# Forsythoside B

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> Markdown URL: https://mediated.wiki/source/Forsythoside_B.md
> Source: https://en.wikipedia.org/wiki/Forsythoside_B
> Source revision: 1330279661
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Short description|Chemical compound}}
{{Drugbox
| drug_name = 
| type = 
| IUPAC_name = <nowiki>[(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</nowiki>
| image = Forsythoside-B_structure.png
| image_class = skin-invert-image
| width = 300
<!--Clinical data-->| alt = 
| caption = 
| tradename = 
| MedlinePlus = 
| licence_EU = 
| licence_US = 
| pregnancy_AU = 
| pregnancy_US = 
| pregnancy_category = 
| legal_US = 
| legal_status = <!--Pharmacokinetic data-->
| bioavailability = 
| metabolism = 
| elimination_half-life = 
| excretion = <!--Identifiers-->
| CAS_number = 81525-13-5
| PubChem = 23928102
| ChEMBL = 
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| UNII = 
| DrugBank = 
| ChemSpiderID = 22912890
<!--Chemical data-->
| C = 34
| H = 44
| O = 19
| SMILES = 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
| StdInChI = 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
| StdInChIKey = 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](/source/Lamiales) such as ''[Marrubium](/source/Marrubium) alysson'', ''[Phlomis](/source/Phlomis) armeniaca'', ''[Scutellaria](/source/Scutellaria) salviifolia'', ''[Phlomoides tuberosa](/source/Phlomoides_tuberosa)'', ''[Phlomoides](/source/Phlomoides) rotata'', ''[Pedicularis](/source/Pedicularis) longiflora'' and ''[Teucrium](/source/Teucrium) chamaedrys'', several of which are used in [Chinese traditional medicine](/source/Chinese_traditional_medicine) in preparations such as '''Shuanghuanglian''' (双黄连). It acts as an inhibitor of inflammatory mediators such as [TNF-alpha](/source/TNF-alpha), [IL-6](/source/Interleukin_6), [IκB](/source/I%CE%BAB) and [NF-κB](/source/NF-%CE%BAB), as well as the temperature sensitive channel [TRPV3](/source/TRPV3), but also activates the [RhoA](/source/Transforming_protein_RhoA)/[ROCK](/source/Rho-associated_protein_kinase) signaling pathway which can cause hypersensitivity reactions when it is injected intravenously.<ref>{{cite journal | vauthors = Caliş I, Hosny M, Khalifa T, Rüedi P | title = Phenylpropanoid glycosides from Marrubium alysson | journal = Phytochemistry | volume = 31 | issue = 10 | pages = 3624–6 | date = October 1992 | pmid = 1368865 | doi = 10.1016/0031-9422(92)83740-p }}</ref><ref>{{cite journal | vauthors = Saracoglu I, Inoue M, Calis I, Ogihara Y | title = Studies on constituents with cytotoxic and cytostatic activity of two Turkish medicinal plants Phlomis armeniaca and Scutellaria salviifolia | journal = Biological & Pharmaceutical Bulletin | volume = 18 | issue = 10 | pages = 1396–400 | date = October 1995 | pmid = 8593444 | doi = 10.1248/bpb.18.1396 | doi-access = free | hdl = 11655/19381 | hdl-access = free }}</ref><ref>{{cite journal | vauthors = Jiang WL, Fu FH, Xu BM, Tian JW, Zhu HB | title = Cardioprotection with forsythoside B in rat myocardial ischemia-reperfusion injury: relation to inflammation response | journal = Phytomedicine | volume = 17 | issue = 8–9 | pages = 635–9 | date = July 2010 | pmid = 19959348 | doi = 10.1016/j.phymed.2009.10.017 }}</ref><ref>{{cite journal | vauthors = Jiang WL, Zhang SP, Zhu HB | title = Forsythoside B protects against experimental sepsis by modulating inflammatory factors | journal = Phytotherapy Research | volume = 26 | issue = 7 | pages = 981–7 | date = July 2012 | pmid = 22147417 | doi = 10.1002/ptr.3668 | s2cid = 32769238 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Dimitrova P, Kostadinova E, Milanova V, Alipieva K, Georgiev M, Ivanovska N | title = Antiinflammatory properties of extracts and compounds isolated from Verbascum xanthophoeniceum Griseb | journal = Phytotherapy Research | volume = 26 | issue = 11 | pages = 1681–7 | date = November 2012 | pmid = 22389249 | doi = 10.1002/ptr.4641 | s2cid = 206428570 }}</ref><ref>{{cite journal | vauthors = Frezza C, Venditti A, Matrone G, Serafini I, Foddai S, Bianco A, Serafini M | title = Iridoid glycosides and polyphenolic compounds from Teucrium chamaedrys L | journal = Natural Product Research | volume = 32 | issue = 13 | pages = 1583–1589 | date = July 2018 | pmid = 29058476 | doi = 10.1080/14786419.2017.1392948 | s2cid = 46602138 | url = https://figshare.com/articles/journal_contribution/5527183 | url-access = subscription }}</ref><ref>{{cite journal | vauthors = Zhang H, Sun X, Qi H, Ma Q, Zhou Q, Wang W, Wang K | title = Pharmacological Inhibition of the Temperature-Sensitive and Ca<sup>2+</sup>-Permeable Transient Receptor Potential Vanilloid TRPV3 Channel by Natural Forsythoside B Attenuates Pruritus and Cytotoxicity of Keratinocytes | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 368 | issue = 1 | pages = 21–31 | date = January 2019 | pmid = 30377214 | doi = 10.1124/jpet.118.254045 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Liu JX, Li X, Yan FG, Pan QJ, Yang C, Wu MY, Li G, Liu HF | display-authors = 6 | title = Protective effect of forsythoside B against lipopolysaccharide-induced acute lung injury by attenuating the TLR4/NF-κB pathway | journal = International Immunopharmacology | volume = 66 | pages = 336–346 | date = January 2019 | pmid = 30521962 | doi = 10.1016/j.intimp.2018.11.033 | s2cid = 56141148 }}</ref><ref>{{cite journal | vauthors = Han J, Zhang Y, Pan C, Xian Z, Pan C, Zhao Y, Li C, Yi Y, Wang L, Tian J, Liu S, Wang D, Meng J, Liang A | display-authors = 6 | title = Forsythoside A and Forsythoside B Contribute to Shuanghuanglian Injection-Induced Pseudoallergic Reactions through the RhoA/ROCK Signaling Pathway | journal = International Journal of Molecular Sciences | volume = 20 | issue = 24 | date = December 2019 | page = 6266 | pmid = 31842335 | doi = 10.3390/ijms20246266|pmc=6940901 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Yan K, Sun X, Wang G, Liu Y, Wang K | title = Pharmacological Activation of Thermo-Transient Receptor Potential Vanilloid 3 Channels Inhibits Hair Growth by Inducing Cell Death of Hair Follicle Outer Root Sheath | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 370 | issue = 2 | pages = 299–307 | date = August 2019 | pmid = 31152005 | doi = 10.1124/jpet.119.258087 | doi-access = free }}</ref>

== See also ==
* [Xiyanping](/source/Xiyanping)

== References ==
{{Reflist}}

Category:Hydroxycinnamic acid esters
Category:Hydroxycinnamic acid glycosides
Category:Polyols

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Adapted from the Wikipedia article [Forsythoside B](https://en.wikipedia.org/wiki/Forsythoside_B) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Forsythoside_B?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.