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Biosynthesis of Abscisic Acid by the Direct Pathway Via Ionylideneethane in a Fungus, Cercospora Cruenta

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Biosynthesis of Abscisic Acid by the Direct Pathway Via Ionylideneethane in a Fungus, Cercospora Cruenta Biosci. Biotechnol. Biochem., 68 (12), 2571–2580, 2004 Biosynthesis of Abscisic Acid by the Direct Pathway via Ionylideneethane in a Fungus, Cercospora cruenta y Masahiro INOMATA,1 Nobuhiro HIRAI,2; Ryuji YOSHIDA,3 and Hajime OHIGASHI1 1Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan 2International Innovation Center, Kyoto University, Kyoto 606-8501, Japan 3Department of Agriculture Technology, Toyama Prefectural University, Toyama 939-0311, Japan Received August 11, 2004; Accepted September 12, 2004 We examined the biosynthetic pathway of abscisic Key words: Cercospora cruenta; abscisic acid; allofar- acid (ABA) after isopentenyl diphosphate in a fungus, nesene; -ionylideneethane; all-E-7,8-dihy- Cercospora cruenta. All oxygen atoms at C-1, -1, -10, and dro- -carotene -40 of ABA produced by this fungus were labeled with 18 18 O from O2. The fungus did not produce the 9Z- A sesquiterpenoid, abscisic acid (ABA, 1), is a plant carotenoid possessing -ring that is likely a precursor hormone which regulates seed dormancy and induces for the carotenoid pathway, but produced new sesqui- dehydration tolerance by reducing the stomatal aper- terpenoids, 2E,4E- -ionylideneethane and 2Z,4E- -ion- ture.1) ABA is biosynthesized by some phytopathogenic ylideneethane, along with 2E,4E,6E-allofarnesene. The fungi in addition to plants,2) but the biosynthetic origin fungus converted these sesquiterpenoids labeled with of isopentenyl diphosphate (IDP) for fungal ABA is 13C to ABA, and the incorporation ratio of 2Z,4E- - different from that for plant ABA (Fig. 1). Fungi use ionylideneethane was higher than that of 2E,4E- - IDP derived from the mevalonate pathway for ABA, ionylideneethane. From these results, we concluded that while higher plants biosynthesize IDP for ABA by the C. cruenta biosynthesized ABA by the direct pathway non-mevalonate pathway.3) For the biosynthetic path- via oxidation of ionylideneethane with molecular oxygen way of ABA after IDP, the carotenoid pathway involv- following cyclization of allofarnesene. This direct path- ing cleavage of 9Z-xanthophyll has been elucidated for way via ionylideneethane in the fungus is consistent with plant ABA.4) In contrast to ABA of higher plants, two that in Botrytis cinerea, except for the positions of pathways, the direct and carotenoid pathways after IDP, double bonds in the rings of biosynthetic intermediates, have been proposed for fungal ABA. The direct pathway suggesting that the pathway is common among ABA- is supposed to contain oxidation of ionylideneethanol by producing fungi. oxidase after cyclization of farnesyl diphosphate Fig. 1. Outline of ABA Biosynthetic Pathway. y To whom correspondence should be addressed. Fax: +81-75-753-6284; E-mail: [email protected] Abbreviations: ABA, abscisic acid; FDP, farnesyl diphosphate; IDP, isopentenyl diphosphate 2572 M. INOMATA et al. Table 1. Relative IntensitiesaÞ and CompositionsbÞ of Molecular Ions of 4 and Methyl Esters of 5 and ABA Isolated from C. cruenta Cultured 18 under O2 Compound 4 Methyl ester of 5 Methyl ester of ABA rel. int. comp. rel. int. comp. rel. int. comp. m=z ion species m=z ion species m=z ion species (%) (%) (%) (%) (%) (%) 222 ½M þ 2þ 3.0 58 288 ½M þ 8þ 1.4 6 286 ½M þ 8þ 0.5 9 220 ½Mþ 2.2 42 286 ½M þ 6þ 4.3 19 284 ½M þ 6þ 0.9 17 284 ½M þ 4þ 7.7 34 282 ½M þ 4þ 1.7 32 282 ½M þ 2þ 6.8 30 280 ½M þ 2þ 1.4 26 280 ½Mþ 2.7 12 278 ½Mþ 0.8 15 a)Relative intensities were corrected by natural 13C-, 2H- and 17O-isotopic abundance. bÞComposition of relative intensities of each ion group. (FDP),5–7) the classical direct pathway in Fig. 1, and the Results and Discussion carotenoid pathway might be similar to that of plant 8) 18 ABA. Sufficient evidence appears to be lacking for Labeling of 4, 5, and ABA with O2 these two pathways, since the intermediates between 18O-Labeling of the intermediates 4 and 5 in addition FDP and ionylideneethanol have not been found for the to ABA was examined. The period of accumulation and direct pathway,9–11) and the immediate precursor car- the location were different between compound 4 on the otenoids have not been found for the carotenoid path- one hand and compound 5 and ABA on the other. way. We found that a phytopathogenic fungus, Botrytis Compound 4 was isolated from the mycelia of C. cruen- 18 cinerea, biosynthesized ABA by the direct pathway via ta cultured under O2 for 7 d, and compound 5 and ionylideneethane.12) In this pathway, FDP is converted ABA were isolated from the medium of the fungus 18 to 2E,4E,6E-allofarnesene (2), 2Z,4E,6E-allofarnesene cultured under O2 for 16 d. Compound 6 was not (3), and (R)-2Z,4E- -ionylideneethane successively, and detected in the mycelia of the fungus during the culture then ionylideneethane is oxidized to ABA with molecu- for 16 d. lar oxygen. Recently, the bcaba1 gene encoding P450 Compound 4 and methyl esters of 5 and ABA were monooxygenase of B. cinerea was identified as the ABA analyzed by EIMS to determine their labeled positions 13) 18 18 biosynthetic gene. This finding is consistent with with O from O2. The relative intensities and oxidation of ionylideneethane with molecular oxygen in compositions of molecular ions of 4 and methyl esters B. cinerea. It is not known whether the direct pathway of 5 and ABA are summarized in Table 1. Compound 4 via ionylideneethane is common among ABA-producing gave molecular ions corresponding to ½M þ 2þ and fungi. This situation led us to investigate the biosyn- ½Mþ at m=z 222 and 220 respectively, indicating that thesis of ABA in another ABA-producing fungus, the oxygen atom at C-1 of 4 was labeled with 18O from 18 Cercospora cruenta. O2. Methyl ester of 5 showed molecular ions corre- C. cruenta is a typical fungus in which the two sponding to ½M þ 8þ, ½M þ 6þ, ½M þ 4þ, ½M þ 2þ, pathways have been proposed for the biosynthesis of and ½Mþ at m=z 288, 286, 284, 282, and 280 ABA. This fungus produces 2Z,4E- -ionylideneethanol respectively. This showed that all four oxygen atoms 0 0 18 18 (4) and 2Z,4E-1 ,4 -dihydroxy- -ionylideneacetic acid of 5 at maximum were labeled with O from O2. ABA (5) as the biosynthetic intermediates of ABA.7,14) The methyl ester gave ½M þ 8þ, ½M þ 6þ, ½M þ 4þ, production of these compounds appears to support the ½M þ 2þ, and ½Mþ ions at m=z 286, 284, 282, 280, direct pathway, but the fungus produces -carotene and and 278 respectively. This showed that all four oxygen an aldehyde-intermediate, 2Z,4E- -ionylideneacetalde- atoms of ABA at maximum were labeled with 18O from 18 18 0 18 18 18 hyde (6), and incorporates O from O2 into C-1, -1 , O2 also. In B. cinerea cultured under O2, O-label and -40 of ABA.8) These facts suggest that ABA of the at C-40 of ABA was lost by exchange with 16O from 16 fungus is biosynthesized by the carotenoid pathway, H2 O due to the acidity of the medium. The remaining although the 9Z-carotenoid possessing -ring that 18O-label at C-40 in C. cruenta is probably due to the pH should be a precursor of 6 has not been found in this of the medium, which was kept between 5.8 and 7.5 fungus. We re-examined the 18O-labeling of ABA with during the culture. Exchange of 40-18O with 16Oof 18 16 12) 18 O2, made precise analysis of ABA-related carotenoids H2 O was less than 7% in this pH range. The O and sesquiterpenoids, and did feeding experiments of labels incorporated into compounds 4, 5, and ABA 18 labeled compounds in C. cruenta to solve the confusion might be derived from H2 O that the fungus formed 18 over the biosynthesis of ABA. This paper reports the from O2 by respiration during culture. This possibility occurrence of the direct pathway via ionylideneethane in appears to be small, since no oxygen atom from water C. cruenta as well as in B. cinerea. was incorporated into ABA in the labeling experiment 18 12) with H2 OinB. cinerea. Thus all oxygen of 4, 5, and Biosynthetic Pathway of Abscisic Acid in Cercospora cruenta 2573 ABA produced by C. cruenta is derived from molecular oxygen, but not from water. The result of 18O-labeling of ABA was different from that reported by Yamamoto et al.8) This difference can be explained by the metabolic rate of 6 to ABA. Accumulation of compound 6 in their cultural condition suggests slow turnover of 6 to ABA. The 18O-label at C- 16 16 1of6 would exchange easily with O from H2 Oina medium via a hydrate of the aldehyde group at C-1. Slow turnover of 6 to ABA should allow this exchange, resulting in a decrease or loss of 1-18Oof6. The temperature (30 C) for the culture used by Yamamoto et al. was higher than the optimum temperature for fungal growth and might affect the biosynthetic rate of ABA. We also observed that all four oxygen atoms of 18 18 ABA were not always labeled with O from O2. When the fungus began to produce ABA at a late period, day 22 after inoculation, two oxygen atoms at C-1 and 0 18 18 -1 were labeled with O from O2, but two oxygen atoms at C-1 and -40 were not (data not shown).
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