An efficient synthesis of the phytoestrogen 8-prenylnaringenin from xanthohumol by a novel demethylation process

Wilhelm, Heike; Wessjohann, Ludger A.

doi:10.1016/j.tet.2006.04.060

Cited by 36 publications

(42 citation statements)

References 28 publications

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“…After debenzylation-decarboxylation of 15c, the ketone in 18 was protected as an acetal. The alcohol (20) obtained by hydrolysis of the acetal (19) was tosylated, and the tosylate (21) was treated with potassium tert-butoxide (tBuOK) to give the olefin (22). After hydrogenation of 22 over palladium on carbone (Pd-C), the obtained acetal (23) was deprotected with iron(III) chloride hexahydrate (FeCl 3 · 6H 2 O) to afford the ketone (24) 15) (Chart 4).…”

Section: Resultsmentioning

confidence: 99%

“…Microwave irradiation of the obtained 30 gave 28 in 80% yield. After selective demethylation of 28 in the usual manner, 20,21) extension of the acetyl group in 16 to the cinnamoyl group was carried out by cross-aldol condensation with benzaldehyde in the presence of t-BuOK to afford 32 in 80% yield. Finally, the double bond of the α,β-unsaturated carbonyl group of 32 was chemoselectively reduced over the isolated double bond at the 6,7-position to give (±)-8-deisopropyladunctin B (9) in 61% yield 22,23) (Chart 6).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of (.+-.)-8-Deisopropyladunctin B

et al. 2012

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis of (.+-.)-8-Deisopropyladunctin B

et al. 2012

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“…Xanthohumol (1), the substrate for the synthesis of isoxanthohumol (2), was isolated from carbon dioxide-extracted hops. It was purified and transformed into 2 according to a modified procedure described by Wilhelm and Wessjohann (2006). Acetyl derivatives of 2 (compounds 3 and 4) were synthesized using different amounts of acetic anhydride in 19.7% and 54% yield, respectively.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and biological evaluation of 4'-O-acetyl-isoxanthohumol and its analogues as antioxidant and antiproliferative agents

et al. 2017

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Isoxanthohumol (2) and its 4'-O-monoacylated (3) and 7,4'-O-diacetylated (4) derivatives were synthesized and evaluated in vitro for their cytotoxic activity against several cancer cell lines of various origins: MCF-7 (breast), A549 (lung), MESSA (uterine sarcoma), LoVo (colon), drug-resistant human cancer cells (MESSA/DX and LoVo/DX), glioblastoma (U-118 MG), and also towards the non-cancerous cell line MCF-10A (normal breast cells). An antiproliferative assay indicates that 7,4'-di-O-acylisoxanthohumol (4) has similar cytotoxicity to its precursor, isoxanthohumol (2), against selected cell lines (A549, MES-SA, MES-SA/5DX, and U-118 MG). Compound 4 was only slightly more cytotoxic to lung, colon, breast (cancerous and normal) and uterine sarcoma (drug sensitive and drug resistant) cell lines compared to its monoacylated derivative (3). Both acylated isoxanthohumols showed preferential activity against tumor cells (MCF-7) and low cytotoxicity to normal cells (MCF-10A), which suggests selectivity of the acylated isoxanthohumols towards cancer cells. Additionally, the activity of the acylated isoxanthohumols was higher than for 2. To the best of our knowledge this is the first report on bioactivity of monoacylated isoxanthohumol (3) and its ester derivatives as antiproliferative compounds in drug resistant cell cultures. Acylation of 2 decreased the antioxidant activity determined by the DPPH method in the order isoxanthohumol (2) >4'-O-acetylisoxanthohumol (3) >7,4'-di-O-acetylisoxanthohumol (4).

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“…However, this is a multi-step process, requiring protection of the 7-OH and 4'-OH hydroxyl groups and therefore the reaction yield was moderate (48%) [24]. An alternative method described by Wilhelm and Wessjohann [25] involves demethylation of isoxanthohumol. The authors tested various demethylation agents and achieved the yield of 92%.…”

Section: Synthesis Of 8-prenylnaringeninmentioning

confidence: 99%

In Vitro Effect of 8-Prenylnaringenin and Naringenin on Fibroblasts and Glioblastoma Cells—Cellular Accumulation and Cytotoxicity

Stompor¹,

Uram²

2017

Preprint

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Gliomas are one of the most aggressive and treatment-resistant types of human cancer. One of the most promising field in gliomas cancer therapy is identification and evaluation of anticancer properties of compounds found in plants i.a. naringenin (N) and 8-prenylnaringenin (8PN). The prenyl group seem to be crucial to the anticancer activity of flavones, which may lead to enhanced cell membrane targeting and thus increased intracellular activity. Unfortunately, 8PN content in hop cones is from 10 to 100 times lower compared to other flavonoids i.e. xanthohumol. In this study we used a simple method for the synthesis of 8PN from isoxanthohumol, via O-demethylation with high, 97% of the isolated yield. Cellular accumulation and cytotoxicity of naringenin and 8-prenylnaringenin in normal (BJ) and cancer cells (U-118 MG) were also examined. Obtained data indicated that 8-prenylnaringenin exhibited higher toxicity against used cell lines than naringenin and both flavones inhibited stronger glioblastoma U-118 MG cells than normal fibroblasts. The anticancer properties of 8PN correlated with its significantly greater (37%), accumulation in glioblastoma cells than in normal fibroblasts. Additionally, naringenin indicated higher selectivity for glioblastoma as it was over 6 times more toxic for cancer than normal cells. Our results provide evidence that examined prenylated and non-prenylated flavanones have different biological activity against normal and cancer cell lines and this phenomenon may be useful in clinical practice to construct new, anticancer drugs for glioblastoma.

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An efficient synthesis of the phytoestrogen 8-prenylnaringenin from xanthohumol by a novel demethylation process

Cited by 36 publications

References 28 publications

Synthesis of (.+-.)-8-Deisopropyladunctin B

Synthesis of (.+-.)-8-Deisopropyladunctin B

Synthesis and biological evaluation of 4'-O-acetyl-isoxanthohumol and its analogues as antioxidant and antiproliferative agents

In Vitro Effect of 8-Prenylnaringenin and Naringenin on Fibroblasts and Glioblastoma Cells—Cellular Accumulation and Cytotoxicity

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An efficient synthesis of the phytoestrogen 8-prenylnaringenin from xanthohumol by a novel demethylation process

Cited by 36 publications

References 28 publications

Synthesis of (.+-.)-8-Deisopropyladunctin B

Synthesis of (.+-.)-8-Deisopropyladunctin B

Synthesis and biological evaluation of 4'-O-acetyl-isoxanthohumol and its analogues as antioxidant and antiproliferative agents

In Vitro Effect of 8-Prenylnaringenin and Naringenin on Fibroblasts and Glioblastoma Cells&mdash;Cellular Accumulation and Cytotoxicity

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In Vitro Effect of 8-Prenylnaringenin and Naringenin on Fibroblasts and Glioblastoma Cells—Cellular Accumulation and Cytotoxicity