Steroids: A Timeless Fascination

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1 GENERAL I ARTICLE Sterids: A Timeless Fascinatin Chlesterl and its Bi-prducts SHari Prasad SHari Prasad teaches medicinal rganic chemistry and rganic spectrscpy t pst graduate students at the Chemistry Department, Central Cllege, Bangalre University, Bangalre. His research includes synthetic and mechanistic rganic chemistry. Sterids are slid rganic cmpunds derived frm all life frms, including micrrganisms, plants and animals_ They btain their generic name 'sterids' frm Greek: steres = slid. Sterids encmpass a wide variety f cmpunds f vital imprtance t life such as sterls, bile acids, sex hrmnes, anti-inflammatry crticid hrmnes, etc. This article highlights sme f the imprtant aspects f chlesterl, the principal sterl f higher animals. Chlesterl is a mlecule that has fascinated scientists and cmmn man alike. Thirteen Nbel Prizes have been awarded t scientists wh have devted majr parts f their careers twards its study. Chlesterl, the first sterid t be islated, was discvered by Michel Eugene Chevreul in Chevreul islated chlesterl frm the nn-sapnifiable prtin f animal lipids. Chlesterl is a C Z7 alchl. It is the principal sterl f higher animals. An average human weighing 80 kg cntains apprximately 250 g f chlesterl. Chlesterl is an essential cnstituent flipid membranes. It is widely distributed in all bdy tissues, especially in the brain and spinal crd. It is als present in animal fats r ils. Keywrds Chlesterl, bi-prducts, bile acids, crticsterids, sex hrmnes. Chlesterl ~ R-E-S-O-N-A-N-C-E--I-F-e-br-u-a-rY

2 GENERAL I ARTICLE The predminant cnstituent f human gall stnes is chlesterl. Chlesterl is primarily synthesized in the liver, frm which it is secreted as a lipprtein cnstituent. Lipprteins are large assemblies f lipids in assciatin with prteins. The tw mst imprtant classes f lipprteins are high density lipprtein (HDL) and lw density lipprtein (LDL). When chlesterl is assciated with high density lipprtein (HDL), it is called gd chlesterl. HDL is respnsible fr the frmatin f a wide variety f ther imprtant biactive sterids. Hwever, when assciated with lw density lipprtein (LDL), it is called bad chlesterl. LDL leads t the frmatin f bld clts, the chief causative agent f heart attacks and strkes. Depsitin fldl n the walls f arteries leads t athersclersis, characterized by the hardening f the arterial walls and thrmbsis. Athersclertic plaques have been fund in excavated Egyptian mummies, indicating the prevalence f chrnic heart disease even in ancient times. Bld chlesterl levels are a gd statistical indicatr f the ptential risk f a heart attack. Chlesterl levels in the bld maybe reduced by using a new class f drugs: The statins which are inhibitrs f the enzyme hydrxymethylglutarylcenzyme-a reductase which is.respnsible fr the prductin f the bdy's natural chlesterl. Lipprteins are large assemblies f lipids in assciatin with prteins. The tw mst imprtant classes f lipprteins are high density lipprtein (HDL) and lw density lipprtein (LDL). The percentage cmpsitin and size f LDL and HDL are given in Table 1. Even thugh chlesterl is fund t have n bilgical activity, it is an imprtant precursr. the bile acids, crticsterids, sex hrmnes, etc. Name Synthesized Size Prtein Phsphl ipids LDL r in (nm) (%) (%) P-lipprtein Bld and liver HDL r a-lipprtein Liver Table 1. Chlesterl (%) (%) \ Triglyceride -R-ES-O-N-A-N--CE--I-F-e-b-rU-a-rY ~

3 GENERAL I ARTICLE COOH Bile Acids \' R\ H Bile Acids R 1 = OH;R2=R3=H : Lithchlic acid R 1 = R3= OH; R 2 = H : Desxychlic acid R 1 = R2 = R3 = OH: Chlic acid R\ = R 2 = - OH; R3= H : Ursdesxychlic acid R 1 = R2 = OH; R3 = H : Chendesxychlic acid R\ = R2 = R3 = H : Chlanic acid Human bile is a glden yellw alkaline liquid. It is prduced in the liver and stred in the gall bladder. Small amunts f bile are regularly secreted int the intestines. Bile acids are the chief cnstituents f the slid matter f bile. Bile acids sterids. Lepld Gmelin are C 24 in 1828 islated an impure preparatin f chlic acid (Gk: chle = bile) frm the nn-sapnifiable part f x-bile. Hans Fischer in 1911 islated anther hard stne-like acid frm gall stnes which he aptly named as lithchlic acid (Gk:liths = stne). Wieland reprted the islatin f desxychlic acid in Bile acids act as detergents and help in emulsifying fats and digestin f fd. Bile acids are frmed frm chlesterl after a series f cmplex bichemical reactins, which bring abut changes in the number f the hydrxyl grups, their cnfiguratin, and the ring cnfrmatins. Bile acids are fund in bile juice as sdium salts f glycine r taurine. Due t the nn-plar steridal nucleus and plar carbxylic acid side chain, bile acids act as detergents and help in emulsifying fats and digestin f fd. Apprximately twenty different bile acids are knwn. Bile acids are imprtant tday as starting materials fr the semi-synthesis f ther medicinal sterids. Chendesxychlic acid and ursdesxychlic acid are used t disslve chlesterl gallstnes as an alternative t surgery. Dehydrchlic acid is used after surgery t imprve bilary drainage. Crticsterids and Sex Hrmnes Chl~sterl als underges a series f bisynthetic degradatins t frm a variety f hrmnes. Sme f the imprtant steridal ~ R-E-S-O-N-A-N-C-E-I--Fe-b-ru-a-rY

4 GENERAL I ARTICLE hrmnes derived frm chl~sterl are the crticsterids and the sex hrmnes. Crticsterids are C 21 units fund in the crtex f the adrenal gland. The imprtant crticsterids are crtisl, crtisne and aldsterne. Crticsterids play an imprtant rle as antiinflammatry and anti-allergic agents. Female sex hrmnes are bradly classified int tw grups: the gestgens and the estrgens. Prgesterne is a C 21 gestgen which regulates the female reprductive cycle. Oestradil and estrne are C I8 estrgens. These estrgens gvern primary female characteristics. The male sex hrmnes termed andrgens include the C I9 units teststerne and dehydrepiandrsterne. Andrgens are respnsible fr primary male characteristics. The levels f these hrmnes are cntrlled by certain plypeptides/glycprteins prduced by the pituitary gland. Crticsterids are cntrlled by crtictrphin (adrencrtictrphic OH crtisl R:- OH crtisne R: C ==0 R aldsterne OH prgesterne estradil R: - OH estrne R: C =0 teststerne dehydrepiandrsterne -R-ES-O-N-A-N-C-E--I-F-e-br-U-a-rY ~ ~-

5 GENERAL, ARTICLE Bx 1. Adlf Ott Reinhld Windaus ( ) Nbel Prize 1928 Heinrich Ott Wieland ( ) Nbel Prize 1927 Ott Paul Hermann Diels ( ) Nbel Prize 1950 hrmne, ACTH), a straight chain plypeptide f 39 amin acid residues. The levels f the sex hrmnes are cntrlled by the glycprtein gnadtrphins: lutein ising hrmne (LH) and fllicle-stimulating hrmne (FSH) f 204 and 210 amin acid residues respectively. Dedicated t Prf K M Sivanandiah, frmer Principal, Central Cllege, Bangalre University, Bangalre, n the ccasin f his 73rd birthday. The authr thanks the UGC and DST fr financial assistance. Address fr Crrespndence SHari Prasad Department f Chemistry Central Cllege Campus Bangalre University Bangalre , India. hariprasad@mycatsindia.cm Three eminent chemists wh pineered steridal chemistry at the turn f the twentieth century were Windaus, Wieland and Diels (Bx 1). Windaus was primarily respnsible fr the initial studies f chlesterl. Wieland gave the structural elucidatin f bile acids and finally the structure f sterids itself as depicted tday. Diels amng ther studies cntributed t the finalizatin f the structure f sterids as derivatives f perhydr-cyclpentanphenanthrene in additin t giving a gd methd t cnstruct six membered cyclic cmpunds by the well-knwn Diels Alder reactin. Suggested Reading [I] [2] /wieland bihtrnl [3] /laureates/1928/windaus-bihtrnl [4] ~ R-ES-O--N-A-N-C-E-'--F-eb-r-u-a-rY

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