altissimacoumarin C | 1388627-66-4

• 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: altissimacoumarin C
• 英文别名: 7-[(2R,3R)-2,3-dihydroxy-3,7-dimethyloct-6-enoxy]-6,8-dimethoxychromen-2-one
• CAS: 1388627-66-4
• 化学式: C₂₁H₂₈O₇
• 分子量: 392.449
• InChiKey: NIDLLNZZMATZKI-IIBYNOLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  altissimacoumarin C 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 吡啶 作用下， 反应 3.0h， 以0.8 mg的产率得到[(2R,3R)-1-(6,8-dimethoxy-2-oxochromen-7-yl)oxy-3-hydroxy-3,7-dimethyloct-6-en-2-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Terpenylated Coumarins As SIRT1 Activators Isolated from Ailanthus altissima

  摘要：

  Four new terpenylated coumarins (1-4) were isolated from the stem bark of Ailanthus altissima by bioactivity-guided fractionation using an in vitro SIRT1 deacetylation assay. Their structures were identified as (2'R,3'R)-7-(2',3'-dihydroxy-3',7'-dimethylocta-6'-enyloxy)-6,8-dimethoxycoumarin (1), 6,8-dimethoxy-7-(3',7'-dimethylocta-2',6'-dienyloxy)coumarin (2), (2'R,3'R,6'R)-7-(2',3'-dihydroxy-6',7'-epoxy-3',7'-dimethyloctaoxy)-6,8-dimethoxycoumarin (3), and (2'R,3'R,4'S,5'S)-6,8-dimethoxy-7-(3',7'-dimethyl-4',5'-epoxy-2'-hydroxyocta-6'-enyloxy)coumarin (4). Compounds 1-4 strongly enhanced SIRT1 activity in an in vitro SIRT1-NAD/NADH assay and an in vivo SIRT1-p53 luciferase assay. These compounds also increased the NAD-to-NADH ratio in HEK293 cells. The present results suggest that terpenylated coumarins from A. altissima have a direct stimulatory effect on SIRT1 deacetylation activity and may serve as lead molecules for the treatment of some age related disorders.

  DOI：

  10.1021/np300258u

文献信息

• Monoterpenoid coumarins and monoterpenoid phenylpropanoids from the root bark of <i>Ailanthus altissima</i>
  作者：Zhi-Kang Duan、Bin Lin、Ye-Qin Du、Chuan Li、Xiao-Qi Yu、Xiao-Bian Xue、Qing-Bo Liu、Shao-Jiang Song、Xiao-Xiao Huang

  DOI：10.1039/d0nj04872k

  日期：——

  Three new monoterpenoid coumarins, zantholin A (3), altissimacoumarin P-Q (5, 6), two new monoterpenoid phenylpropanoids, altissmaphenylpropanoids A-B (2, 4), along with two known compounds (7, 8), were obtained from aqueous EtOH extracts of the root bark of Ailanthus altissima. The assignments of their structures were conducted via extensive analyses of the spectroscopic data. The evidence for the

  三个新单萜香豆素，zantholin A（3），altissimacoumarin PQ（5，6），两个新的单萜苯丙altissmaphenylpropanoids AB（2，4），具有两个公知的化合物（沿7，8），从含水乙醇提取物中得到臭椿的根皮。通过对光谱数据的广泛分析来进行结构分配。从丙酮化物分析中获得了化合物1中相对构型的重新分配的证据，该分析还用于确定化合物2中的相对构型。和6。对化合物3和4的相对立体化学，评估了统计程序（DP4 +）的效用。化合物5的相对构型通过NOE差示光谱法和计算方法验证。结合使用Mosher方法，旋光度计算和合理的生物合成途径来确定化合物1-6的绝对构型。此外，测试了化合物对两种肝癌癌细胞系（HepG2和Hep3B）的抗肿瘤作用。
• Terpenylated Coumarins As SIRT1 Activators Isolated from <i>Ailanthus altissima</i>
  作者：Trong-Tuan Dao、Tien-Lam Tran、Jayeon Kim、Phi-Hung Nguyen、Eun-Hee Lee、Junsoo Park、Ik-Soon Jang、Won-Keun Oh

  DOI：10.1021/np300258u

  日期：2012.7.27

  Four new terpenylated coumarins (1-4) were isolated from the stem bark of Ailanthus altissima by bioactivity-guided fractionation using an in vitro SIRT1 deacetylation assay. Their structures were identified as (2'R,3'R)-7-(2',3'-dihydroxy-3',7'-dimethylocta-6'-enyloxy)-6,8-dimethoxycoumarin (1), 6,8-dimethoxy-7-(3',7'-dimethylocta-2',6'-dienyloxy)coumarin (2), (2'R,3'R,6'R)-7-(2',3'-dihydroxy-6',7'-epoxy-3',7'-dimethyloctaoxy)-6,8-dimethoxycoumarin (3), and (2'R,3'R,4'S,5'S)-6,8-dimethoxy-7-(3',7'-dimethyl-4',5'-epoxy-2'-hydroxyocta-6'-enyloxy)coumarin (4). Compounds 1-4 strongly enhanced SIRT1 activity in an in vitro SIRT1-NAD/NADH assay and an in vivo SIRT1-p53 luciferase assay. These compounds also increased the NAD-to-NADH ratio in HEK293 cells. The present results suggest that terpenylated coumarins from A. altissima have a direct stimulatory effect on SIRT1 deacetylation activity and may serve as lead molecules for the treatment of some age related disorders.