Paeoniflorin

Paeoniflorin

Names
Other names Paeonia moutan Paeony root Peoniflorin
Identifiers
CAS Number	23180-57-6
ChemSpider	390957
Jmol interactive 3D	Image
PubChem	442534
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	480.47 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. It is one of the major constituents of a 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] Paeoniflorin has antiandrogenic properties. Paeoniflorin inhibits the production of testosterone and promotes the activity of aromatase - the enzyme that converts testosterone into estrogen.^[4]

References

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. 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. Grant; Ramasamy (April 2012). "An Update on Plant Derived Anti-Androgens". International Journal of Endocrinology and Metabolism 10 (2): 497–502. doi:10.5812/ijem.3644. PMC 3693613. PMID 23843810.