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(±)-Kituramides A and B, pairs of enantiomeric dopamine dimers from the two-spotted cricket Gryllus bimaculatus.
Bioorganic Chemistry ( IF 4.5 ) Pub Date : 2019-12-24 , DOI: 10.1016/j.bioorg.2019.103554 Seoung Rak Lee 1 , Sang Ah Yi 1 , Ki Hong Nam 1 , Jae Gyu Park 2 , Jae Sam Hwang 3 , Jaecheol Lee 1 , Ki Hyun Kim 1
Bioorganic Chemistry ( IF 4.5 ) Pub Date : 2019-12-24 , DOI: 10.1016/j.bioorg.2019.103554 Seoung Rak Lee 1 , Sang Ah Yi 1 , Ki Hong Nam 1 , Jae Gyu Park 2 , Jae Sam Hwang 3 , Jaecheol Lee 1 , Ki Hyun Kim 1
Affiliation
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Two-spotted cricket Gryllus bimaculatus is one of many cricket species, and it is widely used as a food source for insectivorous animals. Moreover, this species is one of the edible insects approved by the Korea Food and Drug Administration (KFDA). (±)-Kituramides A (1) and B (2), which are pairs of novel enantiomeric dopamine dimers possessing a formamide group, were isolated from the two-spotted cricket, together with four other known biosynthetically related compounds (3-6). The chemical structures of 1 and 2 were elucidated using a combination of 1D and 2D NMR spectroscopic experiments and HR-ESIMS data. Compounds 1 and 2 were identified as racemic mixtures; the enantiomers (+)-1/2 and (-)-1/2 were successfully separated by utilizing a chiral HPLC column. The absolute configurations of (±)-1 and (±)-2 were unambiguously delineated by the application of quantum chemical ECD calculations. Further, these insect-derived substances were evaluated to understand their effects on cytokine expression in adipocytes. Treatment with (-)-1, (+)-2, and (-)-2 during adipocyte differentiation significantly promoted the expression of Leptin and IL-6, which resembles the actions of dopamine.
中文翻译：
（±）-Kituramides A和B，来自两个斑点的G Gryllus bimaculatus的对映体多巴胺二聚体。
二斑Gryllus bimaculatus是许多物种之一，被广泛用作食虫动物的食物来源。此外，该物种是韩国食品药品监督管理局（KFDA）批准的食用昆虫之一。从两个斑点的中分离出（±）-基尿酰胺A（1）和B（2）对，它们是一对具有甲酰胺基的新型对映体多巴胺二聚体，并与其他四种已知的生物合成相关化合物（3-6）分离。 。结合1D和2D NMR光谱实验以及HR-ESIMS数据阐明了1和2的化学结构。化合物1和2被确定为外消旋混合物；对映体（+）-1/2和（-）-1/2通过手性HPLC色谱柱成功分离。（±）-1和（±）-2的绝对构型通过量子化学ECD计算的应用得以明确描述。此外，对这些昆虫来源的物质进行了评估，以了解它们对脂肪细胞中细胞因子表达的影响。在脂肪细胞分化过程中用（-）-1，（+）-2和（-）-2处理可显着促进瘦素和IL-6的表达，这类似于多巴胺的作用。
更新日期：2019-12-25
中文翻译：
（±）-Kituramides A和B，来自两个斑点的G Gryllus bimaculatus的对映体多巴胺二聚体。
二斑Gryllus bimaculatus是许多物种之一，被广泛用作食虫动物的食物来源。此外，该物种是韩国食品药品监督管理局（KFDA）批准的食用昆虫之一。从两个斑点的中分离出（±）-基尿酰胺A（1）和B（2）对，它们是一对具有甲酰胺基的新型对映体多巴胺二聚体，并与其他四种已知的生物合成相关化合物（3-6）分离。 。结合1D和2D NMR光谱实验以及HR-ESIMS数据阐明了1和2的化学结构。化合物1和2被确定为外消旋混合物；对映体（+）-1/2和（-）-1/2通过手性HPLC色谱柱成功分离。（±）-1和（±）-2的绝对构型通过量子化学ECD计算的应用得以明确描述。此外，对这些昆虫来源的物质进行了评估，以了解它们对脂肪细胞中细胞因子表达的影响。在脂肪细胞分化过程中用（-）-1，（+）-2和（-）-2处理可显着促进瘦素和IL-6的表达，这类似于多巴胺的作用。
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