Inhibition of 5α-Reductase and Aromatase by the Ellagitannins Oenothein A and Oenothein B from<i>Epilobium</i>Species

Ducrey, B.; Marston, Andrew; Göhring, S.; Hartmann, Robert C.; Hostettmann, Kurt

doi:10.1055/s-2006-957624

Cited by 85 publications

(62 citation statements)

References 7 publications

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“…Many pharmaceutical drugs include 2-pyrrolidinone compound. 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (41) 1(3,7).1 (9,13 …”

Section: Analysis Of Methanolic Extract On Polar Columnmentioning

confidence: 99%

“…A study (8) has displayed the activity of Epilobium angustifolium L. extract against the LNCaP in human hormone dependent prostate cancer cells. Epilobium angustifolium L. includes Oenothein B, and this component has been analyzed for its inhibition activity of 5-alphareductase and aromatase enzymes that raise benign prostatic hyperplasia, BPH (9). Oenothein B is a dimeric ellagitannin and has also been proved to affect the NEP activity in prostatic cancer progression (10).…”

Section: Introductionmentioning

confidence: 99%

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DNA- Binding, Biological Activities and Chemical Composition of Wild Growing Epilobium angustifolium L. Extracts from Canakkale, Turkey

Sayik¹,

Yusufoğlu²,

Açık³

et al. 2017

Journal of the Turkish Chemical Society, Section A: Chemistry

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Abstract:The usage of Epilobium angustifolium L. in folk medicine against prostate and dermal diseases encouraged us to investigate pBR322 DNA-binding ability, biological activities and chemical composition of wild growing Epilobium angustifolium L.'s methanolic, ethanolic and aqueous extracts from Canakkale, Turkey. DNA-binding activity was studied by agarose gel electrophoresis and chemical composition via GC, GC-MS, HPLC, LC-MS, ICP-MS, and AAS. A detailed literature survey indicates no data on pBR322 plasmid DNA interaction of Epilobium species which is an important criterion for being a potential anticancer agent. Antibacterial and antifungal effects were tested against 11 bacteria and 3 fungi and compared with ampicillin, chloramphenicol, and ketoconazole by agar well diffusion techniques. Total phenolic content was found by Folin-Ciocalteu method, and antioxidant activity was obtained by DPPH and Fe(II)-FZ (ferric-ferrozine) methods. This plant is rich in flavonoids, hormones, fatty acids, and phenolic acids. Si, K, Mg, P, and Mn were the main inorganic elements. Epilobium angustifolium L. with its high DNA-binding activity and rich chemical composition can be an excellent potential anticancer, antimicrobial and antioxidant prodrug.

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“…Many pharmaceutical drugs include 2-pyrrolidinone compound. 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (41) 1(3,7).1 (9,13 …”

Section: Analysis Of Methanolic Extract On Polar Columnmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

DNA- Binding, Biological Activities and Chemical Composition of Wild Growing Epilobium angustifolium L. Extracts from Canakkale, Turkey

Sayik¹,

Yusufoğlu²,

Açık³

et al. 2017

Journal of the Turkish Chemical Society, Section A: Chemistry

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“…However, this flavone was found to be only moderately active in H295R adrenocortical carcinoma cells [127] and was not active using trout ovarian aromatase [128]. The pentahydroxylated flavone, quercetin (37), present in numerous plant species but reported in the aromatase literature as being isolated from Epilobium capense [130] and Morinda citrifolia L. (noni) [131], was found to be moderately active in two microsomal studies [120,122] but only weakly active in another microsomal study [130]. Quercetin (37) was not active in granulose-luteal cells [129], JEG-3 cells [125], H295R adrenocortical carcinoma cells [127], human preadipocyte cells [126], or using trout ovarian aromatase [128].…”

Section: Natural Product Compounds Tested For Aromatase Inhibitionmentioning

confidence: 99%

Natural Products as Aromatase Inhibitors

Balunas¹,

Su²,

Brueggemeier³

et al. 2008

ACAMC

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With the clinical success of several synthetic aromatase inhibitors (AIs) in the treatment of postmenopausal estrogen receptor-positive breast cancer, researchers have also been investigating also the potential of natural products as AIs. Natural products from terrestrial and marine organisms provide a chemically diverse array of compounds not always available through current synthetic chemistry techniques. Natural products that have been used traditionally for nutritional or medicinal purposes (e.g., botanical dietary supplements) may also afford AIs with reduced side effects. A thorough review of the literature regarding natural product extracts and secondary metabolites of plant, microbial, and marine origin that have been shown to exhibit aromatase inhibitory activity is presented herein. Keywordsaromatase inhibitors; natural products; breast cancer; botanical dietary supplements BREAST CANCERWorldwide breast cancer estimates included over one million incident cases and almost 400,000 deaths in the year 2000 [1,2]. In the United States, over 178,000 women were expected to be diagnosed with breast cancer in 2007 with over 40,000 deaths occurring from the disease [3]. In developed countries, mortality from breast cancer has recently begun to decline, primarily due to earlier detection and improved treatments [4,5]. Breast cancer is thought to be a result of inherited genetic predisposition (e.g., mutations in genes such as BRCA-1, p53, PTEN/MMAC1, and/or ATM) and/or environmental factors (e.g., radiation exposure, dietary factors, alcohol consumption, hormonal exposure) [2,6,7]. Numerous genetic mutations are necessary for breast cancer development and progression including the acquisition of the capabilities for self-sufficiency in growth signals, insensitivity to anti-growth signals, evasion of apoptosis, limitless replicative potential, sustained angiogenesis, and tissue invasion and metastasis, known collectively as the "hallmarks of cancer" [8].Numerous molecular targets have been identified as playing a significant role in breast cancer development and progression. Estrogens and the estrogen receptors (ERs) are widely NIH Public Access Author ManuscriptAnticancer Agents Med Chem. Author manuscript; available in PMC 2011 April 12.Published in final edited form as:Anticancer Agents Med Chem. 2008 August ; 8(6): 646-682. NIH-PA Author ManuscriptNIH-PA Author Manuscript NIH-PA Author Manuscript recognized to play an important role in the development and progression of breast cancer, making estrogens and the ERs widely studied molecular targets [9][10][11][12]. Two of the endogenous estrogens found in humans include estradiol and estrone. In pre-menopausal women, estrogens are produced primarily through conversion of androgens in the ovaries while estrogen production in postmenopausal women occurs in only peripheral tissues [13,14]. Estrogens have various effects throughout the body, including positive effects on the brain, bone, heart, liver, and vagina, with negative effects such as increased risk...

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“…However, for treatment of benign prostate hyperplasia, tannins also seem to play a role as 5a-reductase and aromatase were inhibited by the tannins oenotheins A and B. Furthermore, oenothein B inhibited the proliferation of prostate cells, enhanced the neutral endopeptidase in prostate cancer cells, and inhibited hyaluronidase and lipoxygenase (Ducrey et al, 1997;Kiss et al, 2011;Ramstead et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Content of phenolic compounds in wild populations ofEpilobium angustifoliumgrowing at different altitudes

Monschein

Jaindl

Buzimkić

et al. 2015

Pharmaceutical Biology

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Context: Flavonoids are regarded as essential ingredients for the anti-inflammatory activity of Epilobium angustifolium L. (Onagraceae). The metabolic profiles of medicinal plants vary aside from genetic determination due to the influence by external factors. Objectives: This study evaluates the influence of altitudinal variation on the content of flavonoids in E. angustifolium in two consecutive growing periods. Materials and methods: Aerial and herbaceous plant materials were collected at three different altitudes (800, 1000, and 1500 m) during two collection periods. Plant samples (11-13 samples per altitude and year) were extracted with methanol using accelerated solvent extraction (ASE). Identification and quantification of the constituents were achieved by chromatographic means of HPLC-PDA and LC-PDA-MS analyses. Results: Rising concentrations of flavonol 3-O-glycosides could be detected with increasing altitude. The content of the major compound, quercetin 3-O-glucuronide, ranged from 4.4 ± 2.05 (800 m) to 4.9 ± 1.03 (1000 m) and up to 6.6 ± 1.14 mg/g (1500 m). The total amount of flavonol 3-O-glycosides in 73 analyzed samples ranged from 10.7 ± 1.37 up to 17.3 ± 1.99 mg/g. Discussion: Quercetin-3-O-glucuronide can be considered as a potential marker for the increased production of flavonols in herbal parts of E. angustifolium at higher altitudinal levels. Conclusion: The study confirms that environmental factors at higher altitude result in elevated levels of flavonols in aerial plant tissues of E. angustifolium. Specific factors for influencing the flavonoid content have to be clarified in further studies.

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Inhibition of 5α-Reductase and Aromatase by the Ellagitannins Oenothein A and Oenothein B fromEpilobiumSpecies

Cited by 85 publications

References 7 publications

DNA- Binding, Biological Activities and Chemical Composition of Wild Growing Epilobium angustifolium L. Extracts from Canakkale, Turkey

DNA- Binding, Biological Activities and Chemical Composition of Wild Growing Epilobium angustifolium L. Extracts from Canakkale, Turkey

Natural Products as Aromatase Inhibitors

Content of phenolic compounds in wild populations ofEpilobium angustifoliumgrowing at different altitudes

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