Marine anticancer agents: asperdiol, a cembranoid from the gorgonians, Eunicea asperula and E. tourneforti

Weinheimer, Alfred J.; Matson, James A.; Helm, D. van der; Poling, M.

doi:10.1016/s0040-4039(01)93000-x

Cited by 37 publications

(24 citation statements)

References 7 publications

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“…Based on their 1 H-NMR chemical signals, it was possible to make a putative identification of asperdiol in the extract of Plexaurella sp. due to the signals evident in the extract; these signals agree with the chemical shifts for this compound reported by 59 . Chemical shifts at 4.76 and 4.95 ppm correspond to an exomethylene group characteristic of the cembrane skeleton.…”

Section: Discussionsupporting

confidence: 88%

“…Additionally, chemical signals of VIP markers B4_4965 and B4_7686 were found in the 1 H-NMR spectrum of the extract from Plexaurella sp. When comparing these data with those reported in the literature, we detected similarities with the NMR data published for the antineoplastic compound asperdiol 50 . Additionally, an analysis of the marker B2_5118 in the 1 H-NMR spectrum of the extract from P. kukenthali and further comparisons with NMR data reported in the literature allowed us to make a putative identification of this compound as plexaurolone.…”

Section: Confidence Annotation Of Compound Identification Confidencesupporting

confidence: 77%

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Metabolomic study of soft corals from the Colombian Caribbean: PSYCHE and 1H-NMR comparative analysis

Santacruz

Hurtado

Doohan

et al. 2020

Sci Rep

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Marine organisms have evolved to survive against predators in complex marine ecosystems via the production of chemical compounds. Soft corals (cnidaria, Anthozoa, octocorallia) are an important source of chemically diverse metabolites with a broad spectrum of biological activities. Herein, we perform a comparative study between high-resolution proton nuclear magnetic resonance (1 H-nMR) and pure shift yielded by chirp excitation (PSYCHE) experiments to analyze the metabolic profile of 24 soft corals from the Colombian Caribbean to correlate chemical fingerprints with their cytotoxic activity against three cancer cell lines (human cervical carcinoma (SiHa), human prostatic carcinoma (PC3) and human lung adenocarcinoma (A549)). All data obtained were explored using multivariate analysis using principal components analysis (pcA) and orthogonal partial least squares (opLS) analysis. the results did not show a significant correlation between clusters using 1 H-nMR data in the pcA and opLS-DA models and therefore did not provide conclusive evidence; on the other hand, a metabolomic analysis of pSYcHe data obtained under the same parameters revealed that when a decoupled experiment is performed, it was possible to establish a statistically valid correlation between the chemical composition of soft corals and their cytotoxic activity against the PC3 cancer cell line, where the asperdiol and plexaurolone markers were putatively identified and related to the cytotoxic activity presented by extracts of Plexaurella sp. and Plexaura kukenthali, respectively. these results increase the speed, effectiveness and reliability of analyses for the study of this type of complex matrices. Metabolomics studies allow a complete analysis of a set of metabolites that are the substrates and products of metabolism driving essential cellular functions in a given biological system 1. This research has applications in different fields, such as pharmacology, environmental sciences, chemotaxonomy, nutrition and medicine 2. Recently, metabolomic approaches have allowed the understanding of complex biological systems and the biochemical composition of organisms that live in diverse environments, such as marine areas 3. Goulitquer et al. demonstrated that metabolites are important links between genotype and phenotype and are important for studying several biological processes and for analyzing interactions between organisms within communities via mass spectrometry (MS)-based metabolomics 4. In addition, Mohamed A. Farag et al. compared metabolomics results obtained with liquid chromatography coupled to mass spectrometry (LC-MS) with those obtained by nuclear magnetic resonance (NMR) to investigate the metabolism of 16 Sarcophyton species in the context of their genetic diversity and growth habitats 3. The importance of studying marine invertebrates lies in their extraordinary ability to produce a broad variety of chemical compounds with unique chemical structures that in most cases have been correlated with significant biological activities, which ...

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Section: Discussionsupporting

confidence: 88%

Section: Confidence Annotation Of Compound Identification Confidencesupporting

confidence: 77%

Metabolomic study of soft corals from the Colombian Caribbean: PSYCHE and 1H-NMR comparative analysis

Santacruz

Hurtado

Doohan

et al. 2020

Sci Rep

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“…Immerhin bestehen Hinweise, dass sie bei den Koniferen als Wachstumsinhibitoren [2], bei den Korallen als Abwehrstoffe gegen Raubfische [3] und bei den Termiten als Weg-Pheromon wirken [4]. Zudem wird einigen Cembranoiden Antitumor-Aktivitat zugeschrieben [5].…”

Section: Starting From L-serine (-)-(R)-nephthenol ((-)-2) and (-)-(unclassified

Synthese von (−)‐(R)‐Nephthenol und (−)‐(R)‐Cembren A

Schwabe

Farkas

Pfander

1988

Helvetica Chimica Acta

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“…9. The least-squares plane in each case is indicated by a dashed horizontal line and (Ealick, van der Helm & Weinheimer, 1975) Asperdioi A (Weinheimer, Matson, van der Helm & Poling, 1977) Lobophytolide (Karlsson, 1977a) Sinulariolide (Karlsson, 1977b atoms are indicated by their numbers. The figure once again shows the striking similarity between SLN, DSLN and crassin acetate.…”

Section: Structure Determination and Refinementmentioning

confidence: 99%

The molecular structures and absolute configurations of two new marine cembranolides: sinularin and dihydrosinularin

Hossain¹,

Helm²,

Matson³

et al. 1979

Acta Crystallogr Sect B

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ExperimentalThe crystal and molecular structures of two marine diterpene cembranolides, sinularin, C20H3004, and dihydrosinularin, C20H3204, extracted from the soft were collected with Cu Kct radiation at 138 K. The structures were solved by direct methods and refined by least-squares techniques. The final discrepancy factor is 0.036 for all 2221 reflections of sinularin and 0.043 for all 2087 reflections of dihydrosinularin. In each case, the absolute configuration of the molecule was determined by the Bijvoet method using anomalous dispersion of Cu radiation by oxygen atoms. The backbone molecular structure of the two compounds consists of a 14-membered cembrane ring fused to a 6-membered lactone ring and an epoxide function.

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Marine anticancer agents: asperdiol, a cembranoid from the gorgonians, Eunicea asperula and E. tourneforti

Cited by 37 publications

References 7 publications

Metabolomic study of soft corals from the Colombian Caribbean: PSYCHE and 1H-NMR comparative analysis

Metabolomic study of soft corals from the Colombian Caribbean: PSYCHE and 1H-NMR comparative analysis

Synthese von (−)‐(R)‐Nephthenol und (−)‐(R)‐Cembren A

The molecular structures and absolute configurations of two new marine cembranolides: sinularin and dihydrosinularin

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