khanal, T,Park, BH,Tran, TP(2013).Antitumor efficacy of piperine in the treatment of human HER2‑overexpressing breast cancer cells.Food Chem,141,2591-2599.
  23. Duh, CY,Wu, YC,Wang, SK(1990).Cytotoxic pyridone alkaloids from Piper aborescens.Phytochemistry,29,2689-2691.
  24. Duh, CY,Wu, YC,Wang, SK(1990).Cytotoxic pyridone alkaloids from the leaves of Piper aborescens.J Nat Prod,53,1575-1577.
  25. Editorial Board of ‘Zhong Hua Ben Cao’,State Administration of Traditional Chinese Medicine of the People’s Republic of China(1999).Zhong Hua Ben Cao.Shanghai:Shanghai Scientific and Technical Publishers.
  26. Ee, GC,Lim, CM,Lim, CK,Rahmani, M,Shaari, K,Bong, CF(2009).Alkaloids from Piper sarmentosum and Piper nigrum.Nat Prod Res,23,1416-1423.
  27. Ee, GCL,Lim, CM,Rahmani, M,Shaari, K,Bong, CF(2010).Pellitorine, a potential anti‑cancer lead compound against HL60 and MCF‑7 cell lines and microbial transformation of piperine from Piper Nigrum.Molecules,15,2398-2404.
  28. Elban, MA,Chapuis, JC,Li, M,Hecht, SM(2007).Synthesis and biological evaluation of cepharadiones A and B and related dioxoaporphines.Bioorg Med Chem,15,6119-6125.
  29. Eskander, RN,Randall, LM,Sakai, T,Guo, Y,Hoang, B,Zi, X(2012).Flavokawain B, a novel, naturally occurring chalcone, exhibits robust apoptotic effects and induces G2/M arrest of a uterine leiomyosarcoma cell line.J Orthop Res,38,1086-1094.
  30. Golovine, KV,Makhov, PB,Teper, E,Kutikov, A,Canter, D,Uzzo, RG,Kolenko, VM(2013).Piperlongumine induces rapid depletion of the androgen receptor in human prostate cancer cells.The Prostate,73,23-30.
  31. Han, SS,Son, DJ,Yun, H,Kamberos, NL,Janz, S(2013).Piperlongumine inhibits proliferation and survival of Burkitt lymphoma in vitro.Leukemia Res,37,146-154.
  32. Han, SS,Tompkins, VS,Son, DJ,Kamberos, NL,Stunz, LL,Halwani, A(2013).Piperlongumine inhibits LMP1/MYC‑dependent mouse B‑lymphoma cells.Biochem Biophys Res Commun,436,660-665.
  33. Holdsworth, D.(1991).Traditional medicinal plants of Rarotonga, Cook Islands. Part II.Pharm Biol,29,71-79.
  34. Holdsworth, D,Kerenga, K(1987).A survey of medicinal plants in the Simbu Province, Papua New Guinea.Pharm Biol,25,183-187.
  35. Hwang, YP,Yun, HJ,Kim, HG,Han, EH,Choi, JH,Chung, YC(2011).Suppression of phorbol‑12‑myristate‑13‑acetate‑induced tumor cell invasion by piperine via the inhibition of PKC alpha/ERK1/2‑dependent matrix metalloproteinase‑9 expression.Toxicol Lett,203,9-19.
  36. Jarvius, M,Fryknas, M,D’Arcy, P,Sun, C,Rickardson, L,Gullbo, J(2013).Piperlongumine induces inhibition of the ubiquitin‑proteasome system in cancer cells.Biochem Biophys Res Commun,431,117-123.
  37. Ji, T,Lin, C,Krill, LS,Eskander, R,Guo, Y,Zi, XL(2013).Flavokawain B, a kava chalcone, inhibits growth of human osteosarcoma cells through G2/M cell cycle arrest and apoptosis.Mol Cancer,12,55.
  38. Kato, MJ,Furlan, M(2007).Chemistry and evolution of the Piperaceae.Pure Appl Chem,79,529-538.
  39. Kim, KH,Choi, JW,Choi, SU,Ha, SK,Kim, SY,Park, HJ(2011).The chemical constituents of Piper kadsura and their cytotoxic and anti‑neuroinflammtaory activities.J Enzyme Inhib Med Chem,26,254-260.
  40. Kreuter, MH,Yam, J,Berger‑Büter, K(2009).Kreuter MH, Yam J, Berger‑Büter K. The use of extracts or materials extracted from Piper cubeba L. as an effective component in a drug for the treatment of cancer diseases. WO Patent: 2009021347, 2009..
  41. Kuete, V,Krusche, B,Youns, M,Voukeng, I,Fankam, AG,Tankeo, S(2011).Cytotoxicity of some Cameroonian spices and selected medicinal plant extracts.J Ethnopharmacol,134,803-812.
  42. Kuete, V,Sandjo, LP,Wiench, B,Efferth, T(2013).Cytotoxicity and modes of action of four Cameroonian dietary spices ethno‑medically used to treat cancers: Echinops giganteus, Xylopia aethiopica, Imperata cylindrica and Piper capense.J Ethnopharmacol,149,245-253.
  43. Li, S,Lei, Y,Jia, Y,Li, N,Wink, M,Ma, Y(2011).Piperine, a piperidine alkaloid from Piper nigrum re‑sensitizes P‑gp, MRP1 and BCRP dependent multidrug resistant cancer cells.Phytomedicine,19,83-87.
  44. Li, SM,Long, CL,Liu, FY,Lee, S,Guo, Q,Li, R(2006).Herbs for medicinal baths among the traditional Yao communities of China.J Ethnopharmacol,108,59-67.
  45. Li, X,Liu, Z,Xu, X,Blair, CA,Sun, Z,Xie, J(2012).Kava components down‑regulate expression of AR and AR splice variants and reduce growth in patient‑derived prostate cancer xenografts in mice.PloS One,7,e31213.
  46. Lin, E,Lin, WH,Wang, SY,Chen, CS,Liao, JW,Chang, HW(2012).Flavokawain B inhibits growth of human squamous carcinoma cells: Involvement of apoptosis and cell cycle dysregulation in vitro and in vivo.J Nutr Biochem,23,368-378.
  47. Liu, HX,Chen, K,Sun, QY,Yang, FM,Hu, GW,Wang, YH(2013).Nudibaccatumone, a trimer comprising a phenylpropanoid and two sesquiterpene moieties from Piper nudibaccatum.J Nat Prod,76,732-736.
  48. Liu, JM,Pan, F,Li, L,Liu, QR,Chen, Y,Xiong, XX(2013).Piperlongumine selectively kills glioblastoma multiforme cells via reactive oxygen species accumulation dependent JNK and p38 activation.Biochem Biophys Res Commun,437,87-93.
  49. Long, CL,Li, R(2004).Ethnobotanical studies on medicinal plants used by the Red‑headed Yao People in Jinping, Yunnan Province, China.J Ethnopharmacol,90,389-395.
  50. Lopes, AP,Bagatela, BS,Rosa, PC,Nanayakkara, DN,Tavares Carvalho, JC,Maistro, EL(2013).Antioxidant and cytotoxic effects of cude extract, fractions and 4‑nerolidylcathecol from aerial parts of Pothomorphe umbellata L. (Piperaceae).Biomed Res Int,2013,206581.
  51. Ma, J,Jones, SH,Marshall, R,Johnson, RK,Hecht, SM(2004).A DNA‑damaging oxoaporphine alkaloid from Piper caninum.J Nat Prod,67,1162-1164.
  52. Mahanta, P,Ghanim, A,Gopinath, K(1974).Chemical constituents of Piper sylvaticum (Roxb) and Piper boehmerifolium (Wall).J Pharm Sci,63,1160-1161.
  53. Mahavorasirikul, W,Viyanant, V,Chaijaroenkul, W,Itharat, A,Na‑Bangchang, K(2010).Cytotoxic activity of Thai medicinal plants against human cholangiocarcinoma, laryngeal and hepatocarcinoma cells in vitro.BMC Complement Altern Med,10,55.
  54. Mongelli, E,RomanoA,Desmarchelier, C,Coussio, J,Ciccia, G(1999).Cytotoxic 4‑nerolidylcatechol from Pothomorphe peltata inhibits topoisomerase I activity.Planta Med,65,376-378.
  55. Newman, DJ,Cragg, GM(2012).Natural products as sources of new drugs over the 30 years from 1981 to 2010.J Nat Prod,75,311-335.
  56. Orjala, J,Mian, P,Rali, T,Sticher, O.(1998).Gibbilimbols A‑D, cytotoxic and antibacterial alkenylphenols from Piper gibbilimbum.J Nat Prod,61,939-941.
  57. Orjala, J,Wright, AD,Behrends, H,Folkers, G,Sticher, O,Rüegger, H(1994).Cytotoxic and antibacterial dihydrochalcones from Piper aduncum.J Nat Prod,57,18-26.
  58. Ouyang, DY,Zeng, LH,Pan, H,Xu, LH,Wang, Y,Liu, KP(2013).Piperine inhibits the proliferation of human prostate cancer cells via induction of cell cycle arrest and autophagy.Food Chem Toxicol,60,424-430.
  59. Parmar, VS,Jain, SC,Bisht, KS,Jain, R,Taneja, P,Jha, A(1997).Phytochemistry of the genus Piper.Phytochemistry,46,597-673.
  60. Pedersen, ME,Metzler, B,Stafford, GI,Van Staden, J,Jäger, AK,Rasmussen, HB(2009).Amides from Piper capense with CNS activity: A preliminary SAR analysis.Molecules,14,3833-3842.
  61. Peng, CZ,Qi, JJ,Li, XE(2010).Medicinal plants traditionally used by Hani people in Yuanyang, Yunnan, China.Lishizhen Med Mater Med Res,21,428-431.
  62. Raj, L,Ide, T,Gurkar, AU,Foley, M,Schenone, M,Li, XY(2011).Selective killing of cancer cells by a small molecule targeting the stress response to ROS.Nature,475,231-234.
  63. Randhawa, H,Kibble, K,Zeng, H,Moyer, M,Reindl, K(2013).Activation of ERK signaling and induction of colon cancer cell death by piperlongumine.Toxicol in Vitro,17,1626-1633.
  64. Rao, VR,Suresh, G,Babu, KS,Raju, SS,Vishnu vardhan, MV,Ramakrishna, S(2011).Novel dimeric amide alkaloids from Piper chaba Hunter: Isolation, cytotoxic activity, and their biomimetic synthesis.Tetrahedron,67,1885-1892.
  65. Roy, UB,Vijayalaxmi, KK(2013).Evaluation of in vitro antitumor property of ethanolic extract of Piper Nigrum seeds.Int J Innov Res Stud,2,282-302.
  66. Sakai, T,Eskander, RN,Guo, Y,Kim, KJ,Mefford, J,Hopkins, J(2012).Flavokawain B, a kava chalcone, induces apoptosis in synovial sarcoma cell lines.J Orthop Res,30,1045-1050.
  67. Scott, IM,Jensen, HR,Philogene, BJ,Arnason, JT(2008).A review of Piper spp. (Piperaceae) phytochemistry, insecticidal activity and mode of action.Phytochem Rev,7,65-75.
  68. Soladoye, MO,Amusa, N,Raji‑Esan, S,Chukwuma, E,Taiwo, A(2010).Ethnobotanical survey of anti‑cancer plants in Ogun State, Nigeria.Ann Biol Res,1,261-273.
  69. Steiner, G(2000).The correlation between cancer incidence and kava consumption.Hawaii Med J,59,420-422.
  70. Tabudravu, JN,Jaspars, M(2005).Anticancer activities of constituents of kava (Piper methysticum).S Pac J Nat Appl Sci,23,26-29.
  71. Tang, GH,Chen, DM,Qiu, BY,Sheng, L,Wang, YH,Hu, GW(2011).Cytotoxic amide alkaloids from Piper boehmeriaefolium.J Nat Prod,74,45-49.
  72. Tang, YX,Li, XB,Liu, ZB,Simoneau, AR,Xie, J,Zi, XL(2010).Flavokawain B, a kava chalcone, induces apoptosis via up‑regulation of death‑receptor 5 and Bim expression in androgen receptor negative, hormonal refractory prostate cancer cell lines and reduces tumor growth.Int J Cancer,127,1758-1768.
  73. Taylor, P,Arsenak, M,Abad, MJ,Fernandez, A,Milano, B,Gonto, R(2013).Screening of Venezuelan medicinal plant extracts for cytostatic and cytotoxic activity against tumor cell lines.Phytother Res,27,530-539.
  74. Tseng, YC,Xia, NH,Gilbert, MG(1999).Flora of China.Beijing:Science Press.
  75. Umadevi, P,Deepti, K,Venugopal, DV(2013).Synthesis, anticancer and antibacterial activities of piperine analogs.Med Chem Res,22,5466-5471.
  76. Usia, T,Watabe, T,Kadota, S,Tezuka, Y(2005).Potent CYP3A4 inhibitory constituents of Piper cubeba.J Nat Prod,68,64-68.
  77. Valadares, MC,de Carvalho, IC,de Oliveira Junior, L,Vieira Mde, S,Benfica, PL,de Carvalho, FS(2009).Cytotoxicity and antiangiogenic activity of grandisin.J Pharm Pharmacol,61,1709-1714.
  78. Wang, Y,Wang, J,Xiao, X,Shan, Y,Xue, B,Jiang, G(2013).Piperlongumine induces autophagy by targeting p38 signaling.Cell Death Dis,4,e824.
  79. Widowati, W,Wijaya, L,Wargasetia, TL,Bachtiar, I,Yelliantty, Y,Laksmitawati, DR(2013).Antioxidant, anticancer, and apoptosis‑inducing effects of Piper extracts in HeLa cells.J Exp Integr Med,3,225-230.
  80. Xin, YW,Qi, WD,Han, CY.(2009).Xin YW, Qi WD, Han CY. Traditional Chinese medicine for treating respiratory cancer. CN Patent: 101455834 A, 2009..
  81. Yaffe, PB,Doucette, CD,Walsh, M,Hoskin, DW(2013).Piperine impairs cell cycle progression and causes reactive oxygen species‑dependent apoptosis in rectal cancer cells.Exp Mol Pathol,94,109-114.
  82. Yam, J,Kreuter, M,Drewe, J(2008).Piper cubeba targets multiple aspects of the androgen‑signalling pathway. A potential phytotherapy against prostate cancer growth?.Planta Med,74,33-38.
  83. Yang, J,Su, Y,Luo, JF,Gu, W,Niu, HM,Li, Y(2013).New amide alkaloids from Piper longum fruits.Nat Prod Bioprospect,3,277-281.
  84. Yang, SX,Sun, QY,Yang, FM,Hu, GW,Luo, JF,Wang, YH(2013).Sarmentosumols A to F, new mono‑and dimeric alkenylphenols from Piper sarmentosum.Planta Med,79,693-696.
  85. Zainal Ariffin, SH,Wan Omar, WH,Zainal Ariffin, Z,Safian, MF,Senafi, S,Megat Abdul Wahab, R(2009).Intrinsic anticarcinogenic effects of Piper sarmentosum ethanolic extract on a human hepatoma cell line.Cancer Cell Int,9,6.
  86. Zheng, XL,Xing, FW(2009).Ethnobotanical study on medicinal plants around Mt.Yinggeling, Hainan Island, China.J Ethnopharmacol,124,197-210.
被引用次数
  1. Vikas Kumar,Vaishali Yadav,Shyam Sunder Chatterjee,Muhammed Majeed(2016).Preventive potentials of piperlongumine and a Piper longum extract against stress responses and pain.Journal of Traditional and Complementary Medicine,6(4),413-423.