LIPID MAPS

Structure Database (LMSD)

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Common Name

Phytosphingosine

Systematic Name

4R-hydroxysphinganine

Synonyms

4-hydroxysphinganine

LM ID

LMSP01030001

Formula

C₁₈H₃₉NO₃

Exact Mass

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317.292994

Sum Composition

SPB 18:0;O3

Status

Curated

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Classification

Biological Context

Phytosphingosine is a sphingolipid with a hydroxyl group at the C4 position that is found mainly in fungi and plants but also in animals, including humans.^1,2 It is metabolized to odd-numbered fatty acids with 2-hydroxy palmitic acid as an intermediate.³ Phytosphingosine dose-dependently induces cell death of CHO cells and inhibits carbachol-induced activation of phospholipase D (PLD) in CHO cells transfected with C. elegans muscarinic acetylcholine receptors.⁴ It is essential in the heat stress response in S. cerevisiae.⁵ [Matreya, LLC. Catalog No. 1330]

This information has been provided by Cayman Chemical

References

1. Hannun, Y.A., Luberto, C., and Argraves, K.M. Enzymes of sphingolipid metabolism: From modular to integrative signaling. Biochemistry 40(16), 4893-4903 (2001).

2. Kondo, N., Ohno, Y., Yamagata, M., et al. Identification of the phytosphingosine metabolic pathway leading to odd-numbered fatty acids. Nat. Commun. 5, 5338 (2014).

3. Lee, J.S., Min, D.S., Park, C., et al. Phytosphingosine and C2-phytoceramide induce cell death and inhibit carbachol-stimulated phospholipase D activation in Chinese hamster ovary cells expressing the Caenorhabditis elegans muscarinic acetylcholine receptor. FEBS. Lett. 499(1-2), 82-86 (2001).

4. Dickson, R.C. Sphingolipid functions in Saccharomyces cerevisiae: Comparison to mammals. Annu. Rev. Biochem. 67, 27-48 (1998).

5. Schürer, N.Y., Plewig, G., and Elias, P.M. Stratum corneum lipid function. Dermatologica 183(2), 77-94 (1991).