Forino Martino, Pace Simona, Chianese Giuseppina, Santagostini Laura, Werner Markus, Weinigel Christina, Rummler Silke, Fico Gelsomina, Werz Oliver, Taglialatela-Scafati Orazio
Department of Pharmacy, University of Naples Federico II , Via Montesano 49, 80131 Naples, Italy.
Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, University of Jena , Philosophenweg 14, D-07743 Jena, Germany.
J Nat Prod. 2016 Mar 25;79(3):590-7. doi: 10.1021/acs.jnatprod.5b01052. Epub 2016 Feb 26.
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.
啤酒花（蛇麻草）长期以来在传统医学中被用作镇静剂和抗菌剂。最近，人们开始关注该植物提取物的植物雌激素活性以及其中所含异戊烯基化查耳酮的抗炎和化学预防特性。在本研究中，对意大利的“卡斯卡特”啤酒花品种样本进行了研究，通过核磁共振光谱法纯化并鉴定了三种新化合物[4-羟基蛇麻酮（6）、humudifucol（7）和卡斯卡酮（8）]以及四种已知代谢物。值得注意的是，humudifucol（7）是自然界中发现的首个异戊烯基化二聚间苯三酚单宁。由于先前发现天然来源的结构相关间苯三酚可抑制微粒体前列腺素E2合酶（mPGES）-1和5-脂氧合酶（5-LO），因此对分离出的化合物针对这些促炎靶蛋白的生物活性进行了评估。异戊烯基化查耳酮黄腐酚在低 microM 浓度下可抑制这两种酶。
