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Humudifucol and Bioactive Prenylated Polyphenols from Hops (Humulus lupulus cv. “Cascade”)
Journal of Natural Products ( IF 3.3 ) Pub Date : 2016-02-26 00:00:00 , DOI: 10.1021/acs.jnatprod.5b01052 Martino Forino 1 , Simona Pace 2 , Giuseppina Chianese 1 , Laura Santagostini 3 , Markus Werner 2 , Christina Weinigel 4 , Silke Rummler 4 , Gelsomina Fico 5, 6 , Oliver Werz 2 , Orazio Taglialatela-Scafati 1
Journal of Natural Products ( IF 3.3 ) Pub Date : 2016-02-26 00:00:00 , DOI: 10.1021/acs.jnatprod.5b01052 Martino Forino 1 , Simona Pace 2 , Giuseppina Chianese 1 , Laura Santagostini 3 , Markus Werner 2 , Christina Weinigel 4 , Silke Rummler 4 , Gelsomina Fico 5, 6 , Oliver Werz 2 , Orazio Taglialatela-Scafati 1
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Humulus lupulus (hop plant) has long been used in traditional medicine as a sedative and antimicrobial agent. More recently, attention has been devoted to the phytoestrogenic activity of the plant extracts as well as to the anti-inflammatory and chemopreventive properties of the prenylated chalcones present. In this study, an Italian sample of H. lupulus cv. “Cascade” has been investigated and three new compounds [4-hydroxycolupulone (6), humudifucol (7) and cascadone (8)] have been purified and identified by means of NMR spectroscopy along with four known metabolites. Notably, humudifucol (7) is the first prenylated dimeric phlorotannin discovered in nature. Because structurally related phloroglucinols from natural sources were found previously to inhibit microsomal prostaglandin E2 synthase (mPGES)-1 and 5-lipoxygenase (5-LO), the isolated compounds were evaluated for their bioactivity against these pro-inflammatory target proteins. The prenylated chalcone xanthohumol inhibited both enzymes at low μM concentrations.
中文翻译：
蛇麻草中的Humudifucol和生物活性的烯丙基化多酚（Humulus lupulus cv。“ Cascade”）
草（蛇麻草植物）长期以来一直在传统医学中用作镇静剂和抗菌剂。最近，注意力已经集中在植物提取物的植物雌激素活性以及存在的炔丙基查耳酮的抗炎和化学预防特性上。在这项研究中，H。lupulus cv的意大利样本。已经研究了“级联”，并已通过NMR光谱法纯化和鉴定了三种新化合物[4-羟基colupulone （6），humudifucol（7）和Cascadone（8）]以及四种已知的代谢物。值得注意的是，humudifucol（7）是自然界中发现的第一个烯丙基化的二聚邻苯二酚。因为以前发现天然来源的结构相关间苯三酚抑制微粒体前列腺素E 2合酶（mPGES）-1和5-脂氧合酶（5-LO），所以评估了分离的化合物对这些促炎性靶标蛋白质的生物活性。在低μM浓度下，异戊烯化查尔酮黄腐酚可抑制这两种酶。
更新日期：2016-02-26
中文翻译：
蛇麻草中的Humudifucol和生物活性的烯丙基化多酚（Humulus lupulus cv。“ Cascade”）
草（蛇麻草植物）长期以来一直在传统医学中用作镇静剂和抗菌剂。最近，注意力已经集中在植物提取物的植物雌激素活性以及存在的炔丙基查耳酮的抗炎和化学预防特性上。在这项研究中，H。lupulus cv的意大利样本。已经研究了“级联”，并已通过NMR光谱法纯化和鉴定了三种新化合物[4-羟基colupulone （6），humudifucol（7）和Cascadone（8）]以及四种已知的代谢物。值得注意的是，humudifucol（7）是自然界中发现的第一个烯丙基化的二聚邻苯二酚。因为以前发现天然来源的结构相关间苯三酚抑制微粒体前列腺素E 2合酶（mPGES）-1和5-脂氧合酶（5-LO），所以评估了分离的化合物对这些促炎性靶标蛋白质的生物活性。在低μM浓度下，异戊烯化查尔酮黄腐酚可抑制这两种酶。
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