phyllanthin | 10351-88-9

• 物质功能分类: 天然产物 - 木脂素
• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苄基丁烷木脂素
• 英文名称: phyllanthin
• 英文别名: 4-[(2R,3R)-3-[(3,4-Dimethoxyphenyl)methyl]-4-methoxy-2-(methoxymethyl)butyl]-1,2-dimethoxybenzene
• CAS: 10351-88-9；40516-27-6；123808-59-3
• 化学式: C₂₄H₃₄O₆
• 分子量: 418.53
• InChiKey: KFLQGJQSLUYUBF-PMACEKPBSA-N

物化性质

• 熔点：
  96℃
• 沸点：
  530.6±50.0 °C(Predicted)
• 密度：
  1.069
• 溶解度：
  DMF：15 mg/ml； DMSO：10 mg/ml；乙醇：5 mg/ml
• LogP：
  4.110 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 海关编码：
  2909309090

制备方法与用途

概述

叶下珠素（1，1'-[(2S,3S)-2,3-双(甲氧基甲基)-1,4-丁二基]双[3,4-二甲氧基苯]）又叫叶下珠醇。叶下珠（Phyllanthus urinaria L.）为大戟科叶下珠属植物，别名珍珠草、夜合草、阴阳草，是一年生草本，全草入药，是传统的中草药。最早记载于《生草药性备要》中，具有平肝清热、利水解毒的功效，在我国民间常用于治疗小儿疳积、黄疸、肝炎、肠炎、痢疾、肾炎水肿及蛇咬伤等症状。

叶下珠素属于芳基丁烷类木脂素，是结构最简单的一类木脂素。在植物生物合成过程中，此类木脂素是合成其他各类木脂素的基石，并可转化为其他类型的木脂素。

生物活性

Phyllanthin 是从叶下珠（Phyllanthus amarus）中提取的主要生物活性木脂素成分之一，具有显著的抗氧化和保肝作用。

反应信息

• 作为反应物：
  描述：

  phyllanthin 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 以70%的产率得到4-(3,4-Dimethoxyphenyl)-6,7-dimethoxy-3-(methoxymethyl)naphthalene-2-carbaldehyde
  参考文献：
  名称：

  Oxidative aryl-aryl, aryl-benzyl coupling of lignans-reactions of phyllanthin and haloderivatives with ttfa, ddq, li/thf)))): synthesis of dibenzocyclooctadiene system and phyltetralin

  摘要：

  Treatment of phyllanthin (1) with TTFA in TFA gives dibenzocyclooctadiene (2) and phyltetralin (3). Treatment of (1) with DDQ in TFA also affords (2) while with DDQ in acetic acid gives 1-phenylnaphthalenic lignan (4). Synthesis of halophyllanthins (5,6,7) and its Ullmann reaction in ultrasonic condition affords reductive dehalogenated product (1) instead of (2). Treatment of (1) with POCl3 in TCA gives (+) 3,4-diveratryltetrahydrofuran (8) and its conversion to (9) also reported. Treatment of (5) with TTFA/TFA gives (9).

  DOI：

  10.1016/s0040-4020(01)91020-8
• 作为产物：
  描述：

  D,L-2,3-bis(3,4-dimethoxybenzyl)succinic acid anhydride 在 lithium aluminium tetrahydride 、 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 phyllanthin
  参考文献：
  名称：

  Crystalline constituents of euphorbiaceae—VI

  摘要：

  DOI：

  10.1016/s0040-4020(01)82594-1

文献信息

• A sterically encumbered photoredox catalyst enables the unified synthesis of the classical lignan family of natural products
  作者：Edwin Alfonzo、Aaron B. Beeler

  DOI：10.1039/c9sc02682g

  日期：——

  selectively generate carbonyl ylides from electron-rich epoxides. These can undergo concerted [3 + 2] dipolar cycloadditions to afford tetrahydrofurans, which were advanced (2–4 steps) to at least one representative natural product or natural product scaffold within all six subtypes in classical lignans. The application of those synthetic blueprints to the synthesis of heterolignans bearing unnatural

  在这里，我们详细介绍了经典的天然木脂素家族天然产品的统一合成方法，该方法取决于与从自然界生物合成蓝图战略性确定的常见中间体的差异。通过会聚和模块化方法来尝试访问通用中间体的努力导致发现了一种空间受限的光氧化还原催化剂，该催化剂可以从富含电子的环氧化物中选择性地生成羰基化物。这些可以经历一致的[3 + 2]偶极环加成反应，得到四氢呋喃，在经典木脂素的所有六种亚型中，四氢呋喃被推进（2-4个步骤）至至少一种代表性的天然产物或天然产物支架。证明了这些合成蓝图在具有不自然功能的杂木聚糖合成中的应用，
• A polyherbal pharmaceutical composition useful in the treatment of conditions associated with hepatitis E and hepatitis B virus infections
  申请人：Dabur Research Foundation

  公开号：EP0890360A1

  公开（公告）日：1999-01-13

  The invention provides a novel polyherbal composition useful for treating acute Hepatitis E virus infection including acute liver failure due to HEV infection, healthy Hepatitis B virus carriers who develop superadded hepatitis E virus infection, Acute hepatitis B virus infection, and animal hepadna virus, therapeutic effects on hepatitis B virus infection and also used as a hepatoprotective agent, said composition comprising essentially extracts of plants Rheum emodi Wall., Phyllanthus amarus Linn., Eclipta alba Hassk., Andrographis paniculate Nees., and Picrorhiza kurroa Royle ex Benth., and optionally Fumaria officinalis, Tinospora cordifolia Miers., Terminalia chebula Retz., Cichorium intybus Linn., Tephrosea purpurea Linn. and Boerhaavia diffusa Linn.

  本发明提供了一种新型多草药组合物，可用于治疗急性戊型肝炎病毒感染，包括 HEV 感染引起的急性肝衰竭、健康乙型肝炎病毒携带者发生戊型肝炎病毒超级感染、急性乙型肝炎病毒感染和动物hepadna病毒感染，对乙型肝炎病毒感染有治疗作用，还可用作肝保护剂，所述组合物主要包括植物 Rheum emodi Wall、Phyllanthus amarus Linn.、Eclipta alba Hassk.、Andrographis paniculate Nees.和 Picrorhiza kurroa Royle ex Benth.，以及可选的 Fumaria officinalis、Tinospora cordifolia Miers.、Terminalia chebula Retz.、Cichorium intybus Linn.、Tephrosea purpurea Linn.和 Boerhaavia diffusa Linn.提取物。
• Novel phyllanthus extract
  申请人：Phytrix JV, LLC

  公开号：EP2116253A1

  公开（公告）日：2009-11-11

  The present invention relates to a method for the production of an extract of Phyllanthus comprising the steps of: (a) extracting Phyllanthus components with a solvent; (b) fractionating the extract obtained in the preceding step on the basis of hydrophobicity; (c) collecting and combining fractions that correspond in hydrophobicity to elute fractions resulting from 10-50% methanol elution steps, wherein said elute fractions are obtained by low pressure vacuum liquid chromatography (VLC) using a C18 reversed-phase lipophilic column and a water/methanol gradient system, wherein the gradient system is based on an initial elution step of loading said column with 100% water, on intermediate elution steps with gradually decreasing water content and on a terminal elution step loading said column with 100% methanol; and (d) optionally drying the extract obtained in step (c). Further, the invention relates to an extract of Phyllanthus obtainable or obtained by the latter method or a fraction thereof and a Phyllanthus extract or fraction thereof comprising repandusinic acid, wherein the repandusinic acid is present at a concentration of at least 42 mg/g. Also contemplated is a pharmaceutical composition comprising the extract or fraction thereof, the extract of the invention for the prevention and/or treatment of a human immunodeficiency virus (HIV)-associated disease and finally a method to prevent and/or treat the latter.

  本发明涉及一种生产植物提取物的方法，包括以下步骤(a) 用溶剂萃取叶黄素成分； (b) 根据疏水性对上一步得到的提取物进行分馏；(c) 收集并合并疏水性与 10-50%甲醇洗脱步骤产生的洗脱馏分一致的馏分，其中所述洗脱馏分是通过使用 C18 反相亲油柱和水/甲醇梯度系统的低压真空液相色谱法（VLC）获得的，梯度系统基于初始洗脱步骤，用 100%的水加载所述色谱柱，中间洗脱步骤水含量逐渐减少，最后洗脱步骤用 100%的甲醇加载所述色谱柱；(d) 将步骤（c）中得到的提取物进行干燥。此外，本发明还涉及一种可通过后一种方法获得或得到的叶黄素提取物或其馏分，以及一种含有补骨脂酸的叶黄素提取物或其馏分，其中补骨脂酸的浓度至少为 42 毫克/克。还考虑一种药物组合物，该组合物包含本发明用于预防和/或治疗人类免疫缺陷病毒（HIV）相关疾病的提取物或其馏分，以及预防和/或治疗后者的方法。
• COMPOSITIONS COMPRISING PHYLLANTHUS EXTRACT FOR USE IN THE TREATMENT OR PREVENTION OF A SARS-COV-2 INFECTION AND/OR AT LEAST ONE SYMPTOM OF COVID-19
  申请人：HFM - Hybrid Fusion Medicals, GmbH

  公开号：EP3954379A1

  公开（公告）日：2022-02-16

  The present invention relates to a composition comprising or corresponding to a Phyllanthus extract for use in the treatment or prevention of a SARS-CoV-2 infection and/or at least one symptom of COVID-19.

  本发明涉及一种组合物，该组合物包含或对应于一种植物提取物，用于治疗或预防 SARS-CoV-2 感染和/或 COVID-19 的至少一种症状。
• Use of phyllanthus components for the treatment or prophylaxis of infections triggered by flavivirdae
  申请人：——

  公开号：US20020054921A1

  公开（公告）日：2002-05-09

  The invention relates to the use of one or more Phyllanthus components or substances or mixtures of substances obtained therefrom for preventing or treating infectious diseases that are triggered by viruses belonging to the family of Flaviviridae or infectious diseases in which viruses belonging to the family of Flaviviridae are involved in the development or progression thereof. Furthermore, the invention relates to the use of one or more Phyllanthus components or substances or mixtures of substances obtained therefrom for producing a pharmaceutical composition for the prevention or treatment of infectious diseases that are triggered by viruses belonging to the family of Flaviviridae or infectious diseases in which viruses belonging to the family of Flaviviridae are involved in the development or progression thereof. The invention also relates to the use of one or more Phyllanthus components or substances or mixtures of substances obtained therefrom for inhibiting the propagation of viruses belonging to the family of Flaviviridae. Moreover, the invention relates to a method for preventing or treating infectious diseases in a mammal that are triggered by viruses belonging to the family of Flaviviridae or infectious diseases in which viruses belonging to the family of Flaviviridae are involved in the development or progression thereof, wherein one or more Phyllanthus components or substances or mixtures of substances obtained therefrom are administered to the mammal. In addition, the invention relates to a method for inhibiting the propagation of viruses belonging to the family of Flaviviridae, wherein one or more Phyllanthus components or substances or mixtures of substances obtained therefrom are contacted with the viruses. The hepatitis C virus is a preferred virus.

  本发明涉及一种或多种叶黄素成分或物质或由其获得的物质混合物用于预防或治疗由属于黄病毒科的病毒引发的传染性疾病或属于黄病毒科的病毒参与其发展或进展的传染性疾病。此外，本发明还涉及使用一种或多种叶黄素成分或物质或从中获得的物质混合物生产药物组合物，用于预防或治疗由属于黄病毒科的病毒引发的传染性疾病或属于黄病毒科的病毒参与其发展或恶化的传染性疾病。本发明还涉及使用一种或多种叶黄素成分或物质或从中获得的物质混合物来抑制属于黄病毒科的病毒的繁殖。此外，本发明还涉及一种预防或治疗哺乳动物由黄病毒科病毒引发的传染性疾病或黄病毒科病毒参与其发展或恶化的传染性疾病的方法，其中向哺乳动物施用一种或多种叶黄素成分或物质或从中获得的物质混合物。此外，本发明还涉及一种抑制属于黄病毒科的病毒繁殖的方法，其中一种或多种叶黄素成分或物质或从中获得的物质混合物与病毒接触。丙型肝炎病毒是首选病毒。