(+/-)-Kituramides A and B, pairs of enantiomeric dopamine dimers from the two-spotted cricket Gryllus bimaculatus
- Authors
- Lee, Seoung Rak; Yi, Sang Ah; Nam, Ki Hong; Park, Jae Gyu; Hwang, Jae Sam; Lee, Jaecheol; Kim, Ki Hyun
- Issue Date
- Jan-2020
- Publisher
- ACADEMIC PRESS INC ELSEVIER SCIENCE
- Keywords
- Gryllus bimaculatus; Dopamine dimers; ECD calculations; Adipocyte; Leptin; IL-6
- Citation
- BIOORGANIC CHEMISTRY, v.95
- Indexed
- SCIE
SCOPUS
- Journal Title
- BIOORGANIC CHEMISTRY
- Volume
- 95
- URI
- https://scholarworks.bwise.kr/skku/handle/2021.sw.skku/6083
- DOI
- 10.1016/j.bioorg.2019.103554
- ISSN
- 0045-2068
1090-2120
- Abstract
- 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.
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Collections - Pharmacy > Department of Pharmacy > 1. Journal Articles
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