12-epi-lycopodine

• 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: 12-epi-lycopodine
• 英文别名: (1R,2S,10S,13S,15R)-15-methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadecan-11-one
• 化学式: C₁₆H₂₅NO
• 分子量: 247.381
• InChiKey: BCZFSDNVXODRAJ-WZYWGQKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  12-epi-lycopodine 在 间氯过氧苯甲酸 作用下， 生成 (1R,2S,10S,13S,15R)-15-methyl-6-oxido-6-azoniatetracyclo[8.6.0.01,6.02,13]hexadecan-11-one
  参考文献：
  名称：

  鉴定由紫外线照射的副波杆菌血症菌株（来自锯齿状番茄的内生真菌）产生的番茄属生物碱。长寿花

  摘要：

  在Paraboeremia sp。的菌丝体中发现了12- epi- Lycopodine（1），Lycopodium生物碱，Lycopodine（2）和石杉碱A（3）。Lsl3KI076，一种用紫外线照射的副猪嗜血菌菌株。Lsl3，从内生真菌石松藤。变种 longipetiolatum春天。此外，从印度产的Phlegmariurus nummulariifolius（Blume）Ching中分离出了痕量的1，并根据光谱数据阐明了其结构。这是第一份证明新的天然存在的石蒜的报告 生物碱可以从内生真菌获得。

  DOI：

  10.1021/acs.jnatprod.7b00627
• 作为产物：
  描述：

  phlenumdine D 在 盐酸 作用下， 以 水 为溶剂， 反应 49.0h， 以0.5 mg的产率得到12-epi-lycopodine
  参考文献：
  名称：

  Phlenumdines D and E, new Lycopodium alkaloids from Phlegmariurus nummulariifolius, and their regulatory effects on macrophage differentiation during tumor development

  摘要：

  Two new Lycopodium alkaloids, phlenumdines D (1) and E (2), have been isolated from the club moss Phlegmariurus nummulariifolius (Blume) Ching along with ten known compounds (3 -12), and the structures were elucidated by spectroscopic analyses. The absolute configurations of 1 and 2 were established by chemical conversion and modified Mosher's method, respectively. Phlenumdines E (2), A (8), hupermine A (12), and 12-epi-lycopodine-N-oxide (14) exhibited an inhibitory effect on interleukin 10 (IL-10)-induced expression of CD163, a M2 phenotype marker, in human monocyte-derived macrophages (HMDMs).

  DOI：

  10.1016/j.phytol.2018.11.010

文献信息

• Phlenumdines D and E, new Lycopodium alkaloids from Phlegmariurus nummulariifolius, and their regulatory effects on macrophage differentiation during tumor development
  作者：Waka Nakayama、Yukio Fujiwara、Yasuhiro Kosuge、Orawan Monthakantirat、Kazumi Fujikawa、Santi Watthana、Susumu Kitanaka、Toshiaki Makino、Kan’ichiro Ishiuchi

  DOI：10.1016/j.phytol.2018.11.010

  日期：2019.2

  Two new Lycopodium alkaloids, phlenumdines D (1) and E (2), have been isolated from the club moss Phlegmariurus nummulariifolius (Blume) Ching along with ten known compounds (3 -12), and the structures were elucidated by spectroscopic analyses. The absolute configurations of 1 and 2 were established by chemical conversion and modified Mosher's method, respectively. Phlenumdines E (2), A (8), hupermine A (12), and 12-epi-lycopodine-N-oxide (14) exhibited an inhibitory effect on interleukin 10 (IL-10)-induced expression of CD163, a M2 phenotype marker, in human monocyte-derived macrophages (HMDMs).
• Identification of <i>Lycopodium</i> Alkaloids Produced by an Ultraviolet-Irradiated Strain of <i>Paraboeremia</i>, an Endophytic Fungus from <i>Lycopodium serratum</i> var. <i>longipetiolatum</i>
  作者：Kan’ichiro Ishiuchi、Dai Hirose、Takuma Suzuki、Waka Nakayama、Wen-Ping Jiang、Orawan Monthakantirat、Jin-Bin Wu、Susumu Kitanaka、Toshiaki Makino

  DOI：10.1021/acs.jnatprod.7b00627

  日期：2018.5.25

  12-epi-Lycopodine (1), a Lycopodium alkaloid, along with lycopodine (2) and huperzine A (3), were discovered in the mycelium of Paraboeremia sp. Lsl3KI076, a UV-irradiated strain of Paraboeremia sp. Lsl3, an endophytic fungus from Lycopodium serratum Thunb. var. longipetiolatum Spring. Additionally, a trace of 1 was isolated from Phlegmariurus nummulariifolius (Blume) Ching, and the structure was elucidated

  在Paraboeremia sp。的菌丝体中发现了12- epi- Lycopodine（1），Lycopodium生物碱，Lycopodine（2）和石杉碱A（3）。Lsl3KI076，一种用紫外线照射的副猪嗜血菌菌株。Lsl3，从内生真菌石松藤。变种 longipetiolatum春天。此外，从印度产的Phlegmariurus nummulariifolius（Blume）Ching中分离出了痕量的1，并根据光谱数据阐明了其结构。这是第一份证明新的天然存在的石蒜的报告 生物碱可以从内生真菌获得。