Literature DB >> 23268569

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.

Tadeusz F Molinski1, Renata Biegelmeyer, E Paige Stout, Xiao Wang, Mario L C Frota, Amelia T Henriques.   

Abstract

Halisphingosines A (1) and B (2), modified long-chain sphingoid bases, from the marine sponge Haliclona tubifera collected in Brazil, were characterized after conversion to their N-Boc derivatives. The 2R,3R,6R configuration of halisphingosine A, a compound first reported from Haliclona sp. from South Korea, was confirmed using a novel CD approach: deconvolution of exciton coupling from mono- and trinaphthoyl derivatives obtained by derivatization of the natural product. The sensitive CD deconvolution method, applicable to submilligram samples, simultaneously predicted the relative and absolute configuration of three stereocenters in halisphingosine A with precision and accuracy. Halisphingosine B was assigned by correlation to halisphingosine A.

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Year:  2012        PMID： 23268569      PMCID： PMC3969749          DOI： 10.1021/np300744y

Source DB:  PubMed          Journal:  J Nat Prod        ISSN： 0163-3864            Impact factor:   4.050


  17 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.

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

2.  (2R,3R,7Z)-2-Aminotetradec-7-ene-1,3-diol, a new amino alcohol from the caribbean sponge Haliclona vansoesti.

Authors:  C Devijver; M Salmoun; D Daloze; J C Braekman; W H De Weerdt; M J De Kluijver; R Gomez
Journal:  J Nat Prod       Date:  2000-07       Impact factor: 4.050

3.  Antifungal activity of bifunctional sphingolipids. Intramolecular synergism within long-chain alpha,omega-bis-aminoalcohols.

Authors:  Gillian M Nicholas; Ronghua Li; John B MacMillan; Tadeusz F Molinski
Journal:  Bioorg Med Chem Lett       Date:  2002-08-19       Impact factor: 2.823

4.  Picomole scale stereochemical analysis of sphingosines and dihydrosphingosines.

Authors:  A Kawamura; N Berova; V Dirsch; A Mangoni; K Nakanishi; G Schwartz; A Bielawska; Y Hannun; I Kitagawa
Journal:  Bioorg Med Chem       Date:  1996-07       Impact factor: 3.641

5.  Pachastrissamine, a cytotoxic anhydrophytosphingosine from a marine sponge, Pachastrissa sp.

Authors:  Ikuma Kuroda; Musri Musman; Ikuko I Ohtani; Toshio Ichiba; Junichi Tanaka; Dolores Garcia Gravalos; Tatsuo Higa
Journal:  J Nat Prod       Date:  2002-10       Impact factor: 4.050

6.  Long-chain 2H-azirines with heterogeneous terminal halogenation from the marine sponge Dysidea fragilis.

Authors:  Colin K Skepper; Tadeusz F Molinski
Journal:  J Org Chem       Date:  2008-03-06       Impact factor: 4.354

7.  Structure elucidation at the nanomole scale. 1. Trisoxazole macrolides and thiazole-containing cyclic peptides from the nudibranch Hexabranchus sanguineus.

Authors:  Doralyn S Dalisay; Evan W Rogers; Arthur S Edison; Tadeusz F Molinski
Journal:  J Nat Prod       Date:  2009-04       Impact factor: 4.050

8.  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

9.  New azacyclopropene derivatives from Dysidea fragilis collected in Pohnpei.

Authors:  C E Salomon; D H Williams; D J Faulkner
Journal:  J Nat Prod       Date:  1995-09       Impact factor: 4.050

Review 10.  Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols.

Authors:  Sarah T Pruett; Anatoliy Bushnev; Kerri Hagedorn; Madhura Adiga; Christopher A Haynes; M Cameron Sullards; Dennis C Liotta; Alfred H Merrill
Journal:  J Lipid Res       Date:  2008-05-21       Impact factor: 5.922
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  4 in total

1.  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

2.  Sphingosines Derived from Marine Sponge as Potential Multi-Target Drug Related to Disorders in Cancer Development.

Authors:  Renata Biegelmeyer; Rafael Schröder; Douglas F Rambo; Roger R Dresch; João L F Carraro; Beatriz Mothes; José Cláudio F Moreira; Mário L C da Frota Junior; Amélia T Henriques
Journal:  Mar Drugs       Date:  2015-08-25       Impact factor: 5.118

3.  Isolation and Synthesis of a Bacterially Produced Inhibitor of Rosette Development in Choanoflagellates.

Authors:  Alexandra M Cantley; Arielle Woznica; Christine Beemelmanns; Nicole King; Jon Clardy
Journal:  J Am Chem Soc       Date:  2016-03-24       Impact factor: 15.419

4.  National Cancer Institute (NCI) Program for Natural Products Discovery: Rapid Isolation and Identification of Biologically Active Natural Products from the NCI Prefractionated Library.

Authors:  Tanja Grkovic; Rhone K Akee; Christopher C Thornburg; Spencer K Trinh; John R Britt; Matthew J Harris; Jason R Evans; Unwoo Kang; Susan Ensel; Curtis J Henrich; Kirk R Gustafson; Joel P Schneider; Barry R O'Keefe
Journal:  ACS Chem Biol       Date:  2020-04-07       Impact factor: 5.100
  4 in total

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