salpichrolide A | 141895-08-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: salpichrolide A
• 英文别名: (1S,2R,7R,9S,11R)-15-[(1S)-1-[(1S,2R,4R,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-2-methyl-8-oxapentacyclo[9.8.0.02,7.07,9.012,17]nonadeca-4,12(17),13,15-tetraen-3-one
• CAS: 141895-08-1
• 化学式: C₂₈H₃₄O₅
• 分子量: 450.575
• InChiKey: CPHPTFZOHUSPRV-ZSVXBLANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  salpichrolide A 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (4aR,4bS,10bR,12R,12aR)-12,12a-Dihydroxy-4a-methyl-8-[(S)-1-((2R,4R,5S)-4,5,6-trihydroxy-4,5-dimethyl-tetrahydro-pyran-2-yl)-ethyl]-4a,4b,5,6,10b,11,12,12a-octahydro-1H-chrysen-4-one
  参考文献：
  名称：

  New Hydroxylated Withanolides from Salpichroa origanifolia

  摘要：

  From the leaves of Salpichroa origanifolia three new withanolides, (20S,22R,24S,25S,26R)-5 alpha,6 alpha:22,26:24,25-triepoxy-15,26-dihydroxy-17(13-->18)-abeo-ergosta-2,13,15,17-tetraen-1-one (salpichrolide G, 1), (20S,22R,24S,25R)-5 alpha,6 alpha: 22,26-diepoxy-24,25,26-trihydroxy-17(13-->18)abeo-ergosta-2,13,15,17-tetraen-1-one (salpichrolide H, 2), and (20S,22R,25S)-5 alpha,6 alpha:22,26-diepoxy-25,26-dihydroxy-17(13-->18)-abeo-ergosta-2,13,15,17,23-pentaen-1-one (salpichrolide I, 3), were isolated and characterized by spectroscopic methods and with the aid of molecular modeling. The latter two compounds were obtained as an epimeric mixture at C-26.

  DOI：

  10.1021/np970387s

文献信息

• Biotransformation of Salpichrolides A, C, and G by Three Filamentous Fungi
  作者：Ana V. Basso、Viviana E. Nicotra、Andrés Parra、Antonio Martínez、Antonia Fernández-Vivas

  DOI：10.1021/acs.jnatprod.6b00310

  日期：2016.6.24

  of salpichrolide A (1) with Rhizomucor miehei produced hydroxylation in rings B and C (C-7 and C-12) and led to C-5–C-6 epoxide opening, while incubation of salpichrolides C (2) and G (3) with R. miehei led to epoxide opening at the C-24–C-25 and C-5–C-6 positions, respectively. Biotransformation of salpichrolide A (1) with Cunninghamella elegans produced stereoselective hydroxylated, oxidized, and reduced

  salpichrolide A（孵育1）与曼赫根毛霉生产羟化环B和C（C-7和C-12），并导致C-5-C-6环氧化物开环，而salpichrolides孵育C（2）和G（3）与米黑麦芽孢杆菌分别导致C-24–C-25和C-5–C-6位置处的环氧化物开放。Salpichrolide A（1）与秀丽线虫的生物转化在A，B和C环的不同位置和C-5–C-6环氧开口处产生了立体选择性的羟基化，氧化和还原衍生物。此外，从沙必利特A的孵育中获得了C-5–C-6或C-24–C-25位置的选择性环氧化物开口（1）与弯孢菌（Curvularia lunata）。
• Lethal and Sublethal Effects of Withanolides from <i>Salpichroa origanifolia</i> and Analogues on <i>Ceratitis capitata</i>
  作者：Silvina Bado、Graciela Mareggiani、Nicolás Amiano、Gerardo Burton、Adriana S. Veleiro

  DOI：10.1021/jf035508a

  日期：2004.5.1

  Biological effects on Ceratitis capitata were evaluated for several withanolides isolated from Salpichroa origanifolia (Solanaceae), (20S,22R,24S,25S,26R)-5alpha,6alpha:22,26:24,25-triepoxy-26-hydroxy-17(13-->18)-abeo-ergosta-2,13,15,17-tetraen-1 -one (salpichrolide A, 1), (20S,22R,24S,25S,26R)-22,26:24,25-diepoxy-5alpha,6beta,26-trihydroxy-17(13-->18)-abeo-ergosta-2,13,15,17-tetraen-1-one (salpichrolide C, 2), (20S,22R,24S,25S,26R)-5alpha,6alpha;22,26:24,25-triepoxy-15,26-dihydroxy-17(13-->18)abeo-ergosta-2,13,15,17-tetraen-1-one (salpichrolide G, 3), and (20S,22R,24S,25S,26R)-5alpha,6alpha:22,26:24,25-triepoxy-1,26-dihydroxy-17(13-->18)-abeo-ergosta-2,13,15,17-tetraene (salpichrolide B, 5), and for chemically modified analogues. Influence of chemical modifications on development delay was analyzed. The compounds were incorporated into the larval diet and the adults' drinking water. Significant development delays from larvae to puparia were observed in treatments with the natural withanolides salpichrolides A, C, and G (1-3) at a concentration of 500 ppm. Salpichrolide B (5) was the most toxic compound, the highest mortality (95%) being observed at the larval stage. Exposure of adults to drinking water containing natural withanolides 1-3 and 5 produced mortality in all cases.
• Withanolides from <i>Salpichroa origanifolia</i>
  作者：M. Cristina Tettamanzi、Adriana S. Veleiro、Juana R. de la Fuente、Gerardo Burton

  DOI：10.1021/np010010t

  日期：2001.6.1

  Five new withanolides, 5 alpha ,6 alpha :22,26: 24,25-triepoxy-16 alpha ,26-dihydroxy-18(13 --> 17)-abeo-ergosta-2, 13-dien-1-one (salpichrolide N, 1), 5 alpha ,6 alpha :22,26:24,25-triepoxi-15 alpha ,26-dihydroxyergosta-2,16-dien-1-one (salpichrolide L, 2), 5 alpha ,6 alpha :22,26-diepoxi-24,25,26-trihydroxy-17(13 --> 18)-abeo-ergosta-2,13,15,17-tetrarn-1-one (salpichrolide M, 3a), 5 alpha ,6 alpha :22,25:22,26-triepoxy-24-hydroxy-17(13 --> 18)-abeo-ergosta-2,13,15,17-tetraen-1-one (salpichrolide J, 4), and 5 alpha ,6 alpha :22,26-diepoxy-22,24,25-trihydroxy-17(13 --> 18)-abeo-ergosta-2,13,15,17-tetraen-1-one (salpichrolide K, 5), were isolated from the leaves of Salpichroa origanifolia and characterized by a combination of spectroscopic (1D and 2D NMR, MS) and chemical methods.