Phallac acids A and B, new sesquiterpenes from the fruiting bodies of Phallus luteus

Lee, Seoung Rak; Lee, Dahae; Lee, Bum Soo; Ryoo, Rhim; Pang, Changhyun; Kang, Ki Sung; Kim, Ki Hyun

doi:10.1038/s41429-020-0328-z

Cited by 9 publications

(5 citation statements)

References 17 publications

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“…A new trichothecene sesquiterpenoid and tremulane sesquiterpenoid were isolated from Gymnopilus junonius [ 35 ]. The sesquiterpenoid phallacic acid A was isolated from the Phallus luteus species, and its chemical structure was established [ 36 ]. Previously undescribed compounds named incarnatins A-D, incarnolactones A-C, incarnatin E, incarnetic acid, and incarnanin were isolated from Gloeostereum incarnatum [ 19 ].…”

Section: Structure and Chemical Classification Of Terpenes And Terpen...mentioning

confidence: 99%

Therapeutic Potential of Fungal Terpenes and Terpenoids: Application in Skin Diseases

Trepa,

Sułkowska-Ziaja,

Kała

et al. 2024

Molecules

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Terpenes and their derivatives comprise a diverse group of natural compounds with versatile medicinal properties. This article elucidates the general characteristics of fungal terpenes and terpenoids, encompassing their structure and biogenesis. The focal point of this work involves a comprehensive overview of these compounds, highlighting their therapeutic properties, mechanisms of action, and potential applications in treating specific skin conditions. Numerous isolated terpenes and terpenoids have demonstrated noteworthy anti-inflammatory and anti-microbial effects, rivalling or surpassing the efficacy of currently employed treatments for inflammation or skin infections. Due to their well-documented antioxidant and anti-cancer attributes, these compounds exhibit promise in both preventing and treating skin cancer. Terpenes and terpenoids sourced from fungi display the capability to inhibit tyrosinase, suggesting potential applications in addressing skin pigmentation disorders and cancers linked to melanogenesis dysfunctions. This paper further disseminates the findings of clinical and in vivo research on fungal terpenes and terpenoids conducted thus far.

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Section: Structure and Chemical Classification Of Terpenes And Terpen...mentioning

confidence: 99%

Therapeutic Potential of Fungal Terpenes and Terpenoids: Application in Skin Diseases

Trepa,

Sułkowska-Ziaja,

Kała

et al. 2024

Molecules

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“…The pharmacological value of P. luteus came to light when a new sesquiterpene, phallac acid B(2), was isolated from the fruiting bodies of this mushroom [35]. An evaluation of its α-glucosidase inhibitory activity found that phallac acid B(2) has signi cantly greater inhibitory effects on α-glucosidase than acarbose, an enzyme that breaks down carbohydrates in the small intestine.…”

Section: Antiviral E Cacymentioning

confidence: 99%

In vitro anti-influenza virus (H1N1) activity of eleven species of Korean medicinal mushrooms

Ryoo,

Lee

2024

Preprint

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Background: Oseltamivir is the most commonly used antiviral drug for the treatment and prevention of influenza. However, there are growing concerns about its use due to the risk of psychiatric side effects. Methods: Eleven species of edible medicinal mushrooms (Pleurotus ostreatus, Phallus rubrovolvata, Phallus luteus, Morchella esculenta, Grifola frondosa, Sarcodon imbricatus, Tricholoma bakamatsutake, Pachyma hoelen, Sparassis latifolia, Amanita caesareoides, and Marasmius siccus) were collected from forests in Korea to evaluate their anti-influenza A properties. After collection, the identification of each mushroom type was verified with internal transcribed spacer (ITS) gene sequencing using fungal-specific primers. Extracts were prepared by heating dried mushroom powder at 100℃ for 2 h. The cytotoxicity of the extracts was evaluated by MTT assay. The anti-influenza A properties of each extract were evaluated using the ASTM E1052-11 protocol, which is the international standardized approach. Results: The efficacy of the mushroom extracts against influenza A was evaluated using hot mushroom extract solutions, each of which had a concentration of 10 g powdered mushroom per liter of hot water. This ratio was selected as all of the mushrooms had little cytotoxic effect at this concentration. The influenza virus reduction titer of Pleurotus ostreatus was 5.519, with a virus removal efficacy of 99.999%. This was the highest antiviral efficacy among the 11 mushroom species. The virus inhibition titers of Phallus rubrovolvata and P. luteus were 4.477 and 2.247, respectively. Their virus inhibition efficacies were 99.997% and 99.433%, respectively. The efficacy of M. esculenta was 90.303%. The antiviral effects of Grifola% that of G. frondosawas 78.788%, and that of S. imbricatuswas 75.758%. The virus suppression efficacy of Tricholoma bakamatsutake and Pachyma hoelen were 66.667% and 63.636%, respectively. The extract solutions of the remaining three species (Sparassis latifolia, Amanita caesareoides, and Marasmius siccus) all showed a virus reduction efficacy of 60%. Conclusions: This study demonstrates the potential of mushroom extracts for medicinal use as antiviral treatments for influenza A infections.

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“…Compared to the polysaccharides, the bioactive compounds with small molecular weights in D. indusiata have not been sufficiently investigated [ 1 ]. From this mushroom species, three eudesmane-type sesquiterpenes and five monoterpene alcohols were reported to be identified by Kawagishi et al [ 6 , 7 ]; albaflavenone and two derivatives (9,10-dihydroxy-albaflavenone and 5-hydroxy-albaflavenone) were isolated by Huang et al and Zhang et al, respectively [ 8 , 9 ]; two linear sesquiterpene carboxylic acids (Phallac acids A and B) were obtained and determined by Lee et al [ 10 ]. In addition to the terpenoid compounds, Lee et al identified three alkaloids, Dictyoquinazols A, B, and C, from D. indusiata [ 11 ]; and Sharma et al reported the isolation of 5-hydroxymethyl–2-furfural (HMF) [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

“…In addition to the terpenoid compounds, Lee et al identified three alkaloids, Dictyoquinazols A, B, and C, from D. indusiata [ 11 ]; and Sharma et al reported the isolation of 5-hydroxymethyl–2-furfural (HMF) [ 12 ]. The biological investigations revealed that some of these small molecules isolated from D. indusiata possess neuroprotective, anti-tyrosinase, anti-glucosidase, and some anti-inflammatory activities [ 6 , 9 , 10 , 11 , 12 ]. However, the role of small-molecular-weight metabolites in the anti-inflammatory property of the mushroom D. indusiata has yet to be fully elucidated.…”

Section: Introductionmentioning

confidence: 99%

Chemical Constituents of the Mushroom Dictyophora indusiata and Their Anti-Inflammatory Activities

et al. 2023

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As an edible and medicinal fungus, Dictyophora indusiata is well-known for its morphological elegance, distinctive taste, high nutritional value, and therapeutic properties. In this study, eighteen compounds (1–18) were isolated and identified from the ethanolic extract of D. indusiata; four (1–4) were previously undescribed. Their molecular structures and absolute configurations were determined via a comprehensive analysis of spectroscopic data (1D/2D NMR, HRESIMS, ECD, and XRD). Seven isolated compounds were examined for their anti-inflammatory activities using an in vitro model of lipopolysaccharide (LPS)-simulated BV-2 microglial cells. Compound 3 displayed the strongest inhibitory effect on tumor necrosis factor-α (TNF-α) expression, with an IC50 value of 11.9 μM. Compound 16 exhibited the highest inhibitory activity on interleukin-6 (IL-6) production, with an IC50 value of 13.53 μM. Compound 17 showed the most potent anti-inflammatory capacity by inhibiting the LPS-induced generation of nitric oxide (NO) (IC50: 10.86 μM) and interleukin-1β (IL-1β) (IC50: 23.9 μM) and by significantly suppressing induced nitric oxide synthase (iNOS) and phosphorylated nuclear factor-kappa B inhibitor-α (p-IκB-α) expression at concentrations of 5 μM and 20 μM, respectively (p < 0.01). The modes of interactions between the isolated compounds and the target inflammation-related proteins were investigated in a preliminary molecular docking study. These results provided insight into the chemodiversity and potential anti-inflammatory activities of metabolites with small molecular weights in the mushroom D. indusiata.

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Phallac acids A and B, new sesquiterpenes from the fruiting bodies of Phallus luteus

Cited by 9 publications

References 17 publications

Therapeutic Potential of Fungal Terpenes and Terpenoids: Application in Skin Diseases

Therapeutic Potential of Fungal Terpenes and Terpenoids: Application in Skin Diseases

In vitro anti-influenza virus (H1N1) activity of eleven species of Korean medicinal mushrooms

Chemical Constituents of the Mushroom Dictyophora indusiata and Their Anti-Inflammatory Activities

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