Occurrence of the (2R,3S)-Isomer of 2-Amino-3,4-dihydroxybutanoic Acid in the Mushroom Hypsizygus marmoreus,Journal of Agricultural and Food Chemistry

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Occurrence of the (2R,3S)-Isomer of 2-Amino-3,4-dihydroxybutanoic Acid in the Mushroom Hypsizygus marmoreus
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2017-07-24 00:00:00 , DOI: 10.1021/acs.jafc.7b01893
Tomokazu Ito ₁ , Zhuoer Yu ₁ , Issei Yoshino ₂ , Yurina Hirozawa ₁ , Kana Yamamoto ₁ , Kiyotugu Shinoda ₃ , Akira Watanabe ₂ , Hisashi Hemmi ₁ , Yasuhiko Asada ₂ , Tohru Yoshimura ₁

Affiliation

Here, we report the occurrence of the (2R,3S)-isomer of 2-amino-3,4-dihydroxybutanoic acid (d-ADHB) in the fruiting body of an edible mushroom, Hypsizygus marmoreus. This is an unusual example of the accumulation of a d-amino acid whose enantiomer is not a proteinogenic amino acid. We show that d-ADHB occurs specifically in the mushroom H. marmoreus. Other edible mushrooms examined, including Pholiota microspora, Pleurotus eryngii, Mycena chlorophos, Sparassis crispa, Grifola frondosa, Pleurotus ostreatus, and Flammulina velutipes, do not contain detectable levels of d-ADHB. The concentration of d-ADHB in the fruiting body of H. marmoreus is relatively high (approximately 1.3 mg/g of fruiting body) and is comparable to the concentration of some of the most abundant free proteinogenic amino acids. Quantitative analysis of d-ADHB during fruiting body development demonstrated that the amino acid is synthesized during the fruiting body formation period. The absence of the putative precursors of d-ADHB, the (2S,3S)-isomer of ADHB and 2-oxo-tetronate, and the enzyme activities of d-ADHB racemase (2-epimerase) and transaminase suggested that d-ADHB is synthesized by a unique mechanism in this organism. Our data also suggested that the lack of or low expression of a d-ADHB degradation enzyme is a key determinant of d-ADHB accumulation in H. marmoreus.

中文翻译：

蘑菇Hypsizygus marmoreus中2-氨基-3,4-二羟基丁酸的（2 R，3 S）-异构体的发生

在这里，我们报道了2-氨基-3,4-二羟基丁酸（d - ADHB）的（2 R，3 S）-异构体在可食用蘑菇，Hypsizygus marmoreus的子实体中的发生。这是对映体不是蛋白原氨基酸的d-氨基酸积累的不寻常的例子。我们显示d -ADHB专门发生在蘑菇H. marmoreus中。检查了其他可食用蘑菇，包括小孢子菌（Pholiota microspora），杏鲍菇（Pleurotus eryngii），绿霉菌（Mycena chlorophos），松果（Sparassis crispa），灰树花（Grifola frondosa），平菇（Pleurotus ostreatus）和金针菇不包含可检测水平的d -ADHB。的浓度d在子实体-ADHB真姬菇是相对高的（大约1.3毫克子实体/ g）和比得上的一些最丰富的游离蛋白氨基酸的浓度。子实体发育过程中对d -ADHB的定量分析表明，氨基酸是在子实体形成期间合成的。缺少d -ADHB的推定前体，ADHB的（2 S，3 S）异构体和2-氧代-四氢酸酯，以及d的酶活性-ADHB消旋酶（2-表异构酶）和转氨酶表明，d- ADHB是通过这种生物体中的独特机制合成的。我们的数据还表明，d -ADHB降解酶的缺乏或表达水平低下是mar.us中d -ADHB积累的关键决定因素。

更新日期：2017-07-25

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