Lycopodin | 466-61-5

• 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
• 英文名称: Lycopodin
• CAS: 466-61-5；6883-69-8；18688-24-9；33190-30-6
• 化学式: C₁₆H₂₅NO
• 分子量: 247.381
• InChiKey: BCZFSDNVXODRAJ-XACVMBAXSA-N

物化性质

• 熔点：
  114-115°; mp (racemate) 130-131°
• 比旋光度：
  D -24° (alc)
• 沸点：
  125 °C(Press: 0.2 Torr)
• 密度：
  1.18 g/cm3
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

安全信息

• 海关编码：
  2933990090

制备方法与用途

生物活性

Lycopodine，一种石松 (Lycopodium clavatumspores) 孢子重要的生物活性成分，通过调节难治性前列腺癌细胞中 5-脂氧合酶 (5-lipoxygenase)，极化线粒体膜电位而不调节 p53 活性来诱导细胞凋亡。 Lycopodine 通过激活 caspase-3 诱导细胞凋亡来抑制 HeLa 细胞的增殖。

靶点

Caspase-3

5-Lipoxygenase

体外研究

Lycopodine (5.22-78.3 μg/mL; 12 hours) has 50% viability at 57.62±0.086 μg/mL and 51.46±1.43 μg/mL for PC3 and LnCaP, respectively.
Treated with Lycopodine (74-222 mM; 12 hours), the apoptotic index is with respect to the gradual increase in doses for the PC3 and LnCaP cells.
Lycopodine (74-222 mM; 12 hours) induces cell cycle arrest at G0/G1 phase in PC3 and LnCaP cells.
Lycopodine (0-200 µg/mL; 48 hours) shows cytotoxicity to HeLa cells in a dose and time dependent manner. However, Lycopodine shows minimal cytotoxic effects in normal peripheral blood mononuclear cells (PBMC) even at the highest dose (200 µg/mL).
Lycopodine (100, 200 µg/mL; 24 hours) increases level of Bax and decreases the mitochondrial cytochrome c. This is followed by an increase in expression of cytochrome c in cytosolic fraction. Lycopodine also cleaves the caspase-3 in the total cell lysate, while the expression of Bcl-2 is down regulated.

Cell Viability Assay

Cell Line:	PC3 and LnCaP cells
Concentration:	5.22-78.3 μg/mL
Incubation Time:	12 hours
Result:	Reached 50% viability at 57.62±0.086 μg/mL and 51.46±1.43 μg/mL for PC3 and LnCaP, respectively.

Apoptosis Analysis

Cell Line:	PC3 and LnCaP cells
Concentration:	74, 148, 222 mM
Incubation Time:	12 hours
Result:	The apoptotic index was with respect to the gradual increase in doses.

Cell Cycle Analysis

Cell Line:	PC3 and LnCaP cells
Concentration:	74, 148, 222 mM
Incubation Time:	12 hours
Result:	Arrested growth of the cells at G0/G1 phase in the case of PC3 and LnCaP cells.

Cell Cytotoxicity Assay

Cell Line:	Hela cells and PBMC
Concentration:	0-200 µg/mL
Incubation Time:	48 hours
Result:	A linear increase of the cytotoxicity was along with the increase of time of treatment and also of the dose.

Western Blot Analysis

Cell Line:	HeLa cells
Concentration:	100, 200 µg/mL
Incubation Time:	24 hours
Result:	Increased level of Bax and decreased the mitochondrial cytochrome c.

反应信息

• 作为产物：
  描述：

  7-Methyl-2,3,4,6,7,8-hexahydroquinoline 在 sodium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 23.0h， 生成 Lycopodin
  参考文献：
  名称：

  Schumann, Dieter; Mueller, Hans-Juergen; Naumann, Anneliese, Liebigs Annalen der Chemie, 1982, # 9, p. 1700 - 1705

  摘要：

  DOI：