Chemical and Biological Significance of Oenothein B and Related Ellagitannin Oligomers with Macrocyclic Structure

Yoshida, Takashi; Yoshimura, Manabu; Amakura, Yoshiaki

doi:10.3390/molecules23030552

Cited by 42 publications

(35 citation statements)

References 86 publications

(130 reference statements)

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“…Medicinal properties of fireweed extracts have been attributed to the synergic effect of polyphenols and the presence of the most abundant, compound -oenothein B. This substance shows various pharmacological activities, including anti-androgenic, antiproliferative, anticancer, antioxidant, anti-inflammatory, and immunomodulatory properties [5][6][7][8][9][10]. Additionally, E. angustifolium exhibits antimicrobial [11][12][13][14][15], analgesic [16] as well as photoprotective and antiaging [17] activities.…”

Section: Introductionmentioning

confidence: 99%

Fireweed (Epilobium angustifolium L.): botany, phytochemistry and traditional uses. A review

et al. 2019

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Fireweed (Epilobium angustifolium L., Onagraceae) is one of important medicinal plants used especially in the treatment of urogenital disorders, including benign prostatic hyperplasia (BPH) and prostatitis. The therapeutic effects of E. angustifolium extracts comprise antiproliferative, anti-inflammatory, immunomodulatory, antioxidant, and also antimicrobial activities. The aim of the present review was to provide the information on the botany, phytochemistry and traditional uses of E. angustifolium. This plant is a widespread circumboreal species of North America and Eurasia, tolerant in terms of habitat conditions, and often occupying man-made open habitats. Phytochemical studies on E. angustifolium resulted in the identification of about 250 different metabolites, including about 170 substances found for the first time in this plant in the last six years (2014)(2015)(2016)(2017)(2018)(2019). Fireweed has an abundance of polyphenolic compounds, particularly ellagitannins. Oenothein B and quercetin-3-O-glucuronide are proposed as markers for the identification and standardization of the plant raw material. E. angustifolium exhibits significant phytochemical variability in relation to the geographical origin, plant part and time of harvest/vegetation phase. Survey of the ethnobotanical literature showed that the above-mentioned species has been widely used not only as a medicinal, but also as an edible, honey and decorative plant. BOTANY TaxonomyEpilobium (Chamerion) angustifolium is classified to the Onagraceae family, which consists of 22 genera and approximately 650 species. The genus Chamerion (Raf.) Raf. ex Holub (syn. Chamaenerion Ség.) with eight species restricted to the northern hemisphere (mainly in Eurasia) belongs to the Onagroideae subfamily and Epilobieae tribe [18]. Relatively often, it is included in Epilobium L., which is the largest genus in the Onagraceae [19][20][21][22]. However, Chamerion clearly differs from Epilobium in terms of flower structure, leaf arrangement and other features [18,[23][24][25]. Molecular data also show that Chamerion is a separate monophyletic group of plants [26][27][28]. SynonymsThe Plant List [22] provides more than 40 synonyms of the species described, with three of these being the most commonly used: Epilobium angustifolium L., Chamerion angustifolium (L.) Holub and Chamaenerion angustifolium (L.) Scop. According to Holub [23], Chamerion should be considered the correct Latin name of this genus, while Chamaenerion is an illegitimate name. On the other hand, Sennikov [25] recently presented arguments for the restoration of the older name Chamaenerion. However, in Recently, the number of publications concerning the above-mentioned species has increased significantly. Screening of the Scopus database with the keywords of 'Epilobium/Chamerion/Chamaenerion angustifolium' found 416 document results, including 80 articles published in the years of 2014-2019. A new detailed summary is required not only for phytochemistry and pharmacology of E. angustifolium, but also in ...

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Section: Introductionmentioning

confidence: 99%

Fireweed (Epilobium angustifolium L.): botany, phytochemistry and traditional uses. A review

et al. 2019

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“…Oenothera Erythrosepala) and Lythraceae (e.g. Punica granatum L.) (Ito et al, 2014;Yoshida et al, 2018). Additionally, OeB has numerous physiological activities, such as antioxidant, anti-inflammatory activities (Yoshida et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

“…Punica granatum L.) (Ito et al, 2014;Yoshida et al, 2018). Additionally, OeB has numerous physiological activities, such as antioxidant, anti-inflammatory activities (Yoshida et al, 2018). Its existence has a great influence on the development of plant proteolytic products, but the mechanism is not clearly understood.…”

Section: Introductionmentioning

confidence: 99%

Investigation on the inactivation of trypsin by oenothein B: isothermal titration calorimetry and docking studies

Wang

Liang

Liu

et al. 2019

Int J of Food Sci Tech

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Summary The aim of this study was to investigate the inhibitory mechanism of oenothein B (OeB), a unique oligomer ellagitannin with a rigid structure, on porcine trypsin using fluorescence spectroscopy, isothermal titration calorimetry (ITC), circular dichroism (CD) and molecular docking. Trypsin activity was strongly inhibited by OeB in a competitive way. Fluorescence quenching of trypsin by OeB was a static quenching. The CD spectra showed that binding of OeB to trypsin altered trypsin's conformation. The ITC and docking studies revealed that the inhibitory mechanism of OeB occurred via binding to the interior hydrophobic groups of trypsin and the formation of hydrogen bonds with trypsin through binding to the amino acid residues Asn97, His573, Ser195 and Gln192. This study provides a theoretical and computational basis for the precise control of trypsin in food industry. Based on the results, OeB may be used in food technology research as novel bioactive trypsin inhibitor.

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“… 134 – 136 Moreover, oenothein B, which is present in Epilobium in high concentrations (20%–35%), was shown to powerfully inhibit cellular proliferation. 136 – 138 In particular, oenothein B hinders the progression of prostate cancer by inducing the production of neutral endopeptidase (NEP), an enzyme that inactivates the neuropeptides that stimulate neoplastic cellular proliferation. 138 , 139…”

Section: Introductionmentioning

confidence: 99%

“… 136 – 138 In particular, oenothein B hinders the progression of prostate cancer by inducing the production of neutral endopeptidase (NEP), an enzyme that inactivates the neuropeptides that stimulate neoplastic cellular proliferation. 138 , 139…”

Section: Introductionmentioning

confidence: 99%

Inflammatory mechanisms and oxidative stress in prostatitis: the possible role of antioxidant therapy

Paulis¹

2018

RRU

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This article focuses on the role that oxidative stress plays in chronic prostatitis, not only with respect to the known impact on symptoms and fertility but also especially in relation to possible prostate cancer development. Prostatitis is the most common urologic disease in adult males younger than 50 years and the third most common urologic diagnosis in males older than 50 years. If the germ-causing acute prostatitis is not eliminated, the inflammatory process becomes chronic. Persistent inflammation causes ongoing production of large quantities of pro-inflammatory cytokines and both oxygen and nitrogen reactive species, with consequent activation of transcription factor nuclear factor-kappa B (NF-κB) and genes encoding for further production of pro-inflammatory cytokines, chemotactic factors, and growth factors. Confirming the role of oxidative stress in chronic prostatitis, several studies have demonstrated the presence of oxidative stress markers in the genital secretions of patients suffering from the disease. Antioxidants can therefore play an essential role in the treatment of chronic bacterial and non-bacterial prostatitis; in the case of bacterial inflammation, they can be associated with antibiotic therapy. Moreover, due to their anti-inflammatory properties, antioxidants hinder the progression of inflammation and the possible development of prostate cancer.

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Chemical and Biological Significance of Oenothein B and Related Ellagitannin Oligomers with Macrocyclic Structure

Cited by 42 publications

References 86 publications

Fireweed (Epilobium angustifolium L.): botany, phytochemistry and traditional uses. A review

Fireweed (Epilobium angustifolium L.): botany, phytochemistry and traditional uses. A review

Investigation on the inactivation of trypsin by oenothein B: isothermal titration calorimetry and docking studies

Inflammatory mechanisms and oxidative stress in prostatitis: the possible role of antioxidant therapy

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