An unusual spirocyclic isopimarane diterpenoid and other isopimarane diterpenoids from fruiting bodies of Xylaria polymorpha

Shiono, Yoshihito; Matsui, Norika; Imaizumi, Takayuki; Koseki, Takuya; Murayama, Tetsuya; Kwon, Eunsang; Abe, Tomomi; Kimura, Ken

doi:10.1016/j.phytol.2013.05.008

Cited by 13 publications

(4 citation statements)

References 17 publications

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“…The molecular formula for the compound was established to be C 20 H 22 O 4 based on the pseudomolecular ion, [M + H] + of m / z 329.1745 with an accuracy of 0.6 ppm (HRESITOFMS) and the ultraviolet (UV) spectrum displayed absorption bands at λ max 215 and 270 nm. A NMR spectroscopic analysis of the isolated compound and comparison to the data reported for myrocins A-E [ 34 , 35 , 36 , 37 ] allowed for the structural elucidation of a new pimarane-type diterpene, myrocin F ( 1 ) ( Figure 2 ). 1 H, 13 C, HMBC and NOESY data is shown in Table 1 .…”

Section: Resultsmentioning

confidence: 99%

A Dereplication and Bioguided Discovery Approach to Reveal New Compounds from a Marine-Derived Fungus Stilbella fimetaria

et al. 2017

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A marine-derived Stilbella fimetaria fungal strain was screened for new bioactive compounds based on two different approaches: (i) bio-guided approach using cytotoxicity and antimicrobial bioassays; and (ii) dereplication based approach using liquid chromatography with both diode array detection and high resolution mass spectrometry. This led to the discovery of several bioactive compound families with different biosynthetic origins, including pimarane-type diterpenoids and hybrid polyketide-non ribosomal peptide derived compounds. Prefractionation before bioassay screening proved to be a great aid in the dereplication process, since separate fractions displaying different bioactivities allowed a quick tentative identification of known antimicrobial compounds and of potential new analogues. A new pimarane-type diterpene, myrocin F, was discovered in trace amounts and displayed cytotoxicity towards various cancer cell lines. Further media optimization led to increased production followed by the purification and bioactivity screening of several new and known pimarane-type diterpenoids. A known broad-spectrum antifungal compound, ilicicolin H, was purified along with two new analogues, hydroxyl-ilicicolin H and ilicicolin I, and their antifungal activity was evaluated.

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Section: Resultsmentioning

confidence: 99%

A Dereplication and Bioguided Discovery Approach to Reveal New Compounds from a Marine-Derived Fungus Stilbella fimetaria

et al. 2017

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“…Compounds spiropolin A ( 93 ) and myrocin E ( 94 ), with isopimarane-type skeletons, were isolated from the root of Mt. Gassan Xylaria polymorpha , Yamagata Prefecture, Japan [ 33 ]. Eighteen new diterpenes, including xylarinorditerpenes A–R ( 95 – 112 ) with nor-isopimarane skeletons, were isolated from the wood-rotting basidiomycete Fomitopsis betulinus -derived fungus Xylaria longipes HFG1018.…”

Section: Structural and Biological Activity Studiesmentioning

confidence: 99%

Structures and Biological Activities of Secondary Metabolites from Xylaria spp.

Chen,

Yu,

Chen

et al. 2024

JoF

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The fungus genus Xylaria is an important source of drug discoveries in scientific fields and in the pharmaceutical industry due to its potential to produce a variety of structured novel and bioactive secondary metabolites. This review prioritizes the structures of the secondary metabolites of Xylaria spp. from 1994 to January 2024 and their relevant biological activities. A total of 445 new compounds, including terpenoids, nitrogen-containing compounds, polyketides, lactones, and other classes, are presented in this review. Remarkably, among these compounds, 177 compounds show various biological activities, including cytotoxic, antimicrobial, anti-inflammatory, antifungal, immunosuppressive, and enzyme-inhibitory activities. This paper will guide further investigations into the structures of novel and potent active natural products derived from Xylaria and their potential contributions to the future development of new natural drug products in the agricultural and medicinal fields.

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“…9). 43 Notably, the oxidation of SphB 2 via sodium periodate led to the formation of semi-synthetic derivative 15 (Fig. 9).…”

Section: Papermentioning

confidence: 99%

Deciphering the chemical instability of sphaeropsidin A under physiological conditions – degradation studies and structural elucidation of the major metabolite

et al. 2020

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An unusual spirocyclic isopimarane diterpenoid and other isopimarane diterpenoids from fruiting bodies of Xylaria polymorpha

Cited by 13 publications

References 17 publications

A Dereplication and Bioguided Discovery Approach to Reveal New Compounds from a Marine-Derived Fungus Stilbella fimetaria

A Dereplication and Bioguided Discovery Approach to Reveal New Compounds from a Marine-Derived Fungus Stilbella fimetaria

Structures and Biological Activities of Secondary Metabolites from Xylaria spp.

Deciphering the chemical instability of sphaeropsidin A under physiological conditions – degradation studies and structural elucidation of the major metabolite

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