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原人参二醇

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原人参二醇
IUPAC名
(3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol
系统名
(1R,2R,5S,7R,10R,11R,14S,15R,16R)-14-[(1S)-1-hydroxy-1,5-dimethyl-4-hexenyl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.02,7.011,15]heptadecane-5,16-diol

(1R,2R,5S,7R,10R,11R,14S,15R,16R)-2,6,6,10,11-五甲基-14-[(1S)-1,5-二甲基-1-羟基-4-己烯基]四环[8.7.0.02,7.011,15]-5,16-十七烷二醇

别名 Dammar-24-ene-3β,12β,20-triol
识别
缩写 PPD
CAS号 7755-01-3  checkY
PubChem 9920281
ChemSpider 8095918
SMILES
 
  • CC(=CCC[C@@](C)([C@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)O)C)O)C
InChI
 
  • 1/C30H52O3/c1-19(2)10-9-14-30(8,33)20-11-16-29(7)25(20)21(31)18-23-27(5)15-13-24(32)26(3,4)22(27)12-17-28(23,29)6/h10,20-25,31-33H,9,11-18H2,1-8H3/t20-,21+,22-,23+,24-,25-,27-,28+,29+,30+/m0/s1
InChIKey PYXFVCFISTUSOO-VUFVRDRTBZ
ChEBI 76237
性质
化学式 C30H52O3
摩尔质量 460.73 g·mol−1
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

原人参二醇ProtopanaxadiolPPD)是一种甾体化合物,分子式C
30
H
52
O
3
,具有达玛烷骨架。是人参二醇型人参皂苷的骨架分子。[1][2]原人参三醇的不同之处在于,它的6号位没有羟基。

原人参二醇对人体的影响尚不清楚。一项研究表明,它对内皮细胞有迅速的非基因性影响,与糖皮质激素受体雌激素受体β英语Oestrogen receptor beta结合。这项研究还显示,它能使细胞内钙离子浓度增加。[3]

上海中药创新研究中心英语Shanghai Innovative Research Center of Traditional Chinese Medicine的“优欣定”产品内为高纯度原人参二醇,号称是首个单分子抗抑郁中药。药物在2023年5月进入III期实验。[4]II期临床实验结果于2024年11月发布。[5][6]

上中创研的一篇论文描述了此药的口服剂量和IIa期志愿者血浆浓度的线性关系,但未给出半衰期、生物利用率等信息。[7]在大鼠中,本品口服生物利用率约48%,半衰期为6.25小时(作为原人参二、三醇均有的混合提取物喂食)。单独口服时,生物利用率降低到20.7–36.8%。[8]

See also

参考资料

  1. ^ Shibata, S.; Tanaka, O.; Sado, M.; Tsushima, S. The genuine sapogenin of ginseng. Tetrahedron Letters. 1963, 4 (12): 795–800. doi:10.1016/S0040-4039(01)90718-X. 
  2. ^ Tanaka, O.; Nagai, M.; Shibata, S. Stereochemistry of protopanaxadiol, a genuine sapogenin of ginseng. Tetrahedron Letters. 1964, 5 (33–34): 2291–7. doi:10.1016/S0040-4039(00)71705-9. 
  3. ^ Leung; et al. Protopanaxadiol and protopanaxatriol bind to glucocorticoid and oestrogen receptors in endothelial cells. British Journal of Pharmacology. Wiley Online Library. [29 October 2012]. (原始内容存档于2016-03-04). 
  4. ^ 文汇. 全球首个单分子抗抑郁中药进入临床Ⅲ期研究,由人参开发而来_腾讯新闻. news.qq.com. 2023-05-23 (中文(中国大陆)). 
  5. ^ Youxinding. synapse.patsnap.com (英语). 
  6. ^ Dong, Z; Shen, Q; Zhu, H; Yang, Z; Lv, J; Feng, R; Bai, X; Huang, G; Hu, Y; Pan, L; Zhao, G; Jia, W; Wang, X. Efficacy and safety of YOXINTINE for depression: A double-blinded, randomized, placebo-controlled, phase 2 clinical trial.. Phytomedicine : international journal of phytotherapy and phytopharmacology. 14 November 2024, 136: 156204. PMID 39580994. doi:10.1016/j.phymed.2024.156204. 
  7. ^ Ling, J; Yu, Y; Zhu, J; Li, Y; Ling, L; Wang, L; Xu, C; Duan, G. A highly sensitive HPLC-MS/MS method for quantification of 20(S)-protopanaxadiol in human plasma and its application in phase IIa clinical trial of a novel antidepressant agent.. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 15 September 2016, 1031: 214–220. PMID 27507666. doi:10.1016/j.jchromb.2016.07.044. 
  8. ^ Kong, LT; Wang, Q; Xiao, BX; Liao, YH; He, XX; Ye, LH; Liu, XM; Chang, Q. Different pharmacokinetics of the two structurally similar dammarane sapogenins, protopanaxatriol and protopanaxadiol, in rats.. Fitoterapia. April 2013, 86: 48–53. PMID 23391424. doi:10.1016/j.fitote.2013.01.019.