Forsythoside B

Last updated
Forsythoside B
Forsythoside-B structure.png
Identifiers
  • [(2R,3R,4R,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C34H44O19
Molar mass 756.707 g·mol−1
3D model (JSmol)
  • C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)O)O)CO[C@H]4[C@@H]([C@](CO4)(CO)O)O)OCCC5=CC(=C(C=C5)O)O)O)O)O)O
  • InChI=1S/C34H44O19/c1-15-24(41)25(42)26(43)32(50-15)53-29-27(44)31(47-9-8-17-3-6-19(37)21(39)11-17)51-22(12-48-33-30(45)34(46,13-35)14-49-33)28(29)52-23(40)7-4-16-2-5-18(36)20(38)10-16/h2-7,10-11,15,22,24-33,35-39,41-46H,8-9,12-14H2,1H3/b7-4+/t15-,22+,24-,25+,26+,27+,28+,29+,30-,31+,32-,33+,34+/m0/s1
  • Key:JMBINOWGIHWPJI-UNSOMVRXSA-N

Forsythoside B is a natural product from the phenylpropanoid/polyphenolic glycoside group, which is found in a number of plant species in the mint order such as Marrubium alysson, Phlomis armeniaca, Scutellaria salviifolia, Phlomoides tuberosa , Phlomoides rotata, Pedicularis longiflora and Teucrium chamaedrys, several of which are used in Chinese traditional medicine in preparations such as Shuanghuanglian (双黄连). It acts as an inhibitor of inflammatory mediators such as TNF-alpha, IL-6, IκB and NF-κB, as well as the temperature sensitive channel TRPV3, but also activates the RhoA/ROCK signaling pathway which can cause hypersensitivity reactions when it is injected intravenously. [1] [2] [3] [4] [5] [6] [7] [8] [9] [10]

See also

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References

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  7. Zhang H, Sun X, Qi H, Ma Q, Zhou Q, Wang W, Wang K (January 2019). "Pharmacological Inhibition of the Temperature-Sensitive and Ca2+-Permeable Transient Receptor Potential Vanilloid TRPV3 Channel by Natural Forsythoside B Attenuates Pruritus and Cytotoxicity of Keratinocytes". The Journal of Pharmacology and Experimental Therapeutics. 368 (1): 21–31. doi: 10.1124/jpet.118.254045 . PMID   30377214.
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  9. Han J, Zhang Y, Pan C, Xian Z, Pan C, Zhao Y, et al. (December 2019). "Forsythoside A and Forsythoside B Contribute to Shuanghuanglian Injection-Induced Pseudoallergic Reactions through the RhoA/ROCK Signaling Pathway". International Journal of Molecular Sciences. 20 (24): 6266. doi: 10.3390/ijms20246266 . PMC   6940901 . PMID   31842335.
  10. Yan K, Sun X, Wang G, Liu Y, Wang K (August 2019). "Pharmacological Activation of Thermo-Transient Receptor Potential Vanilloid 3 Channels Inhibits Hair Growth by Inducing Cell Death of Hair Follicle Outer Root Sheath". The Journal of Pharmacology and Experimental Therapeutics. 370 (2): 299–307. doi: 10.1124/jpet.119.258087 . PMID   31152005.