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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。
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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和图1。
表 1 胡椒中酰胺类化合物
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。
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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]。
Research on the chemical compositions and their biological activities of Piper nigrum L.
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摘要: 胡椒是属于胡椒科胡椒属的一种常绿攀援藤本植物,它被称为“香料之王”,既能用于食品也能用于医药。胡椒中主要活性物质有以酰胺类化合物为主的生物碱和胡椒精油,以及酚类化合物。本文对胡椒中的化学成分,尤其是酰胺类生物碱,及其生物活性进行了归纳总结。这些研究表明,胡椒作为药食同源的一种植物,具有广泛生物活性,值得进一步研究和深度利用。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.
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Key words:
- Piper nigrum L. /
- chemical composition /
- biological activity /
- alkaloids /
- amide compounds /
- piperine
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表 1 胡椒中酰胺类化合物
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] -
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