Rhamnocitrin

Rhamnocitrin is a flavonoid isolated from astragalus complanatus R. Br. (Sha-yuan-zi)[1]. Rhamnocitrin is a scavenger of DPPH with an IC50 of 28.38 mM. Rhamnocitrin has anti-oxidant, anti-inflammatory and an-tiatherosclerosis activity[2].

Rhamnocitrin is a monomethoxyflavone that is the 7-methyl ether derivative of kaempferol. It has a role as a plant metabolite. It is a trihydroxyflavone, a member of flavonols and a monomethoxyflavone. It derives from a kaempferol.

Thesolution of compound 3 (150 mg, 0.35 mmol) in 7.0 M methaniloc ammonia(2 mL) was stirred at room temperature for 3 h. The solution was diluted withMeOH (4 mL) and neutralized cautiously with 0.5 M HCl (aq)and then left at roomtemperature for 12 h. The abundant resulting precipitate was recovered byfiltration, washed with water and dried over P2O5 under vacuum to give 4 (102 mg, 97percent) asyellow powder, mp:172-173C. IR (cm-1): 3481, 3274, 2926, 2854, 1609, 1587, 1503, 1415, 1355, 1231, 1164. H NMR (400 MHz, DMSO-d6):δ = 12.47 (s, 1H, OH-5), 10.14 (s, 1H, OH-4′), 9.51 (s, 1H, OH-3), 8.08 (d, J= 8.8 Hz, 2H, H-2′, 6′), 6.93 (d, J = 8.8 Hz, 2H, H-3′, 5′), 6.75 (d, J= 2.0 Hz, 1H, H-8), 6.35 (d, J = 2.0 Hz, 1H, H-6), 3.86 (s, 3H, OCH3-7).13CNMR (150 MHz, DMSO-d6): δ = 176.04 (C-4), 164.91 (C-7), 160.38 (C-5), 159.32 (C-4′), 156.11 (C-9), 147.28 (C-2), 135.96 (C-3), 129.58 (C-2′, 6′), 121.58 (C-1′), 115.46 (C-3′, 5′), 104.04 (C-10), 97.46 (C-6), 92.03 (C-8), 56.02(OCH3-7).ESI-HRMS: 299.0568 [M−H]−(calcd.for C16H11O6:299.0561).Thesolution of compound 3 (150 mg, 0.35 mmol) in 7.0 M methaniloc ammonia(2 mL) was stirred at room temperature for 3 h. The solution was diluted withMeOH (4 mL) and neutralized cautiously with 0.5 M HCl (aq)and then left at roomtemperature for 12 h. The abundant resulting precipitate was recovered byfiltration, washed with water and dried over P2O5 under vacuum to give 4 (102 mg, 97percent) asyellow powder, mp:172-173C. IR (cm-1): 3481, 3274, 2926, 2854, 1609, 1587, 1503, 1415, 1355, 1231, 1164. H NMR (400 MHz, DMSO-d6):delta = 12.47 (s, 1H, OH-5), 10.14 (s, 1H, OH-4?), 9.51 (s, 1H, OH-3), 8.08 (d, J= 8.8 Hz, 2H, H-2?, 6?), 6.93 (d, J = 8.8 Hz, 2H, H-3?, 5?), 6.75 (d, J= 2.0 Hz, 1H, H-8), 6.35 (d, J = 2.0 Hz, 1H, H-6), 3.86 (s, 3H, OCH3-7).13CNMR (150 MHz, DMSO-d6): delta = 176.04 (C-4), 164.91 (C-7), 160.38 (C-5), 159.32 (C-4?), 156.11 (C-9), 147.28 (C-2), 135.96 (C-3), 129.58 (C-2?, 6?), 121.58 (C-1?), 115.46 (C-3?, 5?), 104.04 (C-10), 97.46 (C-6), 92.03 (C-8), 56.02(OCH3-7).ESI-HRMS: 299.0568 [M'H]?(calcd.for C16H11O6:299.0561).

Molecular Weight:300.26
XLogP3:2.2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:300.06338810
Monoisotopic Mass:300.06338810
Topological Polar Surface Area:96.2
Heavy Atom Count:22
Complexity:465
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes