New cytotoxic steroids from the gorgonian Isis hippuris . Structure–activity studies

González, Noemí; Barral, Miguel A.; Rodrı́guez, Jaime; Jiménez, Carlos

doi:10.1016/s0040-4020(01)00223-x

Cited by 55 publications

(47 citation statements)

References 12 publications

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“…The cytotoxicity IC 50 value of 5 against A549 was ca. tenfold larger than the reported one [4], which might be caused by methodological errors and other factors.…”

contrasting

confidence: 64%

“…-Both Isis minorbrachyblasta and I. hippuris belong to the Isis genus, Isididae family of gorgonian corals. There are reports that I. hippuris is unique concerning its steroidal constituents that can be characterized as of the hippurin or hippuristanol type having a spiroketal [1 -4], of the gorgosterol type possessing a cyclopropane [5 -7], and of the hippuristerone type containing a 3-keto function [4] [8]. These types also differ in the side-chain alkylation pattern.…”

mentioning

confidence: 99%

“…These types also differ in the side-chain alkylation pattern. Some of these compounds have been reported to have significant biological activities, e.g., hippuristanol and (2a)-2-hydroxyhippuristanol showed 50% inhibition (in vitro) of DBA/MC fibrosarcoma at 0.8 and 0.1 mg/ml [2], several hippuristanol-type steroids showed potent cytotoxicity against P-388, A549, HT29, and MEL28 cancer cell lines [4], and several gorgosterol-type steroids showed moderate activity against drug-resistant cells (KBC2) expressing P-glycoprotein [7]. However, there were no reports about the chemical constituents of Isis minorbrachyblasta.…”

mentioning

confidence: 99%

“…However, there were no reports about the chemical constituents of Isis minorbrachyblasta. In our present investigation on the chemical constituents of the South China Sea gorgonian I. minorbrachyblasta Zou 1991, two new steroids, (1a,3b,7a,11a,12b)-gorgost-5-ene-1,3,7,11,12-pentol 12-acetate (1) and 11-O-acetyl-22-epihippuristanol (2), and a new alkaloid, 2,3,5,6,11,11b-hexahydro-2-hydroxy-1H-indolizino [8,7-b]indole-2-carboxylic acid (3), were obtained, together with the three known compounds 22-epihippuristanol (4) [4], hippuristanol (5) [2] [4], and tryptamine (6) [9]. The cytotoxicity of 1, 5, and the…”

mentioning

confidence: 99%

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New Steroids and a New Alkaloid from the Gorgonian Isis minorbrachyblasta: Structures, Cytotoxicity, and Antilarval Activity

Miao

Gao

et al. 2010

Helvetica Chimica Acta

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Two new polyoxygenated steroids, (1a,3b,7a,11a,12b)-gorgost-5-ene-1,3,7,11,12-pentol 12-acetate (1) and 11-O-acetyl-22-epihippuristanol (2), and a new alkaloid, 2,3,5,6,11,11b-hexahydro-2-hydroxy-1H-indolizino [8,7-b]indole-2-carboxylic acid (3), together with three known compounds, 22-epihippuristanol (4), hippuristanol (5), and tryptamine (6), were isolated from the EtOH/CH 2 Cl 2 extracts of the South China Sea gorgonian Isis minorbrachyblasta. The structures of the new compounds were determined by spectroscopic methods. Compound 1 showed weak cytotoxicity against A549, HONE1, and HeLa cancer cell lines and strong antilarval activity towards Bugula neritina larvae with an EC 50 value of 5.8 mg/ml. Compound 5 showed moderate cytotoxicity against A549, HONE1, and HeLa cell lines, and the epimer mixture 4/5 (weight ratio 3 : 2) exhibited potent cytotoxicity against A549 and HONE1 cell lines with IC 50 values of 4.2 and 4.8 mg/ml, which indicated that epimers 4 and 5 might have a synergistic effect on their cytotoxicity against A549 and HONE1 cell lines.Introduction. -Both Isis minorbrachyblasta and I. hippuris belong to the Isis genus, Isididae family of gorgonian corals. There are reports that I. hippuris is unique concerning its steroidal constituents that can be characterized as of the hippurin or hippuristanol type having a spiroketal [1 -4], of the gorgosterol type possessing a cyclopropane [5 -7], and of the hippuristerone type containing a 3-keto function [4] [8]. These types also differ in the side-chain alkylation pattern. Some of these compounds have been reported to have significant biological activities, e.g., hippuristanol and (2a)-2-hydroxyhippuristanol showed 50% inhibition (in vitro) of DBA/MC fibrosarcoma at 0.8 and 0.1 mg/ml [2], several hippuristanol-type steroids showed potent cytotoxicity against P-388, A549, HT29, and MEL28 cancer cell lines [4], and several gorgosterol-type steroids showed moderate activity against drug-resistant cells (KBC2) expressing P-glycoprotein [7]. However, there were no reports about the chemical constituents of Isis minorbrachyblasta. In our present investigation on the chemical constituents of the South China Sea gorgonian I. minorbrachyblasta Zou 1991, two new steroids, (1a,3b,7a,11a,12b)-gorgost-5-ene-1,3,7,11,12-pentol 12-acetate (1) and 11-O-acetyl-22-epihippuristanol (2), and a new alkaloid, 2,3,5,6,11,11b-hexahydro-2-hydroxy-1H-indolizino [8,7-b]indole-2-carboxylic acid (3), were obtained, together with the three known compounds 22-epihippuristanol (4) [4], hippuristanol (5) [2] [4], and tryptamine (6) [9]. The cytotoxicity of 1, 5, and the

show abstract

“…The cytotoxicity IC 50 value of 5 against A549 was ca. tenfold larger than the reported one [4], which might be caused by methodological errors and other factors.…”

contrasting

confidence: 64%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

New Steroids and a New Alkaloid from the Gorgonian Isis minorbrachyblasta: Structures, Cytotoxicity, and Antilarval Activity

Miao

Gao

et al. 2010

Helvetica Chimica Acta

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“…143 The drug has potent activity against tumor cell lines and studies have focused on manufacturing it synthetically. [144][145][146] Further preclinical development of hippuristanol and its derivatives is awaited.…”

Section: Hippuristanolmentioning

confidence: 99%

The biological and therapeutic relevance of mRNA translation in cancer

2011

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Protein synthesis is a tightly regulated process that enables post-transcriptional control of gene expression. Dysregulation of this process is associated with the development and progression of cancers because components of the translational machinery function at the point of convergence of aberrant cell signaling pathways. Drugs designed to inhibit mRNA translation are currently in preclinical and early clinical development, and are likely to provide effective anticancer strategies in the future. In this Review, we summarize the main components of translation and describe how alterations in these proteins and their principle upstream signaling pathways can impact on cancer. The first inhibitors of translation, drugs designed to target eIF4E, have been trialed in hematologic malignancies, while antisense oligonucleotides against eIF4E are also due to enter clinical trials. Here, we discuss the mode of action of drugs designed to inhibit mRNA translation and other promising therapies that are in preclinical development with the aim of becoming anticancer agents.

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Cnidaria and Ctenophora–1

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: General Introduction Simplified Classification of Cnidaria Hermatypic and Ahermatypic Corals: Coral Bleaching General Information on Metabolites of Cnidaria Membrane Constituents and Secondary Metabolites of Octocorallia (Anthozoa) Prostaglandins and Prostanoids Phospholipid Fatty Acids, Glycolipids, and Other Lipidic Derivatives General Remarks on the Sterols of Octocorallia Gorgosterol and Other Cyclopropane‐Containing Sterols 19‐Oxygenated‐ and 19‐ nor ‐Steroids Polyoxygenated Steroids Sterones and Chlorinated Sterones Sulfur‐Containing Steroids Cyclized Side‐Chain Sterols Secosterols Sterosides, Pregnane, and nor ‐Pregnane Derivatives Sesquiterpenic Hydrocarbons Halogen‐, Nitrogen‐, and Sulfur‐Containing Sesquiterpenes Sesquiterpenes with Original Carbon Skeletons Examples of Sesquiterpenes with a Classical Carbon Skeleton General Account of Diterpenes Linear and Monocyclic Diterpenes General Information on Bicyclic Diterpenes Chlorinated Diterpenes Other examples of Briarane Derivatives Nitrogen‐Containing Diterpenes of Cladiellane/Eunicellane: Eleutherobin and Analogs, Labiatamides Other Examples of Cladiellane/Eunicellane Diterpenes Diterpenes of Serrulatane and Other Bicyclic Carbon Skeletons Bicyclic C 5 /C 11 Diterpenes Bicyclic Diterpenes Containing a Cyclopropane Some Other Examples of Bicyclic Diterpenes General Account of Tricyclic Diterpenes Pseudopterosins, Other Amphilectane Derivatives and Analogs Other Examples of Tricyclic and Tetracyclic Diterpenes Comments on the Origin of Terpenes Non‐Terpenic Nitrogenous Derivatives of Octocorallia Uncommon Sulfur‐Containing Compounds

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New cytotoxic steroids from the gorgonian Isis hippuris . Structure–activity studies

Cited by 55 publications

References 12 publications

New Steroids and a New Alkaloid from the Gorgonian Isis minorbrachyblasta: Structures, Cytotoxicity, and Antilarval Activity

New Steroids and a New Alkaloid from the Gorgonian Isis minorbrachyblasta: Structures, Cytotoxicity, and Antilarval Activity

The biological and therapeutic relevance of mRNA translation in cancer

Cnidaria and Ctenophora–1

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