Three new sesquiterpenes from the fungus Stereum sp. YMF1.1686

doi:10.1016/j.phytol.2016.01.006

Phytochemistry Letters

Volume 15, March 2016, Pages 186-189

https://doi.org/10.1016/j.phytol.2016.01.006 Get rights and content

Highlights

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The chemical constituents of the fungus Stereum sp. YMF1.1686 were investigated.
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New sesquiterpenes sterostreins R, S and T were obtained.
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Their structures were characterized by extensive 2D-NMR studies.

Abstract

A basidiomycete fungus, Stereum sp. YMF1.1686, was studied for its ability to produce new sesquiterpenes on nutrient-enriched cultivation media. Three new sesquiterpenes sterostrein R (1), sterostrein S (2) and sterostrein T (3), along with two known compounds sterostrein A (4) and sterostrein C (5) were isolated from the EtOAc extract of a culture broth of Stereum sp. YMF1.1686.

Graphical abstract

Introduction

The discovery of novel secondary metabolites is a goal of both pharmaceutical and natural product chemists. While fungi are well-established sources for such substances, the increasing number of new compounds impressively demonstrated that the potential of fungi’ to produce a high proportion of unknown natural products is far from being exploited. Fungi of the Stereum genus belong to the Stereaceae family (Basidiomycetes), which is one of the major sources of structurally diverse sesquiterpenes (Abraham, 2001). A series of interesting sesquiterpenoid skeletons has been obtained from Stereum, including hirsutane (Yoo et al., 2006, Liermann et al., 2010, Qi et al., 2014, Qi et al., 2015, Ma et al., 2014), cadinane (Li et al., 2006, Li et al., 2008, Zheng et al., 2013, Ma et al., 2014, Bunyapaiboonsri et al., 2014), drimane (Kim et al., 2006), isolactarane (Opatz et al., 2008), norilludalane (Isaka et al., 2011, Isaka et al., 2012) and stereumane (Li et al., 2011). In recent years, many other compounds have been reported from Stereum such as phenol derivatives (Duan et al., 2015), depside (Wang et al., 2014) and benzoate derivatives (Ma et al., 2014); some of them have even demonstrated antibacterial activity (Aqueveque et al., 2015, Ma et al., 2014) and cytotoxicity (Ma et al., 2014). To obtain a comprehensive understanding of the chemical composition of the genus Stereum, we analyzed the constituents of Stereum sp. YMF1.1686 in the present work. Three new sesquiterpenes (1–3) and two known compounds (4–5) (Fig. 1) were isolated. This work has enriched the study of secondary metabolites of the genus Stereum.

Section snippets

Results and discussion

Compound 1 was obtained as a pale yellow gum. The HR-ESI-MS data indicated a molecular formula of C₁₅H₂₂O₅ based on the [M + H]⁺ ion signal at m/z 283.1539 ([M + H]⁺, calc. 283.1546). The NMR data (Table 1) revealed five quaternary carbons at δ_C 43.2, 70.6, 132.1, 153.3 and 199.3; four methines at δ_C 84.6, 48.4, 55.9 and 91.8; three methylenes and three methyls, suggesting that compound 1 was an illudalane-type sesquiterpene compound (Isaka et al., 2011, Isaka et al., 2012, Li et al., 2014). MS and

General experimental procedures

UV spectra were measured on a Shimadzu UV-2401PC spectrophotometer (λ_max (log ε) in nm). Optical rotations were measured with a Jasco DIP-370 digital polarimeter. NMR spectra were obtained with a Bruker DRX-500 and Bruker Avance III-600 NMR spectrometers with TMS as an internal standard. ESI-MS and HR-ESI-MS were recorded on a Finnigan LCQ-Advantage and VG Auto-Spec-3000 mass spectrometer, respectively. EI-MS was recorded on an Agilent G6230 spectrometer. Column chromatography (CC) was

Acknowledgment

This work was supported by grants from the “973” Program of China (2013CB127505), the NSFC (31360028, 31560016), the Young Academic and Technical Leader Raising Foundation of Yunnan Province (2010CI023), the Natural Science Foundation of Yunnan Province (2013FB003).

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There are more references available in the full text version of this article.

Cited by (10)

Biological and chemical diversity go hand in hand: Basidiomycota as source of new pharmaceuticals and agrochemicals
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Citation Excerpt :
Recently, three novel sterostreins, sterostrein R (196), S (197), and sterostrein T (198) have been extracted from submerged cultures of Stereum sp. YMF1.1686 isolated in China, Yunnan Province (Tian et al., 2016). The same research group also studied another Stereum species, Stereum insigne CGMCC5.57, and isolated a novel dihydrobenzofuran (199; Fig. 12), as well as six known metabolites, which constitute the first secondary metabolites from this species (Tian et al., 2017).
The Basidiomycota constitutes the second largest higher taxonomic group of the Fungi after the Ascomycota and comprises over 30.000 species. Mycelial cultures of Basidiomycota have already been studied since the 1950s for production of antibiotics and other beneficial secondary metabolites. Despite the fact that unique and selective compounds like pleuromutilin were obtained early on, it took several decades more until they were subjected to a systematic screening for antimicrobial and anticancer activities. These efforts led to the discovery of the strobilurins and several hundreds of further compounds that mainly constitute terpenoids. In parallel the traditional medicinal mushrooms of Asia were also studied intensively for metabolite production, aimed at finding new therapeutic agents for treatment of various diseases including metabolic disorders and the central nervous system. While the evaluation of this organism group has in general been more tedious as compared to the Ascomycota, the chances to discover new metabolites and to develop them further to candidates for drugs, agrochemicals and other products for the Life Science industry have substantially increased over the past decade. This is owing to the revolutionary developments in –OMICS techniques, bioinformatics, analytical chemistry and biotechnological process technology, which are steadily being developed further. On the other hand, the new developments in polythetic fungal taxonomy now also allow a more concise selection of previously untapped organisms. The current review is dedicated to summarize the state of the art and to give an outlook to further developments.
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The genus Stereum is a rich source of sesquiterpenoids (Abraham, 2001; Qi et al., 2015). To date, the hirsutane (Yoo et al., 2006; Ma et al., 2014), sterpurane (Xie et al., 1992), cadinane (Liu et al., 2010), stereumane (Li et al., 2011), isolactarane (Opatz et al., 2008) and illudalane (Tian et al., 2016) sourced sesquiterpenes have been reported in the literature from this genus. More than eight species of the genus have had their chemical constituents reported (Tian et al., 2017).
The chemical constituents of the fungus Stereum rugosum ATCC64657 were studied. Two new sesquiterpenes, namely, sterostreins S (1) and W (2), as well as 10 known compounds, were isolated from the EtOAc extract of the fungal culture broth. The structures of the compounds were elucidated by HRMS, and 1D, 2D-NMR spectroscopy analysis. This is the first report on the chemical constituents of the fungus Stereum rugosum.
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Fungi of the genus Stereum, family Stereaceae (Basidiomycetes), contain diverse and interesting secondary metabolites. Many new sesquiterpenoids produced by Stereum have been identified, including hirsutane-type (Ma et al., 2014; Qi et al., 2015), illudalane-type (Isaka et al., 2011, 2012; Li et al., 2014; Tian et al., 2016a,b), isolactarane-type (Opatz et al., 2008), cadinane-type (Zheng et al., 2013; Ma et al., 2014; Bunyapaiboonsri et al., 2014), and stereumane-type (Li et al., 2011). Other compounds produced by Stereum include dihydrobenzofuran (Tian et al., 2016a,b), lactones (Kang and Kim, 2016), phenol derivatives (Duan et al., 2015), benzoate derivatives (Ma et al., 2014), and depside (Wang et al., 2014).
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Phytochemistry Letters

Highlights

Abstract

Graphical abstract

Introduction

Section snippets

Results and discussion

General experimental procedures

Acknowledgment

References (19)

Cadinane sesquiterpenoids from the basidiomycete Stereum cf. sanguinolentum BCC 22926

Phytochemistry

Two new phenol derivatives from Stereum hirsutum FP-91666

J. Asian Nat. Prod. Res.

Sterostreins F–O, illudalanes and norilludalanes from cultures of the basidiomycete Stereum ostrea BCC 22955

Phytochemistry

Stereumin A–E, sesquiterpenoids from the fungus Stereum sp. CCTCC AF 207024

Phytochemistry

Two new sesquiterpenes from the fungus Stereum sp. NN048997

Phytochem. Lett.

New benzoate derivatives and hirsutane type sesquiterpenoids with antimicrobial activity and cytotoxicity from the solid-state fermented rice by the medicinal mushroom Stereum hirsutum

Food. Chem.

Stucturally diverse sesquiterpenes produced by a chinese Tibet fungus Stereum hirsutum and their cytotoxic and Immunosuppressant activities

Org. Lett.

Stereumins K–P, sesquiterpenes from the fungus Stereum sp. CCTCC AF 007

Phytochemistry

Bioactive sesquiterpenes produced by fungi: are they useful for humans as well?

Curr. Med. Chem.

Cited by (10)

Biological and chemical diversity go hand in hand: Basidiomycota as source of new pharmaceuticals and agrochemicals

Chemical constituents of the fungus Stereum rugosum ATCC64657

Chemical constituents from the fungus Stereum sp. YMF1.04183

A new compound from Stereum insigne CGMCC5.57

Production of minor ginsenosides by combining Stereum hirsutum and cellulase

Natural disesquiterpenoids: an overview of their chemical structures, pharmacological activities, and biosynthetic pathways

Short communicationThree new sesquiterpenes from the fungus Stereum sp. YMF1.1686

Highlights

Abstract

Graphical abstract

Introduction

Section snippets

Results and discussion

General experimental procedures

Acknowledgment

Phytochemistry

J. Asian Nat. Prod. Res.

Phytochemistry

Phytochemistry

Phytochem. Lett.

Food. Chem.

Org. Lett.

Phytochemistry

Bioactive sesquiterpenes produced by fungi: are they useful for humans as well?

Curr. Med. Chem.

Short communication
Three new sesquiterpenes from the fungus Stereum sp. YMF1.1686