Synthesis and characterization of novel astragalin galactosides using β-galactosidase from Bacillus circulans

Han, Songhee; Nguyen, Thi Thanh Hanh; Hur, Jaewon; Kim, Nahyun M.; Kim, Seong Bo; Hwang, Kyeong Hwan; Moon, Young Hwan; Kang, Choon-Gil; Chung, Byoungsang; Kim, Young Min; Kim, Tae Sung; Park, Jun Seong; Kim, Doman

doi:10.1016/j.enzmictec.2017.05.003

Cited by 19 publications

(12 citation statements)

References 36 publications

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“…Notably, kaempferol is a flavonoid phytochemical, which exists in a variety of fruits and vegetables, including onions, kale, broccoli, apples, cherries, berries, tea and red wine (40,41). Kaempferol has multiple bioactivities, including antitumor effects, an antioxidant activity, and an anti-inflammatory function (17)(18)(19)(20). In addition, kaempferol has induced apoptotic and autophagic cell death and/or cell cycle arrest in various tumor cell lines, including colon, liver, gastric and bladder cancer cells (25,27,(42)(43)(44)(45)(46)(47).…”

Section: Discussionmentioning

confidence: 99%

“…Kaempferol is a flavonoid phytochemical found in fruits and vegetables and in some traditional Chinese medicines (TCM) (14)(15)(16). Kaempferol has been reported to exert biological activities such as anti-inflammatory (17,18), antioxidant (19,20), cardioprotective (19) and antitumor (21)(22)(23). Kaempferol has been demonstrated to provide chemopreventive effects on different tumor systems including tumor initiation, promotion, and progression (24,25).…”

Section: Introductionmentioning

confidence: 99%

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Kaempferol inhibits angiogenic ability by targeting VEGF receptor-2 and downregulating the PI3K/AKT, MEK and ERK pathways in VEGF-stimulated human umbilical vein endothelial cells

et al. 2018

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Anti-angiogenesis is one of the most general clinical obstacles in cancer chemotherapy. Kaempferol is a flavonoid phytochemical found in many fruits and vegetables. Our previous study revealed that kaempferol triggered apoptosis in human umbilical vein endothelial cells (HUVECs) by ROS‑mediated p53/ATM/death receptor signaling. However, the anti‑angiogenic potential of kaempferol remains unclear and its underlying mechanism warranted further exploration in VEGF‑stimulated HUVECs. In the present study, kaempferol significantly reduced VEGF‑stimulated HUVEC viability. Kaempferol treatment also inhibited cell migration, invasion, and tube formation in VEGF‑stimulated HUVECs. VEGF receptor‑2 (VEGFR‑2), and its downstream signaling cascades (such as AKT, mTOR and MEK1/2‑ERK1/2) were reduced as determined by western blotting and kinase activity assay in VEGF‑stimulated HUVECs after treatment with kaempferol. The present study revealed that kaempferol may possess angiogenic inhibition through regulation of VEGF/VEGFR‑2 and its downstream signaling cascades (PI3K/AKT, MEK and ERK) in VEGF-stimulated endothelial cells.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Kaempferol inhibits angiogenic ability by targeting VEGF receptor-2 and downregulating the PI3K/AKT, MEK and ERK pathways in VEGF-stimulated human umbilical vein endothelial cells

et al. 2018

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“…This shortcoming has restricted clinical applications of astragalin. Lately, astragalin-galactoside was proposed as a solution to the inadequate clinical application[26].This study reveals for the first time that Ast-Gal induces the phenotypic and functional maturation of bone marrow-derived DCs. Ast-Gal significantly increased the expression of several maturation-related surface markers, such as co-stimulatory molecules (CD80 and CD86) and MHC class II molecule on DCs.…”

mentioning

confidence: 84%

“…This drawback results in its slow absorption, inadequate and variable bioavailability, gastrointestinal mucosal toxicity, and delayed development as a prescription drug [24,25]. Recently, astragalin-galactoside (Ast-Gal) became known as an alternative that can overcome this problem [26]. However, the effects of Ast and Ast-Gal on the maturation and activation of DCs are not well studied.…”

Section: The Activation and Differentiation Of Th Cells Distinguishementioning

confidence: 99%

Hydrophilic Astragalin Galactoside Induces T Helper Type 1-Mediated Immune Responses via Dendritic Cells

Jeon¹,

Lee²,

Kim³

et al. 2018

Preprint

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A flavonoid Astragalin (kaempferol-3-O-β-D-glucopyranoside, Ast) has several biological activities including anti-oxidant, anti-HIV, and anti-allergic effects. Nonetheless, its insolubility in hydrophilic solvents imposes restrictions on its therapeutic applications. In this study, we investigated the effects of water-soluble astragalin-galactoside (kaempferol-3-O- β-D-isomaltotrioside, Ast-Gal) on dendritic cell (DC) maturation and T helper (Th) cell-mediated immune responses. Ast-Gal significantly increased maturation and activation of DCs through up-regulation of surface markers, such as CD80, CD86, and MHC II in a dose-dependent manner, while Ast had little effects. Also, Ast-Gal-treated DCs markedly secreted immune-stimulating cytokines such as IL-1β, IL-6, and IL-12. Importantly, Ast-Gal strongly increased expression of IL-12, a polarizing cytokine of Th1 cells. In a co-culture system of DCs and CD4+ T cells, Ast-Gal-treated DCs preferentially differentiates naïve CD4+ T cells into Th1 cells. The addition of neutralizing IL-12 mAb to cultures of Ast-Gal-treated DCs and CD4+ T cells significantly increased IFN- γ production, thereby indicating that Ast-Gal-stimulated DCs enhance the Th1 response through IL-12 production by DCs. Injection with Ast-Gal-treated DCs in mice increased IFN-γ-secreting Th1 cell population. Collectively, these findings indicate that hydrophilically modified astragalin can enhance Th1-mediated immune responses via DCs, and point to a possible application of water-soluble astragalin-galactoside as an immune adjuvant.

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“…This drawback results in its slow absorption, inadequate and variable bioavailability, gastrointestinal mucosal toxicity, and delayed development as a prescription drug [ 23 , 24 ]. Recently, astragalin-galactoside (Ast-Gal) became known as an alternative that can overcome this problem [ 25 ]. However, the effects of Ast and Ast-Gal on the maturation and activation of DCs are not well studied.…”

Section: Introductionmentioning

confidence: 99%

Hydrophilic Astragalin Galactoside Induces T Helper Type 1-Mediated Immune Responses via Dendritic Cells

Jeon

Lee

Kim

et al. 2018

IJMS

Self Cite

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A flavonoid Astragalin (kaempferol-3-O-β-d-glucopyranoside, Ast) has several biological activities including anti-oxidant, anti-HIV, and anti-allergic effects. Nonetheless, its insolubility in hydrophilic solvents imposes restrictions on its therapeutic applications. In this study, we investigated the effects of water-soluble astragalin-galactoside (kaempferol-3-O-β-d-isomaltotrioside, Ast-Gal) on murine bone marrow-derived dendritic cell (DC) maturation and T helper (Th) cell-mediated immune responses. Ast-Gal significantly increased maturation and activation of DCs through the upregulation of surface markers, such as cluster of differentiation (CD)80, CD86, and Major histocompatibility complex (MHC) II in a dose-dependent manner, while Ast had little effects. Additionally, Ast-Gal-treated DCs markedly secreted immune-stimulating cytokines such as interleukin (IL)-1β, IL-6, and IL-12. Importantly, Ast-Gal strongly increased expression of IL-12, a polarizing cytokine of Th1 cells. In a co-culture system of DCs and CD4+ T cells, Ast-Gal-treated DCs preferentially differentiates naïve CD4+ T cells into Th1 cells. The addition of neutralizing IL-12 monoclonal antibody (mAb) to cultures of Ast-Gal-treated DCs and CD4+ T cells significantly decreased interferon (IFN)-γ production, thereby indicating that Ast-Gal-stimulated DCs enhance the Th1 response through IL-12 production by DCs. Injection with Ast-Gal-treated DCs in mice increased IFN-γ-secreting Th1 cell population. Collectively, these findings indicate that hydrophilically modified astragalin can enhance Th1-mediated immune responses via DCs and point to a possible application of water-soluble astragalin-galactoside as an immune adjuvant.

show abstract

Synthesis and characterization of novel astragalin galactosides using β-galactosidase from Bacillus circulans

Cited by 19 publications

References 36 publications

Kaempferol inhibits angiogenic ability by targeting VEGF receptor-2 and downregulating the PI3K/AKT, MEK and ERK pathways in VEGF-stimulated human umbilical vein endothelial cells

Kaempferol inhibits angiogenic ability by targeting VEGF receptor-2 and downregulating the PI3K/AKT, MEK and ERK pathways in VEGF-stimulated human umbilical vein endothelial cells

Hydrophilic Astragalin Galactoside Induces T Helper Type 1-Mediated Immune Responses via Dendritic Cells

Hydrophilic Astragalin Galactoside Induces T Helper Type 1-Mediated Immune Responses via Dendritic Cells

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