Steroid Wiki

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Steroid

From Wikipedia, the free encyclopedia

(Redirected from Steroidogenesis)

This article is about the family of polycyclic chemical compounds. For the performance-enhancing substances, seeAnabolic steroid. For the scientific journal, see Steroids(journal).

This article may be too technicalfor most readers to undershelpimprovethis article to make it understandale to non!e"perremoving the technical details. The talk pagemay containsuggestions. (October !"#)

Steroid ring system$ The parent %&' steroid ring system (hydrocaron frame#ork) is

sho#n #ith *P%'!approved ring lettering and atom numering. +-$/0f

% steroidis an organic compound#ith four rings arranged in a specificconfiguration.

1"amples include the dietary lipidcholesterol, the se"hormonesestradioland testosterone +2-$345and the anti!inflammatorydrug de"amethasone.+6-Steroids have t#o principal iological functions$certain steroids (such as cholesterol) are important components of cellmemranes#hich alter memrane fluidity,and many steroids are signalingmolecules#hich activate steroid hormone receptors.

The steroid core structureis composed of seventeen caronatoms, onded in four7fused7 rings$ three si"!memer cyclohe"anerings (rings %, & and ' in the firstillustration) and one five!memer cyclopentanering (the ring). Steroids vary y thefunctional groups attached to this four!ring core and y theo"idation stateof therings. Sterolsare forms of steroids #ith a hydro"ylgroup at position three and a

skeleton derived from cholestane.+8-+-$/0f

+0-

They can also vary more markedly ychanges to the ring structure (for e"ample, ring scissions#hichproduce secosteroidssuch as vitamin 6).

9undreds of steroids are found in plants, animalsand fungi. %ll steroids aremanufactured in cells from the sterols lanosterol(animals and fungi)or cycloartenol(plants). :anosterol and cycloartenol are derived from the cycli;ationofthe triterpenes


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Space!filling representation

&all!and!stick representation

0>!dihydroprogesterone (0>!9P), a steroid. The shape of the four rings of most

steroids is illustrated (caron atoms in lack, o"ygens in red and hydrogens in grey).

The apolar7sla7 of hydrocaronin the middle (grey, lack) and the polargroups at

opposing ends (red) are common features of natural steroids. 0>!9Pis an

endogenous steroid hormoneand aiosyntheticintermediate.

Contents

+hide-

?omenclature

2Species distriution and function

6Types

o 6.ntact ring system

o 6.2'leaved, contracted, and e"panded rings

8&iological significance

0Pharmacological action

=&iosynthesis and metaolism

o =.@evalonate path#ay
https://en.wikipedia.org/wiki/Apolarhttps://en.wikipedia.org/wiki/Hydrocarbonhttps://en.wikipedia.org/wiki/Ketonehttps://en.wikipedia.org/wiki/5%CE%B1-Dihydroprogesteronehttps://en.wikipedia.org/wiki/Steroid_hormonehttps://en.wikipedia.org/wiki/Steroid_hormonehttps://en.wikipedia.org/wiki/Biosynthesishttps://en.wikipedia.org/wiki/Steroidhttps://en.wikipedia.org/wiki/Steroid#Nomenclaturehttps://en.wikipedia.org/wiki/Steroid#Species_distribution_and_functionhttps://en.wikipedia.org/wiki/Steroid#Typeshttps://en.wikipedia.org/wiki/Steroid#Intact_ring_systemhttps://en.wikipedia.org/wiki/Steroid#Cleaved.2C_contracted.2C_and_expanded_ringshttps://en.wikipedia.org/wiki/Steroid#Biological_significancehttps://en.wikipedia.org/wiki/Steroid#Pharmacological_actionhttps://en.wikipedia.org/wiki/Steroid#Biosynthesis_and_metabolismhttps://en.wikipedia.org/wiki/Steroid#Mevalonate_pathwayhttps://en.wikipedia.org/wiki/Apolarhttps://en.wikipedia.org/wiki/Hydrocarbonhttps://en.wikipedia.org/wiki/Ketonehttps://en.wikipedia.org/wiki/5%CE%B1-Dihydroprogesteronehttps://en.wikipedia.org/wiki/Steroid_hormonehttps://en.wikipedia.org/wiki/Biosynthesishttps://en.wikipedia.org/wiki/Steroidhttps://en.wikipedia.org/wiki/Steroid#Nomenclaturehttps://en.wikipedia.org/wiki/Steroid#Species_distribution_and_functionhttps://en.wikipedia.org/wiki/Steroid#Typeshttps://en.wikipedia.org/wiki/Steroid#Intact_ring_systemhttps://en.wikipedia.org/wiki/Steroid#Cleaved.2C_contracted.2C_and_expanded_ringshttps://en.wikipedia.org/wiki/Steroid#Biological_significancehttps://en.wikipedia.org/wiki/Steroid#Pharmacological_actionhttps://en.wikipedia.org/wiki/Steroid#Biosynthesis_and_metabolismhttps://en.wikipedia.org/wiki/Steroid#Mevalonate_pathway


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o =.2Steroidogenesis

o =.6%lternative path#ays

'ataolism and e"cretion

/solation, structure determination, and methods of analysis

5'hemical synthesis

3Research a#ards

See also

2References

6Further reading

81"ternal links

?omenclature+edit-

% gonane (steroid nucleus)

% gonane, the simplest steroid, is composed of seventeen caronatoms in caron!caron onds forming four fused ringsin a three!dimensional shape. Thethree cyclohe"anerings (%, &, and ' in the first illustration) form the skeleton ofa perhydroderivative of phenanthrene. The ring has acyclopentanestructure. Whenthe t#o methyl groups and eight caron side chains(at '!, as sho#n for cholesterol)are present, the steroid is said to have a cholestane frame#ork. The t#o common 0>and 0A stereoisomeric forms of steroids e"ist ecause of differences in the side of thelargely planar ring system #here the hydrogen (9) atom at caron!0 is attached, #hichresults in a change in steroid %!ring conformation.

1"amples of steroid structures are$
https://en.wikipedia.org/wiki/Steroid#Steroidogenesishttps://en.wikipedia.org/wiki/Steroid#Alternative_pathwayshttps://en.wikipedia.org/wiki/Steroid#Catabolism_and_excretionhttps://en.wikipedia.org/wiki/Steroid#Isolation.2C_structure_determination.2C_and_methods_of_analysishttps://en.wikipedia.org/wiki/Steroid#Chemical_synthesishttps://en.wikipedia.org/wiki/Steroid#Research_awardshttps://en.wikipedia.org/wiki/Steroid#See_alsohttps://en.wikipedia.org/wiki/Steroid#Referenceshttps://en.wikipedia.org/wiki/Steroid#Further_readinghttps://en.wikipedia.org/wiki/Steroid#External_linkshttps://en.wikipedia.org/w/index.php?title=Steroid&action=edit&section=1https://en.wikipedia.org/wiki/Gonanehttps://en.wikipedia.org/wiki/Carbonhttps://en.wikipedia.org/wiki/Fused_compoundhttps://en.wikipedia.org/wiki/Fused_compoundhttps://en.wikipedia.org/wiki/Chirality_(chemistry)https://en.wikipedia.org/wiki/Cyclohexanehttps://en.wikipedia.org/wiki/Hydrogenationhttps://en.wikipedia.org/wiki/Phenanthrenehttps://en.wikipedia.org/wiki/Cyclopentanehttps://en.wikipedia.org/wiki/Side_chainhttps://en.wikipedia.org/wiki/Steroid#Steroidogenesishttps://en.wikipedia.org/wiki/Steroid#Alternative_pathwayshttps://en.wikipedia.org/wiki/Steroid#Catabolism_and_excretionhttps://en.wikipedia.org/wiki/Steroid#Isolation.2C_structure_determination.2C_and_methods_of_analysishttps://en.wikipedia.org/wiki/Steroid#Chemical_synthesishttps://en.wikipedia.org/wiki/Steroid#Research_awardshttps://en.wikipedia.org/wiki/Steroid#See_alsohttps://en.wikipedia.org/wiki/Steroid#Referenceshttps://en.wikipedia.org/wiki/Steroid#Further_readinghttps://en.wikipedia.org/wiki/Steroid#External_linkshttps://en.wikipedia.org/w/index.php?title=Steroid&action=edit&section=1https://en.wikipedia.org/wiki/Gonanehttps://en.wikipedia.org/wiki/Carbonhttps://en.wikipedia.org/wiki/Fused_compoundhttps://en.wikipedia.org/wiki/Chirality_(chemistry)https://en.wikipedia.org/wiki/Cyclohexanehttps://en.wikipedia.org/wiki/Hydrogenationhttps://en.wikipedia.org/wiki/Phenanthrenehttps://en.wikipedia.org/wiki/Cyclopentanehttps://en.wikipedia.org/wiki/Side_chain


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Testosterone,

the principal

male se"

hormoneand

ananaolic

steroid

'holic acid, a ile acid,

sho#ing the caro"ylic

acidand

additional hydro"yl

groupsoften present

e"amethasone,

a

syntheticcorticost

eroiddrug

:anosterol,

the iosyntheticprecursor

to animal steroids. The

numer of carons (63)

indicates

itstriterpenoidclassificatio

n.

Progesterone, a steroid

hormone involved in the

female menstrual cycle,

pregnancy, and

emryogenesis

@edrogestone, a

synthetic drug #itheffects similar to

progesterone

A!Sitosterol, a plant or phytosterol,#ith a fully ranched hydrocaron

side chain at '! and an hydro"yl

group at '!6

n addition to the ring scissions (cleavages), e"pansionsandcontractions(cleavage andreclosing to a larger or smaller rings)Ball variations in the caron!caron ondframe#orkBsteroids can also vary$

in the ond orders#ithin the rings,

in the numer of methyl groups attached to the ring (and, #hen present, on the

prominent side chain at '),

in the functional groups attached to the rings and side chain, and

in the configurationof groups attached to the rings and chain. +2-$245
https://en.wikipedia.org/wiki/Testosteronehttps://en.wikipedia.org/wiki/Sex_steroidhttps://en.wikipedia.org/wiki/Sex_steroidhttps://en.wikipedia.org/wiki/Anabolic_steroidhttps://en.wikipedia.org/wiki/Anabolic_steroidhttps://en.wikipedia.org/wiki/Cholic_acidhttps://en.wikipedia.org/wiki/Bile_acidhttps://en.wikipedia.org/wiki/Carboxylic_acidhttps://en.wikipedia.org/wiki/Carboxylic_acidhttps://en.wikipedia.org/wiki/Carboxylic_acidhttps://en.wikipedia.org/wiki/Hydroxyl_grouphttps://en.wikipedia.org/wiki/Hydroxyl_grouphttps://en.wikipedia.org/wiki/Dexamethasonehttps://en.wikipedia.org/wiki/Corticosteroidhttps://en.wikipedia.org/wiki/Corticosteroidhttps://en.wikipedia.org/wiki/Lanosterolhttps://en.wikipedia.org/wiki/Biosynthetichttps://en.wikipedia.org/wiki/Triterpenoidhttps://en.wikipedia.org/wiki/Progesteronehttps://en.wikipedia.org/wiki/Medrogestonehttps://en.wikipedia.org/wiki/Beta-Sitosterolhttps://en.wikipedia.org/wiki/Phytosterolhttps://en.wikipedia.org/wiki/Ring_expansionhttps://en.wikipedia.org/wiki/Ring_contractionhttps://en.wikipedia.org/wiki/Ring_contractionhttps://en.wikipedia.org/wiki/Bond_orderhttps://en.wikipedia.org/wiki/Chirality_(chemistry)https://en.wikipedia.org/wiki/Steroid#cite_note-Lednicer_2011-2https://en.wikipedia.org/wiki/Steroid#cite_note-Lednicer_2011-2https://en.wikipedia.org/wiki/Testosteronehttps://en.wikipedia.org/wiki/Sex_steroidhttps://en.wikipedia.org/wiki/Sex_steroidhttps://en.wikipedia.org/wiki/Anabolic_steroidhttps://en.wikipedia.org/wiki/Anabolic_steroidhttps://en.wikipedia.org/wiki/Cholic_acidhttps://en.wikipedia.org/wiki/Bile_acidhttps://en.wikipedia.org/wiki/Carboxylic_acidhttps://en.wikipedia.org/wiki/Carboxylic_acidhttps://en.wikipedia.org/wiki/Hydroxyl_grouphttps://en.wikipedia.org/wiki/Hydroxyl_grouphttps://en.wikipedia.org/wiki/Dexamethasonehttps://en.wikipedia.org/wiki/Corticosteroidhttps://en.wikipedia.org/wiki/Corticosteroidhttps://en.wikipedia.org/wiki/Lanosterolhttps://en.wikipedia.org/wiki/Biosynthetichttps://en.wikipedia.org/wiki/Triterpenoidhttps://en.wikipedia.org/wiki/Progesteronehttps://en.wikipedia.org/wiki/Medrogestonehttps://en.wikipedia.org/wiki/Beta-Sitosterolhttps://en.wikipedia.org/wiki/Phytosterolhttps://en.wikipedia.org/wiki/Ring_expansionhttps://en.wikipedia.org/wiki/Ring_contractionhttps://en.wikipedia.org/wiki/Bond_orderhttps://en.wikipedia.org/wiki/Chirality_(chemistry)https://en.wikipedia.org/wiki/Steroid#cite_note-Lednicer_2011-2


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For instance, sterolssuch as cholesterol and lanosterol have an hydro"ylgroupattached at position '!6, #hile testosteroneandprogesteronehave a caronyl(o"o sustituent) at '!6C of these, lanosterolalone has t#o methyl groups at '!8 andcholesterol (#ith a '!0 to '!= doule ond) differs from testosterone and progesterone(#hich have a '!8 to '!0 doule ond).

'holesterol,

a prototypicalanimal sterol.

This structural lipidand key

steroid iosyntheticprecursor.+-$/0f

0>!cholestane, a common

steroid core

Steroid 0> and

0Astereoisomers+-$/=f

Species distriution and function+edit-

The follo#ing are some common categories of steroids. n eukaryotes, steroids arefound in fungi, animals, and plants. Fungal steroids include theergosterols.

%nimal steroids include compounds of verterateand insectorigin, the latterincluding ecdysteroidssuch as ecdysterone(controlling molting in some species).Derterate e"amples include the steroid hormonesand cholesterolC the latter is a

structural component of cell memranes#hich helps determine the fluidity of cellmemranesand is a principal constituent of pla


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+/-4 #here its origin from eukaryotesis conEectured+5-4 and the more!commonpentacyclic triterpinoidhopanoidframe#ork.+3-

Types+edit-

Intact ring system+edit-

t is also possile to classify steroids ased on their chemical composition. nee"ample of ho# @eS9performs this classification is availale at the Wikipedia @eS9catalog. 1"amples of this classification include$

'holecalciferol(vitamin 6), an e"ample of a 5,3!secosteroid

'yclopamine, an e"ample of a comple" '!nor!!homosteroid

Class Example Number of carbon atoms

'holestanes 'holesterol 2

'holanes 'holic acid 28

Pregnanes Progesterone 2
https://en.wikipedia.org/wiki/Steroid#cite_note-pmid12519197-8https://en.wikipedia.org/wiki/Eukaryotehttps://en.wikipedia.org/wiki/Eukaryotehttps://en.wikipedia.org/wiki/Steroid#cite_note-pmid20333205-9https://en.wikipedia.org/wiki/Triterpenehttps://en.wikipedia.org/wiki/Hopanehttps://en.wikipedia.org/wiki/Hopanehttps://en.wikipedia.org/wiki/Steroid#cite_note-pmid21531832-10https://en.wikipedia.org/w/index.php?title=Steroid&action=edit&section=3https://en.wikipedia.org/w/index.php?title=Steroid&action=edit&section=4https://en.wikipedia.org/wiki/Medical_Subject_Headingshttps://en.wikipedia.org/wiki/Wikipedia:MeSH_D04#MeSH_D04.808_---_steroidshttps://en.wikipedia.org/wiki/Wikipedia:MeSH_D04#MeSH_D04.808_---_steroidshttps://en.wikipedia.org/wiki/Cholecalciferolhttps://en.wikipedia.org/wiki/Secosteroidhttps://en.wikipedia.org/wiki/Cyclopaminehttps://en.wikipedia.org/wiki/Cholestanehttps://en.wikipedia.org/wiki/Cholanehttps://en.wikipedia.org/wiki/Pregnanehttps://en.wikipedia.org/wiki/Steroid#cite_note-pmid12519197-8https://en.wikipedia.org/wiki/Eukaryotehttps://en.wikipedia.org/wiki/Steroid#cite_note-pmid20333205-9https://en.wikipedia.org/wiki/Triterpenehttps://en.wikipedia.org/wiki/Hopanehttps://en.wikipedia.org/wiki/Steroid#cite_note-pmid21531832-10https://en.wikipedia.org/w/index.php?title=Steroid&action=edit&section=3https://en.wikipedia.org/w/index.php?title=Steroid&action=edit&section=4https://en.wikipedia.org/wiki/Medical_Subject_Headingshttps://en.wikipedia.org/wiki/Wikipedia:MeSH_D04#MeSH_D04.808_---_steroidshttps://en.wikipedia.org/wiki/Wikipedia:MeSH_D04#MeSH_D04.808_---_steroidshttps://en.wikipedia.org/wiki/Cholecalciferolhttps://en.wikipedia.org/wiki/Secosteroidhttps://en.wikipedia.org/wiki/Cyclopaminehttps://en.wikipedia.org/wiki/Cholestanehttps://en.wikipedia.org/wiki/Cholanehttps://en.wikipedia.org/wiki/Pregnane


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%ndrostanes Testosterone 5

1stranes 1stradiol /

The gonane (steroid nucleus) is the parent !caron tetracyclic hydrocaron molecule#ith no alkylsidechains.+-

Cleaved, contracted, and expanded rings+edit-

Secosteroids (:atin seco, 7to cut7) are a suclass of steroidal compoundsresulting,iosyntheticallyor conceptually, from scission (cleavage) of parent steroid

rings (generally one of the four). @aEor secosteroid suclasses are defined y thesteroid caron atoms #here this scission has taken place. For instance, the prototypicalsecosteroid cholecalciferol, vitamin 6(sho#n), is in the 5,3!secosteroid suclass andderives from the cleavage of caron atoms '!5 and '!3 of the steroid &!ringC 0,=!secosteroids and 6,8!steroids are similar.+2-

?orsteroids(nor!, :. normaC 7normal7 in chemistry, indicating caron removal) +6-andhomosteroids (homo!, Greek homosC 7same7, indicating caron addition) are structuralsuclasses of steroids formed from iosynthetic steps. The former involves en;ymic ringe"pansion!contractionreactions, and the latter is accomplished (iomimetically) or(more fre


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Pharmacological action+edit-

T#o classes of drugstarget the mevalonate path#ay$ statins(used to reduce elevatedcholesterol levels) andisphosphonates(used to treat a numer of one!degenerativediseases).

&iosynthesis and metaolism+edit-

The hundreds of steroids found in animals, fungi, and plantsare madefrom lanosterol(in animals and fungiC see e"amples aove) or cycloartenol(in plants).:anosterol and cycloartenol derive from cycli;ationof thetriterpenoids


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@evalonate path#ay

The mevalonate, or 9@G!'o% reductase path#ay egins #ith acetyl!'o%and ends#ith dimethylallyl pyrophosphate(@%PP) and isopentenyl pyrophosphate(PP).@%PP and PP donate isopreneunits, #hich are assemled and modified toformterpenesand isoprenoids+5-(a large class of lipids, #hich includethe carotenoidsand form the largest class of plantnatural products.+23-9ere, theisoprene units are Eoined to make s


10/16

among species. The maEor classes of steroid hormones, #ith prominent memers ande"amples of related functions, are$

Progestogens$

Progesterone, #hich regulates cyclical changes in the endometriumoftheuterusand maintains a pregnancy

'orticosteroids(corticoids)$

%ldosterone, a mineralocorticoid#hich helps regulatelood pressure

'ortisol, a glucocorticoid#hose functions include immunosuppression

%ndrogens$

Testosterone, #hich contriutes to the development and maintenance of

male secondary se" characteristics

1strogens$

1strogen, #hich contriutes to the development and maintenance of

female secondary se" characteristics

9uman steroidogenesis occurs in a numer of locations$

Progestogens are the precursors of all other human steroids, and all human

tissues #hich produce steroids must first convert cholesterol to pregnenolone. Thisconversion is the rate!limiting step of steroid synthesis, #hich occurs insidethe mitochondrionof the respective tissue.+28-

'orticosteroids are produced in the adrenal corte".

1strogen and progesterone are made primarily in the ovaryand

the placentaduring pregnancy, and testosteronein the testes.

Testosterone is also converted to estrogen to regulate the supply of each in

females and males.

Some neuronsand gliain thecentral nervous system('?S) e"press

the en;ymesre


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n plants and acteria, the non!mevalonate path#ayusespyruvateand glyceraldehyde6!phosphateas sustrates.+5-+20-

'ataolism and e"cretion+edit-

Steroids are primarily o"idi;ed y cytochrome P803 o"idaseen;ymes, such

as 'HP6%8. These reactions introduce o"ygen into the steroid ring, allo#ing thecholesterol to e roken up y other en;ymes into ile acids. +2=-These acids can then eeliminated y secretion from the liverin ile.+2-The e"pression of the o"idasegene cane upregulatedy the steroid sensor PIR#hen there is a high lood concentration ofsteroids.+2/-Steroid hormones, lacking the side chain of cholesterol and ile acids, aretypically hydro"ylatedat various ring positions or o"idi;ed at the position, conEugted#ith sulfate orglucuronic acidand e"creted in the urine.+25-

solation, structure determination, and methods of analysis+edit-

Steroid isolation, depending on conte"t, is the isolation of chemical matter re


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52 ('hemistry) 9einrich tto Wieland4 'onstitution of ile acids and sterols

and their connection to vitamins+68-

52/ ('hemistry)%dolf tto Reinhold Windaus4 'onstitution of sterols and their

connection to vitamins+60-

565 ('hemistry)%dolf &utenandtand :eopold Ru;icka4 solation and structural

studies of steroid se" hormones, and related studies on higher terpenes+6=-

503 (Physiology or @edicine) 1d#ard 'alvin Jendall, Tadeus Reichstein,

andPhilip 9ench4 Structure and iological effects of adrenal hormones+6-

5=0 ('hemistry) Roert &urns Wood#ard4 n part, for the synthesis of

cholesterol, cortisone, and lanosterol+6/-

5=5 ('hemistry) erek &artonand dd 9assel4 evelopment of the concept of

conformation in chemistry, emphasi;ing the steroid nucleus+65-

50 ('hemistry) Dladimir Prelog4 n part, for developing methods to determine

the stereochemical course of cholesterol iosynthesis from mevalonicacidvia s


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. K Lump up to$abcd.. $oss and the *or+ing arty of the A-/0oint ommission on /iochemical 1omenclature ("232).41omenclature ofsteroids, recommendations "2324(5F). ure 6 Appl. hem.61("!)% "7389"3.doi%"!."8#":pac"232;""!"738.Also a&ailable 'ith the same authors (andyear) at4A-/ 0oint ommission on /iochemical 1omenclature (0/1).

The nomenclature of steroids. 8-"!88."232.tb"#3.?.$5;!;!22.?ote, the article co!authors, the WorkingParty of the *P%'!*& L'&?, #ere P. Jarlson (chairman), L.R. &ull, J. 1ngel, L.FriedM, 9.W. Jircher, J.:. :oening, G.P. @oss, G. PopENk and @.R.*skokovic.Also a&ailable online at4The 1omenclature of Steroids4. @ondon,/


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$icrobiology 47()% >7"93". doi%"!."!>;:j."8;#-2#3.!!8.!88!2.?.$5"#"2"27.

5. ump up !5esmond =, ribaldo S (!!2). 4hylogenomics of sterolsynthesis% insights into the origin, e&olution, and di&ersity of a +ey eu+aryotic

feature4. enome /iology and =&olution 1% 8;>93". doi%"!."!28:gbe:e&p!8;. $3"7>8!.$5!888!#.

3. ump up !Siedenburg , 0endrosse+ 5 (0un !""). 4SGualene-hopenecyclases4. Applied and =n&ironmental $icrobiology 77(")% 82!#9"#. doi%"!.""3:A=$.!!8!!-"". $8"8";!. $5"#8"38.

. ump up !=dgren (22)!!"!"-3. $5"!7"#8;>.

2. ump up !Banson 0< (0un !"!). 4Steroids% partial synthesis in medicinalchemistry4. 1atural roduct 2->;>;->.

/. ump up !rocho's+i @@, Iu B, *hite


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5. K Lump up to$abCuEuyama T, Seto B (Apr !!8). 45i&ersity of thebiosynthesis of the isoprene units4. 1atural roduct ;.doi%"!."!!7:/F!7!8882. $5">#"78;7.

2. K Lump up to$abSchroepfer 0 ("23"). 4Sterol biosynthesis4. Annual.!!. $5";7#2;27.

20. ump up !@ichtenthaler BC (0un "222). 4The "-deo?y-d-?ylulose-#-

phosphate path'ay of isoprenoid biosynthesis in plants4. Annual


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25. ump up !Steimer T. 4Steroid Bormone $etabolism4. *BO ollaboratingentre in =ducation and

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