Dinosterol

Dinosterol
Names
	IUPAC name (3β,4α,5α,22E)-4,23-Dimethylergost-22-en-3-ol
Identifiers
CAS Number	58670-63-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	4945298 ;
PubChem CID	6441076;
UNII	91FGT6HJ59 ;
	InChI 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 Key: LPFIPZJIWTZLEY-DAABMGJCSA-N ; 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;
	SMILES 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
Chemical formula	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).
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	Infobox references

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

Volkman, J.K. (2003). "Sterols in microorganisms". Appl. Microbiol. Biotechnol. 60 (5): 495–506. doi:10.1007/s00253-002-1172-8. PMID 12536248.
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.
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.CS1 maint: multiple names: authors list (link)
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.
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.CS1 maint: multiple names: authors list (link)
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.CS1 maint: multiple names: authors list (link)
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.CS1 maint: multiple names: authors list (link)
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.CS1 maint: multiple names: authors list (link)
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.
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.
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.CS1 maint: multiple names: authors list (link)
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.CS1 maint: multiple names: authors list (link)

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[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.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.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.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.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.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.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.CS1 maint: multiple names: authors list (link)