ArticleLipids2009
Isorhizochalin: a minor unprecedented bipolar sphingolipid of stereodivergent biogenesis from the Rhizochalina incrustata.
Article in Lipids, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
9 citing papers in PubMed.
- Dual Biological Potential: Anticancer and Antibacterial Activities of Bis-α, ω-Bifunctional Sphingolipids from the Marine Sponge Oceanapia ramsayi.ChemMedChem · 2025Article
- Structure Diversity and Properties of Some Bola-like Natural Products.Marine drugs · 2024Review
- Secondary Metabolites from Marine Sponges of the GenusMarine drugs · 2022Review
- Liposomal Circular Dichroism (L-CD) of Arenoyl Derivatives of Sphingolipids. Amplification of Cotton Effects in Ordered Lipid Bilayers.Marine drugs · 2017Article
- Halisphingosines A and B, modified sphingoid bases from Haliclona tubifera. Assignment of configuration by circular dichroism and van't Hoff's principle of optical superposition.Journal of natural products · 2013Article
- D-Glucosamine-derived synthons for assembly of L-threo-sphingoid bases. Total synthesis of rhizochalinin C.The Journal of organic chemistry · 2013Article
- Glycosides from marine sponges (Porifera, Demospongiae): structures, taxonomical distribution, biological activities and biological roles.Marine drugs · 2012Review
- Synthesis and chain-dependent antifungal activity of long-chain 2H-azirine-carboxylate esters related to dysidazirine.Bioorganic & medicinal chemistry letters · 2010Article
- Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: an update for 2009-2010.Mass spectrometry reviewsReview
Corrections and comments
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Authors and funding
9 authors.
Funding
Abstract
Isorhizochalin (1) was isolated as its peracetate from the EtOH extract of the sponge Rhizochalina incrustata. Its structure and absolute stereochemistry were elucidated as (2S,3R,26R,27R)-2,27-diamino-3-O-beta-D: -galactopyranosyl-oxy-26-hydroxyoctacosan-18-one by extensive NMR, MS studies, chemical transformations, including micromolar-scale Baeyer-Villiger oxidation, and by analysis of CD spectra of isorhizochalinin perbenzoate (2b). Isorhizochalin is an unprecedented C-2 epimer of rhizochalin having an erythro configuration at the glycosylated 2-amino-3-alkanol alpha-terminus in contrast with a canonical threo configuration for other representatives of this structural group. Probable biogenesis of 1 is discussed in the context of known sphingolipid biosynthesis beginning with condensation of alanine with a fatty acyl CoA thioester. The aglycone, isorhizochalinin (2a), shows cytotoxicity against human leukemia HL-60 and THP-1 cells with IC(50) values of 2.90 and 2.20 microM, respectively.
Indexed as
Identifiers
19882184What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.