Molnár Péter, Kawase Masami, Satoh Kazue, Sohara Yoshitaka, Tanaka Toru, Tani Satoru, Sakagami Hiroshi, Nakashima Hideki, Motohashi Noboru, Gyémánt Nóra, Molnár Joseph
Department of Biochemistry and Medical Chemistry, University of Pécs Medical School, Pécs, H-7601 Hungary.
Phytother Res. 2005 Aug;19(8):700-7. doi: 10.1002/ptr.1735.
Carotenoid fractions were extracted from red paprika, Valencia orange peel and the peel of Golden delicious apple. Thus, hypophasic carotenoids of paprika (PM1), orange (PM3) and apple (PM4), and epiphasic extractions of paprika (PM2) and apple (PM5) were obtained by extraction, saponification and partition between MeOH-H(2)O (9:1) (hypophasic) and hexane (epiphasic). A high content of capsanthin was quantified in hypophasic carotenoids (PM1) from red spice paprika, whereas the hypophasic fractions from orange (PM3) and apple (PM4) were mainly composed of violaxanthin, zeaxanthin and lutein. On the other hand, a high content of beta,beta-carotene and beta-cryptoxanthin was found in epiphasic fractions (PM2 and PM5). The extracts were studied for their anti-Helicobacter pylori (H. pylori), anti-human immunodeficiency virus (HIV), cytotoxic, multidrug resistance (MDR) reversal and radical scavenging activity. Among five PM extracts and beta,betacarotene, PM4 showed potent anti-H. pylori activity (MIC(50) = 36 microg/mL), comparable to metronidazole (MIC(50) = 45 microg/mL). The extracts were inactive against HIV. PM3 and PM4 showed slightly higher cytotoxic activity against three human tumor cell lines (squamous cell carcinoma HSC-2, HSC-3, submandibular gland carcinoma HSG) and human promyelocytic leukemic HL-60 cells than against three normal human oral cells (gingival fibroblast HGF, pulp cell HPC, periodontal ligament fibroblast HPLF), suggesting a tumor-specific cytotoxic activity. PM1, PM3 and PM4 displayed much higher MDR-reversing activity than (+/-)-verapamil. ESR spectroscopy demonstrated that PM1-5 and beta,beta-carotene produced little or no detectable radical under alkaline conditions and did not scavenge the O(2) (-) produced by the hypoxanthine and xanthine oxidase reaction. On the other hand, PM1 and PM2 scavenged efficiently 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, whereas singlet oxygen was also quenched efficiently by PM5 and PM2. The data suggest the potential importance of carotenoids as possible anti-H. pylori and MDR reversal agents. The active principles in the carotenoid extract might differ, depending upon the types of fruits and vegetables.
从红辣椒、瓦伦西亚橙皮和金冠苹果皮中提取类胡萝卜素组分。通过在甲醇 - 水（9:1）（下层相）和己烷（上层相）之间进行萃取、皂化和分配，得到了辣椒的下层相类胡萝卜素（PM1）、橙子的下层相类胡萝卜素（PM3）、苹果的下层相类胡萝卜素（PM4），以及辣椒的上层相提取物（PM2）和苹果的上层相提取物（PM5）。在红辣椒的下层相类胡萝卜素（PM1）中定量测定出高含量的辣椒红素，而橙子（PM3）和苹果（PM4）的下层相组分主要由紫黄质、玉米黄质和叶黄素组成。另一方面，在上层相组分（PM2和PM5）中发现了高含量的β,β - 胡萝卜素和β - 隐黄质。对提取物进行了抗幽门螺杆菌（H. pylori）、抗人类免疫缺陷病毒（HIV）、细胞毒性、多药耐药（MDR）逆转和自由基清除活性的研究。在五种PM提取物和β,β - 胡萝卜素中，PM4表现出强效的抗幽门螺杆菌活性（MIC50 = 36 μg/mL），与甲硝唑（MIC50 = 45 μg/mL）相当。提取物对HIV无活性。PM3和PM4对三种人类肿瘤细胞系（鳞状细胞癌HSC - 2、HSC - 3、下颌下腺癌HSG）和人类早幼粒细胞白血病HL - 60细胞的细胞毒性活性略高于对三种正常人类口腔细胞（牙龈成纤维细胞HGF、牙髓细胞HPC、牙周膜成纤维细胞HPLF），表明具有肿瘤特异性细胞毒性活性。PM1、PM3和PM4表现出比（±） - 维拉帕米更高的MDR逆转活性。电子自旋共振光谱表明，PM1 - 5和β,β - 胡萝卜素在碱性条件下产生很少或没有可检测到的自由基，并且不能清除次黄嘌呤和黄嘌呤氧化酶反应产生的O2（ - ）。另一方面，PM1和PM2能有效清除1,1 - 二苯基 - 2 - 苦基肼（DPPH）自由基，而PM5和PM2也能有效淬灭单线态氧。数据表明类胡萝卜素作为可能的抗幽门螺杆菌和MDR逆转剂具有潜在的重要性。类胡萝卜素提取物中的活性成分可能因水果和蔬菜的种类而异。
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