Caulerpenyne and Related Bis‐enol Esters Are Novel‐Type Inhibitors of Human 5‐Lipoxygenase

Richter, P; Schubert, Gregor; Schaible, Anja; Çavaş, Levent; Werz, Oliver; Pohnert, Georg

doi:10.1002/cmdc.201402065

Cited by 7 publications

(4 citation statements)

References 25 publications

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“…caulerpenyne has also been reported [70]. Caulerpenyne is a highly bioactive molecule, presenting anticancer activity, cell grown inhibition, neurotoxic activity, and inhibiting lipoxygenases, among others [71][72][73][74]. Some shelled sacoglossans are also rich in monoterpenoids, which they can obtain from their algal food and further transform into more bioactive compounds.…”

Section: Linear Monoterpenoidsmentioning

confidence: 99%

Terpenoids in Marine Heterobranch Molluscs

Ávila

2020

Marine Drugs

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Heterobranch molluscs are rich in natural products. As other marine organisms, these gastropods are still quite unexplored, but they provide a stunning arsenal of compounds with interesting activities. Among their natural products, terpenoids are particularly abundant and diverse, including monoterpenoids, sesquiterpenoids, diterpenoids, sesterterpenoids, triterpenoids, tetraterpenoids, and steroids. This review evaluates the different kinds of terpenoids found in heterobranchs and reports on their bioactivity. It includes more than 330 metabolites isolated from ca. 70 species of heterobranchs. The monoterpenoids reported may be linear or monocyclic, while sesquiterpenoids may include linear, monocyclic, bicyclic, or tricyclic molecules. Diterpenoids in heterobranchs may include linear, monocyclic, bicyclic, tricyclic, or tetracyclic compounds. Sesterterpenoids, instead, are linear, bicyclic, or tetracyclic. Triterpenoids, tetraterpenoids, and steroids are not as abundant as the previously mentioned types. Within heterobranch molluscs, no terpenoids have been described in this period in tylodinoideans, cephalaspideans, or pteropods, and most terpenoids have been found in nudibranchs, anaspideans, and sacoglossans, with very few compounds in pleurobranchoideans and pulmonates. Monoterpenoids are present mostly in anaspidea, and less abundant in sacoglossa. Nudibranchs are especially rich in sesquiterpenes, which are also present in anaspidea, and in less numbers in sacoglossa and pulmonata. Diterpenoids are also very abundant in nudibranchs, present also in anaspidea, and scarce in pleurobranchoidea, sacoglossa, and pulmonata. Sesterterpenoids are only found in nudibranchia, while triterpenoids, carotenoids, and steroids are only reported for nudibranchia, pleurobranchoidea, and anaspidea. Many of these compounds are obtained from their diet, while others are biotransformed, or de novo biosynthesized by the molluscs. Overall, a huge variety of structures is found, indicating that chemodiversity correlates to the amazing biodiversity of this fascinating group of molluscs.

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Section: Linear Monoterpenoidsmentioning

confidence: 99%

Terpenoids in Marine Heterobranch Molluscs

Ávila

2020

Marine Drugs

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“…It is characterized by its “central troponoid bridging” bisindole structure ( Su et al, 1997 ). Caulerpenyne is a sesquiterpenoid-structured secondary metabolite which has some bioactivities such as antiproliferative and apoptotic activities ( Cavas et al, 2006 ) and inhibitors of lipoxygenase ( Cengiz et al, 2011 ) and 5-lipoxygenase ( Richter et al, 2014 ), etc. Secondary metabolites of genus Caulerpa are responsible for complex modulation network induced in AMPK, ER Stress, mitochondrial stress, PTP1B inhibition and cell cycle stop pathways, metabolic reprogramming in cancer cells, apoptosis and cell cycle arrest in cancer metabolism ( Mehra et al, 2019 ).…”

Section: Introductionmentioning

confidence: 99%

In-silico molecular interactions among the secondary metabolites of Caulerpa spp. and colorectal cancer targets

et al. 2022

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Caulerpa spp. secrete more than thirty different bioactive chemicals which have already been used in cancer treatment research since they play a pivotal role in cancer metabolism. Colorectal cancer is one of the most common cancer types, thus using novel and effective chemicals for colorectal cancer treatment is crucial. In the cheminformatics pipeline of this study, ADME-Tox and drug-likeness tests were performed for filtering the secondary metabolites of Caulerpa spp. The ligands which were selected from the ADME test were used for in silico molecular docking studies against the enzymes of the oxidative branch of the pentose phosphate pathway (glucose-6-phosphate dehydrogenase and 6-phosphoglutarate dehydrogenase), which is of great importance for colorectal cancer, by using AutoDock Vina. Pharmacophore modeling was carried out to align the molecules. Molecular dynamic simulations were performed for each target to validate the molecular docking studies and binding free energies were calculated. According to the ADME test results, 13 different secondary metabolites were selected as potential ligands. Molecular docking studies revealed that vina scores of caulerpin and monomethyl caulerpinate for G6PDH were found as −10.6 kcal mol-1, −10.5 kcal mol-1, respectively. Also, the vina score of caulersin for 6PGD was found as −10.7 kcal mol-1. The highest and the lowest binding free energies were calculated for monomethyl caulerpinate and caulersin, respectively. This in silico study showed that caulerpin, monomethyl caulerpinate, and caulersin could be evaluated as promising marine phytochemicals against pentose phosphate pathway enzymes and further studies are recommended to investigate the detailed activity of these secondary metabolites on these targets.

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“…Moreover, LOX products, leukotrienes, and lipoxins, have a part in significant metabolic functions such as organelle degradation (25), transcription regulation (26), and possibly tumor cell metastasis (27). Therefore, the inhibition of LOXs is considered an important target for the treatment of LOX-related diseases (5)(6)(7)16,(28)(29)(30)(31)(32)(33)(34)(35). There are some reports which show the results of LOX inhibition studies in the literature.…”

Section: Introductionmentioning

confidence: 99%

Can soybean lipoxygenases be real models for mammalian lipoxygenases? A bioinformatics approach

Cengiz

Çavaş

2021

Journal of the Turkish Chemical Society Section A: Chemistry

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Soybean lipoxygenase-1 is one of well-studied enzymes because it is considered as a model enzyme for mammalian lipoxygenases. In general, the soybean lipoxygenase-1 is used in the test of inhibitory activities of various compounds. The present study provides a bioinformatics approach for comparison of various lipoxygenases in the databases. Their various physical and chemical parameters such as molecular weight, theoretical pI, amino acid composition, aliphatic index, and grand average of hydropathicity and the multiple sequence alignments of the lipoxygenases were computed by using several bioinformatics tools. In order to see phylogenetic relationships among lipoxygenases, a phylogenetic tree was constructed. The first three most abundant amino acids in soybean lipoxygenase-1 and 15-lipoxygenase (human) are L (10.3 %), S (7.4 %), A (6.7 %) and L (13.3 %), G (7.4 %), V (7.1 %), respectively. According to the phylogenetic tree, the soybean lipoxygenases are within separate clade compared to the mammalian lipoxygenases. In conclusion, soybean lipoxygenase-1 may not fully characterize the human lipoxygenase-15 since there are remarkable sequence-based differences, which are obtained by using bioinformatics tools between soybean lipoxygenase-1 and lipoxygenases from other sources especially from human. In this context, the researchers, who are aware of the problems described above and who have similar concerns, have begun to use recombinant DNA technology to produce recombinant human lipoxygenase-15 enzyme.

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Caulerpenyne and Related Bis‐enol Esters Are Novel‐Type Inhibitors of Human 5‐Lipoxygenase

Cited by 7 publications

References 25 publications

Terpenoids in Marine Heterobranch Molluscs

Terpenoids in Marine Heterobranch Molluscs

In-silico molecular interactions among the secondary metabolites of Caulerpa spp. and colorectal cancer targets

Can soybean lipoxygenases be real models for mammalian lipoxygenases? A bioinformatics approach

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