海葱葡苷 | 507-60-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 海葱葡苷
• 中文别名: 红海葱
• 英文名称: [(3S,6R,8S,9R,10R,13R,14R,17R)-8,14-dihydroxy-10,13-dimethyl-17-(6-oxopyran-3-yl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,6,7,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-yl] acetate
• 英文别名: Scilliroside
• CAS: 507-60-8
• 化学式: C₃₂H₄₄O₁₂
• 分子量: 620.7
• InChiKey: LSMIOFMZNVEEBR-ICLSSMQGSA-N

物化性质

• 熔点：
  168-170°
• 比旋光度：
  D20 -59 to -60° (methanol)
• 沸点：
  581.69°C (rough estimate)
• 密度：
  1.1882 (rough estimate)
• 颜色/状态：
  Long prisms from dilute methanol
• 溶解度：
  In water, 1.43X10+4 mg/L at 25 °C (est)
• 蒸汽压力：
  2.06X10-23 mm Hg at 25 °C (est)
• 旋光度：
  Specific optical rotation: -59 to -60 deg at 20 °C/D (methanol)
• 分解：
  When heated to decomposition it emits acrid smoke and irritating fumes.

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  44
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  192
• 氢给体数：
  6
• 氢受体数：
  12

ADMET

毒理性

• 毒性总结

识别和使用：Scilliroside是一种固体；一种自13世纪以来使用的杀鼠剂。人类暴露和毒性：无数据。动物研究：单次亚致死剂量50微克/大鼠导致带状鼠的心脏生理发生变化。观察到心肌复极化延迟和心肌组织压力。S-T段升高超过等电位轴，诊断近期心肌梗死。它引起心动过速。推测死亡可能是由于心肌复极化延迟和心动过速。除了啮齿类动物之外，其他哺乳动物不太可能中毒。注射苷类物质会导致典型洋地黄效应：心脏冲动传导改变和心律失常。

IDENTIFICATION AND USE: Scilliroside is a solid; a rodenticide that has been used since the 13th century. HUMAN EXPOSURE AND TOXICITY: There are no data. ANIMAL STUDIES: A single sublethal dose 50 ug/rat brought about changes in cardiac physiology of bandicoot rats. Delayed myocardial repolarization and stress on cardiac tissues were noticed. Elevation of S-T segment above the isoelectric axis diagnostic of recent myocardial infarction was observed. It induced tachycardia. It is inferred that deaths may be due to delayed myocardial repolarization and tachycardia. Mammals, other than rodents, are unlikely to be poisoned. Injection of the glycosides leads to effects typical of digitalis: alterations in cardiac impulse conduction and arrhythmias.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

石房蛤毒素在组织粘膜表面应用时，以浓度依赖性的方式刺激了大鼠远端和近端结肠的阳离子依赖短路电流（Isc）。远端结肠对毒素表现出更高的敏感性。石房蛤毒素诱导的Isc被钒酸根阻断，但对乌本苷或海葱苷有抗性，这表明将钒酸根敏感的H+/K+-ATP酶转化为电离阳离子转运体。在基底侧膜去极化的组织中进行阳离子替代实验表明，石房蛤毒素诱导的电导对Na+>K+>Li+的渗透性明显。免疫组化对照实验确认顶膜上不存在Na+/K+-ATP酶。因此，石房蛤毒素的成孔作用不仅限于Na+/K+-ATP酶，也观察到了与结肠H+/K+-ATP酶的关联。

Palytoxin stimulated a cation-dependent short-circuit current (Isc) in rat distal and proximal colon in a concentration-dependent fashion when applied to the mucosal surface of the tissue. The distal colon exhibited a higher sensitivity to the toxin. The palytoxin-induced Isc was blocked by vanadate but was resistant to ouabain or scilliroside, suggesting the conversion of a vanadate-sensitive H+/K+-ATPase into an electrogenic cation transporter. Cation substitution experiments with basolaterally depolarized tissues suggested an apparent permeability of the palytoxin-induced conductance of Na+>K+>Li+. Immunohistochemical control experiments confirmed the absence of the Na+/K+-ATPase in the apical membrane. Consequently, the pore-forming action of palytoxin is not restricted to Na+/K+-ATPase but is also observed with the colonic H+/K+-ATPase.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

在大鼠降结肠的粘膜下组织培养中，通过静水压力梯度引起的扩张增加了短路电流（Isc）。在含有粘膜下神经丛的粘膜下组织中，Isc的增加是双相的，自发恢复到基线的一半时间约为200秒。在没有粘膜下神经丛的粘膜组织中，时间过程是单相的。粘膜下组织中的Isc增加被磷脂酶A2的抑制剂喹尼克林、吲哚美辛、四氢毒伞素或阿托品所抑制；这些化合物每一种也都消除了反应的第二阶段。相比之下，只有吲哚美辛在粘膜组织中有效地减少了Isc的增加。在两种准备中，对扩张的反应都被海葱苷抑制，通过用葡萄糖酸盐替代Cl-，以及给予呋塞米或氯化通道阻断剂9-乙炔基酸。结果表明，通过引起前列腺素的释放，扩张间接地（即通过粘膜下神经丛介导）和直接在上皮细胞上引起氯分泌。

Distension of the rat colon descendens in vitro by a hydrostatic gradient induced an increase in short-circuit current (Isc). In a mucosa-submucosa preparation containing the plexus submucosus, the increase in Isc was biphasic with a half-time of about 200 s for the spontaneous returning to the baseline. The time course was monophasic in a mucosa preparation without the plexus submucosus. The increase in Isc in the mucosa-submucosa preparation was inhibited by an inhibitor of phospholipase A2, quinacrine, and by indomethacin, tetrodotoxin or atropine; each of these compounds also abolished the second phase of the response. In contrast, only indomethacin was effective in reducing the increase in Isc in the mucosa preparation. In both preparations the response to distension was inhibited by scilliroside, by replacement of Cl- with gluconate, and by administration of frusemide or the chloride channel blocker, anthracene-9-carboxylic acid. The results indicate that distension induces chloride secretion by causing the release of prostaglandins, which act indirectly, i.e. mediated by the submucosal plexus, and directly at the epithelium.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

这项研究的目的旨在评估特定抗洋地黄毒苷Fab片段在急性中毒中对毒扁豆碱和前毒扁豆碱的绑定和中和能力。测定的表观亲和常数分别为毒扁豆碱2.6 x 10^8 M^-1，前毒扁豆碱为3.8 x 10^7 M^-1。这些结果与这些毒素在体内可能的中和作用相一致。

The purpose of this study was to evaluate the capacity of specific anti-digoxin Fab fragments to bind to and neutralize scilliroside and proscillaridin in acute poisoning. Apparent affinity constants were determined with values of 2.6 10(8)M-1 for scilliroside and 3.8 10(7)M-1 for proscillaridin. These results are in accordance with a possible in-vivo neutralization of these toxins.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

实验室动物：急性暴露/ 单次亚致死剂量的Vacor（1毫克/大鼠）或Silmurin（50微克/大鼠）导致袋狸大鼠的心脏生理发生了不同的变化。观察到心肌复极化延迟和心肌组织压力增加。S-T段升高超过等电位轴，这是近期心肌梗死的诊断标志。Vacor和Silmurin引起了心跳的不同变化；Vacor中毒导致心动过缓，而Silmurin导致心动过速。推测Vacor的死亡可能是由于心动过缓伴随房室传导阻滞，而Silmurin的死亡可能是由于心肌复极化延迟和心动过速。

/LABORATORY ANIMALS: Acute Exposure/ A single sublethal dose of Vacor (1 mg/rat) or Silmurin (50 ug/rat) brought about dissimilar changes in cardiac physiology of bandicoot rats. Delayed myocardial repolarization and stress on cardiac tissues were noticed. Elevation of S-T segment above the isoelectric axis diagnostic of recent myocardial infarction was observed. Vacor and Silmurin induced differential changes in heartbeat; Vacor poisoning resulted in bradycardia, whereas Silmurin tachycardia. It is inferred that Vacor deaths may be due to bradycardia associated with atrioventricular block and that of Silmurin to delayed myocardial repolarization and tachycardia.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

红海葱是一种很少使用的灭鼠剂，由生长在东地中海国家的一种小型卷心菜植物的内部部分组成。其毒性自古代以来就已为人所知，可能是由心脏糖苷引起的。出于几个原因，除了啮齿类动物之外的哺乳动物不太可能中毒：(1) 红海葱具有强烈的催吐作用，因此会呕吐的动物（啮齿类动物不会）不太可能保留毒药；(2) 糖苷从肠道吸收的效率不高； (3) 吸收的糖苷会迅速排泄。注射糖苷会导致类似于洋地黄的效果：心脏冲动传导的改变和心律失常。

Red squill is a little-used rodenticide, consisting of the inner portions of a small cabbage plant grown in eastern Mediterranean countries. Its toxic properties have been known since ancient times and are probably due to cardiac glycosides. For several reasons, mammals other than rodents are unlikely to be poisoned: (1) red squill is intensely nauseant, so that animals which vomit (rodents do not) are unlikely to retain the poison; (2) the glycoside is not efficiently absorbed from the gut; and (3) absorbed glycoside is rapidly excreted. Injection of the glycosides leads to effects typical of digitalis: alterations in cardiac impulse conduction and arrhythmias.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(a)
• 危险品标志：
  T+
• 安全说明：
  S36/37,S45
• 危险类别码：
  R28
• 包装等级：
  I
• 危险类别：
  6.1(a)
• 危险品运输编号：
  UN 2810

反应信息

• 作为反应物：
  描述：

  海葱葡苷 在 甲醇 、 钯 作用下， 生成 3β-β-D-glucopyranosyloxy-8,14-dihydroxy-5ξ,14β-buf-20(22)-enolide
  参考文献：
  名称：

  ÜberScillirosid，纳格·纳格·斯佩菲菲奇·维克萨姆斯·礼物赠送给罗滕·梅兹维贝尔。（18. MitteilungüberHerzglukoside）

  摘要：

  DOI：

  10.1002/hlca.19420250108

文献信息

• [EN] MICROBIOCIDAL OXADIAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'OXADIAZOLE MICROBIOCIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2017157962A1

  公开（公告）日：2017-09-21

  Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially fungicides.

  式(I)的化合物，其中取代基如权利要求1所定义，作为杀虫剂特别是杀菌剂有用。
• [EN] INSECTICIDAL TRIAZINONE DERIVATIVES<br/>[FR] DÉRIVÉS DE TRIAZINONE INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2013079350A1

  公开（公告）日：2013-06-06

  Compounds of the formula (I) or (I'), wherein the substituents are as defined in claim 1, are useful as pesticides.

  式(I)或(I')的化合物，其中取代基如权利要求1所定义的那样，可用作杀虫剂。
• Novel insecticides
  申请人：Syngenta Participations AG

  公开号：EP2540718A1

  公开（公告）日：2013-01-02

  Compounds of formula I wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts and all stereoisomers and tautomeric forms of the compounds of formula I can be used as insecticides and can be prepared in a manner known per se.

  式I的化合物 其中取代基如权利要求1所定义，并且式I化合物的农药可接受盐以及所有立体异构体和互变异构形式可用作杀虫剂，并且可以按照已知的方法制备。
• Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto
  申请人：Dow AgroSciences LLC

  公开号：US20180279612A1

  公开（公告）日：2018-10-04

  This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions against such pests. These pesticidal compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula (“Formula One”).

  这份披露涉及具有对节肢动物门、软体动物门和线虫门害虫具有杀虫效用的分子领域，用于生产此类分子的过程，用于此类过程的中间体，含有此类分子的杀虫组合物，以及使用此类杀虫组合物对抗此类害虫的过程。这些杀虫组合物可以用作螨虫剂、杀虫剂、螨虫剂、软体动物杀虫剂和线虫杀虫剂。本文件披露了具有以下式（“式一”）的分子。
• [EN] MOLECULES HAVING PESTICIDAL UTILITY, AND INTERMEDIATES, COMPOSITIONS, AND PROCESSES, RELATED THERETO<br/>[FR] MOLÉCULES PRÉSENTANT UNE UTILITÉ EN TANT QUE PESTICIDE, ET LEURS INTERMÉDIAIRES, COMPOSITIONS ET PROCÉDÉS
  申请人：DOW AGROSCIENCES LLC

  公开号：WO2017040194A1

  公开（公告）日：2017-03-09

  This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions aga inst such pests. These pesticidal compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula ("Formula One").

  这份披露涉及具有对节肢动物门、软体动物门和线虫门害虫有用的分子领域，用于生产这种分子的过程，用于这种过程的中间体，含有这种分子的杀虫剂组合物，以及使用这种杀虫剂组合物对抗这些害虫的过程。这些杀虫剂组合物可以用作螨虫剂、杀虫剂、螨虫剂、软体动物杀虫剂和线虫杀虫剂。本文件披露了具有以下化学式（“化学式一”）的分子。