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Keywords = illudalane

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12 pages, 1435 KiB  
Article
Chemistry and Bioactivity of the Deep-Water Antarctic Octocoral Alcyonium sp.
by Anne-Claire D. Limon, Hiran M. L. W. Patabendige, Ala Azhari, Xingmin Sun, Dennis E. Kyle, Nerida G. Wilson and Bill J. Baker
Mar. Drugs 2022, 20(9), 576; https://doi.org/10.3390/md20090576 - 14 Sep 2022
Cited by 6 | Viewed by 2627
Abstract
Chemical investigation of an Antarctic deep-water octocoral has led to the isolation of four new compounds, including three illudalane sesquiterpenoids (13) related to the alcyopterosins, a highly oxidized steroid, alcyosterone (5), and five known alcyopterosins (4 [...] Read more.
Chemical investigation of an Antarctic deep-water octocoral has led to the isolation of four new compounds, including three illudalane sesquiterpenoids (13) related to the alcyopterosins, a highly oxidized steroid, alcyosterone (5), and five known alcyopterosins (4, 69). The structures were established by extensive 1D and 2D NMR analyses, while 9 was verified by XRD. Alcyopterosins are unusual for their nitrate ester functionalization and have been characterized with cytotoxicity related to their DNA binding properties. Alcyopterosins V (3) and E (4) demonstrated single-digit micromolar activity against Clostridium difficile, an intestinal bacterium capable of causing severe diarrhea that is increasingly associated with drug resistance. Alcyosterone (5) and several alcyopterosins were similarly potent against the protist Leishmania donovani, the causative agent of leishmaniasis, a disfiguring disease that can be fatal if not treated. While the alcyopterosin family of sesquiterpenes is known for mild cytotoxicity, the observed activity against C. difficile and L. donovani is selective for the infectious agents. Full article
(This article belongs to the Section Structural Studies on Marine Natural Products)
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9 pages, 2271 KiB  
Article
Antiproliferative Illudalane Sesquiterpenes from the Marine Sediment Ascomycete Aspergillus oryzae
by Raha Orfali, Shagufta Perveen, Muhammad Farooq Khan, Atallah F. Ahmed, Mohammad A. Wadaan, Areej Mohammad Al-Taweel, Ali S. Alqahtani, Fahd A. Nasr, Sobia Tabassum, Paolo Luciano, Giuseppina Chianese, Jyh-Horng Sheu and Orazio Taglialatela-Scafati
Mar. Drugs 2021, 19(6), 333; https://doi.org/10.3390/md19060333 - 10 Jun 2021
Cited by 9 | Viewed by 3652
Abstract
The new asperorlactone (1), along with the known illudalane sesquiterpene echinolactone D (2), two known pyrones, 4-(hydroxymethyl)-5-hydroxy-2H-pyran-2-one (3) and its acetate 4, and 4-hydroxybenzaldehyde (5), were isolated from a culture of Aspergillus [...] Read more.
The new asperorlactone (1), along with the known illudalane sesquiterpene echinolactone D (2), two known pyrones, 4-(hydroxymethyl)-5-hydroxy-2H-pyran-2-one (3) and its acetate 4, and 4-hydroxybenzaldehyde (5), were isolated from a culture of Aspergillus oryzae, collected from Red Sea marine sediments. The structure of asperorlactone (1) was elucidated by HR-ESIMS, 1D, and 2D NMR, and a comparison between experimental and DFT calculated electronic circular dichroism (ECD) spectra. This is the first report of illudalane sesquiterpenoids from Aspergillus fungi and, more in general, from ascomycetes. Asperorlactone (1) exhibited antiproliferative activity against human lung, liver, and breast carcinoma cell lines, with IC50 values < 100 µM. All the isolated compounds were also evaluated for their toxicity using the zebrafish embryo model. Full article
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9 pages, 908 KiB  
Article
Cytotoxic Illudalane Sesquiterpenes from the Wood-Decay Fungus Granulobasidium vellereum (Ellis & Cragin) Jülich
by Christina L. Nord, Audrius Menkis and Anders Broberg
Molecules 2014, 19(9), 14195-14203; https://doi.org/10.3390/molecules190914195 - 9 Sep 2014
Cited by 22 | Viewed by 10612
Abstract
Seven illudalane sesquiterpenes were obtained from the wood decomposing fungus Granulobasidium vellereum: granuloinden A, granuloinden B and dihydrogranuloinden, along with the previously known compounds radulactone, pterosin M, echinolactone A and D. Granuloinden B showed potent cytotoxic activity against the Huh7 and MT4 [...] Read more.
Seven illudalane sesquiterpenes were obtained from the wood decomposing fungus Granulobasidium vellereum: granuloinden A, granuloinden B and dihydrogranuloinden, along with the previously known compounds radulactone, pterosin M, echinolactone A and D. Granuloinden B showed potent cytotoxic activity against the Huh7 and MT4 tumor cell lines (CC50 values of 6.7 and 0.15 µM, respectively), whereas granuloinden A and dihydrogranuloinden had no or moderate activity. Full article
(This article belongs to the Section Natural Products Chemistry)
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