New polyoxygenated steroids exhibiting reversal of multidrug resistance from the gorgonian Isis hippuris

Tanaka, Junichi; Trianto, Agus; Musman, Musri; Issa, Hassan; Ohtani, Ikuko I.; Ichiba, Toshio; Higa, Tatsuo; Yoshida, Wesley Y.; Scheuer, Paul J.

doi:10.1016/s0040-4020(02)00625-7

Cited by 55 publications

(62 citation statements)

References 18 publications

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“…Some of them (compounds 16-20) have been tested against KB-C2 overexpressing P-gp cells and showed moderate activity at the concentration of 3 μM by inhibiting the growth of this resistance cell line. Compounds 17 and 18 were the most potent against KB-C2 cells [62].…”

Section: Polyoxygenated Steroids and Derivativesmentioning

confidence: 96%

“…A number of polyoxygenated steroids has been isolated from gorgonians (Isis hippuris [62] and Leptogorgia sarmentosa [63]), soft corals (Sarcophyton sp. [64] and Sinularia sp.…”

Section: Polyoxygenated Steroids and Derivativesmentioning

confidence: 99%

“…[64] and Sinularia sp. [65]), echinoderms, and sponges [62]. Interestingly, all the polyoxygenated steroids investigated for antitumor [66], antibacterial [64], antifungal [64], and reversing MDR [62] activities contain the characteristic 3β,5α,6β-hydroxyl moiety.…”

Section: Polyoxygenated Steroids and Derivativesmentioning

confidence: 99%

“…Interestingly, all the polyoxygenated steroids investigated for antitumor [66], antibacterial [64], antifungal [64], and reversing MDR [62] activities contain the characteristic 3β,5α,6β-hydroxyl moiety. Among these derivatives are a spiroketal hippurinstanol (14), hippuristerone (15), which possesses a 3-keto group, and the cyclopropane-containing gorgosterols (16)(17)(18)(19)(20) (Figure 4) [62,64]. Polyoxygenated steroids 14-20 also differ in the side chains.…”

Section: Polyoxygenated Steroids and Derivativesmentioning

confidence: 99%

“…Among these derivatives are a spiroketal hippurinstanol (14), hippuristerone (15), which possesses a 3-keto group, and the cyclopropane-containing gorgosterols (16)(17)(18)(19)(20) (Figure 4) [62,64]. Polyoxygenated steroids 14-20 also differ in the side chains.…”

Section: Polyoxygenated Steroids and Derivativesmentioning

confidence: 99%

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Marine Natural Products as Models to Circumvent Multidrug Resistance

et al. 2016

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Multidrug resistance (MDR) to anticancer drugs is a serious health problem that in many cases leads to cancer treatment failure. The ATP binding cassette (ABC) transporter P-glycoprotein (P-gp), which leads to premature efflux of drugs from cancer cells, is often responsible for MDR. On the other hand, a strategy to search for modulators from natural products to overcome MDR had been in place during the last decades. However, Nature limits the amount of some natural products, which has led to the development of synthetic strategies to increase their availability. This review summarizes the research findings on marine natural products and derivatives, mainly alkaloids, polyoxygenated sterols, polyketides, terpenoids, diketopiperazines, and peptides, with P-gp inhibitory activity highlighting the established structure-activity relationships. The synthetic pathways for the total synthesis of the most promising members and analogs are also presented. It is expected that the data gathered during the last decades concerning their synthesis and MDR-inhibiting activities will help medicinal chemists develop potential drug candidates using marine natural products as models which can deliver new ABC transporter inhibitor scaffolds.

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Section: Polyoxygenated Steroids and Derivativesmentioning

confidence: 96%

“…A number of polyoxygenated steroids has been isolated from gorgonians (Isis hippuris [62] and Leptogorgia sarmentosa [63]), soft corals (Sarcophyton sp. [64] and Sinularia sp.…”

Section: Polyoxygenated Steroids and Derivativesmentioning

confidence: 99%

Section: Polyoxygenated Steroids and Derivativesmentioning

confidence: 99%

Section: Polyoxygenated Steroids and Derivativesmentioning

confidence: 99%

Section: Polyoxygenated Steroids and Derivativesmentioning

confidence: 99%

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Marine Natural Products as Models to Circumvent Multidrug Resistance

et al. 2016

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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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Cnidaria and Ctenophora–2

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: Membrane Constituents and Secondary Metabolites of Hexacorallia (Anthozoa) Fatty Acids, Oxylipins, and Acetylenic Derivatives Sterols and Ecdysteroids Terpenes Carotenoids of Sea Anemones Aromatic Derivatives Ceramides and Lipidic α‐Amino Acids Examples of Nitrogenous Pigments: Zoanthoxanthins and Calliactine Palytoxins ( PTXs ) Mycosporines Betaines, Phosphobetaines, Purines, and Other Nitrogen‐Containing Derivatives Zoanthamine Alkaloids Cytolysins, Neuropeptides, and Other Venoms of Sea Anemones Venoms and Other Metabolites of Medusozoa Some Data on the Cubozoa and Other Jellyfish Bioluminescence of Jellyfish and Other Cnidaria Some Results on the Secondary Metabolites of Other Hydrozoa Ctenophora

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New polyoxygenated steroids exhibiting reversal of multidrug resistance from the gorgonian Isis hippuris

Cited by 55 publications

References 18 publications

Marine Natural Products as Models to Circumvent Multidrug Resistance

Marine Natural Products as Models to Circumvent Multidrug Resistance

Cnidaria and Ctenophora–1

Cnidaria and Ctenophora–2

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