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Antimicrobial Isoflavones and Derivatives from Erythrina (Fabaceae): Structure Activity Perspective (Sar & Qsar) on Experimental and Mined Values Against Staphylococcus Aureus.
Antibiotics ( IF 4.3 ) Pub Date : 2020-04-30 , DOI: 10.3390/antibiotics9050223
Nicholas J Sadgrove 1, 2 , Tiago B Oliveira 3 , Gugulethu P Khumalo 2 , Sandy F van Vuuren 4 , Ben-Erik van Wyk 2
Affiliation  

Prenylated (iso)flavonoids, -flavans and pterocarpans from taxa in Erythrina are repeatedly flagged as potent antimicrobial compounds. In the current study, bark from E. lysistemon was extracted and seven isoflavone derivatives were purified: erybraedin A (1), phaseollidin (2), abyssinone V-4' methyl ether (3), eryzerin C (4), alpumisoflavone (5), cristacarpin (6) and lysisteisoflavone (7). Minimum inhibition concentration (MIC) values were determined against a range of species of bacteria (skin pathogens), then values for another 67 derivatives from Erythrina, only against Staphylococcus aureus, were mined from the literature. Of the seven isolates, MIC values widely ranged from 1-600 μg/mL, with no obvious pattern of selectivity for Gram-types. Nevertheless, using the mined and experimentally determined values against S. aureus, Klekota-Roth fragments (Structure Activity Relationship: SAR) were determined then used as molecular descriptors to make a 'decision tree' based on structural characters inspired by the classes of antimicrobial potency (classes A-D). Furthermore, to make quantitative predictions of MIC values (Quantitative SAR: QSAR) 'pace regression' was utilized and validated (R² = 0.778, Q² = 0.727 and P² = 0.555). Evidently, the position and degree of prenylation is important; however, the presence of hydroxyl groups at positions 5 and 7 in ring A and 4' in ring B is associated with lower MIC values. While antimicrobial results continue to validate the traditional use of E. lysistemon extracts (or Erythrina generally) in therapeutic applications consistent with anti-infection, it is surprising that this class of compound is not being utilized more often in general industry applications, such as food or cosmetic preservation, or in topical antimicrobial creams. Prenylated (iso)flavonoids are derived from several other Genera, such as Dorstenia (Moraceae), Ficus (Moraceae), Glycyrrhiza (Fabaceae), Paulownia (Lamiales) or Pomifera (Moraceae).

中文翻译:

erythrina(Fabaceae)的抗菌异黄酮及其衍生物:针对金黄色葡萄球菌的实验值和挖掘值的结构活性观点(Sar和Qsar)。

刺桐属中的类群的烯丙基化的(异)类黄酮,-黄酮类和翼果类被反复标记为有效的抗菌化合物。在当前的研究中,提取了来自溶血性大肠杆菌的树皮,并纯化了七种异黄酮衍生物:erybraedin A(1),Phaseollidin(2),Abyssinone V-4'甲醚(3),eryzerin C(4),alphumisoflavone(5) ),木犀草苷(6)和溶胞异黄酮(7)。确定针对一系列细菌(皮肤病原体)的最小抑菌浓度(MIC)值,然后从文献中获得来自刺桐的另外67种衍生物的值,仅针对金黄色葡萄球菌。在这七个分离株中,MIC值范围广泛,在1-600μg/ mL之间,对革兰氏类型没有明显的选择性模式。不过,使用针对金黄色葡萄球菌的经挖掘和实验确定的值,然后确定Klekota-Roth片段(结构活度关系:SAR),作为分子描述符,根据受抗菌效力类别(AD类)启发的结构特征制作“决策树”。此外,为了对MIC值进行定量预测(定量SAR:QSAR),使用了“步伐回归”并进行了验证(R 2 = 0.778,Q 2 = 0.727和P 2 = 0.555)。显然,异戊二烯的位置和程度很重要。但是,在环A的5和7位以及环B的4'位置上存在羟基与较低的MIC值有关。虽然抗菌结果继续验证了溶血性大肠杆菌提取物(或一般而言为刺桐)在抗感染方面的传统应用,令人惊讶的是,这类化合物在诸如食品或化妆品防腐剂之类的一般工业应用中,或在局部抗菌霜中不被更频繁地使用。烯丙基化的(异)黄酮类化合物衍生自数个其他属,例如Dorstenia(桑科),Ficus(桑科),甘草(Fabaceae),泡桐(Lamiales)或Pomifera(桑科)。
更新日期:2020-04-30
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