Research Progress in Chemical Components and Pharmacological Effectiveness of Piper hancei Maxim
Lei Haipeng1*, Zhou Bin2 and Chen Xianqiang3
1Department of Biology and Chemistry, City University of Hong Kong, Kowloon, Hong Kong, People's Republic of China
2School of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang, PR China
3State Key Laboratory of Quality Research in Chinese Medicine and Institute of Chinese Medical Sciences, University of Macau, PR China
- *Corresponding Author:
- Lei Haipeng
Department of Biology and Chemistry, City University of Hong Kong
Kowloon, Hong Kong, People's Republic of China
Tel: 34424490
E-mail: haipelei@cityu.edu.hk
Received date: 10/08/2015; Accepted date: 28/08/2015; Published date: 01/09/2015
Visit for more related articles at Research & Reviews: Journal of Chemistry
Abstract
Objective: To compile the various research reporting active chemical components of Piper hancei Maxim, as well as their pharmacological effects. Results: Up to now, the chemical components isolated from Piper hancei include mainly alkaloids, lignans etc. Pharmacological references show that it has antiplatelet activities, anti-inflammation, antimicrobial, antioxidation, antitumor and insecticidal activity. Conclusion: To lay the basis of literature and inspired ideas on Piper hancei.
Keywords
Piper hancei maxim, Chemical constituents, Pharmacological
Introduction
We live in an age where human health problems are changing dramatically. Modern medicine has greatly enhanced life expectancy and offered a cure for most of the deadliest communicable disease. Yet, because of the ageing population and increasingly unhealthy lifestyles, new crises are surfacing. Cardiovascular disorders, hypertension, cancers and diabetes appear today in unprecedented and alarming proportions. With the failure of classic medicinal methods to cure some of these new leading killer diseases, medicinal plants and natural products offer an alternative not to be overlooked.
Plants are already vital components of human diet, but are now becoming essential medicinal elements throughout the word as well. They represents the only medicinal alternative for many living in under-developed countries and although access to the modern medicine is not a problem in developed countries, an important proportion of the population also makes use of medicinal plants for historical and cultural reasons [1]. For these reasons, plants represent an important economic market whose growing popularity has naturally attracted the attention of scientist since decades [2].
With more than 1000 species represented in the Piperaceae family, a genus Piper is present in traditional medicine all over the world. Behind the notorious pepper spice lies a plant whose various biological effects have been reported to include antitumor, anticancer, anti-platelet aggregation, hepatotoxicity, hepatoprotective effects, anti-obesity, immune-enhancing and anti-inflammatory [3]. In the last few decades, several studies have been carried out in order to identify the biological actives compounds of these medicinal plants.
Of particular interest is Piper hanceiMaxim., a piper species whose plants grow in forests, mostly by climbing on trees or rocks. It is distributed throughout Zhejiang, Fujian, Hubei, Guangdong, Guangxi, Yunnan province in china. The plant is currently used to treat several illnesses including rheumatism, wind-cold, cough as well as more serious pathology such as influenza and dysmenorrhea [4].
The purpose of this review is to provide comprehensive information about the phytochemistry and the pharmacological effects of Piper hancei Maxim. A list of the 35 active compounds that have been found in Piper hancei are listed here, along with some of their most relevant biological activities, are listed here. These activities includes, not extensively, anti-platelet [5], antiinflammatory [6,7], antibacterial [8], antioxidant [9,10], anticancer [11], cytotoxic effects [12,13].
Although these discoveries represent only the tip of the iceberg as to what has been gathered on Piper hancei, it compiles the most significant insights on the potential of the plant for medicinal applications. This review intends to provide an important resource for investigators planning future studies on this extraordinary plant
Phytochemical of Piper hancei.
The chemical constituents of Piper hancei can be separated in three groups. The most prominent group of active species family regroups the alkaloids/amides molecules. A second group contains the lignans and neolignans compounds. The third group is a miscellaneous gathering of other actives molecules. These constituents of Piper hancei plant are summarized in Tables 1, 2 and 3, and their chemical structures are shown in Figures 1, 2 and 3.
Alongside the compounds listed in these tables, Lai et al. used GC-MS to analysis the essential oil from Piper hancei and identified 26 additional compounds from it, mostly terpenes and phenols. These compounds includes α-pinene, 1,8-cineole, linalool and terpinyl acetate whose percentage represent 56.45% of the oil composition [14]. These compounds are however not listed here.
Alkaloids/Amides: Table 1 – Figure 1.
Table 1: Alkaloids/Amides.
Figure 1: Chemical structure of compounds listed in Table 1.
Lignans/Neolignans: Table 2 – Figure 2.
Table 2: Lignans/Neolignans.
Figure 2: Chemical structure of compounds listed in Table 2.
Others: Table 3 – Figure 3.
Figure 3: Chemical structure of compounds listed in Table 3.
Biological Activity
Antiplatelet Activity
Platelet-activating factors (PAF) are phospholipid molecules that are involved in the mediation of inflammation and patelet aggregation [34]. A couple of studies have reported the screening of large library of constituents from Piper hancei for their potential antiplatelet activity [5,35]. Han‘s group reported that Hancinone B, Hancinone C, Kadsurenone, Futoamide were PFA receptor antagonists. The ethanolic extract from Piper hancei was also reported to inhibit both PAF induced rabbit platelet aggregation and PAF induced inflammatory reaction [5,34].
Anti-inflammatory Activity
Lin et al. reported that Piper kadsura Ohwi, which is always substituted for Piper haicen or Piper puberulum (Benth.) in the market, have anti-inflammatory activity [29,44]. Han et al. have found three compounds with anti-inflammatory activity from Piper hancei[10]. Kim evaluated the anti-neuroinflammatory activities by assessing nitric oxide (NO) production in LPS-activated BV-2 cells; a microglia cell line [6,7]. The result showed that Kadsurenone had anti-neuroinflammatory activities.
Antimicrobial Activity
Pellitorin, Veratric acid, β-Sitosterol, Daucosterin and Stigmast-4-ene-3,6-dione which are found in Piper hancei, but Piper cubeba, Piper retrofractum and Piper Sarmentoum, all were found to have antimicrobial activities [8,45]. Pellitorin showed moderate to strong growth inhibition against Listeria monocytogenes, with (Minimum inhibitory concentration, MICs) between 62.5 and 125 μg/mL [46]. In vitro bioassay show that Daucosterin exhibited antibacterial activity [47]. Veratric acid showed the antibacterial activities mainly against gram positive germs [8].
Antioxidant Activity
Crotepoxide, isolated from Piper hancei and the root of Panax notoginseng has been found to exhibit antioxidant activity [10]. Pajak et al. reported that vanillic acid showed antioxidant activity and evaluated using 2,2-azinobis (3-ethyl-benzothiazoline-6- sulfonic acid, (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) assays [9]. Furthermore, Yao’s group studies shown that syringic acid also have antioxidant activity [42,48].
Anticancer Activity
Do’s group reported that piperine not only inhibited proliferation, but also HER2 gene expression at a transcriptional level. It also induces apoptosis through caspase-3 activation and PARP cleavage and was found to efficiently kill breast cancer cells [27]. Pradeep et al. studies showed that piperine have a dose-dependent anticancer activity against B16F-10 melanoma cell and inhibited transcription factors such as ATF-2, c-Fos and CREB [11].
Cytotoxicity
Aristolactam A IIIa, Nigrinodine and Guineensine were found to have cytotoxic activity against human cervical carcinoma HeLa cells, as evaluated by three different cytotoxicity assays [12,13]. Nigrinodine showed cytotoxic activity against CCRF-CEM, HL- 60, PC-3, P-388, HT-29, A549 and HA22T cells [49].
Insecticidal Activity
Pipercide, isolated from Piper hancei, showed toxicity against female adults of Culex pipiens pallens and Aedesaegypti with an LD50 value of 3.2 μg/female and 2.0 μg/female, respectively [50]. Piperovatine showed important antiprotozoal activity against the amastigote and promastigote forms of L. amazonensis [51].
Other Biological Activity
Retrofractamide A and piperine were found to have a hepatoprotective effect on D-galactosamine (d-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. Guineensine was significantly inhibited anti-HBV against with Hep G 2.2.15 cell line in vitro [52]. Chingchengenamide A was shown to have antidepressant activity [32].
Conclusions
Here, an attempt was made to compile relevant information about both the phytochemistry and the pharmacology of the Piper hancei. The review highlight’s the medicinally significant constituents of the plant and provides a useful database for researchers in the field.
References
- Gutierrez RM, Gonzalez AM, Hoyo-Vadillo C. Alkaloids from Piper: a review of its phytochemistry and pharmacology. Mini-Rev Med Chem 2013; 13: 163-193.
- Parmar VS, Jain SC, Bisht KS, Jain R, Taneja P, et al. Phytochemistry of the genus Piper. Phytochemistry 1997; 46: 597-673.
- Rahman MA, Mossa JS, Al-Said MS, Al-Yahya MA. Medicinal plant diversity in the flora of Saudi Arabia 1: a report on seven plant families. Fitoterapia 2004; 75: 149-161.
- State Administration of Traditional Chinese Medicine. Chinese MateriaMedica. Shanghai Science and Technology Press.
- Li Changlin, Ma Jian,Wang Yin, et al. Preliminary study on PFA-antagonists of ethanol extracts from piper hancei. Physiological Science Basic & Clinical Medicine 1987; 5:316-317.
- Kim KH, Choi JW, Choi SU, Ha SK, Kim SY , et al. The chemical constituents of Piper kadsura and their cytotoxic and anti-neuroinflammtory activities. Journal of Enzyme Inhibition and Medicinal Chemistry 2011; 26: 254-260.
- Kim KH, Choi JW, Ha SK, Kim SY, Lee KR. Neolignans from Piper kadsura and their anti-neuroinflammatory activity. Bioorganic & Medicinal Chemistry Letters 2010; 20: 3186-3187.
- Medini F,Ksouri R, Falleh H, Megdiche W, Trabelsi N, et al. Effects of physiological stage and solvent on polyphenol composition, antioxidant and antimicrobial activities of Limoniumdensiflorum. Journal of Medicinal Plants Research 2011; 5: 6719-6730.
- Pajak P, Socha R, Galkowska D, Roznowski J, Fortuna T. Phenolic profile and antioxidant activity in selected seeds and sprouts. Food Chemistry 2014; 143:300-306.
- Han GQ, Wei LH, Li CL, Qiao L, Jia YZ, et al. The isolation and identification of PAF inhibitors from Piper wallichii (Miq.) Hand-Mazz and P. hancei Maxim. Yao XueXueBao 1989; 6:438-443
- Pradeep CR, Kuttan G. Piperine is a potent inhibitor of nuclear factor-kappaB (NF-kappaB), c-Fos, CREB, ATF-2 and proinflammatory cytokine gene expression in B16F-10 melanoma cells. International immunopharmacology 2004; 4: 1795-803.
- Li YZ, Tong AP, Huang J. Two New Norlignans and a New Lignanamide from Peperomiatetraphylla. Chemistry & Biodiversity 2012; 9: 769-776.
- Marques JV, Kitamura RO, Lago JH, Young MC, Guimarães EF, et al. Antifungal Amides from Piper scutifoliumand Piper hoffmanseggianum. Journal of Natural Products 2007; 70: 2036-2039.
- Lai XP, Liu, XC, Chen JN, et al.The chemical constituents of volatile oil from Piper hancei. Journal of Chinese Medicinal Materials 1995; 10: 519-520.
- Zhou Liang, Yang Jun-Shan, TuGuang-Zhang. Study on chemical components of piper hance [J]. Chinese pharmaceutical Journal 2005; 40: 184-185.
- Chen S, Huang HY, Cheng MJ, Ishikawa T, Chang HS, et al. Neolignans and phenylpropanoids from the roots of Piper taiwanense and their antiplatelet and antitubercular activities. Phytochemistry 2013; 93:203-209.
- Chen S, Huang HY, Cheng MJ, Ishikawa T, Chang HS, et al. Neolignans and phenylpropanoids from the roots of Piper taiwanense and their antiplatelet and antitubercular activities. Phytochemistry 2013; 93:203-209.
- Lee W, Yoo H, Kim JA, Lee S, Jee JG, et al. Barrier protective effects of piperlonguminine in LPS-induced inflammation in vitro and in vivo. Food and Chemical Toxicology 2013; 58:149-157.
- Matsuda H, Ninomiya K, Morikawa T, Yasuda D, Yamaguchi I, et al. Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides. Bioorganic & Medicinal Chemistry 2009; 17: 7313-7323.
- Gwendoline CL, Chyi ML, Mawardi R, Khozirah S, Joseph Bong CF. Pellitorine, a potential anti-cancer lead compound against HL60 and MCT-7 cell lines and microbial transformation of piperine from Piper nigrum. Molecules 2010; 15:398-404.
- Rondest J, Das BC, Polonsky J. N-(p-Hydroxyphenethyl)-p-hydroxycinnamamide, a new natural amide isolated fromEvodiabelahe. Bulletin de la SocieteChimique de France 1968; 6: 2411-2414.
- Sarrnaizul E, Borjiihan G, Sun Z. The preparation and antihyperlipidaemic assay of piperlonguminine in vivo. Phytochemistry Letters 2013; 6: 101-105.
- Lee W, Yoo H, Kim JA, Lee S, Jee JG, et al. Barrier protective effects of piperlonguminine in LPS-induced inflammation in vitro and in vivo. Food and Chemical Toxicology 2013; 58:149-157.
- Matsuda H, Ninomiya K, Morikawa T, Yasuda D, Yamaguchi I, et al. Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides. Bioorganic & Medicinal Chemistry 2009; 17: 7313-7323.
- Gwendoline CL, Chyi ML, Mawardi R, Khozirah S, Joseph Bong CF. Pellitorine, a potential anti-cancer lead compound against HL60 and MCT-7 cell lines and microbial transformation of piperine from Piper nigrum. Molecules 2010; 15:398-404.
- Nesterenko V, Putt KS, Hergenrother PJ. Identification from a Combinatorial Library of a Small Molecule that Selectively Induces Apoptosis in Cancer Cells. Journal of the American Chemical Society, 2003; 125: 14672-14673.
- Regasini LO, Cotinguiba F, Morandim ADA, Kato MJ, Scorzoni L, et al. Antimicrobial activity of Piper arboreum and Piper tuberculatum (Piperaceae) against opportunistic yeasts. African Journal of Biotechnology 2009; 8: 2866-2870.
- Tang GH, Chen DM, Qiu BY, Sheng L, Wang YH, et al. Cytotoxic Amide Alkaloids from Piper boehmeriaefolium. Journal of Natural Products 2011; 74: 45-49.
- Matsuda H, Ninomiya K, Morikawa T, Yasuda D, Yamaguchi I, et al. Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-α-induced cell death in mouse hepatocytes. Bioorganic & Medicinal Chemistry Letters 2008; 18: 2038-2042.
- Khom S, Strommer B, Schöffmann A, Hintersteiner J, Baburin I, et al. GABAA receptor modulation by piperine and a non-TRPV1 activating derivative. Biochemical Pharmacology 2013; 85: 1827-1836.
- Do MT, Kim HG, Choi JH, Khanal T, Park BH, et al. Antitumor efficacy of piperine in the treatment of human HER2-overexpressing breast cancer cells. Food Chemistry 2013; 141: 2591-2599.
- Wei K, Li W, Koike K, Pei Y, Chen Y, et al. New amide alkaloids from the roots of Piper nigrum. Journal of Natural Products 2004; 67: 1005-1009.
- Lin LC, Shen CC, Shen YC, Tsai TH. Anti-inflammatory neolignans from Piper kadsura. Journal of Natural Products 2006; 69: 842-844.
- Han GQ. Study on PFA-antagonists from Chinese herb medicinal. China Academic Journal 1995; 2:35-40.
- Zhou L, Yang J, Tu G. Study on chemical components of Piper hancei. ZhongguoYaoxueZazhi 2005; 40: 184-185.
- Wei A, Zhou D, Ruan J, Cai Y, Xiong C, et al. Study on the contents of aristololactams in Piper wallichii and their renal cytotoxicities. Journal of Food and Drug Analysis 2011; 19: 349-354.
- Xie H, Yan MC, Jin D, Liu JJ, Yu M, et al. Studies on antidepressant and antinociceptive effects of ethyl acetate extract from Piper laetispicumand structure-activity relationship of its amide alkaloids. Fitoterapia, 2011; 82: 1086-1092.
- Chauhan R, Ruby KM, Dwivedi J. Secondary metabolites found in Bergenia species: a compendious review. International Journal of Pharmacy and Pharmaceutical Sciences 2013; 5: 9-16.
- Lei HP, Chen XQ, Qiao CF, Liu Y, Zhao J. Chemical Constituents from the Twigs of Piper hancei. Journal of Chinese Medicinal Materials 2014; 37:72-74.
- Singh P, Singh IN, Mondal SC, Singh L, Garg VK. Platelet-activating factor (PAF)-antagonists of natural origin. Fitoterapia 2013; 84:180-201.
- Han GQ, Li SM, Li CL, Springer JP, Hwang SB, et al. Neolignans from Piper hancei Maxim. Yao XueXueBao 1986; 21:361-365.
- Li SM, Han GQ, Arison BH, Chang MN, et al. Studies on the chemical constituents of Piper hancei Maxim (II). Yao XueXueBao 1987; 22: 196-202.
- Mohamad H, Lajis NH, Abas F, Ali AM, Sukari MA, et al. Antioxidative Constituents of Etlingeraelatior. Journal of Natural Products 2005; 68: 285-288.
- Chauhan R, Ruby KM, Dwivedi J. Secondary metabolites found in Bergenia species: a compendious review. International Journal of Pharmacy and Pharmaceutical Sciences 2013; 5: 9-16.
- Hsu CL, Fang SC, Yen GC. Anti-inflammatory effects of phenolic compounds isolated from the flowers of NymphaeamexicanaZucc. Food & Function 2013; 4: 1216-1222.
- Zhang CR, Aldosari SA, Vidyasagar P S, Nair KM, Nair MG, et al. Antioxidant and anti-inflammatory assays confirm bioactive compounds in Ajwa date fruit. Journal of Agricultural and Food Chemistry 2013; 61: 5834-5840.
- Bach SM, Perotti ME, Merep AP, Marcial GE, Grau A, et al. Chemical constituents, anti-inflammatory and antioxidant activities of bark extracts from PrunustucumanensisLillo. Natural Product Research 2013; 27: 916-919.
- Yao Y, Yang X, Tian J, Liu C, Cheng X, et al. Antioxidant and antidiabetic activities of black mung bean (Vignaradiata L.) [J]. Journal of Agricultural and Food Chemistry 2013; 61: 8104-8109.
- Chen JJ, Duh CY, Huang HY, et al.Cytotoxic constituents of Piper sintenensis. Helvetica ChimicaActa 2003; 86: 2058-2064.
- Park IK. Insecticidal activity of isobutylamides derived from Piper nigrum against adult of two mosquito species,Culexpipienspallens and Aedesaegypti. Natural Product Research 2012; 26: 2129-2131.
- Mohamad H, Lajis NH, Abas F, Ali AM, Sukari MA, et al. Antioxidative Constituents of Etlingeraelatior. Journal of Natural Products 2005; 68: 285-288.
- SunS,Yu L, Liu J. Comparison on Pharmacological Effects of Kadsura Pepper (piper kadsura) with That of Its substitutes.Chinese Herbal Medicines 1998; 10: 677-679.