Natalenamides A-C, Cyclic Tripeptides from the Termite-Associated Actinomadura sp RB99
- Authors
- Lee, Seoung Rak; Lee, Dahae; Yu, Jae Sik; Benndorf, Rene; Lee, Sullim; Lee, Dong-Soo; Huh, Jungmoo; de Beer, Z. Wilhelm; Kim, Yong Ho; Beemelmanns, Christine; Kang, Ki Sung; Kim, Ki Hyun
- Issue Date
- Nov-2018
- Publisher
- MDPI
- Keywords
- fungus-growing termite; Actinomadura sp.; tripeptides; natalenamides A-C; skin-whitening effects
- Citation
- MOLECULES, v.23, no.11
- Journal Title
- MOLECULES
- Volume
- 23
- Number
- 11
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/3134
- DOI
- 10.3390/molecules23113003
- ISSN
- 1420-3049
- Abstract
- In recent years, investigations into the biochemistry of insect-associated bacteria have increased. When combined with analytical dereplication processes, these studies provide a powerful strategy to identify structurally and/or biologically novel compounds. Non-ribosomally synthesized cyclic peptides have a broad bioactivity spectrum with high medicinal potential. Here, we report the discovery of three new cyclic tripeptides: natalenamides A-C (compounds 1-3). These compounds were identified from the culture broth of the fungus-growing termite-associated Actinomadura sp. RB99 using a liquid chromatography (LC)/ultraviolet (UV)/mass spectrometry (MS)-based dereplication method. Chemical structures of the new compounds (1-3) were established by analysis of comprehensive spectroscopic methods, including one-dimensional (H-1 and C-13) and two-dimensional (H-1-H-1-COSY, HSQC, HMBC) nuclear magnetic resonance spectroscopy (NMR), together with high-resolution electrospray ionization mass spectrometry (HR-ESIMS) data. The absolute configurations of the new compounds were elucidated using Marfey's analysis. Through several bioactivity tests for the tripeptides, we found that compound 3 exhibited significant inhibitory effects on 3-isobutyl-1-methylxanthine (IBMX)-induced melanin production. The effect of compound 3 was similar to that of kojic acid, a compound extensively used as a cosmetic material with a skin-whitening effect.
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Collections - 한의과대학 > 한의예과 > 1. Journal Articles
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