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Isolation of antiosteoporotic compounds from seeds of Sophora japonica.

Abdallah HM, Al-Abd AM, Asaad GF, Abdel-Naim AB, El-halawany AM - PLoS ONE (2014)

Bottom Line: SPH (15 mg/kg) did not significantly increase the serum level of osteocalcin (OC) compared to OVX 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.The drug showed thicker bony trabeculae, more osteoid, and more osteoblastic rimming compared to OVX group.

View Article: PubMed Central - PubMed

Affiliation: Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah, Saudi Arabia; Department of Pharmacognosy, Faculty of Pharmacy, Cairo University, Cairo, Egypt.

ABSTRACT
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. 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.

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Chemical structure for compounds isolated from Sophora japonica seeds.
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pone-0098559-g001: Chemical structure for compounds isolated from Sophora japonica seeds.

Mentions: The methanol extract of S. japonica seeds was partitioned with chloroform and the remaining water soluble portion was fractionated on a Diaion HP-20 column to afford 25%, 50%, and 100% methanol fractions. The 50% methanol fraction was purified on several silica gel, ODS and Sephadex LH-20 columns to produce seven compounds. The identification of isolated compounds was achieved systematically by trying the response of the isolated compounds to different spray reagents using thin layer chromatography (TLC) aiming to identify the nature of the compounds. 1H NMR study was carried out for all compounds to, un-ambiguously, identify its structure. Compounds with more than one sugar moiety such as compounds 3–6 were further subjected to 13C NMR measurement to clearly identify site of sugar attachment (Figure S1–S5). The identity of compounds was confirmed by comparing NMR data with previously reported ones as (Figure S1–S5, Table S1), genistin (1) [16], sophoricoside (2) [17], sophorabioside (3), sophoraflavonoloside (4), genistein 7,4’-di-O-β-D-glucopyransoide (5) [18], kaempferol 3-O-α–L-rhamnopyranosyl(1→6)β-D-glucopyranosyl(1→2)β-D-glucopyranoside (6) [19], and rutin (7) (Fig. 1). Purity of all isolated compounds was confirmed through HPLC analysis. The purity of compounds 4–6 was over 92%, while that of the remaining compounds was over 95% as indicated by their HPLC chromatograms (Figure S6).


Isolation of antiosteoporotic compounds from seeds of Sophora japonica.

Abdallah HM, Al-Abd AM, Asaad GF, Abdel-Naim AB, El-halawany AM - PLoS ONE (2014)

Chemical structure for compounds isolated from Sophora japonica seeds.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4043785&req=5

pone-0098559-g001: Chemical structure for compounds isolated from Sophora japonica seeds.
Mentions: The methanol extract of S. japonica seeds was partitioned with chloroform and the remaining water soluble portion was fractionated on a Diaion HP-20 column to afford 25%, 50%, and 100% methanol fractions. The 50% methanol fraction was purified on several silica gel, ODS and Sephadex LH-20 columns to produce seven compounds. The identification of isolated compounds was achieved systematically by trying the response of the isolated compounds to different spray reagents using thin layer chromatography (TLC) aiming to identify the nature of the compounds. 1H NMR study was carried out for all compounds to, un-ambiguously, identify its structure. Compounds with more than one sugar moiety such as compounds 3–6 were further subjected to 13C NMR measurement to clearly identify site of sugar attachment (Figure S1–S5). The identity of compounds was confirmed by comparing NMR data with previously reported ones as (Figure S1–S5, Table S1), genistin (1) [16], sophoricoside (2) [17], sophorabioside (3), sophoraflavonoloside (4), genistein 7,4’-di-O-β-D-glucopyransoide (5) [18], kaempferol 3-O-α–L-rhamnopyranosyl(1→6)β-D-glucopyranosyl(1→2)β-D-glucopyranoside (6) [19], and rutin (7) (Fig. 1). Purity of all isolated compounds was confirmed through HPLC analysis. The purity of compounds 4–6 was over 92%, while that of the remaining compounds was over 95% as indicated by their HPLC chromatograms (Figure S6).

Bottom Line: SPH (15 mg/kg) did not significantly increase the serum level of osteocalcin (OC) compared to OVX 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.The drug showed thicker bony trabeculae, more osteoid, and more osteoblastic rimming compared to OVX group.

View Article: PubMed Central - PubMed

Affiliation: Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah, Saudi Arabia; Department of Pharmacognosy, Faculty of Pharmacy, Cairo University, Cairo, Egypt.

ABSTRACT
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. 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.

Show MeSH
Related in: MedlinePlus