Rhizochalinin A, a new antileukemic two-headed sphingolipid from the sponge Rhizochalina incrustata

Makarieva, Tatyana N.; Zakharenko, Alexander M.; Denisenko, V. A.; Dmitrenok, Pavel S.; Guzii, Alla G.; Shubina, Larisa K.; Kapustina, I. I.; Fedorov, Sergey N.

doi:10.1007/s10600-007-0164-4

Cited by 7 publications

(12 citation statements)

References 5 publications

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“…Rhizochalin and its analogs and derivatives were extracted, purified and prepared as described previously [1,[7][8][9] and were pure in accordance with NMR, MS, TLC, and HPLC data. Briefly, the fresh collection of the sponges R. incrustata was immediately lyophilized and kept at -20°C.…”

Section: Rhizochalin or Its Analogs And Derivativesmentioning

confidence: 99%

“…1) [1], a series of related natural products have been reported [2][3][4][5][6][7][8][9][10]. Two-headed sphingolipid-like compounds differ from classical sphingolipids in the presence of polar groups in a,x-positions.…”

Section: Introductionmentioning

confidence: 99%

“…Rhizochalin and analogs were reported to possess antibacterial, antifungal, and cytotoxic activities [2][3][4][5][6][7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

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Marine Two‐Headed Sphingolipid‐Like Compound Rhizochalin Inhibits EGF‐Induced Transformation of JB6 P⁺ Cl41 Cells

Fedorov¹,

Makarieva²,

Guzii³

et al. 2009

Lipids

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Rhizochalin [(2R,3R,26R,27R)-2,27-diamino-3-hydroxy-26-[(2R,3R,4S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy]octacosan-11-one], an antimicrobial and cytotoxic marine two-headed sphingolipid-like natural product, isolated from the sponge Rhizochalina incrustata, and some related compounds were studied as anticarcinogenic and proapoptotic agents. The corresponding effects were tested on the mouse skin epidermal JB6 P(+) Cl 41 cell line, its stable transfectants, THP-1, HeLa, and SNU-C4 human tumor cells using a variety of assessments, including cell viability (MTS), flow cytometry, anchorage-independent soft agar, and luciferase assays. At 5-10 muM concentrations, rhizochalin was effective as an inhibitor of the malignant transformation of JB6 P(+) Cl 41 cells or colony formation of human tumor cells, which exerted its action, at least in part, through the induction of p53-dependent apoptosis. Structure-activity relationship study showed aglycon of rhizochalin to be the most active while peracetylated aglycon was the least active among the compounds studied.

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Section: Rhizochalin or Its Analogs And Derivativesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Marine Two‐Headed Sphingolipid‐Like Compound Rhizochalin Inhibits EGF‐Induced Transformation of JB6 P⁺ Cl41 Cells

Fedorov¹,

Makarieva²,

Guzii³

et al. 2009

Lipids

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“…''Two-headed'' (bipolar) sphingolipids from some sponges are unusual tail-to-tail dimeric natural products related to sphingosine, in which a carbon backbone contains two end groups, both formally derived from alanine [1][2][3][4][5][6][7], or different end groups, one formally derived from serine and the opposite terminus from alanine [3,8,9]. Additional variation includes replacement of the aminoalkanol terminus with an isoquinoline ring system [10].…”

Section: Introductionmentioning

confidence: 99%

Isorhizochalin: a Minor Unprecedented Bipolar Sphingolipid of Stereodivergent Biogenesis from the Rhizochalina incrustata

Makarieva

Zakharenko

Dmitrenok

et al. 2009

Lipids

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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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“…1), isolated in 1989 by our group from the Madagascarian sponge Rhizochalin incrustata. 6) The group of two-headed sphingolipids includes a limited number of compounds: Rhz, Rhz A, Rhz C, Rhz D and rhizochalinin A from the marine sponge Rhizochalina incrustata, [6][7][8][9][10] oceanapiside from Oceanapia phillipensis, 11) oceanalin A, Rhz B, and rhizochalinin B from Oceanapia sp., 7,12) calyxoside from Calyx sp., 13) leucettamols A and B from Leucetta leptorhapsis 14) and compound BRS1 from an unidentified sponge. 15) Their structures have been established on the basis of spectroscopic data and chemical transformations.…”

mentioning

confidence: 99%

Differential Induction of Apoptosis of Leukemic Cells by Rhizochalin, Two Headed Sphingolipids from Sponge and Its Derivatives

Jin

Shastina

Park

et al. 2009

Biological & Pharmaceutical Bulletin

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Rhizochalinin A, a new antileukemic two-headed sphingolipid from the sponge Rhizochalina incrustata

Cited by 7 publications

References 5 publications

Marine Two‐Headed Sphingolipid‐Like Compound Rhizochalin Inhibits EGF‐Induced Transformation of JB6 P⁺ Cl41 Cells

Marine Two‐Headed Sphingolipid‐Like Compound Rhizochalin Inhibits EGF‐Induced Transformation of JB6 P⁺ Cl41 Cells

Isorhizochalin: a Minor Unprecedented Bipolar Sphingolipid of Stereodivergent Biogenesis from the Rhizochalina incrustata

Differential Induction of Apoptosis of Leukemic Cells by Rhizochalin, Two Headed Sphingolipids from Sponge and Its Derivatives

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Rhizochalinin A, a new antileukemic two-headed sphingolipid from the sponge Rhizochalina incrustata

Cited by 7 publications

References 5 publications

Marine Two‐Headed Sphingolipid‐Like Compound Rhizochalin Inhibits EGF‐Induced Transformation of JB6 P+ Cl41 Cells

Marine Two‐Headed Sphingolipid‐Like Compound Rhizochalin Inhibits EGF‐Induced Transformation of JB6 P+ Cl41 Cells

Isorhizochalin: a Minor Unprecedented Bipolar Sphingolipid of Stereodivergent Biogenesis from the Rhizochalina incrustata

Differential Induction of Apoptosis of Leukemic Cells by Rhizochalin, Two Headed Sphingolipids from Sponge and Its Derivatives

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Marine Two‐Headed Sphingolipid‐Like Compound Rhizochalin Inhibits EGF‐Induced Transformation of JB6 P⁺ Cl41 Cells

Marine Two‐Headed Sphingolipid‐Like Compound Rhizochalin Inhibits EGF‐Induced Transformation of JB6 P⁺ Cl41 Cells