New 8-C-p-Hydroxylbenzylflavonol Glycosides from Pumpkin (Cucurbita moschata Duch.) Tendril and Their Osteoclast Differentiation Inhibitory Activities

Abstract

Six new 8-C-p-hydroxybenzylflavonol glycosides were isolated from a hot water extract of pumpkin (Cucurbita moschata Duch.) tendril and elucidated as 8-C-p-hydroxybenzylquercetin 3-O-rutinoside, 8-C-p-hydroxybenzoylquercetin 3-O-β-D-glucopyranoside, 8-C-p-hydroxybenzylkaempferol 3-O-(α-L-rhamnopyranosyl(1→6)-β-D-galactopyranoside, 8-C-p-hydroxybenzoylkaempferol 3-O-rutinoside, 8-C-p-hydroxybenzylisorhamnetin 3-O-rutinoside, and 8-C-p-hydroxybenzylisorhamnetin 3-O-(α-L-rhamnopyranosyl(1→6)-β-D-galactopyranoside. Their chemical structures were determined using nuclear magnetic resonance (NMR) and electrospray ionization-mass spectrometer (ESIMS) analyses. The 8-C-p-hydroxybenzylflavonol glycosides were found to inhibit the receptor activator of nuclear factor-κB (RANKL)-induced osteoclast differentiation of bone marrow derived macrophage (BMDM), an osteoclast progenitor. Additionally, 8-C-p-hydroxybenzylflavonol glycosides effectively reduced the expression of osteoclast-related genes, such as tartrate-resistant acid phosphatase, cathepsin K, nuclear factor activated T-cell cytoplasmic 1, and dendritic cell specific transmembrane protein in RANKL-treated BMDMs. These results indicate that the 8-C-p-hydroxybenzylflavonol glycosides may be the main components responsible for the osteoclast differentiation inhibitory effect of pumpkin tendril.

The Influence of Ripeness on the Phenolic Content, Antioxidant and Antimicrobial Activities of Pumpkins (Cucurbita moschata Duchesne)

“…The chemical composition and biological properties of different parts of C. moschata have been examined in many investigations confirming that pumpkins have a wide range of bioactivities, such as anti-diabetes, anti-inflammation, hepatoprotective, anticancer, and anti-obesity properties [15][16][17][18][19][20][21][22]. These properties are generally attributedto the content of phenolic acids [23].…”

Pro-Osteogenic Properties of Violina pumpkin (Cucurbita moschata) Leaf Extracts: Data from In Vitro Human Primary Cell Cultures

“…A large body of evidence has been collected to show the potential of plant derivatives for the prevention and treatment of bone lesions [ 12 , 13 , 14 ]. Despite various discrepancies in the literature, there is agreement in attributing the positive effects of plant extracts, including those of the pumpkin tendrils, on the bone repair process, to antioxidant and anti-inflammatory action, and to the ability to increase angiogenesis and cell proliferation and differentiation [ 13 , 15 , 16 , 17 ]. Consistently with those observations, the few characteristics of pumpkin leaf extracts known prior to our study suggested that it would be reasonable to investigate their effects on bone cells.…”

Orientin suppresses osteoclastogenesis and ameliorates ovariectomy‐induced osteoporosis via suppressing ROS production

“…Natural flavonoid compounds are increasingly being recognized for their ability to reduce osteoclast activity and ameliorate critical osteoclastogenesis pathways (Kim et al, 2020 ). Fenugreek's major bioactive component, Orientin, is a C‐glycosyl flavonoid with numerous bioactivities and therapeutic benefits, including anti‐inflammatory, antidiabetes, antioxidative, and autophagy‐inducing properties (Kim et al, 2020 ; Thangaraj et al, 2019 ; Zhang et al, 2022 ). Zhang confirmed that in vitro, Ori could inhibit TBHP‐induced oxidative stress in cells from the rat nucleus pulposus (Zhang et al, 2022 ).…”