Pseudoginsenoside F11

Last updated
Pseudoginsenoside F11
Pseudoginsenoside F11.svg
Names
IUPAC name
(24R)-3β,12β,25-Trihydroxy-20,24-epoxydammaran-6α-yl α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside
Systematic IUPAC name
(2S,3R,4R,5R,6S)-2-{[(2R,3R,4S,5S,6R)-1-({(1S,3aR,3bR,5S,5aR,7S,9aR,9bR,11R,11aR)-7,11-Dihydroxy-1-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethylhexadecahydro-5H-cyclopenta[a]phenanthren-5-yl}oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol
Other names
Ginsenoside A1
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.208.747 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 683-240-4
PubChem CID
  • InChI=1S/C42H72O14/c1-19-28(46)30(48)32(50)35(52-19)55-33-31(49)29(47)23(18-43)54-36(33)53-22-17-41(8)24(39(6)13-11-25(45)37(2,3)34(22)39)16-21(44)27-20(10-14-40(27,41)7)42(9)15-12-26(56-42)38(4,5)51/h19-36,43-51H,10-18H2,1-9H3/t19-,20-,21+,22-,23+,24+,25-,26+,27-,28-,29+,30+,31-,32+,33+,34-,35-,36+,39+,40+,41+,42-/m0/s1
    Key: JBGYSAVRIDZNKA-NKECSCAMSA-N
  • C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@H]3C[C@@]4([C@H](C[C@H]([C@H]5[C@]4(CC[C@@H]5[C@@]6(CC[C@@H](O6)C(C)(C)O)C)C)O)[C@@]7([C@@H]3C([C@H](CC7)O)(C)C)C)C)CO)O)O)O)O)O
Properties
C42H72O14
Molar mass 801.024 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pseudoginsenoside F11 is a chemical natural product found in American ginseng (Panax quinquefolius) but not in Asian ginseng (Panax ginseng), although it has similar properties to the Asian ginseng compound ginsenoside Rf. [1] The molecule is a triterpenoid saponin member of the dammarane family and contains a four-ring rigid skeleton. [1] Compounds in the ginsenoside family are found almost exclusively in plants of the genus Panax. A wide variety of difficult-to-characterize in vitro effects have been reported for the compounds in isolation. [2] [3] Pseudoginsenoside F11 and its derivatives are sometimes referred to as having an ocotillol-type skeleton structure. [1] [4]

Studies in mice have identified antagonistic effects on the actions of other well-characterized drugs, such as scopolamine, [5] morphine, [6] [7] and methamphetamine. [8]

References

  1. 1 2 3 Qi, LW; Wang, CZ; Yuan, CS (June 2011). "Ginsenosides from American ginseng: chemical and pharmacological diversity". Phytochemistry. 72 (8): 689–99. Bibcode:2011PChem..72..689Q. doi:10.1016/j.phytochem.2011.02.012. PMC   3103855 . PMID   21396670.
  2. ↑ Attele, AS; Wu, JA; Yuan, CS (1 December 1999). "Ginseng pharmacology: multiple constituents and multiple actions". Biochemical Pharmacology. 58 (11): 1685–93. doi:10.1016/s0006-2952(99)00212-9. PMID   10571242.
  3. ↑ Christensen, LP (2009). "Ginsenosides chemistry, biosynthesis, analysis, and potential health effects". Advances in Food and Nutrition Research. 55: 1–99. doi:10.1016/S1043-4526(08)00401-4. PMID   18772102.
  4. ↑ Fuzzati, N (5 December 2004). "Analysis methods of ginsenosides". Journal of Chromatography B. 812 (1–2): 119–33. doi:10.1016/j.jchromb.2004.07.039. PMID   15556492.
  5. ↑ Li, Z; Guo, YY; Wu, CF; Li, X; Wang, JH (April 1999). "Protective effects of pseudoginsenoside-F11 on scopolamine-induced memory impairment in mice and rats". The Journal of Pharmacy and Pharmacology. 51 (4): 435–40. doi: 10.1211/0022357991772484 . PMID   10385216. S2CID   12905089.
  6. ↑ Li, Z; Wu, CF; Pei, G; Guo, YY; Li, X (July 2000). "Antagonistic effect of pseudoginsenoside-F11 on the behavioral actions of morphine in mice". Pharmacology Biochemistry and Behavior. 66 (3): 595–601. doi:10.1016/s0091-3057(00)00260-4. PMID   10899376. S2CID   40882518.
  7. ↑ Hao, Y; Yang, JY; Wu, CF; Wu, MF (April 2007). "Pseudoginsenoside-F11 decreases morphine-induced behavioral sensitization and extracellular glutamate levels in the medial prefrontal cortex in mice". Pharmacology Biochemistry and Behavior. 86 (4): 660–6. doi:10.1016/j.pbb.2007.02.011. PMID   17368734. S2CID   32919832.
  8. ↑ Wu, CF; Liu, YL; Song, M; Liu, W; Wang, JH; Li, X; Yang, JY (August 2003). "Protective effects of pseudoginsenoside-F11 on methamphetamine-induced neurotoxicity in mice". Pharmacology Biochemistry and Behavior. 76 (1): 103–9. doi:10.1016/s0091-3057(03)00215-6. PMID   13679222. S2CID   20865626.
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