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And Even-Length, Medium-Chain Fatty Acids in Plants (Amino Adds/Elongtin) ANTOANETA B

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And Even-Length, Medium-Chain Fatty Acids in Plants (Amino Adds/Elongtin) ANTOANETA B Proc. Nadl. Acad. Sci. USA Vol. 91, pp. 11437-11441, November 1994 Biochemistry A pathway for the biosynthesis of straight and branched, odd- and even-length, medium-chain fatty acids in plants (amino adds/elongtin) ANTOANETA B. KROUMOVA, ZHIYI XIE, AND GEORGE J. WAGNER* Plant Physiology/Biochemistry/Molecular Biology Program, Agronomy Department, University of Kentucky, Lexington, KY 40546-0091 Communicated by Martin Gibbs, July 25, 1994 ABSTRACT Pathways and enzymes offatty acid synthase- and even-length scFAs are synthesized via modified mediated, long-even-chain (generally C16-C20) fatty add syn- branched-chain amino acid (bcAA) metabolism in tobacco thesis are well studied, and general metabolism involved in trichome glands (6, 7). It is possible that at least branched and short-chain (Cs-C7) fatty acid biosynthesis is also understood. odd-length mcFAs are formed in this tissue similarly. Alter- In contrast, mechanism of medinm-chain (C#-C14) fatty acid natively, primers derived from bcAA metabolism may be synthesis are unclear. Recent work suggests involvement of elongated by fatty acid synthase (FAS), as suggested for chain-elongation-terminating thloesterases in medium-chain tomato trichomes (8) and tobacco epidermis (9). fatty acid formation in oilseeds and animals. We have shown The classical pathway for bcAA (Val, Leu, Ileu) biosyn- that iso- and anteiso-branched and straigbt, odd- and even- thesis in microorganisms (and largely by inference in plants, length, short-chain fatty adds esterifled in plant-trichome- ref. 10) is shown in the shaded areas of Fig. 1. Key activities gland-produced sucrose esters are synthesized by using carbon involved in branched-chain formation (reactions 1, 1A, and 2) skeletons provided by modified branched-chain amino acid are those catalyzing leucine biosynthesis in all organisms and metabolism/catablis. The principal enzymes involved are those leading to short-chain alcohols in mutant yeasts (12) those catalyzing leucine biosynthesis in all organisms and those and alkyl acids in Clostridium species (products often serving leading to short-chain alohols in mutant yeasts and alkyl adds as mammalian pheromones, ref. 13). Enzymes catalyzing in Clostffdium species (products often serving as mammalian reactions 1, 1A, 2, and 3 are 2-isopropylmalate synthase (EC pheromones). Here we provide evidence that Clo-C2 straight 4.1.3.12), 3-isopropylmalate dehydratase (EC 4.2.1.33), medim-chain and Cloa-Ci branched medium-chain acyl acids 3-isopropylmalate dehydrogenase (EC 1.1.1.85), and 2-oxo- of tomato, Ce-Cs straight-chain acyl acids of Petunia, and C6 isovalerate dehydrogenase (acylating) (EC 1.2.1.25), respec- and Cs branched acyl acds of Nicotiana glutinosa are formed tively; the last is often referred to as 2-oxoacid dehydroge- by a-ketoacld elongation without participation of fatty acid nase. Modified trivial names for these enzymes (which are synthase- ated reactions or -independent thioesterases. well characterized as leucine biosynthetic enzymes in micro- This derent metabolism suggests greater integration ofamino bial systems) were offered previously (7), taking into account acid and fatty acid metabolism than previously considered and the apparent broad substrate specificity of plant-trichome- provides other avenues to study and manipulate not only gland enzymes for the alkyl portion of2-ketoacid substrates. straght even-length but also odd- and even-length stiht and In earlier studies of the biosynthesis of scFAs (C4-C7) branched medium-chain fatty acid biosynthesis. esterified in trichome-exudated sucrose esters oftobacco we concluded that a lack of transamination of 2-oxoacids to focused on to amino acids results (after reactions 1, 1A, 2, and 3) in Considerable effort is currently attempts modify CoA-activated derivatives for esterification to sucrose (6, 7). plants and microbes to over-produce medium-chain fatty acids For example, 2-oxo-3-methylvaleric acid (C6) leads to 2-oxo- (mcFAs) for commercial and dietary use (1). The value of 4-methylhexanoic acid (C7), which when oxidatively decar- biologically derived mcFAs and their conjugates lies in their boxylated (reaction 3) yields 3-methylvaleryl-CoA (C6). As favorable properties for application as renewable and biode- shown in Fig. 1, 2-oxo-3-methylbutyric acid-derived from gradable components of surfactants, adhesives, emulsifiers, pyruvate-can yield iso-branched products, and 2-oxobu- edible oils, flavorants, finrances, and natural product pesti- tyric acid-derived from pyruvate or threonine-can yield cides. mcFAs are found in microorganisms; in mammalian anteiso-branched or straight-chain products. Acetate donates milk, blood, and other tissues; and in certain vegetable oils carbon in two possible ways, in the 3-isopropylmalate syn- and, together with short-chain fatty acids (scFAs), are com- thase reaction (reaction 1) or, in the case of iso- or anteiso- ponents of a large variety of volatile and nonvolatile esters branched product formation, additionally via hydroxyethyl produced by plants, including sugar esters secreted by tri- thiamine pyrophosphate (HETPP), as cosubstrate in the chomes ofSolanaceae species. Esters containing mcFAs and the ab- scFAs are often key factors in plant-pollinator and plant-pest acetolactate synthase reaction (Fig. 1). Presumably interactions (2, 3). Sugar esters can constitute >2% ofleafdry sence of acyl-CoA oxidase (11) in trichome glands prevents weight in certain tomato and tobacco varieties producing catabolism of CoA products via bcAA catabolism. .10% of leaf dry weight as exudate and -25% of exudate as Our objective in the present study was to determine if sugar esters. mcFAs of trichome-exudated sugar esters formed in certain Mechanisms for synthesis oflong-chain fatty acids (lcFAs) Solanaceous species are produced by FAS, FAS- and in plants are well studied (1). In contrast, metabolism leading thioesterase-mediated reactions, or by an alternative path- to the biosynthesis of mcFAs is not well understood (4, 5), way. To distinguish among these possibilities we used a particularly that catalyzing the formation of branched and classical radiotracer approach, including chemical degrada- odd-length mcFAs. Straight, iso-, and antiso-branched, odd- Abbreviations: aKAE, a-ketoacid elongation; mcFA, medium-chain fatty acid; scFA, short-chain fatty acid; FAS, fatty acid synthase; The publication costs ofthis article were defrayed in part by page charge bcAA, branched-chain amino acid; IcFA, long-chain fatty acid; payment. This article must therefore be hereby marked "advertisement" HETPP, hydroxyethyl thiamine pyrophosphate. in accordance with 18 U.S.C. §1734 solely to indicate this fact. *To whom reprint requests should be addressed. 11437 Downloaded by guest on October 3, 2021 11438 Biochemistry: Kroumova et al. Proc. Natl. Acad. Sci. USA 91 (1994) CoA-SIl NAD T ill THR CO2 ,COSCo -CH NAD4 (4c( \-SI (3 C'(C(I I r.5Ii CH51CCOOH -_ (1 Si~~~~st~~2~~~ll\ I/A CI IA 1 T (-. - ( R r ~~~~~~2-X~li .t'(i.T..i:ci5S..( .O(.} ` F) yruvatc L A .,i -.' %'. ALS I cel~l Ii - II 1.t I" ''llr V t Accialdecl\vdc j 'N -lCt2 v 'C ,-:i'lt.cl,' tt)p -'A 3 VAL -a- 2-xo-w3 Mceultyric Acetale 11.FT 2_n-oxo-e,. Val]enIit 3 i I 3 1 T IA I 4- 2 Mcl'reopiin'lC'ov\ -. I 1' 4 C-Ic iLI r -ICcA' 2-O.xo-4 Mel 1c'xaTnoCC IlU _ 2-oxo-4 MeValeric 3 *. I P I i ._- )ic-l- 1 lc 1A 1 3-McValcrvl(.eA 3 2 1 I-MieLul3xr'ICoA 3 -e N5C) N.IC! fleptiol? 2- oxo-5 Melkxanoic 3 I !C' >) I I i c II(vI + 4-MeValcr'lICoA ( i 4N- C; -o\ix-6 Mc )cti't xoK:- NCf 1li1TC( 2- xo-6 Mel lept, iC 3 ""1 1li)v1(`oAiu-N I "-cIi ptmanoviC(-)A 3 i I S-Me clxatio'dCoA 1-oo. TcnC 2-oxo-7 MeOctanoic 3 i 6-Mel leptanoviC'A 2-oxo-8 MeNotianeic -s -i \O0- )od ccCiano Cic 1t ''11( 1 ;3 i 7-McOctarnox lCoA 2-oxo-9 MeDeciIOIC 3 .- T- ideci - T i 8-MeNonzlaariovlCoA 2-oxo-10 MeUndecanoia 1 3 J 9-MeDecaanovlCAcA 2-oxo- 1 I MeDodecanoic 3 I10-Metind3lecanlovlCoA FIG. 1. Reactions in the biosynthesis of bcAAs (shaded areas) and the proposed a-ketoacid elongation (aKAE) pathway for biosynthesis ofbranched and straight mcFAs and scFAs in trichome glands. The conversion ofpyruvate to 2-oxobutyrate and then to 2-oxovalerate via cycling of ketoacid products in aKAE can lead, minimally, to synthesis of straight-chain fatty acid derivatives up to C12 and anteiso derivatives up to Cs. Similar cycling from 2-oxo-3-methylbutyric acid leads to iso-branched products up to C12. Reaction 3 describes the first step in the catabolism of oxoacids derived from valine, leucine, and isoleucine by deamination (11). Threonine donates carbon to anteiso- and straight-chain CoA products via threonine-deaminase-catalyzed formation of 2-oxobutyric acid (6, 7). Lines under atoms of carbon skeletons at top indicate the position of label derived from [2-14C]acetate. The metabolic sequences from pyruvate through valeryl-CoA, methylbutyryl-CoA, and 3-methylvaleryl-CoA were concluded from previous work (6, 7). Superscripted letters represent principal sugar ester alkyl groups formed (and labeled from [2-14C]acetate, shown here) in trichome glands of tomato (T), petunia (P), and Nicotiana glutinosa (G). The relative labeling from [2-14C]acetate of extended acyl moieties in sucrose esters formed in these plant systems is denoted by the relative size of T, P, and G after products. ALS, position of acetolactate synthase. tion analysis of recovered, purified, free fatty acids. Acids and other labels used were from ICN. Standard acids were were radiolabeled in vivo and recovered from trichome- from Aldrich Chem (Metuchen, NJ) or Chemica Alta (Ed- exudated sugar esters by saponification. The resulting free monton, AB, Canada). Carbo-sorb was from the Packard.
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