Sesquiterpenoids and an ergosterol from cultures of the fungus Daedaleopsis tricolor

Zhao, Jing; Feng, Tao; Li, Zhenghui; Dong, Zhibao; Zhang, Hongbin; Liu, Ji‐Kai

doi:10.1007/s13659-013-0065-0

Cited by 9 publications

(5 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compounds 1 – 5 were identified as demethylincisterol A 3 ( 1 ) [ 19 ], (20 S ,22 E ,24 R )-ergosta-7,22-dien-3β,5α,6β-triol ( 2 ) [ 20 ], (24 S )-ergosta-7-ene-3β,5α,6β-triol ( 3 ) [ 21 ], 5α,6α-epoxy-(22 E ,24 R )-ergosta-7,22-dien-3β-ol ( 4 ) [ 22 ], and 5α,6α-epoxy-(24 R )-ergosta-7-en-3β-ol ( 5 ) [ 23 ] ( Figure 3 ) by comparing their NMR spectroscopic data with reported values from previously published studies and LC/MS data ( Figures S1–S10 ). This is the first report regarding the presence of the identified ergosterol derivatives ( 1 – 5 ) in D. confragosa.…”

Section: Resultsmentioning

confidence: 99%

“…Based on the LC-MS/MS analysis and bioactivity-guided fractionation, the n-hexaneand CH 2 Cl 2 -soluble fractions were subjected to analysis using sequential column chromatography, as well as preparative and semi-preparative HPLC, which resulted in the isolation of five ergosterol derivatives (1-5) (Figure 2). Compounds 1-5 were identified as demethylincisterol A 3 (1) [19], (20S,22E,24R)ergosta-7,22-dien-3β,5α,6β-triol (2) [20], (24S)-ergosta-7-ene-3β,5α,6β-triol (3) [21], 5α,6αepoxy-(22E,24R)-ergosta-7,22-dien-3β-ol (4) [22], and 5α,6α-epoxy-(24R)-ergosta-7-en-3β-ol (5) [23] (Figure 3) by comparing their NMR spectroscopic data with reported values from previously published studies and LC/MS data (Figures S1-S10). This is the first report regarding the presence of the identified ergosterol derivatives (1-5) in D. confragosa.…”

Section: Isolation and Chemical Characterization Of The Compoundsmentioning

confidence: 99%

See 1 more Smart Citation

Identification of Antibacterial Sterols from Korean Wild Mushroom Daedaleopsis confragosa via Bioactivity- and LC-MS/MS Profile-Guided Fractionation

Lee

Kang

et al. 2022

Molecules

View full text Add to dashboard Cite

As part of an ongoing natural product chemical research for the discovery of bioactive secondary metabolites with novel structures, wild fruiting bodies of Daedaleopsis confragosa were collected and subjected to chemical and biological analyses. We subjected the fractions derived from the methanol extract of the fruiting bodies of D. confragosa to bioactivity-guided fractionation because the methanol extract of D. confragosa showed antibacterial activity against Helicobacter pylori strain 51, according to our bioactivity screening. The n-hexane and dichloromethane fractions showed moderate to weak antibacterial activity against H. pylori strain 51, and the active fractions were analyzed for the isolation of antibacterial compounds. Liquid chromatography-tandem mass spectrometry (LC–MS/MS) analysis revealed that the n-hexane fraction contains several compounds which are absent in the other fractions, so the fraction was prioritized for further fractionation. Through chemical analysis of the active n-hexane and dichloromethane fractions, we isolated five ergosterol derivatives (1–5), and their chemical structures were determined to be demethylincisterol A3 (1), (20S,22E,24R)-ergosta-7,22-dien-3β,5α,6β-triol (2), (24S)-ergosta-7-ene-3β,5α,6β-triol (3), 5α,6α-epoxy-(22E,24R)-ergosta-7,22-dien-3β-ol (4), and 5α,6α-epoxy-(24R)-ergosta-7-en-3β-ol (5) by NMR spectroscopic analysis. This is the first report on the presence of ergosterol derivatives (1–5) in D. confragosa. Compound 1 showed the most potent anti-H. pylori activity with 33.9% inhibition, rendering it more potent than quercetin, a positive control. Compound 3 showed inhibitory activity comparable to that of quercetin. Distribution analysis of compound 1 revealed a wide presence of compound 1 in the kingdom Fungi. These findings indicate that demethylincisterol A3 (1) is a natural antibiotic that may be used in the development of novel antibiotics against H. pylori.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Isolation and Chemical Characterization Of The Compoundsmentioning

confidence: 99%

Identification of Antibacterial Sterols from Korean Wild Mushroom Daedaleopsis confragosa via Bioactivity- and LC-MS/MS Profile-Guided Fractionation

Lee

Kang

et al. 2022

Molecules

View full text Add to dashboard Cite

show abstract

“…Interestingly, extensive investigations of its constituents have revealed various metabolites such as terpenoids and saccharides [25][26][27][28]. In the present study, we disclosed nine cyclohumulanoids from the culture broth of this fungus collected in the Shirakami metabolites such as terpenoids and saccharides [25][26][27][28]. In the present study, we disclo nine cyclohumulanoids from the culture broth of this fungus collected in the Shiraka mountainous area (Sirakami-Sanchi) of Japan, which UNESCO designated as a Wo Heritage Site in 1993 [29].…”

Section: Introductionmentioning

confidence: 99%

“…Daedaleopsis tricolor ( D . tricolor ) is one of the common basidiomycetes, wood-rotting fungi found in Europe [ 22 , 23 , 24 , 25 ] and Asia [ 26 , 27 , 28 ]. This fungus is not toxic but generally inedible.…”

Section: Introductionmentioning

confidence: 99%

“…This fungus is not toxic but generally inedible. Interestingly, extensive investigations of its constituents have revealed various metabolites such as terpenoids and saccharides [ 25 , 26 , 27 , 28 ]. In the present study, we disclosed nine cyclohumulanoids from the culture broth of this fungus collected in the Shirakami mountainous area (Sirakami-Sanchi) of Japan, which UNESCO designated as a World Heritage Site in 1993 [ 29 ].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Cyclohumulanoid Sesquiterpenes from the Culture Broth of the Basidiomycetous Fungus Daedaleopsis tricolor

et al. 2021

View full text Add to dashboard Cite

A series of cyclohumulanoids, i.e., tricocerapicanols A–C (1a–1c), tricoprotoilludenes A (2a) and B (3), tricosterpurol (4), and tricoilludins A–C (5–7) were isolated along with known violascensol (2b) and omphadiol (8) from the culture broth of Daedaleopsis tricolor, an inedible but not toxic mushroom. The structures were fully elucidated on the basis of NMR spectroscopic analysis, and the suggested relative structures were confirmed via density functional theory (DFT)-based chemical shift calculations involving a DP4 probability analysis. In the present study, the 1H chemical shifts were more informative than the 13C chemical shifts to distinguish the diastereomers at C-11. The absolute configurations of 1–5 were determined by comparing the experimental and calculated electronic circular dichroism (ECD) spectra. For 6 and 7, the same chirality was assigned according to their biosynthetic similarities with the other compounds. The successful assignment of some Cotton effects was achieved by utilizing DFT calculations using simple model compounds. The plausible biosynthesis of 1–7 was also discussed on the basis of the structural commonality and general cyclohumulanoid biosynthesis. Compounds 2a and 5 were found to simultaneously induce hyphal swelling and branching at 5.0 μg/mL against a test fungus Cochliobolus miyabeanus.

show abstract

Secondary Metabolites from Higher Fungi

Chen

Liu

2017

Progress in the Chemistry of Organic Natural Products

View full text Add to dashboard Cite

Secondary metabolites of higher fungi (mushrooms) are an underexplored resource compared to plant-derived secondary metabolites. An increasing interest in mushroom natural products has been noted in recent years. This chapter gives a comprehensive overview of the secondary metabolites from higher fungi, with 765 references highlighting the isolation, structure elucidation, biological activities, chemical syntheses, and biosynthesis of pigments, nitrogen-containing compounds, and terpenoids from mushrooms. Mushroom toxins are also included in each section.In a section on pigments of higher fungi, pigments are classified into four categories, namely, those from the shikimate-chorismate, acetate-malonate, and mevalonate biosynthetic pathways, and pigments containing nitrogen, with 145 references covering the years 2010-2016.In a section on other nitrogen-containing compounds of higher fungi, compounds are categorized primarily into nitrogen heterocycles, nucleosides, non-protein amino acids, cyclic peptides, and sphingolipids, with 65 references covering the years 2010-2016. In turn, in a section describing terpenoids of higher fungi, the sesquiterpenoids and diterpenoids are thoroughly elaborated, spanning the years 2001-2016, and 2009-2016, respectively. The divergent biosynthetic pathways from farnesyl pyrophosphate to sesquiterpenoids are also described. Selected triterpenoids with novel structures and promising biological activities, including lanostanes and ergostanes, are reported from the genus Ganoderma, and the fungi Antrodia cinnamomea and Poria cocos. In addition, cucurbitanes and saponaceolides are also compiled in this section.

show abstract

Sesquiterpenoids and an ergosterol from cultures of the fungus Daedaleopsis tricolor

Cited by 9 publications

References 8 publications

Identification of Antibacterial Sterols from Korean Wild Mushroom Daedaleopsis confragosa via Bioactivity- and LC-MS/MS Profile-Guided Fractionation

Identification of Antibacterial Sterols from Korean Wild Mushroom Daedaleopsis confragosa via Bioactivity- and LC-MS/MS Profile-Guided Fractionation

Cyclohumulanoid Sesquiterpenes from the Culture Broth of the Basidiomycetous Fungus Daedaleopsis tricolor

Secondary Metabolites from Higher Fungi

Contact Info

Product

Resources

About