Literature DB >> 19882184

Isorhizochalin: a minor unprecedented bipolar sphingolipid of stereodivergent biogenesis from the Rhizochalina incrustata.

Tatyana N Makarieva1, Alexander M Zakharenko, Pavel S Dmitrenok, Alla G Guzii, Vladimir A Denisenko, Alexandra S Savina, Doralyn S Dalisay, Tadeusz F Molinski, Valentin A Stonik.   

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.

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Year:  2009        PMID： 19882184     DOI： 10.1007/s11745-009-3360-0

Source DB:  PubMed          Journal:  Lipids        ISSN： 0024-4201            Impact factor:   1.880


  11 in total

1.  (-)-Rhizochalin is a Dimeric Enantiomorphic (2R)-Sphingolipid: Absolute Configuration of Pseudo-C(2v)-Symmetric Bis-2-amino-3-alkanols by CD We thank Jeff de Ropp and John MacMillan (University of California, Davis) for assistance with the 600 and 400 MHz (1)H NMR spectra, respectively; Gillian Nicholas (University of California, Davis) for measurement of the CD spectra of 7 a, b; Rich Kondrat (University of California, Riverside Mass Spectrometry Facility) for chemical ionization MS; and Carlito Lebrilla and Yongming Xie (University of California, Davis) for matrix-assisted laser desorption/ionization MS. This work was supported by the National Institutes of Health (NIH; grant no. AI 39987). The NMR spectrometers were funded in part by the National Science Foundation (grant no. CHE-9808183; 400 MHz apparatus) and the NIH (grant no. RR11973; 600 MHz apparatus). CD=circular dichroism.

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Journal:  Angew Chem Int Ed Engl       Date:  2000-11-17       Impact factor: 15.336

2.  Oceanapiside, an antifungal bis-alpha,omega-amino alcohol glycoside from the marine sponge Oceanapia phillipensis.

Authors:  G M Nicholas; T W Hong; T F Molinski; M L Lerch; M T Cancilla; C B Lebrilla
Journal:  J Nat Prod       Date:  1999-12       Impact factor: 4.050

3.  BRS1, a C30 bis-amino, bis-hydroxy polyunsaturated lipid from an Australian calcareous sponge that inhibits protein kinase C.

Authors:  R H Willis; D J de Vries
Journal:  Toxicon       Date:  1997-07       Impact factor: 3.033

4.  Oceanalin A, a hybrid alpha,omega-bifunctionalized sphingoid tetrahydroisoquinoline beta-glycoside from the marine sponge Oceanapia sp.

Authors:  Tatyana N Makarieva; Vladimir A Denisenko; Pavel S Dmitrenok; Alla G Guzii; Elena A Santalova; Valentin A Stonik; John B Macmillan; Tadeusz F Molinski
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

5.  Marine two-headed sphingolipid-like compound rhizochalin inhibits EGF-induced transformation of JB6 P+ Cl41 cells.

Authors:  Sergey N Fedorov; Tatyana N Makarieva; Alla G Guzii; Larisa K Shubina; Jong Y Kwak; Valentin A Stonik
Journal:  Lipids       Date:  2009-07-05       Impact factor: 1.880

6.  Differential induction of apoptosis of leukemic cells by rhizochalin, two headed sphingolipids from sponge and its derivatives.

Authors:  Jun-O Jin; Valeria Shastina; Joo-In Park; Jin-Yeong Han; Tatyana Makarieva; Sergey Fedorov; Valery Rasskazov; Valentin Stonik; Jong-Young Kwak
Journal:  Biol Pharm Bull       Date:  2009-06       Impact factor: 2.233

7.  Absolute configuration of the alpha,omega-bifunctionalized sphingolipid leucettamol A from Leucetta microrhaphis by deconvoluted exciton coupled CD.

Authors:  Doralyn S Dalisay; Sachiko Tsukamoto; Tadeusz F Molinski
Journal:  J Nat Prod       Date:  2009-03-27       Impact factor: 4.050

8.  Alanine is a precursor in the biosynthesis of fumonisin B1 by Fusarium moniliforme.

Authors:  B E Branham; R D Plattner
Journal:  Mycopathologia       Date:  1993-11       Impact factor: 2.574

9.  Rhizochalins C and D from the sponge Rhizochalina incrustata. A rare threo-sphingolipid and a facile method for determination of the carbonyl position in alpha,omega-bifunctionalized ketosphingolipids.

Authors:  Tatyana N Makarieva; Pavel S Dmitrenok; Alexander M Zakharenko; Vladimir A Denisenko; Alla G Guzii; Ronghua Li; Colin K Skepper; Tadeusz F Molinski; Valentin A Stonik
Journal:  J Nat Prod       Date:  2007-12-06       Impact factor: 4.050

10.  Leucettamol A: a new inhibitor of Ubc13-Uev1A interaction isolated from a marine sponge, Leucetta aff. microrhaphis.

Authors:  Sachiko Tsukamoto; Tomoharu Takeuchi; Henki Rotinsulu; Remy E P Mangindaan; Rob W M van Soest; Kazuyo Ukai; Hisayoshi Kobayashi; Michio Namikoshi; Tomihisa Ohta; Hideyoshi Yokosawa
Journal:  Bioorg Med Chem Lett       Date:  2008-10-31       Impact factor: 2.823
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  7 in total

1.  Synthesis and chain-dependent antifungal activity of long-chain 2H-azirine-carboxylate esters related to dysidazirine.

Authors:  Colin K Skepper; Doralyn S Dalisay; Tadeusz F Molinski
Journal:  Bioorg Med Chem Lett       Date:  2010-02-01       Impact factor: 2.823

Review 2.  Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: an update for 2009-2010.

Authors:  David J Harvey
Journal:  Mass Spectrom Rev       Date:  2014-05-26       Impact factor: 10.946

3.  D-Glucosamine-derived synthons for assembly of L-threo-sphingoid bases. Total synthesis of rhizochalinin C.

Authors:  Jaeyoung Ko; Tadeusz F Molinski
Journal:  J Org Chem       Date:  2012-12-27       Impact factor: 4.354

4.  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.

Authors:  Tadeusz F Molinski; Renata Biegelmeyer; E Paige Stout; Xiao Wang; Mario L C Frota; Amelia T Henriques
Journal:  J Nat Prod       Date:  2012-12-26       Impact factor: 4.050

Review 5.  Glycosides from marine sponges (Porifera, Demospongiae): structures, taxonomical distribution, biological activities and biological roles.

Authors:  Vladimir I Kalinin; Natalia V Ivanchina; Vladimir B Krasokhin; Tatyana N Makarieva; Valentin A Stonik
Journal:  Mar Drugs       Date:  2012-08-10       Impact factor: 6.085

6.  Liposomal Circular Dichroism (L-CD) of Arenoyl Derivatives of Sphingolipids. Amplification of Cotton Effects in Ordered Lipid Bilayers.

Authors:  Tadeusz F Molinski; Caroline D Broaddus; Brandon I Morinaka
Journal:  Mar Drugs       Date:  2017-12-20       Impact factor: 5.118

Review 7.  Secondary Metabolites from Marine Sponges of the Genus Oceanapia: Chemistry and Biological Activities.

Authors:  Meng-Juan Xu; Lin-Jing Zhong; Jun-Kun Chen; Qing Bu; Lin-Fu Liang
Journal:  Mar Drugs       Date:  2022-02-16       Impact factor: 5.118
  7 in total

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