Photostable Abscisic Acid Agonists with a Geometrically Rigid Cyclized Side Chain
Photostable Abscisic Acid Agonists with a Geometrically Rigid Cyclized Side Chain
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具有几何刚性环化侧链的光稳定脱落酸激动剂
DOI：
10.1021/acs.jafc.1c06321
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发表时间：
2022
影响因子：
6.1
通讯作者：
Todoroki Yasushi
中科院分区：
文献类型：
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作者：
Takeuchi Jun;Mimura Saya;Ohnishi Toshiyuki;Todoroki Yasushi
植物激素脱落酸（ABA）在对影响作物生长和生产力的非生物胁迫的适应性反应中起着核心作用。然而，ABA的光不稳定性限制了其在农业中的应用。为了克服这一缺点，在本研究中，我们开发了光稳定的ABA类似物，即(+)-BP2A化合物系列（化合物5 - 9），其中ABA的二烯酸侧链被苯基乙酸取代。所有BP2A类似物在302 nm的UV-B照射下比ABA表现出更高的稳定性，化合物6和7即使在阳光下也几乎不分解。在生理实验中，BP2A (+)-BP2A和BP2A α，β-不饱和羰基减少的(+)-化合物7表现出aba样活性，包括抑制种子萌发和诱导拟南芥耐旱性。生化研究表明，与(+)-BP2A不同，(+)-化合物7在体外不能激活pyrabactin resistance-like （PYL）受体，而在植物体内可转化为(+)-BP2A，提示其具有前药PYL激动剂的功能。（+）-化合物7对番茄、莴苣和水稻的种子萌发有抑制作用。因此，该化合物代表了一种潜在的植物生长调节剂，可在农业领域诱导aba型反应。
The plant hormone abscisic acid (ABA) plays a central role in adaptive responses to abiotic stresses that adversely affect crop growth and productivity. However, ABA photoinstability limits its use in agriculture. To overcome this drawback, in this study, we developed photostable ABA analogues, the (+)-BP2A compound series (compounds5–9), in which the dienoic acid side chain of ABA was replaced with phenylacetic acid. All BP2A analogues showed higher stability against UV-B irradiation at 302 nm than ABA, and compounds6and7barely decomposed even under sunlight. In physiological assays, (+)-BP2A and (+)-compound7, in which the α,β-unsaturated carbonyl group of BP2A was reduced, exhibited ABA-like activities, including inhibition of seed germination and induced drought tolerance inArabidopsis. Biochemical studies revealed that (+)-compound7, unlike (+)-BP2A, did not activate pyrabactin resistance-like (PYL) receptorsin vitroand was converted to (+)-BP2A in plants, suggesting that it functions as a prodrug PYL agonist. Furthermore, (+)-compound7inhibited seed germination of tomato, lettuce, and rice. Thus, this compound represents a potential plant growth regulator that induces ABA-type responses in agricultural fields.