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

Lipids

Volumn 44, Issue 12, 2009, Pages 1155-1162

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

^a PACIFIC INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Absolute configuration; CD; Cytotoxity; HPLC; HRESI; Marine sponge; NMR; Rhizochalina incrustata; Sphingolipids; Two headed sphingolipid

Indexed keywords

ACYL COENZYME A; ALANINE; ALCOHOL; ANTINEOPLASTIC AGENT; ISORHIZOCHALIN; ISORHIZOCHALININ; ISORHIZOCHALININ PERACETATE; ISORHIZOCHALININ PERBENZOATE; RHIZOCHALININ; RHIZOCHALININ D; RHIZOCHALININ PERACETATE; SPHINGOLIPID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BAEYER VILLIGER REACTION; BIOGENESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN HL 60; CHEMICAL MODIFICATION; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; EPIMER; HETERONUCLEAR MULTIPLE BOND CORRELATION; HUMAN; HUMAN CELL; IC 50; MASS SPECTROMETRY; METHANOLYSIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; RHIZOCHALINA INCRUSTATA; SPONGE (PORIFERA); STEREOCHEMISTRY;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CIRCULAR DICHROISM; FATTY ALCOHOLS; GALACTOSIDES; HL-60 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PORIFERA; SPHINGOLIPIDS; STEREOISOMERISM;

RHIZOCHALINA;

EID: 71149106861     PISSN: 00244201     EISSN: 15589307     Source Type: Journal    
DOI: 10.1007/s11745-009-3360-0     Document Type: Article

References (21)

1. TN Makarieva VA Denisenko VA Stonik YM Milgrom YV Rashkes 1989 Rhizochalin, a novel secondary metabolite of mixed biosynthesis from the sponge Rhizochalina incrustata Tetrahedron Lett 30 6581 6584 10.1016/S0040-4039(01) 89027-4 1:CAS:528:DyaK3cXpsFOlsA%3D%3D
2. TN Makarieva AG Guzii VA Denisenko PS Dmitrenok EA Santalova EV Pokanevich TF Molinski VA Stonik 2005 Rhizochalin A, a novel two-headed sphingolipid from the sponge Rhizochalina incrustata J Nat Prod 68 255 257 10.1021/np049710z 1:CAS:528:DC%2BD2MXptlSktw%3D%3D 15730256 (Pubitemid 40299818)
3. TN Makarieva PS Dmitrenok AM Zakharenko VA Denisenko AG Guzii R Li CK Skepper TF Molinski VA Stonik 2007 Rhizochalins C and D from the sponge Rhizochalina incrustata. A rare threo-sphingolipid and a facile method for determination of the carbonyl position in α, ω-bifunctionalized ketosphingolipids J Nat Prod 70 1991 1998 10.1021/np0704811 1:CAS:528: DC%2BD2sXhtlyqs7bO 18052325
4. TN Makarieva AM Zakharenko VA Denisenko PS Dmitrenok AG Guzii LK Shubina II Kapustina SN Fedorov 2007 Rhizochalinin A, a new antileukemic two-headed sphigolipid from the sponge Rhizochalina incrustata Chem Nat Comp 43 468 469 10.1007/s10600-007-0164-4 1:CAS:528:DC%2BD2sXht1yisLrM (Pubitemid 350100148)
5. TN Makarieva AG Guzii VA Denisenko PS Dmitrenok VA Stonik 2008 New two-headed sphingolipid-like compounds from the marine sponge Oceanapia sp Rus Chem Bull 57 669 673 10.1007/s11172-008-0106-8 1:CAS:528:DC%2BD1MXjt1WhsLY%3D
6. F Kong DJ Faulkner 1993 Leucettamols A and B, two antimicrobial lipids from the calcareous sponge Leucetta microraphis J Org Chem 58 970 971 10.1021/jo00056a037 1:CAS:528:DyaK3sXpvVensA%3D%3D
7. RH Willis DJ De Vries 1997 BRS1, a C30 bis-amino, bis-hydroxy polyunsaturated lipid from an Australian calcareous sponge that inhibits protein kinase C Toxicon 35 1125 1129 10.1016/S0041-0101(96)00218-8 1:CAS:528:DyaK2sXks1Wkt70%3D 9248010 (Pubitemid 27304198)
8. GM Nicholas TW Hong TF Molinski ML Lerch MT Cancilla CB Lebrilla 1999 Oceanapiside, an antifungal bis-α, ω-amino alcohol glycoside from the marine sponge Oceanapia phillipensis J Nat Prod 62 1678 1681 10.1021/np990190v 1:CAS:528:DyaK1MXmvVSqsbo%3D 10654417 (Pubitemid 30030615)
9. BN Zhou MP Mattern RK Johnson DG Kingston 2001 Structure and stereochemistry of a novel bioactive sphingolipid from a Calyx sp Tetrahedron 57 9549 9554 10.1016/S0040-4020(01)00958-9 1:CAS:528:DC%2BD3MXotlWqs7w%3D (Pubitemid 33055637)
10. TN Makarieva VA Denisenko PS Dmitrenok AG Guzii EA Santalova VA Stonik JB MacMillan TF Molinski 2005 Oceanalin A, a hybrid α, ω- bifunctionalized sphingoid tetrahydroisoquinoline β-glycoside from the marine sponge Oceanapia sp Org Lett 7 2897 2900 10.1021/ol050796c 1:CAS:528:DC%2BD2MXkslSgt7o%3D 15987164 (Pubitemid 40992591)
11. + Cl41 cells Lipids 44 777 785 10.1007/s11745-009-3322-6 1:CAS:528:DC%2BD1MXhtFaqt77J 19579043
12. JO Jin VV Shastina JI Park JY Han TN Makarieva SN Fedorov VA Rasskazov VA Stonik JY Kwak 2009 Differential induction of apoptosis of leukemic cells by rhizochalin two headed sphingolipids from sponge and its derivatives Biol Pharm Bull 32 956 962
13. S Tsukamoto T Takeuchi H Rotinsulu REP Mangindaan RWM Van Soest K Ukai H Kobayashi M Namikoshi T Ohta H Yokosawa 2008 Leucettamol A: a new inhibitor of Ubc13-Uev1A interaction isolated from a marine sponge, Leucetta aff. microrhaphis Bioorg Med Chem Lett 18 6319 6320 10.1016/j.bmcl.2008.10.110 1:CAS:528:DC%2BD1cXhsVWjs7nN 19006668
14. AG Guzii TN Makarieva VA Denisenko PS Dmitrenok YV Burtseva VB Krasokhin VA Stonik 2008 Topsentiasterol sulfates with novel iodinated and chlorinated side chains from the marine sponge Topsentia sp Tetrahedron Lett 49 7191 7193 10.1016/j.tetlet.2008.10.007 1:CAS:528:DC%2BD1cXhtlWlurfP
15. JA Baltrop TC Owen AH Cory JG Cory 1991 5-(3-Carboxymethoxyphenyl)-2-(4, 5-dimethylthiazolyl)-3-(4-sulfophenyl) tetrazolium, inner salt (MTS) and related analogs of 3-(4,5-dimethylthiazolyl)-2,5-diphenyltetrazolium bromide (MTT) reducing to purple water-soluble formazans as cell-viability indicators Bioorg Med Chem Lett 1 611 614 10.1016/S0960-894X(01)81162-8
16. Makarieva TN, Denisenko VA, Svetashev VI, Vysotsky MV, Stonik VA (1989) Cerebrosides from the Far-Eastern sponge Hymenyacidon assimilis. Chem Nat Comp 634-638 (in Russian)
17. GM Nicholas TF Molinski 2000 Enantiodivergent biosynthesis of the dimeric sphingolipid oceanapiside from the marine sponge Oceanapia phillipensis. Determination of remote stereochemistry J Am Chem Soc 122 4011 4019 10.1021/ja994215o 1:CAS:528:DC%2BD3cXisVKktb0%3D (Pubitemid 30304831)
18. 2v-symmetric bis-2-amino-3-alkanols by CD Angew Chem Int Ed Engl 39 4076 4079 10.1002/1521-3773(20001117)39:22<4076::AID-ANIE4076>3.0.CO;2-D 1:CAS:528:DC%2BD3cXosF2ntb0%3D 11093210
19. DS Dalisay S Tsukamoto TF Molinski 2009 Absolute cofiguration of the α, ω-bifunctionalized sphingolipid Leucettamol A from Leucetta microrhaphis by deconvoluted exciton coupled CD J Nat Prod 72 353 359 10.1021/np800549n 1:CAS:528:DC%2BD1MXhtVSqsbY%3D 19159253
20. 2 backbone Tetrahedron Lett 35 6819 6822 10.1016/0040-4039(94)85013-5 1:CAS:528:DyaK2cXmsFGntbo%3D (Pubitemid 24278512)
21. BE Branham RD Plattner 1993 Alanine is a precursor in the biosynthesis of fumonisin B-1 by Fusarium moniliforme Mycopathologia 124 99 104 10.1007/BF01103109 1:CAS:528:DyaK2cXmtVSmu7c%3D 8008046