Prenylated isoflavones from <i>Cudrania tricuspidata</i> inhibit NO production in RAW 264.7 macrophages and suppress HL-60 cells proliferation

Anh, Hoang Le Tuan; Tuan, Do Thanh; Trang, Đỗ Thị; Tài, Bùi Hữu; Nhiệm, Nguyễn Xuân; Yến, Phạm Hải; Kiệm, Phan Văn; Minh, Châu Văn; Đức, Trần Minh; Kang, Hee Kyoung; Kim, Youn Chul; Kim, Young Ho

doi:10.1080/10286020.2016.1232253

Cited by 11 publications

(4 citation statements)

References 25 publications

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“…The 13 C NMR spectrum displayed a total of 22 carbon resonances, including two methyls, three sp 3 methylenes, five sp 2 methines, and 12 sp 2 quaternary carbons. These spectroscopic features were very similar to those of cudraisoflavone L, which was recently isolated from the same genus and shared the same molecular formula with 4 [26]. Their structural difference was only due to the location of the prenyl group and the hydroxyethyl moiety.…”

Section: Resultssupporting

confidence: 74%

Polysubstituted Isoflavonoids from Spatholobus suberectus, Flemingia macrophylla, and Cudrania cochinchinensis

Wang¹,

Zheng²,

Ren³

et al. 2017

Nat. Prod. Bioprospect.

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Four hitherto unknown polysubstituted isoflavonoids, including three isoflavans: 7,4′-dihydroxy-8,2′,3′-trimethoxyisoflavan (1), 7,2′,4′-trihydroxy-8,3′-dimethoxyisoflavan (2), and 7,2′,4′-trihydroxy-5-methoxyisoflavan (3), and one prenylated isoflavone cudraisoflavone M (4) were isolated from the ethanol extracts of Spatholobus suberectus (for 1 and 2), Flemingia macrophylla (for 3), and Cudrania cochinchinensis (for 4), respectively. Their structures were established on the basis of extensive spectroscopic analysis. Compounds 1 and 4 exhibited weak cytotoxic activity against five human cancer cell lines (HL-60, A-549, SMMC-7721, MCF-7, and SW-480).Graphical Abstract Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-017-0121-2) contains supplementary material, which is available to authorized users.

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Section: Resultssupporting

confidence: 74%

Polysubstituted Isoflavonoids from Spatholobus suberectus, Flemingia macrophylla, and Cudrania cochinchinensis

Wang¹,

Zheng²,

Ren³

et al. 2017

Nat. Prod. Bioprospect.

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“… 2017 ; Tuan Anh et al. 2017 ). Our previous report showed that the compounds isolated from this plant display anti-neuroinflammatory effects (Yoon et al.…”

Section: Introductionmentioning

confidence: 99%

Anti-neuroinflammatory effects of cudraflavanone A isolated from the chloroform fraction of Cudrania tricuspidata root bark

Kim

Quang

et al. 2018

Pharmaceutical Biology

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Context:Cudrania tricuspidata Bureau (Moraceae) is an important source of traditional Korean and Chinese medicines used to treat neuritis and inflammation.Objective: The anti-neuroinflammatory effects of cudraflavanone A isolated from a chloroform fraction of C. tricuspidata were investigated in LPS-induced BV2 cells.Materials and methods: Cudraflavanone A was isolated from the root of C. tricuspidata, and its structure was determined by MS and NMR data. Cytotoxicity of the compound was examined by MTT assay, indicating no cytotoxicity at 5–40 μM of cudraflavanone A. NO concentration was measured by the Griess reaction, and the levels of PGE2, cytokines and COX-2 enzyme activity were measured by each ELISA kit. The mRNA levels of cytokines were analysed by quantitative-PCR. The expression of iNOS, COX-2, HO-1, NF-κB, MAPKs and Nrf2 was detected by Western blot.Results: Cudraflavanone A had no major effect on cell viability at 40 μM indicating 91.5% viability. It reduced the production of NO (IC50 = 22.2 μM), PGE2 (IC50 = 20.6 μM), IL-1β (IC50 = 24.7 μM) and TNF-α (IC50 = 33.0 μM) in LPS-stimulated BV2 cells. It also suppressed iNOS protein, IL-1β and TNF-α mRNA expression. These effects were associated with the inactivation of NF-κB, JNK and p38 MAPK pathways. This compound mediated its anti-neuroinflammatory effects by inducing HO-1 protein expression via increased nuclear translocation of Nrf2.Discussion and conclusions: The present study suggests a potent effect of cudraflavanone A to prevent neuroinflammatory diseases. Further investigation is necessary to elucidate specific molecular mechanism of cudraflavanone A.

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“…Through this, a study was conducted to find out the effect of 6,8-diprenylorobol, which is one of the Cudrania tricuspidata extracts showing various effects. 6,8-Diprenylorobol belongs to the class of flavonoids and can be extracted from the leaves of Cudrania tricuspidata [ 13 ]. 6,8-Diprenylorobol exhibits anti-cell proliferation, anticancer, antifungal and anti-Helicobacter pylori activities [ 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

Inhibitory Effects of 6,8-Diprenylorobol on Endometriosis Progression in Humans by Disrupting Calcium Homeostasis and Mitochondrial Function

Song

Lim

2022

Antioxidants

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6,8-Diprenylorobol is a flavonoid compound extracted from Cudrania tricuspidata. It has various biological functions, such as inhibiting melanin synthesis and inducting cell death in cancerous cells. In addition, Cudrania tricuspidata is known to be effective in female diseases, and previous studies have shown anticancer effects in cervical cancer, a female reproductive disease. Outside of that, Cudrania tricuspidata has various physiological effects. However, the effect of 6,8-diprenylorobol is not well known in other benign and chronic diseases, even in endometriosis, which commonly arises in the female reproductive tract. In the present study, we determined the inhibitory effects of 6,8-diprenylorobol on the growth of endometriosis VK2/E6E7 and End1/E6E7 cells. Results indicated that 6,8-diprenylorobol suppressed cellular proliferation and increased the disruption of the cell cycle, mitochondrial membrane potential (MMP), generation of reactive oxygen species, and Ca2+ homeostasis in both endometriosis cells. However, the proliferation of normal stromal cells isolated from endometrial tissue was not altered by 6,8-diprenylorobol. The change in Ca2+ levels was estimated in fluo-4- or rhod-2-stained VK2/E6E7 and End1/E6E7 cells after the treatment of the intracellular calcium regulators 2-aminoethoxydiphenyl borate (2-APB) and ruthenium red (RUR) with 6,8-diprenylorobol. A combination of 6,8-diprenylorobol with each regulator decreased the calcium accumulation in endometriosis cells. Furthermore, Western blot analysis indicated that 6,8-diprenylorobol inactivated AKT pathways, whereas it activated P38 MAPK pathways. In addition, 6,8-diprenylorobol decreased mitochondrial respiration, leading to the reduction in ATP production in VK2/E6E7 and End1/E6E7 cells. Collectively, our results suggested that 6,8-diprenylorobol might be a potential therapeutic agent or adjuvant therapy for the management of endometriosis.

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Prenylated isoflavones from Cudrania tricuspidata inhibit NO production in RAW 264.7 macrophages and suppress HL-60 cells proliferation

Cited by 11 publications

References 25 publications

Polysubstituted Isoflavonoids from Spatholobus suberectus, Flemingia macrophylla, and Cudrania cochinchinensis

Polysubstituted Isoflavonoids from Spatholobus suberectus, Flemingia macrophylla, and Cudrania cochinchinensis

Anti-neuroinflammatory effects of cudraflavanone A isolated from the chloroform fraction of Cudrania tricuspidata root bark

Inhibitory Effects of 6,8-Diprenylorobol on Endometriosis Progression in Humans by Disrupting Calcium Homeostasis and Mitochondrial Function

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