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Dinosterol

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Dinosterol
Names
IUPAC name
(3β,4α,5α,22E)-4,23-Dimethylergost-22-en-3-ol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C30H52O/c1-18(2)21(5)19(3)17-20(4)24-11-12-26-23-9-10-25-22(6)28(31)14-16-30(25,8)27(23)13-15-29(24,26)7/h17-18,20-28,31H,9-16H2,1-8H3/b19-17+/t20-,21-,22+,23+,24-,25+,26+,27+,28+,29-,30+/m1/s1 checkY
    Key: LPFIPZJIWTZLEY-DAABMGJCSA-N checkY
  • InChI=1/C30H52O/c1-18(2)21(5)19(3)17-20(4)24-11-12-26-23-9-10-25-22(6)28(31)14-16-30(25,8)27(23)13-15-29(24,26)7/h17-18,20-28,31H,9-16H2,1-8H3/b19-17+/t20-,21-,22+,23+,24-,25+,26+,27+,28+,29-,30+/m1/s1
    Key: LPFIPZJIWTZLEY-DAABMGJCBY
  • O[C@H]3CC[C@@]4([C@@H]2[C@H]([C@@H]1CC[C@H]([C@@H](\C=C(/C)[C@H](C)C(C)C)C)[C@@]1(C)CC2)CC[C@H]4[C@@H]3C)C
Properties
C30H52O
Molar mass 428.745 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Dinosterol is a type of steroid produced by several genera of dinoflagellates. It is a 4α-methyl sterol (4α,23,24-trimethyl-5α-cholest-22E-en-3β-ol), a derivative of dinosterane, rarely found in other classes of protists.[1]

This sterol and others have been considered as class-specific, being biomarkers for dinoflagellates, although dinosterol is produced in minor amounts by a small number of other phytoplankton, such as the marine diatom Navicula speciosa.[2] and Prymnesiophytes of the genus Pavlova.[3]

Dinosterols show similar abundances as dinocysts.[4] Other studies found a nonlinear [5] or did not find a direct link between dinocyst abundances and sterol concentrations.[6]

Dinosterol has been used as indicator for dinoflagellate production in the Cariaco Basin.[7][8]

Hydrogen isotope ratios in dinosterols can serve to reconstruct salinity semi-quantitatively.[9]

Some studies have shown that certain dinoflagellates produce sterols that have the potential to serve as genera-specific biomarkers.[10][11] Recent work showed that dinoflagellate genera, which formed discrete clusters in the 18S rDNA-based phylogeny, shared similar sterol compositions. This suggested that the sterol compositions of dinoflagellates are explained by the evolutionary history of this lineage.[12]

References

  1. ^ Volkman, J.K. (2003). "Sterols in microorganisms". Appl. Microbiol. Biotechnol. 60 (5): 495–506. doi:10.1007/s00253-002-1172-8. PMID 12536248.
  2. ^ J.K. Volkman; S.M. Barrett; G.A. Dunstan; S.W. Jeffrey (1993). "Geochemical significance of the occurrence of dinosterol and other 4-methyl sterols in a marine diatom". Organic Geochemistry. 20: 7–15. doi:10.1016/0146-6380(93)90076-N.
  3. ^ Volkman, P. Kearney, S.W. Jeffrey (1990). "A new source of 4-methyl sterols and 5[alpha](H)-stanols in sediments: prymnesiophyte microalgae of the genus Pavlova". Organic Geochemistry. 15 (5): 489–497. doi:10.1016/0146-6380(90)90094-G.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ M. Mouradian; R.J. Panetta; A. de Vernal; Y. Gélinas (2007). "Dinosterols or dinocysts to estimate dinoflagellate contributions to marine sedimentary organic matter?". Limnology and Oceanography. 52 (6): 2569–2581. doi:10.4319/lo.2007.52.6.2569.
  5. ^ MARRET, F., AND J. SCOURSE (2003). "Control of modern dinoflagel- late cyst distribution in the Irish and Celtic seas by seasonal stratification dynamics". Mar. Micropaleontol. 47 (1–2): 101–116. doi:10.1016/S0377-8398(02)00095-6.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. ^ SANGIORGI, F., D. FABBRI, M. COMANDINI, G. GABBIANELLI, AND E. TAGLIAVINI (2005). "The distribution of sterols and organic- walled dinoflagellate cysts in surface sediments of the North- western Adriatic Sea (Italy)". Estuar. Coast. Shelf Sci. 64 (2–3): 395–406. doi:10.1016/j.ecss.2005.03.005. hdl:1874/11455.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ^ Werne, J. P., D. J. Hollander, T. W. Lyons, and L. C. Peterson (2000). "Climate-induced variations in productivity and planktonic ecosystem structure from the Younger Dryas to Holocene in the Cariaco Basin, Venezuela". Paleoceanography. 15: 19–29. doi:10.1029/1998PA000354.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  8. ^ Dahl, K. A., D. J. Repeta, and R. Goericke (2004). "Reconstructing the phytoplankton community of the Cariaco Basin during the Younger Dryas cold event using chlorin steryl esters" (PDF). Paleoceanography. 19: n/a. doi:10.1029/2003PA000907. hdl:1912/3423.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  9. ^ Sachs, J.P.; Schwab, V. (2011). "Hydrogen isotope in dinosterol from the Chesapeake Bay Estuary". Geochimica et Cosmochimica Acta. 75 (2): 444–459. doi:10.1016/j.gca.2010.10.013.
  10. ^ Leblond, J.D.; Chapman, P.J. (2002). "A survey of the sterol composition of the marine dinoflagellates Karenia brevis, Karenia mikimotoi, and Karlodinium micrum: distribution of sterols within other members of the class Dinophyceae". J. Phycol. 38 (4): 670–682. doi:10.1046/j.1529-8817.2002.01181.x.
  11. ^ Giner, J-L., Faraldos, J.A. and Boyer, G.L. (2003). "Novel sterols of the toxic dinoflagellate Karenia brevis (Dinophyceae): a defensive function for unusual marine sterols?". J. Phycol. 39 (2): 315–319. doi:10.1046/j.1529-8817.2003.01254.x.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  12. ^ Leblond, J.D., Lasiter, A.D., Li, C., Logares, R., Rengefors, K., & Evens, T.J. (2010). "A data mining approach to dinoflagellate clustering according to sterol composition: correlations with evolutionary history". International Journal of Data Mining and Bioinformatics. 4 (4): 431–451. doi:10.1504/IJDMB.2010.034198.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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