Chemistry:Forsythoside B

Forsythoside B
Identifiers
	IUPAC name [(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	81525-13-5;
PubChem CID	23928102;
ChemSpider	22912890;
Chemical and physical data
Formula	C34H44O19
Molar mass	756.707 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	InChI 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;

Short description: Chemical compound

Forsythoside B is a natural product from the phenylpropanoid glycoside group, which is found in a number of plant species 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]

References

↑ "Phenylpropanoid glycosides from Marrubium alysson". Phytochemistry 31 (10): 3624–6. October 1992. doi:10.1016/0031-9422(92)83740-p. PMID 1368865.
↑ "Studies on constituents with cytotoxic and cytostatic activity of two Turkish medicinal plants Phlomis armeniaca and Scutellaria salviifolia". Biological & Pharmaceutical Bulletin 18 (10): 1396–400. October 1995. doi:10.1248/bpb.18.1396. PMID 8593444.
↑ "Cardioprotection with forsythoside B in rat myocardial ischemia-reperfusion injury: relation to inflammation response". Phytomedicine 17 (8–9): 635–9. July 2010. doi:10.1016/j.phymed.2009.10.017. PMID 19959348.
↑ "Forsythoside B protects against experimental sepsis by modulating inflammatory factors". Phytotherapy Research 26 (7): 981–7. July 2012. doi:10.1002/ptr.3668. PMID 22147417.
↑ "Antiinflammatory properties of extracts and compounds isolated from Verbascum xanthophoeniceum Griseb". Phytotherapy Research 26 (11): 1681–7. November 2012. doi:10.1002/ptr.4641. PMID 22389249.
↑ "Iridoid glycosides and polyphenolic compounds from Teucrium chamaedrys L". Natural Product Research 32 (13): 1583–1589. July 2018. doi:10.1080/14786419.2017.1392948. PMID 29058476. https://figshare.com/articles/journal_contribution/5527183.
↑ "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. January 2019. doi:10.1124/jpet.118.254045. PMID 30377214.
↑ "Protective effect of forsythoside B against lipopolysaccharide-induced acute lung injury by attenuating the TLR4/NF-κB pathway". International Immunopharmacology 66: 336–346. January 2019. doi:10.1016/j.intimp.2018.11.033. PMID 30521962.
↑ "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. December 2019. doi:10.3390/ijms20246266. PMID 31842335.
↑ "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. August 2019. doi:10.1124/jpet.119.258087. PMID 31152005.

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Original source: https://en.wikipedia.org/wiki/Forsythoside B. Read more

[1] "Phenylpropanoid glycosides from Marrubium alysson". Phytochemistry 31 (10): 3624–6. October 1992. doi:10.1016/0031-9422(92)83740-p. PMID 1368865.

[2] "Studies on constituents with cytotoxic and cytostatic activity of two Turkish medicinal plants Phlomis armeniaca and Scutellaria salviifolia". Biological & Pharmaceutical Bulletin 18 (10): 1396–400. October 1995. doi:10.1248/bpb.18.1396. PMID 8593444.

[3] "Cardioprotection with forsythoside B in rat myocardial ischemia-reperfusion injury: relation to inflammation response". Phytomedicine 17 (8–9): 635–9. July 2010. doi:10.1016/j.phymed.2009.10.017. PMID 19959348.

[4] "Forsythoside B protects against experimental sepsis by modulating inflammatory factors". Phytotherapy Research 26 (7): 981–7. July 2012. doi:10.1002/ptr.3668. PMID 22147417.

[5] "Antiinflammatory properties of extracts and compounds isolated from Verbascum xanthophoeniceum Griseb". Phytotherapy Research 26 (11): 1681–7. November 2012. doi:10.1002/ptr.4641. PMID 22389249.

[6] "Iridoid glycosides and polyphenolic compounds from Teucrium chamaedrys L". Natural Product Research 32 (13): 1583–1589. July 2018. doi:10.1080/14786419.2017.1392948. PMID 29058476. https://figshare.com/articles/journal_contribution/5527183.

[7] "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. January 2019. doi:10.1124/jpet.118.254045. PMID 30377214.

[8] "Protective effect of forsythoside B against lipopolysaccharide-induced acute lung injury by attenuating the TLR4/NF-κB pathway". International Immunopharmacology 66: 336–346. January 2019. doi:10.1016/j.intimp.2018.11.033. PMID 30521962.

[9] "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. December 2019. doi:10.3390/ijms20246266. PMID 31842335.

[10] "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. August 2019. doi:10.1124/jpet.119.258087. PMID 31152005.

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Identifiers

IUPAC name [(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	81525-13-5
PubChem CID	23928102
ChemSpider	22912890
Chemical and physical data
Formula	C₃₄H₄₄O₁₉
Molar mass	756.707 g·mol⁻¹
3D model (JSmol)	Interactive image
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
InChI 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

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