Interconverting flavanone glucosides and other phenolic compounds in Lippia salviaefolia Cham. ethanol extracts
Interconverting flavanone glucosides and other phenolic compounds in Lippia salviaefolia Cham. ethanol extracts
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DOI：
10.1016/j.phytochem.2011.07.004
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发表时间：
2011-11-01
期刊：
影响因子：
3.8
通讯作者：
Siqueira Silva, Dulce Helena
中科院分区：
文献类型：
--
作者：
Funari, Cristiano Soleo;Passalacqua, Thais Gaban;Siqueira Silva, Dulce Helena
四种相互转化的黄烷酮糖苷[（2 R）-和（2S）-3 ′，4 ′，5，6-四羟基黄烷酮7-O-β-D-吡喃葡萄糖苷，和（2 R）-和（2S）-3 ′，4 ′，5，8-四羟基黄烷酮7-O-β-D-吡喃葡萄糖苷]，以及八种已知的类黄酮[柚苷元、阿西柏苷元、樱花素、6-羟基毛地黄素7-O-β-D-葡萄糖苷，（2 R）-和（2S）-圣草酚7-O-β-D-吡喃葡萄糖苷、芳香藤素和根皮素]，三种苯丙素苷[圣草苷B。从Lippia salviaefolia Cham地上部分的乙醇提取物中分离并鉴定了[alyssonoside和verbascoside]和环氧木脂素落叶松树脂醇4 '-O-β-D-吡喃葡萄糖苷。本文的植物化学研究是由初步的抗氧化剂测试，即，β-胡萝卜素保护和2，2-二苯基-1-苦基肼（DPPH）自由基清除活性。测定粗提物、其活性级分和分离的化合物对细胞内活性氧（ROS）和人胚肾HEK-293和人黑色素瘤M14癌细胞生长的影响。Aromadendrin和根皮素能够抵消HEK-293细胞中由氧化剂叔丁基过氧化氢（t-BOOH）诱导的ROS升高，而根皮素在1 μ M时强烈保护HEK-293细胞免受ROS损伤。此外，根皮素在20-40 μ M时在HEK-293和M14细胞中都表现出显著的生长抑制作用，并在20 μ M时在M14细胞中诱导浓度依赖性凋亡，表明对恶性细胞的选择性作用。由于它们的平衡，使用10和2D NMR、HPLC-CD-PDA和GMS分析研究了四种相互转化的黄烷酮苷。(C)2011爱思唯尔有限公司保留所有权利。
Four interconverting flavanone glycosides [(2R)- and (2S)-3',4',5,6-tetrahydroxyflavanone 7-O-beta-D-glucopyranoside, and (2R)- and (2S)-3',4',5,8-tetrahydroxyflavanone 7-O-beta-D-glucopyranoside], in addition to eight known flavonoids [naringenin, asebogenin, sakuranetin, 6-hydroxyluteolin 7-O-beta-D-glucoside, (2R)- and (25)-eriodictyol 7-O-beta-D-glucopyranoside, aromadendrin and phloretin], three phenylpropanoid glycosides [forsythoside B. alyssonoside and verbascoside] and the epoxylignan lariciresinol 4'-O-beta-D-glucopyranoside were isolated and identified in the EtOH extract of the aerial parts of Lippia salviaefolia Cham. The phytochemical study herein was guided by preliminary antioxidant tests, namely, beta-carotene protection and 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging activity. The crude extracts, their active fractions and the isolated compounds were assayed against intracellular reactive oxygen species (ROS) and human embryonic kidney HEK-293 and human melanoma M14 cancer cell growth. Aromadendrin and phloretin were able to counteract elevation of ROS induced by the oxidant t-butylhydroperoxide (t-BOOH) in HEK-293 cells, whereas phloretin strongly protected HEK-293 cells from ROS damage at 1 mu M. Additionally, phloretin exhibited a significant growth inhibitory effect at 20-40 mu M in both HEK-293 and M14 cells and induced a concentration dependent apoptosis at 20 mu M in M14 cells, suggesting a selective action towards malignant cells. Due to their equilibria, the four interconverting flavanone glycosides were studied using 10 and 2D NMR, HPLC-CD-PDA and HRMS analyses. (C) 2011 Elsevier Ltd. All rights reserved.