Kaempferol-3-O-alpha-L-rhamnopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranoside

PLoS One. 2014 Jun 3;9(6):e98559.

Isolation of antiosteoporotic compounds from seeds of Sophora japonica.[Pubmed: 24892557 ]

Chemical investigation of Sophora japonica seeds resulted in the isolation of seven metabolites identified as: genistin (1), sophoricoside (2), sophorabioside (3), sophoraflavonoloside (4), genistein 7,4'-di-O-β-D-glucopyransoide (5), Kaempferol-3-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (6) and rutin (7). Compounds 1, 2 and 5 showed significant estrogenic proliferative effect in MCF-7 cell in sub-cytotoxic concentration range. Compounds 1 and 2 showed minimal cell membrane damaging effect using LDH leakage assay. Accordingly, compound 2 (sophoricoside, (SPH)) was selected for further in-vivo studies as a potential anti-osteoporosis agent. The anti-osteoporotic effect of SPH was assessed in ovarectomized (OVX) rats after oral administration (15 mg/kg and 30 mg/kg) for 45 days compared to estradiol (10 µg/kg) as a positive control. Only in a dose of 30 mg/kg, SPH regained the original mechanical bone hardness compared to normal non-osteoporotic group. However, SPH (15 mg/kg) significantly increased the level of alkaline phosphatase (ALP) to normal level. Treatment with SPH (30 mg/kg) increased the level of ALP to be higher than normal group. SPH (15 mg/kg) did not significantly increase the serum level of osteocalcin (OC) compared to OVX group. On the other hand, treatment with SPH (30 mg/kg) significantly increased the level of OC to 78% higher than normal non-ovarectomized animals group. In addition, SPH (15 mg/kg) decreased the bone resorption marker, acid phosphatase (ACP) to normal level and SPH (30 mg/kg) further diminished the level of serum ACP.
CONCLUSIONS:
Histopathologically, sophoricoside ameliorated the ovarectomy induced osteoporosis in a dose dependent manner. The drug showed thicker bony trabeculae, more osteoid, and more osteoblastic rimming compared to OVX group.

J Asian Nat Prod Res. 2002 Jun;4(2):123-8.

Isolation and identification of antioxidants from Sophora japonica.[Pubmed: 12067157 ]

METHODS AND RESULTS:
A new flavonol triglycoside, Kaempferol-3-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (1), as well as two known kaempferol 3-O-[alpha-L-rhamnopyranosyl-(1 --> 6)]-[beta-D-glucopyranosyl-(1 --> 2)]-beta-D-glucopyranoside (2) and kaempferol 3-O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranoside-7-O-alpha-L-rhamnopyranoside (3), were isolated from the n-BuOH extract of the pericarps of Sophora japonica by bioassay-guided fractionation. The structure of compound 1 was established by UV, IR, MS, and one- and two-dimensional NMR spectroscopy, including DEPT, NOESY, DQF-COSY, TOCSY, HMQC, and HMBC experiments.
CONCLUSIONS:
Compounds 1-3 showed antioxidative activity in DPPH and cytochrome-c assay using HL-60 cell system.