Lanosterol

Structural formula
General
Surname	Lanosterol
other names	(3 S , 5 R , 10 S , 13 R , 14 R , 17 R ) -4,4,10,13,14-pentamethyl-17 - [(2 R ) -6-methylhept-5-en-2- yl] -2,3,5,6,7,11,12,15,16,17-decahydro-1 H -cyclopenta [ a ] phenanthren-3-ol ( IUPAC ) ; Lanosta-8,24-dien-3 β -ol; 4,4,14 α- trimethyl-5 α -cholesta-8,24-dien-3 β -ol; Cryptosterol; LANOSTEROL ( INCI ) ;
Molecular formula	C 30 H 50 O
Brief description	White dust
External identifiers / databases
EC number	201-214-9
ECHA InfoCard	100.001.105
PubChem	246983
ChemSpider	216175
DrugBank	DB03696
Wikidata	Q414996
properties
Molar mass	426.73 g mol −1
Physical state	firmly
Melting point	140-141 ° C
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Lanosterol (also: lanosterol ) is a naturally occurring chemical compound . Chemically, it is a steroid . It is produced in eukaryotes as an intermediate product in the biosynthesis of cholesterol (in plants, however, this role is largely taken over by cycloartenol ). In larger quantities it is a component of wool wax ( lat.Adeps lanae , hence the name), in which it is derived from cholesterol and the Lanostan derivatives dihydrolanosterol (Lanost-8-en-3 β -ol), agnosterol (Lanosta-7,9 ( 11), 24-trien-3 β -ol) and dihydroagnosterol (Lanosta-7,9 (11) -dien-3 β -ol).

Current research suggests that lanosterol could be used to prevent and treat cataracts .

history

The structure of lanosterol was elucidated by a Swiss team led by W. Voser in 1950 using classical methods.

Occurrence and extraction

Lanosterol is an intermediate product of cholesterol biosynthesis in all eukaryotes . Sheep sweat it out with the wool wax , from which it can be obtained in larger quantities. The separation of the mixture from other triterpenes is difficult and takes place via fractional crystallization and chromatography of the acetates .

Woodward successfully synthesized lanosterol from cholesterol in over a dozen steps after his team achieved the total synthesis of cholesterol themselves.

biosynthesis

The biological synthesis of lanosterol takes place in a remarkable multiple ring closure reaction from ( S ) -squalene-2,3-epoxide, which is catalyzed by the enzyme lanosterol synthase :

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Reactions

Lanosterol is able to enter into various chemical reactions. Under the influence of phosphorus pentachloride, the A-ring is rearranged to form a five-membered ring; the C8-C9 double bond cannot be hydrogenated directly, but can be shifted to C7-C8 in an acidic medium; further dehydrogenation with selenium dioxide , N- bromo succinimide or perbenzoic acid gives the 7,9 (11) -diene, which can be further oxidized to the enone or diketone.

Individual evidence

↑ entry to lanosterol in CosIng database of the European Commission, accessed on 2 April 2020th
↑ ^a ^b ^c ^d Datasheet Lanosterol from sheep wool, ~ 97%, powder from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).
↑ Waldemar Ternes , Alfred Täufel, Lieselotte Tunger, Martin Zobel (eds.): Food Lexicon . 4th, comprehensively revised edition. Behr, Hamburg 2005, ISBN 3-89947-165-2 , pp. 1035 ( limited preview in Google Book search).
↑ Kolesnikova MD, Xiong Q, Lodeiro S, Hua L, Matsuda SP: Lanosterol biosynthesis in plants . In: Arch. Biochem. Biophys. . 447, No. 1, March 2006, pp. 87-95. doi : 10.1016 / j.abb.2005.12.010 . PMID 16445886 .
↑ Entry on lanosterol. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.
↑ Ling Zhao, Xiang-Jun Chen, Jie Zhu, Yi-Bo Xi, Xu Yang, Li-Dan Hu, Hong Ouyang, Sherrina H. Patel, Xin Jin, Danni Lin, Frances Wu, Ken Flagg, Huimin Cai, Gen Li , Guiqun Cao, Ying Lin, Daniel Chen, Cindy Wen, Christopher Chung, Yandong Wang, Austin Qiu, Emily Yeh, Wenqiu Wang, Xun Hu, Seanna Grob, et al .: Lanosterol reverses protein aggregation in cataracts . In: Nature . July 2015. doi : 10.1038 / nature14650 .
^ W. Voser, M. Montavon, Hs. H. Günthard, O. Jeger, L. Ruzicka: On the knowledge of the triterpenes. Part 156. On the constitution of the lanostadienol . In: Helv. Chim. acta . 33, No. 6, 1950, pp. 1893-10. doi : 10.1002 / hlca.19500330658 .
^ ^A ^b Sujata V. Bhat, Bhimsen A. Nagasampagi, Meenakshi Sivakumar: Chemistry of natural products Birkhäuser, 2005. ISBN 3-540-40669-7 , p. 47ff
↑ Woodward RB, Patchett AA, Barton DHR, Yves DHJ, Kelly RB: The Synthesis of Lanosterol (Lanostadienol) . In: J. chem. Soc. . 1957, pp. 1131-44. doi : 10.1039 / JR9570001131 .

Web links

Wikibooks: Biochemistry and Pathobiochemistry: Cholesterol Biosynthesis - Learning and Teaching Materials

[CosIng-1] try to lanosterol in CosIng database of the European Commission, accessed on 2 April 2020th

[Sigma-2] Datasheet Lanosterol from sheep wool, ~ 97%, powder from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).

[3] Waldemar Ternes , Alfred Täufel, Lieselotte Tunger, Martin Zobel (eds.): Food Lexicon . 4th, comprehensively revised edition. Behr, Hamburg 2005, ISBN 3-89947-165-2 , pp. 1035 ( limited preview in Google Book search).

[4] Kolesnikova MD, Xiong Q, Lodeiro S, Hua L, Matsuda SP: Lanosterol biosynthesis in plants . In: Arch. Biochem. Biophys. . 447, No. 1, March 2006, pp. 87-95. doi : 10.1016 / j.abb.2005.12.010 . PMID 16445886 .

[Römpp-5] Entry on lanosterol. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.

[LingZhao2015-6] Ling Zhao, Xiang-Jun Chen, Jie Zhu, Yi-Bo Xi, Xu Yang, Li-Dan Hu, Hong Ouyang, Sherrina H. Patel, Xin Jin, Danni Lin, Frances Wu, Ken Flagg, Huimin Cai, Gen Li , Guiqun Cao, Ying Lin, Daniel Chen, Cindy Wen, Christopher Chung, Yandong Wang, Austin Qiu, Emily Yeh, Wenqiu Wang, Xun Hu, Seanna Grob, et al .: Lanosterol reverses protein aggregation in cataracts . In: Nature . July 2015. doi : 10.1038 / nature14650 .

[7] W. Voser, M. Montavon, Hs. H. Günthard, O. Jeger, L. Ruzicka: On the knowledge of the triterpenes. Part 156. On the constitution of the lanostadienol . In: Helv. Chim. acta . 33, No. 6, 1950, pp. 1893-10. doi : 10.1002 / hlca.19500330658 .

[cn-8] A ^b Sujata V. Bhat, Bhimsen A. Nagasampagi, Meenakshi Sivakumar: Chemistry of natural products Birkhäuser, 2005. ISBN 3-540-40669-7 , p. 47ff

[9] Woodward RB, Patchett AA, Barton DHR, Yves DHJ, Kelly RB: The Synthesis of Lanosterol (Lanostadienol) . In: J. chem. Soc. . 1957, pp. 1131-44. doi : 10.1039 / JR9570001131 .