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Search Results (3)

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Keywords = merosesquiterpene

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25 pages, 6627 KB  
Article
Natural Merosesquiterpenes Activate the DNA Damage Response via DNA Strand Break Formation and Trigger Apoptotic Cell Death in p53-Wild-Type and Mutant Colorectal Cancer
by Apisada Jiso, Philipp Demuth, Madeleine Bachowsky, Manuel Haas, Nina Seiwert, Daniel Heylmann, Birgit Rasenberger, Markus Christmann, Lea Dietrich, Thomas Brunner, Riyanti, Till F. Schäberle, Anuchit Plubrukarn and Jörg Fahrer
Cancers 2021, 13(13), 3282; https://doi.org/10.3390/cancers13133282 - 30 Jun 2021
Cited by 11 | Viewed by 4310
Abstract
Colorectal cancer (CRC) is a frequently occurring malignant disease with still low survival rates, highlighting the need for novel therapeutics. Merosesquiterpenes are secondary metabolites from marine sponges, which might be useful as antitumor agents. To address this issue, we made use of a [...] Read more.
Colorectal cancer (CRC) is a frequently occurring malignant disease with still low survival rates, highlighting the need for novel therapeutics. Merosesquiterpenes are secondary metabolites from marine sponges, which might be useful as antitumor agents. To address this issue, we made use of a compound library comprising 11 isolated merosesquiterpenes. The most cytotoxic compounds were smenospongine > ilimaquinone ≈ dactylospontriol, as shown in different human CRC cell lines. Alkaline Comet assays and γH2AX immunofluorescence microscopy demonstrated DNA strand break formation in CRC cells. Western blot analysis revealed an activation of the DNA damage response with CHK1 phosphorylation, stabilization of p53 and p21, which occurred both in CRC cells with p53 knockout and in p53-mutated CRC cells. This resulted in cell cycle arrest followed by a strong increase in the subG1 population, indicative of apoptosis, and typical morphological alterations. In consistency, cell death measurements showed apoptosis following exposure to merosesquiterpenes. Gene expression studies and analysis of caspase cleavage revealed mitochondrial apoptosis via BAX, BIM, and caspase-9 as the main cell death pathway. Interestingly, the compounds were equally effective in p53-wild-type and p53-mutant CRC cells. Finally, the cytotoxic activity of the merosesquiterpenes was corroborated in intestinal tumor organoids, emphasizing their potential for CRC chemotherapy. Full article
(This article belongs to the Special Issue The Tumor Suppressor TP53 in Colorectal Carcinoma)
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7 pages, 849 KB  
Article
A New Sesquiterpenoid Aminoquinone from an Indonesian Marine Sponge
by Walter Balansa, Ute Mettal, Zerlina G. Wuisan, Anuchit Plubrukarn, Frans G. Ijong, Yang Liu and Till F. Schäberle
Mar. Drugs 2019, 17(3), 158; https://doi.org/10.3390/md17030158 - 8 Mar 2019
Cited by 23 | Viewed by 6519
Abstract
Sponges are a well-known bioresource for bioactive compounds. In this study, antibacterial activity-guided fractionation of the extract from an Indonesian marine Dactylospongia elegans sponge led to the discovery of four merosesquiterpenoids, namely, a new sesquiterpenoid aminoquinone nakijiquinone V (1), along with [...] Read more.
Sponges are a well-known bioresource for bioactive compounds. In this study, antibacterial activity-guided fractionation of the extract from an Indonesian marine Dactylospongia elegans sponge led to the discovery of four merosesquiterpenoids, namely, a new sesquiterpenoid aminoquinone nakijiquinone V (1), along with illimaquinone (2), smenospongine (3), and dyctioceratine C (4). The structure of compound 1 was elucidated by 1D and 2D NMR as well as by LC-HRESIMS data analysis. Compounds 2–4 showed moderate to low antimicrobial activity against Bacillus megaterium DSM32 with a minimum inhibitory concentration (MIC) of 32 μg/mL, 32 μg/mL, and 64 μg/mL, respectively. Furthermore, compounds 2 and 3 both inhibited Micrococcus luteus ATCC 4698 with a MIC of 32 μg/mL. In conclusion, the isolated merosesquiterpenoids, which are known for their cytotoxic effects, showed antibacterial activity and prompt future structure activity relationship (SAR) studies concerning the various bioactivities observed for this group of natural products. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Sponges)
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10 pages, 2348 KB  
Article
Merosesquiterpene Congeners from the Australian Sponge Hyrtios digitatus as Potential Drug Leads for Atherosclerosis Disease
by Huda A. Wahab, Ngoc B. Pham, Tengku S. Tengku Muhammad, John N. A. Hooper and Ronald J. Quinn
Mar. Drugs 2017, 15(1), 6; https://doi.org/10.3390/md15010006 - 27 Dec 2016
Cited by 13 | Viewed by 6134
Abstract
A study of the chemical constituents from the Australian Sponge Hyrtios digitatus has provided a perspective on the connection between the chemistry and biology of the puupehenones, a unique and unusual class of merosesquiterpenes. In this study, a new tetracyclic merosesquiterpene, 19-methoxy-9,15-ene-puupehenol ( [...] Read more.
A study of the chemical constituents from the Australian Sponge Hyrtios digitatus has provided a perspective on the connection between the chemistry and biology of the puupehenones, a unique and unusual class of merosesquiterpenes. In this study, a new tetracyclic merosesquiterpene, 19-methoxy-9,15-ene-puupehenol (1) was isolated from the marine sponge Hyrtios digitatus along with the known 20-methoxy-9,15-ene-puupehenol (2). Their structures were elucidated on the basis of spectroscopic data (1H and 13C NMR) in combination with experimental electronic circular dichroism (ECD) data. Compounds 1 and 2 are active at 1.78 μM and 3.05 μM, respectively, on Scavenger Receptor-Class B Type 1 HepG2 (SR-B1 HepG2) stable cell lines, targeting atherosclerosis disease. Full article
(This article belongs to the Collection Bioactive Compounds from Marine Invertebrates)
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