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Two novel fomannosane-type sesquiterpenoids from the culture of the basidiomycete Agrocybe salicacola

ABSTRACT: Two novel fomannosane-type sesquiterpenoids, agrocybins H (1) and I (2), together with a known compound illudosin (3), were isolated from the culture broth of the mushroom Agrocybe salicacola. Their structures were elucidated by extensive spectroscopic analysis. The relative stereochemistry of 1 was determined by the use of single crystal X-ray crystallographic diffraction.

Electronic Supplementary Material

Supplementary material is available for this article at 10.1007/s13659-012-0031-2 and is accessible for authorized users.

SUBMITTER: Liu L

PROVIDER: S-EPMC4131595 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Unusual illudin-type sesquiterpenoids from cultures of Agrocybe salicacola

Project description:Seven new illudin-type sesquiterpenoids, agrocybins A–G (1–7), along with three known analogues (8–10), have been isolated from the culture broth of the fungus Agrocybe salicacola. Their structures were elucidated on the basis of extensive spectroscopic data analysis and comparison with data reported in the literature. The relative stereoconfigurations of 1 and 6 were elucidated by the X-ray crystallographic diffraction analysis. Compound 1 was highly cyclized containing seven chiral carbons which arranged compactly in six rings. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-011-0018-4 and is accessible for authorized users.

| S-EPMC4131650 | biostudies-literature

Two new drimane sesquiterpenoids from cultures of the basidiomycete Trichaptum biforme

Project description:Two new drimane sesquiterpenoids (1 and 2), as well as five known compounds (3–7), were isolated from the basidiomycete Trichaptum biforme. The structures of new compounds were elucidated by extensive spectroscopic methods, and the known compounds were identified by comparing their spectroscopic data with those reported in the literature. The cytotoxicities results against five human cancer cell lines of compounds 1 and 2 were negligible. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-013-0030-y and is accessible for authorized users.

| S-EPMC4131575 | biostudies-literature

Illudane Sesquiterpenoids from Edible Mushroom <i>Agrocybe salicacola</i> and Their Bioactivities.

Project description:To comprehensively understand the chemical constituents of the edible mushroom Agrocybe salicacola and their biological functions, a phytochemical separation of the cultural broth of A. salicacola led to the isolation of four new illudane sesquiterpenoids, agrocybins H-K (1-4), along with 10 known analogues (5-14). Compounds 2-4 were racemates of which 2 and 3 were further separated into single enantiomers as 2a/2b and 3a/3b. All new structures with absolute configurations were elucidated on the basis of an extensive spectroscopic analysis and quantum chemistry calculations. Compound 1 possesses a new carbon skeleton that might be derived from the protoilludane backbone. Compounds 1, 5, 8, and 9 show a certain degree of cytotoxicity to five human cancer cell lines. Compound 1 shows a mild inhibitory effect on nitric oxide production with an IC50 value of 31.4 μM. It is concluded that A. salicacola is rich in illudin derivatives with potential bioactivity prospects, which would make A. salicacola a good material of medicine and food homology.

| S-EPMC7469647 | biostudies-literature

Six novel steroids from culture of basidiomycete Polyporus ellisii

Project description:Graphical abstract Investigation of the culture of basidiomycete Polyporus ellisii led to the isolation of a novel compound 3β,9α,15α-trihydroxy-(22E,24R)-10(5→4)-abeo-ergosta-6,8(14),22-trien-5-one (1) with a new 5/7/6/5 ring system of ergosterol skeleton. In addition, five new steroids, 5β,6β-epoxy-3β,7α,9α-trihydroxy-(22E,24R)-ergosta-8(14),22-dien-15-one (2), 5β,6β-epoxy-3β,7α-dihydroxy-(22E,24R)-ergosta-8(14),22-dien-15-one (3), 5α,6α-epoxy-3β,9α,15α-trihydroxy-(22E,24R)-ergosta-8(14),22-dien-7-one (4), 15α-acetoxy-(22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (5), 15β-methoxy-(22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (6), along with four known ergosterols (7–10), were obtained. All structures were elucidated based on 1D and 2D NMR spectral data. New compounds were evaluated for cytotoxicity against five human cancer cell lines, only compound 4 was found to exhibit a favorable cytotoxicity profile toward all tested tumor cell lines. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-012-0058-4 and is accessible for authorized users.

| S-EPMC4131608 | biostudies-literature

Five new 5,6-seco-tremulane sesquiterpenoids from the basidiomycete Conocybe siliginea

Project description:Five new 5,6-seco-tremulane sesquiterpenoids (1–5), as well as three known analogues (6–8), were isolated from the basidiomycete Conocybe siliginea. The structures of new compounds were elucidated by extensive spectroscopic methods. The known compounds were identified by comparing their spectroscopic data with those reported in the literature. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-013-0003-1 and is accessible for authorized users.

| S-EPMC4131662 | biostudies-literature

Non-isoprenoid botryane sesquiterpenoids from basidiomycete Boletus edulis and their cytotoxic activity

Project description:Three non-isoprenoid botryane sesquiterpenoids, named boledulins A-C (1–3), have been isolated from the cultures of basidiomycete Boletus edulis Bull. The structures were established by means of spectroscopic methods. Boledulin A (1) exhibited moderate inhibitory activity against five human cancer cell lines. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-011-0005-9 and is accessible for authorized users.

| S-EPMC4131704 | biostudies-literature

Calamene-Type Sesqui-, Mero-, and Bis-sesquiterpenoids from Cultures of <i>Heimiomyces</i> sp., a Basidiomycete Collected in Africa.

Project description:New meroterpenoids bis-heimiomycins A-D (1-4) and heimiomycins D and E (5 and 6) were isolated from solid rice cultures of Heimiomyces sp., while new calamene-type sesquiterpenoids heimiocalamene A (7) and B (8) were isolated from shake cultures, respectively. Structures of the metabolites were elucidated by 1D and 2D NMR in addition to HRESIMS data. While relative configurations were assigned by ROESY data, absolute configurations were derived from the structurally related, previously described calamenes, which we herein name heimiocalamenes C-E (9-11). A plausible biosynthetic pathway was proposed for 1-6, with a radical reaction connecting their central para-benzoquinone building block to calamene-sesquiterpenoids. Based on the assumption of a common biosynthesis, we reviewed the structure of the known nitrogen-containing derivative 11, calling the validity of the originally proposed structure into question. Subsequently, the structure of 11 was revised by analysis of HMBC and ROESY NMR data. Only heimiomycin D (5) displayed cytotoxic effects against cell line KB3.1.

| S-EPMC9972471 | biostudies-literature

Expression, gene cloning, and characterization of five novel phytases from four basidiomycete fungi: Peniophora lycii, Agrocybe pediades, a Ceriporia sp., and Trametes pubescens.

Project description:Phytases catalyze the hydrolysis of phosphomonoester bonds of phytate (myo-inositol hexakisphosphate), thereby creating lower forms of myo-inositol phosphates and inorganic phosphate. In this study, cDNA expression libraries were constructed from four basidiomycete fungi (Peniophora lycii, Agrocybe pediades, a Ceriporia sp., and Trametes pubescens) and screened for phytase activity in yeast. One full-length phytase-encoding cDNA was isolated from each library, except for the Ceriporia sp. library where two different phytase-encoding cDNAs were found. All five phytases were expressed in Aspergillus oryzae, purified, and characterized. The phytases revealed temperature optima between 40 and 60 degrees C and pH optima at 5.0 to 6.0, except for the P. lycii phytase, which has a pH optimum at 4.0 to 5.0. They exhibited specific activities in the range of 400 to 1,200 U. mg, of protein(-1) and were capable of hydrolyzing phytate down to myo-inositol monophosphate. Surprisingly, (1)H nuclear magnetic resonance analysis of the hydrolysis of phytate by all five basidiomycete phytases showed a preference for initial attack at the 6-phosphate group of phytic acid, a characteristic that was believed so far not to be seen with fungal phytases. Accordingly, the basidiomycete phytases described here should be grouped as 6-phytases (EC 3.1.3.26).

| S-EPMC93222 | biostudies-literature

Isolation and synthesis of two antiproliferative calamenene-type sesquiterpenoids from Sterculia tavia from the Madagascar rain forest.

Project description:Investigation of the endemic Madagascan plant Sterculia taiva Baill. (Malvaceae) for antiproliferative activity against the A2780 ovarian cancer cell line led to the isolation of two new bioactive calamenene-type sesquiterpenoids, named tavinin A (2) and epi-tavinin A (3) together with the known sesquiterpenoid mansonone G (1). The structures of the two new compounds were elucidated based on analysis of their 1D and 2D NMR spectra and mass spectrometric data, and were confirmed by de novo synthesis. The three isolated sesquiterpenoids (1-3) had modest antiproliferative activities against the A2780 ovarian cancer cell line, with IC(50) values of 10.2, 5.5 and 6.7 μM, respectively.

| S-EPMC3508347 | biostudies-literature

Two new guaiane sesquiterpenoids from Daphne holosericea (Diels) Hamaya.

Project description:Two new sesquiterpenoids with guaiane skeletons-holosericin A (1) and holosericin B (2)-were isolated from the medicinal plant Daphne holosericea (Diels) Hamawa (Thymelaeceae). Their structures were elucidated by 1D and 2D-NMR spectroscopy, as well as HR-ESI-MS data. Compounds 1 and 2 were evaluated for inhibitory activities against acetylcholinesterase and compound 2 showed a moderate activity with 31% inhibition.

| S-EPMC6271883 | biostudies-literature

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