Paeoniflorin

Paeoniflorin
Names
	Other names Paeonia moutan; Paeony root; Peoniflorin
Identifiers
CAS Number	23180-57-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	390957;
ECHA InfoCard	100.041.327
PubChem CID	442534;
UNII	21AIQ4EV64 ;
CompTox Dashboard (EPA)	DTXSID2042648 ;
	InChI InChI=1S/C23H28O11/c1-20-9-22(29)13-7-23(20,32-18-16(27)15(26)14(25)12(8-24)31-18)21(13,19(33-20)34-22)10-30-17(28)11-5-3-2-4-6-11/h2-6,12-16,18-19,24-27,29H,7-10H2,1H3/t12-,13-,14-,15+,16-,18+,19-,20+,21+,22-,23+/m1/s1 Key: YKRGDOXKVOZESV-WRJNSLSBSA-N; InChI=1/C23H28O11/c1-20-9-22(29)13-7-23(20,32-18-16(27)15(26)14(25)12(8-24)31-18)21(13,19(33-20)34-22)10-30-17(28)11-5-3-2-4-6-11/h2-6,12-16,18-19,24-27,29H,7-10H2,1H3/t12-,13-,14-,15+,16-,18+,19-,20+,21+,22-,23+/m1/s1 Key: YKRGDOXKVOZESV-WRJNSLSBBV;
	SMILES O=C(OC[C@@]35[C@@H]4[C@]1(O)O[C@H]5O[C@@](C1)([C@@]3(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C4)C)c6ccccc6;
Properties
Chemical formula	C23H28O11
Molar mass	480.466 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Paeoniflorin is a chemical compound which is one of the major constituents of an herbal medicine derived from Paeonia lactiflora.^[1] It can also be isolated from the fresh water fern Salvinia molesta.^[2]

In Paeonia, it can form new compounds with addition of phenolic substituents.^[3] In a study in female rats, paeoniflorin was found to inhibit the production of testosterone within the ovaries, however does not significantly affect the production of Estradiol.^[4] In mice, paeoniflorin was shown to protect against neuroinflammation and depression-like behavior induced by IFN alpha.^[5]

References

^ Yan, D.; Saito, K.; Ohmi, Y.; Fujie, N.; Ohtsuka, K. (2004). "Paeoniflorin, a novel heat shock protein–inducing compound". Cell Stress & Chaperones. 9 (4): 378–89. doi:10.1379/CSC-51R.1. PMC 1065277. PMID 15633296.
^ Choudhary, M. I.; Naheed, N.; Abbaskhan, A.; Musharraf, S. G.; Siddiqui, H.; Atta-Ur-Rahman (2008). "Phenolic and other constituents of fresh water fern Salvinia molesta". Phytochemistry. 69 (4): 1018–1023. Bibcode:2008PChem..69.1018C. doi:10.1016/j.phytochem.2007.10.028. PMID 18177906.
^ Tanaka, T.; Kataoka, M.; Tsuboi, N.; Kouno, I. (2000). "New monoterpene glycoside esters and phenolic constituents of Paeoniae radix, and increase of water solubility of proanthocyanidins in the presence of paeoniflorin". Chemical & Pharmaceutical Bulletin. 48 (2): 201–207. doi:10.1248/cpb.48.201. PMID 10705504.
^ Takeuchi, Toru; Nishii, Osamu; Okamura, Takashi; Yaginuma, Tsutomu (1991). "Effect of Paeoniflorin, Glycyrrhizin and Glycyrrhetic acid on Ovarian Androgen Production". The American Journal of Chinese Medicine. 19 (1): 73–8. doi:10.1142/S0192415X91000119. PMID 1897494.
^ Paeoniflorin ameliorates interferon-alpha-induced neuroinflammation and depressive-like behaviors in mice.

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[1] Yan, D.; Saito, K.; Ohmi, Y.; Fujie, N.; Ohtsuka, K. (2004). "Paeoniflorin, a novel heat shock protein–inducing compound". Cell Stress & Chaperones. 9 (4): 378–89. doi:10.1379/CSC-51R.1. PMC 1065277. PMID 15633296.

[2] Choudhary, M. I.; Naheed, N.; Abbaskhan, A.; Musharraf, S. G.; Siddiqui, H.; Atta-Ur-Rahman (2008). "Phenolic and other constituents of fresh water fern Salvinia molesta". Phytochemistry. 69 (4): 1018–1023. Bibcode:2008PChem..69.1018C. doi:10.1016/j.phytochem.2007.10.028. PMID 18177906.

[3] Tanaka, T.; Kataoka, M.; Tsuboi, N.; Kouno, I. (2000). "New monoterpene glycoside esters and phenolic constituents of Paeoniae radix, and increase of water solubility of proanthocyanidins in the presence of paeoniflorin". Chemical & Pharmaceutical Bulletin. 48 (2): 201–207. doi:10.1248/cpb.48.201. PMID 10705504.

[4] Takeuchi, Toru; Nishii, Osamu; Okamura, Takashi; Yaginuma, Tsutomu (1991). "Effect of Paeoniflorin, Glycyrrhizin and Glycyrrhetic acid on Ovarian Androgen Production". The American Journal of Chinese Medicine. 19 (1): 73–8. doi:10.1142/S0192415X91000119. PMID 1897494.

[5] Paeoniflorin ameliorates interferon-alpha-induced neuroinflammation and depressive-like behaviors in mice.

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Names

Other names Paeonia moutan Paeony root Peoniflorin
Identifiers
CAS Number	23180-57-6^Y
3D model (JSmol)	Interactive image
ChemSpider	390957
ECHA InfoCard	100.041.327
PubChem CID	442534
UNII	21AIQ4EV64^Y
CompTox Dashboard (EPA)	DTXSID2042648
InChI InChI=1S/C23H28O11/c1-20-9-22(29)13-7-23(20,32-18-16(27)15(26)14(25)12(8-24)31-18)21(13,19(33-20)34-22)10-30-17(28)11-5-3-2-4-6-11/h2-6,12-16,18-19,24-27,29H,7-10H2,1H3/t12-,13-,14-,15+,16-,18+,19-,20+,21+,22-,23+/m1/s1 Key: YKRGDOXKVOZESV-WRJNSLSBSA-N InChI=1/C23H28O11/c1-20-9-22(29)13-7-23(20,32-18-16(27)15(26)14(25)12(8-24)31-18)21(13,19(33-20)34-22)10-30-17(28)11-5-3-2-4-6-11/h2-6,12-16,18-19,24-27,29H,7-10H2,1H3/t12-,13-,14-,15+,16-,18+,19-,20+,21+,22-,23+/m1/s1 Key: YKRGDOXKVOZESV-WRJNSLSBBV
SMILES O=C(OC[C@@]35[C@@H]4[C@]1(O)O[C@H]5O[C@@](C1)([C@@]3(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C4)C)c6ccccc6
Properties
Chemical formula	C₂₃H₂₈O₁₁
Molar mass	480.466 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references