中美菊素C | 16838-87-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 中美菊素C
• 英文名称: zaluzanin C
• 英文别名: (3aS,6aR,8S,9aR,9bS)-8-hydroxy-3,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• CAS: 16838-87-2
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: XFVLNEYIZGZDHP-PEDHHIEDSA-N

物化性质

• 熔点：
  95-96 °C
• 沸点：
  439.9±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  中美菊素C 在 叔丁基过氧化氢 、 selenium(IV) oxide 作用下， 生成
  参考文献：
  名称：

  Developing new herbicide models from allelochemicals

  摘要：

  DOI：

  10.1002/(sici)1096-9063(199906)55:6<662::aid-ps3>3.0.co;2-q
• 作为产物：
  描述：

  山道年 在 双氧水 、 potassium carbonate 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 56.5h， 生成 中美菊素C
  参考文献：
  名称：

  Studies on the syntheses of sesquiterpene lactones. 11. The syntheses of 3-epizaluzanin C, zaluzanin C, zaluzanin D, and related compounds 3.alpha.-hydroxyguaia-1(10),4(15),11(13)-trieno-12,6.alpha.-lactone and 3.alpha.-hydroxyguaia-4(15),9,11(13)-trieno-12,6.alpha.-lactone

  摘要：

  DOI：

  10.1021/jo00269a039

文献信息

• Synthesis and anticancer studies of Michael adducts and Heck arylation products of sesquiterpene lactones, zaluzanin D and zaluzanin C from <i>Vernonia arborea</i>
  作者：Tushar R. Valkute、Eswar K. Aratikatla、Neha A. Gupta、S. Ganga、Manas K. Santra、Asish K. Bhattacharya

  DOI：10.1039/c8ra06238b

  日期：——

  2 were isolated from the leaves of Vernonia arborea. Several diverse Michael adducts (3–22) and Heck arylation analogs (23–34) of 1 have been synthesized by reacting with various amines and aryl iodides, respectively and were assayed for their in vitro anticancer activities against human breast cancer cell lines MCF7 and MDA-MB-231. Among all the synthesized analogs, Michael adducts 9 and 10 showed

  从斑鸠菊的叶子中分离出含有α-亚甲基-γ-内酯、zaluzanin D 1和zaluzanin C 2的倍半萜内酯。通过分别与各种胺和芳基碘化物反应合成了几种不同的迈克尔加合物 ( 3-22 ) 和1的Heck 芳基化类似物 ( 23-34 )，并测定了它们对人乳腺癌细胞系 MCF7和MDA-MB-231。在所有合成的类似物中，迈克尔加合物9和10与1相比显示出更好的抗癌活性。然而，在这些化合物中，只有10对正常乳腺上皮 MCF10A 细胞的细胞毒性作用最小。我们详细的机理研究表明，化合物9和10通过诱导细胞凋亡发挥其抗增殖活性，从而抑制癌细胞增殖，化合物10可能是设计潜在抗癌化合物的先导化合物。
• Sesquiterpene lactones from Diaspananthus uniflorus (SCH. BIP.) KITAM.
  作者：SHIGERU ADEGAWA、TOSHIO MIYASE、AKIRA UENO

  DOI：10.1248/cpb.35.1479

  日期：——

  Five new guaiane-type sesquiterpene lactones, diaspanolides A (V) and B (VI) and diaspanosides A (VIII), B (IX) and C (X), have been isolated from Diaspananthus uniflorus (SCH. BIP.) KITAM. (Compositae), together with five known compounds, costunolide (I), reynosin (II), dehydrocostuslactone (III), 11, 13α-dihydrozaluzanin C (IV) and glucozaluzanin C (VII). The structures were determined on the basis of spectral data and some chemical transformations.

  从 Diaspananthus uniflorus (SCH. BIP.) KITAM.（菊科）中分离出五种新的愈创木型倍半萜内酯，即 diaspanolides A (V)和 B (VI)，以及 diaspanosides A (VIII)、B (IX)和 C (X)。(Compositae)中分离出来，同时分离出的还有五种已知化合物：costunolide (I)、reynosin (II)、dehydrocostuslactone (III)、11, 13α-dihydrozaluzanin C (IV) 和 glucozaluzanin C (VII)。这些化合物的结构是根据光谱数据和一些化学变化确定的。
• TOTAL SYNTHESES OF ZALUZANIN C, ZALUZANIN D, AND 3-EPIZALUZANIN C
  作者：Masayoshi Ando、Hiroaki Yamaoka、Kahei Takase

  DOI：10.1246/cl.1982.501

  日期：1982.4.5

  The biologically active guaianolides, zaluzanin C and zaluzanin D, and the stereoisomeric guaianolide, 3-epizaluzanin C, have been synthesized by two different procedures. The stereochemistry at C3 of zaluzanin C has been established to be S configuration by this synthesis.

  通过两种不同的程序合成了具有生物活性的愈创木酚内酯--扎鲁扎宁 C 和扎鲁扎宁 D，以及立体异构愈创木酚内酯--3-表扎鲁扎宁 C。通过这种合成方法，确定了扎鲁扎宁 C C3 的立体化学结构为 S 构型。
• Bioprospection of Phytotoxic Plant-Derived Eudesmanolides and Guaianolides for the Control of <i>Amaranthus viridis</i>, <i>Echinochloa crus-galli</i>, and <i>Lolium perenne</i> Weeds
  作者：Jesús G. Zorrilla、David M. Cárdenas、Carlos Rial、José M.G. Molinillo、Rosa M. Varela、Marco Masi、Francisco A. Macías

  DOI：10.1021/acs.jafc.3c06901

  日期：2024.1.24

  phytotoxicities of a selection of eudesmanolides and guaianolides, including natural products and new derivatives obtained by semisynthesis from plant-isolated sesquiterpene lactones, were evaluated in bioassays against three weeds of concern in agriculture (Amaranthus viridis L., Echinochloa crus-galli L., and Lolium perenne L.). Both eudesmanolides and guaianolides were active against the root and

  在生物测定中，针对农业中关注的三种杂草（Amaranthus viridis L.、Echinochloa crus-galli L. 和 Lolium perenne）评估了一系列 Eudesmanolides 和 guajanolides 的植物毒性，包括天然产物和通过植物分离倍半萜内酯半合成获得的新衍生物L.).Eudesmanolides 和 愈创木内酯 均对所有物种的根和芽生长具有活性，其中 eudesmanolides 普遍表现出改进的活性。用作阳性对照的除草剂获得的 IC50 值（分别在根和芽生长时，A. viridis：27.8 和 85.7 μM;E. crus-galli：167.5 和 288.2 μM;L. perenne： 99.1 和 571.4 μM）在大多数病例中得到改善。讨论了结构-活性关系，发现 A 环和 C-13 的羟基化以及羟基的位置、数量和方向以及
• Sesquiterpene Lactones with Potential Use as Natural Herbicide Models. 2. Guaianolides
  作者：Francisco A. Macías、Juan C. G. Galindo、Diego Castellano、Raúl F. Velasco

  DOI：10.1021/jf0005364

  日期：2000.11.1

  A structure-activity study to evaluate the effect of 17 guaianolide sesquiterpene lactones (in a range of 100-0.001 muM) on the growth and germination of several mono- and dicotyledon target species is accomplished. Results are compared with those obtained in the same bioassay with an internal standard, the commercial herbicide Logran, to validate the results with a known active formulation and to compare the results with a commercial product to test their potential use as natural herbicide models. Specific conditions for the selective mono- or polyhydroxylation of guaianolides using the SeO2/tert-butyl hydroperoxide system are presented and discussed. The high regio- and stereoselectivities of the reaction are explained through the specific structural requirements of the bulky first adduct formed during the ene reaction. These compounds appear to have deeper effects on the growth of either monocots or dicots than the previously tested germacranolides. Otherwise, the lactone group seems to be necessary for the activity, though it does not necessarily need to be unsaturated. However, the presence of a second and easily accessible unsaturated carbonyl system greatly enhances the inhibitory activity. Lipophilicity and the stereochemistry of the possible anchoring sites are also crucial factors for the activity. Finally, the levels of growth inhibition obtained with some compounds on dicots or monocots are totally comparable to those of Logran and allow proposing them as lead compounds.