Abstract
Sterols are produced via the ubiquitous isoprenoid pathway which also gives rise to an array of products such as the dolichols and ubiquinone, or components of important molecules such as isopentenyl adenine, heme A, and farnesylated proteins (Ras). Although there are major groups of organisms that cannot produce sterols including insects, parasitic nematodes, and pythiaceous fungi, sterols are widely distributed in nature, where they are required for the growth and/or reproduction of essentially all eukaryotic organisms. With few exceptions, prokaryotes cannot synthesize sterols and, except for some mycoplasmas, they are not required for growth or reproduction. Specific sterols tend to be produced as end products and accumulate in the major groups of organisms, e.g., cholesterol in mammals, and sitosterol in many plants along with cholesterol, stigmasterol, and campesterol. Families of algae tend to accumulate specific sterols such as cholesterol in the red algae (Rhodophyceae) and fucosterol in the brown algae (Phaeophyceae), and others have several predominant sterols which may include 24-methyl and 24-ethylcholesterol and cholesterol (Patterson 1991).
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References
Andreasen AA, Stier TJB (1953) Anaerobic nutrition of Saccharomyces cerevisiae. J Cell Comp Physiol 41: 23–26
Aoyama Y, Yoshida Y, Hata S, Nishino T, Katsuki H, Maitra US, Mohan VP, Sprinson DB (1983) J Biol Chem 258: 9040–9042
Arthington BA, Bennett LG, Skatrud PL, Guynn CJ, Barbuch RJ, Ulbright CE, Bard M (1991) Cloning, description, and sequence of the gene encoding yeast C-5 sterol desaturase. Gene 102: 39–44
Ashman WH, Barbuch RJ, Ulbright CE, Jarrett HW, Bard M (1991) Cloning and disruption of the yeast C-8 sterol isomerase gene. Lipids 26: 628–632
Augustyn OPH, Koch JLF, Ferrerira D (1992) Differentiation between yeast species and strains within species by cellular fatty acid analysis: a feasible technique? Syst Appl Microbial 15: 105–115
Baloch RI, Mercer EI, Wiggins TE, Baldwin BC (1984) Inhibition of ergosterol biosynthesis in Saccharomyces cerevisiae and Ustilago maydis by tridemorph, fenpropimorph and fenpropidin. Phytochemistry 23: 2219
Bard M (1972) Biochemical and genetic aspects of nystatin resistance in Saccharomyces cerevisiae. J Bacteriol 111: 649–657
Bard M, Lees ND, Turi T, Croft D, Cofrin L, Barbuch R, Koegel C, Loper JC (1993) Sterol synthesis and viability of ergll (cytochrome P-450 lanosterol demethylase) mutations in Saccharomyces cerevisiae and Candida albicans. Lipids 28: 963–967
Barton DHR, Collie JET, Widdowson DA, Bard M, Woods RA (1974) Biosynthesis of terpenes and steroids. Part IX. The sterols of some mutant yeasts and their relationship to be biosynthesis of ergosterol. Chem Soc Perk Trans 1: 1326–1333
Basson ME, Thorness M, Rine J (1986) Saccharomyces cerevisiae contains two functional genes encoding 3hydroxy-3-methylglutaryl coenzyme A reductase. Proc Natl Acad Sci USA 83: 5553–5567
Benveniste P (1986) Sterol biosynthesis. Annu Rev Plant Physiol 37: 275–308
Berg D, Plempel M (eds) (1988) Sterol biosynthesis inhibitors: pharmaceutical and agrochemical aspects. Ellis Harwood, Chichester
Bil1heimer JT, Reinhart MP (1990) Intracellular trafficking of sterols. In: Hilderson HG (ed) Subcellular biochemistry intracellular transfer of lipid molecules, vol 16. Plenum, New York, pp 301–331
Bloch KE (1983) Sterol structure and membrane function. In: Fasman GD (ed) CRC Crit Rev Biochem 14: 47–92
Bloch KE (1987) Summing up. Annu Rev Biochem 56: 1–19
Blomquist G, Andersson B, Andersson K, Brondz I (1992) Analysis of fatty acids. A new method for characterization of moulds. J Microbial Methods 16: 59–68
Butko P, Hapala I, Nemecz G, Schroeder F (1992) Sterol domains in phospholipid membranes: dehydroergosterol polarization measures molecular sterol transfer. J Biochem Biophys Methods 24: 15–37
Casey WM, Keesler GA, Parks LW (1992) Regulation of partitioned sterol biosynthesis in Saccharomyces cerevisiae. J Bacteriol 174: 7283–7288
Chambon C, Ladeveze V, Oulmonden A, Servous M, Karst F (1990) Isolation and properties of yeast mutants in farnesyl diphosphate synthetase. Curr Genet 18: 41–46
Chambon C, Ladeveze V, Servouse M, Blanchard L, Javelot C, Vladescu B, Karst F (1991) Sterol pathway in yeast. Identification and properties of mutant strains defective in mevalonate diphosphate decarboxylase and farnesyl diphosphate synthetase. Lipids 26: 633–636
Connerton IF, Dean SM, Butters JA, Loeffler RST, Hollomon DW (1991) RIP as a tool in the analysis of P-450 and sterol biosynthesis in Neurospora crassa. Biochem Soc Trans 19: 779–802
Croxen R, Goosey MW, Keon JPR, Hargreaves JA (1994) Isolation of an Ustilago maydis gene encoding 3hydroxy-3-methylglutaryl coenzyme A reductase and expression of a C-terminal truncated form in Escherichia coli. Microbiology 140: 2363–2370
Dahl C, Dahl J (1988) Cholesterol and cell function In: Yeagle PL (ed) Biology of cholesterol. CRC Press, Boca Raton, pp 147–170
Dahl C, Dahl J, Bloch K (1980) Sterols in membranes: growth characteristics and membrane properties of Mycoplasma capricolum cultured on cholesterol and lanosterol. Biochemistry 19: 1462–1467
Dahl C, Biemann H-P, Dahl J (1987) A protein kinase antigenetically related to pp 60v-src involved in yeast cell cycle control: positive in vivo regulation by sterol. Proc Natl Acad Sci USA 84: 4012–4016
Dahl J, Dahl C (1985) Stimulation of cell proliferation and polyphosphoinositol metabolism in Saccharomyces cerevisiae by ergosterol. Biochem Biophys Res Commun 113: 844–850
Dahl JS, Dahl CE, Bloch K (1981) Effect of cholesterol on macromolecular synthesis and fatty acid uptake by Mycoplasma capricolum. J Biol Chem 256: 87–91
Demel RA, de Kruijff B (1976) The function of sterols in membranes. Biochim Biophys Acta 457: 109–132
Erwin JA (1973) Comparative biochemistry of fatty acids in eukaryotic organisms. In: Erwin JA (ed) Lipids and biomembranes of eukaryotic microorganisms. Academic Press, New York, pp 41–143
Fegueur M, Richard L, Charles AD, Karst F (1991) Isolation and primary structure of the ERG9 gene of Saccharomyces cerevisiae encoding squalene synthetase. Curr Genet 20: 365–372
Gaber RF, Copple DM, Kennedy BK, Vidal M, Bard M (1989) The yeast gene ERG6 is required for normal membrane function but is not essential for biosynthesis of the cell-cycle-sparking sterol. Mol Cell Biol 9: 34473456
Goosey MW, Moore DJ (1991) Sterol biochemistry in filamentous fungi: a coming of age. Biochem Soc Trans 19: 769–773
Grindle M (1973) Sterol mutants of Neurospora crassa: their isolation, growth characteristics and resistance to polyene antibiotics. Mol Gen Genet 120: 283–290
Grindle M (1974) The efficiency of various mutagens and polyene antibiotics for the induction and isolation of sterol mutants of Neurospora crassa. Mol Gen Genet 130: 81–90
Grindle M, Farrow R (1978) Sterol content and enzyme defects of nystatin-resistant mutants. Mol Gen Genet 165: 305–308
Gullub EG, Liu K, Dayan J, Adlersberg M, Sprinson DB (1977) The mutants deficient in heure biosynthesis and a heme mutant additionally blocked in cyclization of 2,3oxidosqualene. J Biol Chem 252: 2846–2854
Hendrix JW (1970) Sterols in growth and reproduction of fungi. Annu Rev Phytopathol 8: 111–130
Hippe S (1991) Influence of fungicides on fungal fine structure. In: Mendgen K, Lesemann DE (eds) Electron microscopy of plant pathogens. Springer, Berlin Heidelberg New York, pp 317–331
Hollomon DW (1993) Resistance to azole fungicides in the field. Biochem Soc Trans 21: 1047–1051
Howell SA, Mallet AI, Noble WC (1990) A comparison of the sterol content of multiple isolates of the Candida albicans Darlington strain with other clinically azolesensitive and resistant strains. J Appl Bacteriol 69: 692696
Hull SE, Woolfson MM (1976) Crystal structure of ergosterol monohydrate. Acta Cryst B32: 2370–2373
Ikeguchi T (1919) A new sterol. J Biol Chem 40: 175–182
Ishida N, Aoyama Y, Hatanaka R, Oyama Y, Imajo S, Ishiuguro M, Oshima T, Nakazato H, Noguchi T, Martra US, Mohan VP, Sprinson DB, Yoshida Y (1988) A single amino acid substitution converts cytochrome P-450146M to an active from P4505G1: Complete primary structures deduced from cloned DNAs. Biochem Biophys Res Commun 155: 317–323
Julmanop C, Takano Y, Takemoto JY, Miyakawa T (1993) Protection by sterols against the cytotoxicity of syringomycin in the yeast Saccharomyces cerevisiae. J Gen Microbiol 139: 2323–2327
Kalb VK, Woods CW, Tuse TG, Dey CR, Sutter TR, Loper JC (1987) Primary structure of the P450 lanosterol demethylase gene from Saccharomyces cerevisiae. DNA 6: 529–537
Karst F, Lacroute F (1977) Ergosterol biosynthesis in Saccharomyces cerevisiae mutants deficient in the early steps of the pathway. Mol Gen Genet 154: 259–277
Kelly SL, Quail MA, Rowe J, Kelly DE (1992) Sterol 14ademethylase: Target for azole antifungals. In: Fernandez PB (ed) New approaches for antifungal drugs. Brikhauser, Boston, pp 155–187
Kelly SL, Kenna S, Arnaldi, Kelly DE (1994) Studies on azole-induced cell death in Saccharomyces cerevisiae. FEMS Microbial Lett 115: 219–222
Kerkenaar A (1990) Inhibition of the sterol A’4 — reductase and 48 — A’ isomerase in fungi. Biochem Soc Trans 18: 59–61
Koller W (1992) Antifungal agents with target sites in sterol functions and biosynthesis. In: Koller W (cd) Target sites of fungicidal action. CRC Press, London, pp 119–206
Ladbrooke BO, Williams RM, Chapman D (1968) Studies on lecithin-cholesterol-water interaction by differential scanning calorimetery and x-ray diffraction. Biochim Biophys Acta 150: 333–340
Lai MH, Bard M, Pierson CA, Alexander JF, Goebl M, Carter GT, Kirsch DR (1994) The identification of a gene family in the Saccharomyces cerevisiae ergosterol biosynthesis pathway. Gene 140: 41–49
Lechevalier H, Lechevalier MP (1988) Chemotaxonomic use of lipids an overview. In: Ratledge C, Wilkinson SG (eds) Microbial lipids, vol 1. Academic Press, London. pp 869–902
Lorenz RT, Parks LW (1989) Structural discrimination in the sporting function of sterols in the yeast Saccharomyces cerevisiae. J Bacteriol 171: 6169–6173
Lorenz RT, Parks LW (1991) Involvement of heme components in sterol metabolism of Saccharomyces cerevisiae. Lipids 26: 598–603
Lorenz RT, Parks LW (1992) Cloning, sequencing and description of the gene encoding sterol C-14 reductase in Saccharomyces cerevisiae. DNA Cell Biol 11: 685692
Marcireau C, Guilloton M, Karst F (1990) In vivo effects of fenpropimorph on the yeast Saccharomyces cerevisiae and determination of the molecular basis of the antifungal property. Antimicrob Agents Chemother 34: 989–993
Marcireau C, Guyonnet D, Karst F (1992) Construction and growth properties of a yeast strain defective in sterol 14-reductase. Curr Genet 22: 267–272
McCammon MT, Hartman MA, Bottema CD, Parks LW (1984) Sterol methylation in Saccharomyces cerevisiae. J Bacteriol 157: 475–483
Mead JF, Alfen-Slater RB, Howton DR, Popjak G (1986) Lipids: chemistry, biochemistry, nutrition. Plenum Press, New York, 295 pp
Mercer EI (1991) Morpholine antifungals and their mode of action. Biochem Soc Trans 19: 788–793
Mercer I (1984) The biosynthesis of ergosterol. Pesti Sci 15: 133–155
Mercer I (1993) Inhibitors of sterol biosynthesis and their applications. Prog Lipid Res 32: 357–416
Mishra P, Prasad R (1990) An overview of lipids of Candida albicans. Prog Lipid Res 29: 65–85
Morris DC, Safe S, Subden RE (1974) Detection of ergosterol and episterol isomers in nystatin-resistant mutants of Neurospora crassa. Biochem Genet 12: 459466
Muller MM, Kantola R, Kitunen V (1994) Combining sterol and fatty acid profiles for the characterization of fungi. Mycol Res 98: 593–603
Nes DW (1987) Biosynthesis and requirement for sterols in the growth and reproduction of Oomycetes In: Fuller G, Nes WD (eds) Ecology and metabolism of plant lipids. ACS Symp Ser 325, Washington, DC, pp 304–328
Nes RW, Dhanuka IC (1988) Inhibition of sterol synthesis by A5 — sterols in a sterol auxotroph of yeast defective in oxidosqualene cyclase and cytochrome P-450. J Biol Chem 263: 11844–11850
Nes WD, Jenssen GG, Crumley FG, Kalinowska M, Akihisa T (1983) The structural requirements for membrane function in Saccharomyces cerevisiae. Arch Biochem Biophys 300: 724–733
Nes WD, Parker SR, Crumley PG, Ross SA (1993) Regulation of phytosterol biosynthesis. In: Moore TS (ed) Lipid metabolism in plants. CRC Press, Boca Raton, pp 389426
Nes WR, McKean ML (1977) The biochemistry of steroids and other isopentenoids. Univ Park Press, Baltimore, MD
Nes WR, Nes WD (1980) Lipids in evolution. Plenum Press, New York
Nes WR, Sekula BC, Nes WD, Adler JH (1978) The functional importance of structural features of ergosterol in yeast. J Biol Chem 253: 6218–6225
Oulmouden A, Karst F (1990) Isolation of ERG12 gene of Saccharomyces cerevisiae encoding mevalonate kinase. Gene 88: 253–257
Oulmouden A, Karst F (1991) Nucleotide sequence of the ERG12 gene of Saccharomyces cerevisiae encoding mevalonate kinase. Curr Genet 19: 9–14
Parker SR, Nes WD (1992) Regulation of sterol biosynthesis and its phylogenetic implications. ACS Symp Ser 497: 110
Parks LW (1978) Metabolism of sterols in yeast. CRC Crit Rev Microbiol 6: 300–341
parks LW, Weete JD (1991) Fungal Sterols. In: Patterson GW, Nes WD (eds) Physiology and biochemistry of sterols. Am Oil Chem Soc, Champaign, pp 158–171
Patterson GW (1991) Sterols of algae. In: Patterson GW, Nes WD (eds) Physiology and biochemistry of sterols. Am Oil Chem Soc, Champaign, pp 118–169
Patterson GW, Nes WD (eds) (1991) Physiology and bio- chemistry of sterols. Am Oil Chem Soc, Champaign
Pesti M, Campbell JM, Peberdy JF (1981) Alteration of ergosterol content and chitin synthase activity in Candida albicans. Curr Microbiol 5: 187–190
Pinto WJ, Nes WR (1983) Stereochemical specificity for sterols in Saccharomyces cerevisiae. J Biol Chem 258: 4472–4476
Pinto WJ, Lozano R, Sekula BC, Nes WR (1983) Stereochemically distinct roles for sterol in Saccharomyces cerevisiae. Biochem Biophys Res Commun 112: 47–54
Pommer EH (1984) Chemical structure-fungicidal activity relationships in substituted morpholines. Pestic Sci 15: 285–295
Quinn PJ (1981) The fluidity of cell membrane and its regulation. Prog Biophys Mol Biol 38: 1–104
Ramgopal M, Bloch K (1983) Sterol synergism in yeast. Proc Natl Acad Sci USA 80: 712–715
Ramgopal M, Zundel M, Bloch K (1990) Sterol effects on phospholipid biosynthesis in the yeast strain GL7. J Lipid Res 31: 653–658
Rodriguez RJ, Parks LW (1983) Structural and physiological features of sterols necessary to satisfy the bulk membrane and sparking sterol requirements in yeast auxotrophs. Arch Biochem Biophys 225: 861–871
Rodriguez RJ, Taylor FR, Parks LW (1982) A requirement for ergosterol to permit growth of yeast sterol auxotrophs on cholesterol. Biochem Biophys Res Commun 106: 435–441
Rodriguez RJ, Low C, Bottema CDK, Parks LW (1985) Multiple functions for sterols in Saccharomyces cerevisiae. Biochime Biophys Acta 837: 336–343
Rodwell VW, Nordstrom JL, Mitschelen JJ (1976) Regula- tion of HMG-CoA reductase. Adv Lipid Res 14: 1–74
Rosenheim O, Webster TA (1927) The parent substance of vitamin D. Biochem J 21: 389–397
Ryder NS (1985) Effect of allylamine antimycotic agents on fungal sterol biosynthesis measured by sterol side-chain methylation. J Gen Microbiol 131: 1595–1602
Ryder NS (1988) Mode of action of allylamines. In: Berg D, Plempel M (eds) Sterol biosynthesis inhibitors. Ellis Harwood, Chichester, pp 151–167
Ryder NS (1990) Inhibition of squalene epoxidase and sterol-side chain methylation by allyamines. Biochem Soc Trans 18: 45–46
Ryder NS (1991) Squalene epoxidase as a target for the allylamines. Biochem Soc Trans 19: 774–777
Sancholle M, Dargent R, Weete JD, Rushing AE, Miller KS, Montant C (1988) Effects of triazoles on fungi VI Ultrastructure of Taphrina deformans. Mycologia 80: 162–175
Schroepfer GJ (1981) Sterol biosynthesis. Annu Rev Biochem 50: 585–621
Semer R, Gelerinter E (1979) A spin label study of the effects on egg lecithin bilayers. Chem Phys Lipids 23: 201–211
Servouse M, Mons N, Baillangeat JL, Karst F (1984) Isolation and characterization of yeast mutants blocked in mevalonic acid formation. Biochem Biophys Res Commun 123: 424–430
Shaw R (1966) The polyunsaturated fatty acids of microorganisms. Adv Lipid Res 4: 107–174
Shimizu S, Kawashima H, Wada M, Yamada H (1992) Occurrence of a novel sterol, 24, 25-methylenecholest-5ene-3ß-ol, in Mortierella alpina 1S-4. Lipids 27: 481–483
Shimokawa O, Nakayama H (1991) Phenotype of Candida albicans sterol mutants deficient in A57 isomerization or A5 desaturation. J Med Vet Mycol 29: 53–56
Shimokawa O, Kato Y, Nakayama H (1986) Accumulation of 14-methyl sterols and defective hyphal growth in Candida albicans. J Med Vet Mycol 24: 327–336
Shimokawa O, Kato Y, Kawano K, Nakayama H (1989) Accumulation of 14a-methylergosta-8,24(28)-dien43, 6a-diol in 14a-demethylation mutants of Candida albicans: genetic evidence for the involvement of 5desaturase. Biochim Biophys Acta 1003: 15–19
Siperstein MD (1984) Role of cholesterogenesis and isoprenoid synthesis in DNA replication and cell growth. J Lipid Res 25: 1462–1467
Smedley-MacLean I, Thomas EM (1920) The nature of yeast fat. Biochem J 1: 483–493
Stutz A (1988) Synthesis and structure activity correlation within allylamine antibiotics. Ann NY Acad Sci 544: 4662
Takemoto JY, Yu Y, Stock SD, Migakawa T (1993) Yeast genes involved in growth inhibition by Pseudimonas syringae pv syringae syringomycin family Lipodepsipetides. FEMS Microb Lett 114: 339–342
Tauret C (1889) Sur un nouveau principe immediat de l’ergot deseigle ergosterine. C R Seances Acad Sci 108: 98–100
Taylor FR, Rodriquez FJ, Parks LW (1983) Requirement for a second sterol biosynthetic mutation for viability of a C-14 demethylation defect in Saccharomyces cerevisiae. J Bacteriol 155: 64–68
Thorness M, Schafer W, D’Ari L, Rine J (1989) Positive and negative transcriptional control by heme of genes encoding 3-hydroxy-3-methylglutaryl coenzyme A in Saccharomyces cerevisiae. Mol Cell Biol 9: 5702–5712
Trocha PJ, Jasne SJ, Sprinson DB (1977) Yeast mutant blocked in removing the methyl group of lanosterol at C14: separation of sterols by high pressure liquid chromatography. Biochemistry 16: 4721–4726
Van den Bossche H (1985) Biochemical targets for antifungal azole derivatives: hypothesis on mode of ac-
tion. In: McGinnis MR (ed) Current topics in medical mycology, vol 1. Springer, Berlin Heidelberg New York, pp 313–351
Van den Bossche H, Marichal P, Garrens K, Bellens D, Moereels H, Janssen PAJ (1990) Mutation in cytochrome P-450 dependent 14a-demethylase results in decreased affinity for azole antifungals. Biochem Soc Trans 18: 56–59
Weete JD (1980) Lipid biochemistry of fungi and other organisms. Plenum Press, New York
Weete JD (1987) Mechanism of fungal growth suppression by inhibitors of ergosterol biosynthesis. In: Fuller G, Nes WD (eds) Ecology and metabolism of plant lipids. ACS Symp Ser 325: 268–287, Am Chem Soc, Washington. DC
Weete JD (1989) Structure and function of sterols in fungi. Adv Lipid Res 23: 115–167
Weete JD, Wise ML (1987) Effects of triazloes on fungi: V response by a naturally tolerant species, Mucor rouxii. Exp Mycol 11: 214–222
Weete JD, Fuller MS, Huang MQ, Gandhi S (1989) Fatty acids and sterols of selected Hypochytriomycetes and Chytridiomycetes. Exp Mycol 13: 183–195
Woods RA (1971) Nystatin-resistant mutants of yeast: alteration in sterol content. J Bacteriol 108: 69–73
Yeagle PL (1991) Modulation of membrane function by cholesterol. Biochimie 73: 1303–1310
Yoshida Y (1988) Cytochrome P-450 of fungi: Primary target for azole antifungal agents. In: McGinnis MR (ed) Current topics in medical mycology, vol 2. Springer, Berlin Heidelberg New York, p 388
Yoshida Y, Aoyama Y, Nishino T, Katsuki H, Maitre US, Mohan VP, Sprinson DB (1985) Special properties of a novel cytochrome P-450 of a Saccharomyces cerevisiae mutant SG1. A cytochrome P-450 species having a nitrogenous ligand trans to thiolate. Biochem Biophys Res Commun 127: 623–628
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Weete, J.D., Gandhi, S.R. (1996). Biochemistry and Molecular Biology of Fungal Sterols. In: Brambl, R., Marzluf, G.A. (eds) Biochemistry and Molecular Biology. The Mycota, vol 3. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-10367-8_20
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