Taxonomic group: bacteria / Firmicutes (Phylum: Firmicutes)
 
The structure was elucidated in this paper
NCBI PubMed ID: 35877757
Publication DOI: 10.3390/md20070464
Journal NLM ID: 101213729
Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: H.J. Shin <shinhjkiost.ac.kr>
Institutions: Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyang-ro, Yeongdo-gu, Busan 49111, Korea, Department of Marine Biotechnology, University of Science and Technology (UST), 217 Gajungro, Yuseong-gu, Daejeon 34113, Korea, Laboratory Animal Resource Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanjiro, Cheongju 28116, Korea, Department of Marine Biotechnology, Nhatrang Institute of Technology Research and Application, Vietnam Academy of Science and Technology, 02 Hung Vuong, Nha Trang 650000, Vietnam

Three new glycosylated secondary metabolites, including a new indole alkaloid, pityriacitrin D (1), and two new trehalose lipids (2 and 3), together with three known compounds (4-6) were isolated from two marine-derived bacterial strains, Bacillus siamensis 168CLC-66.1 and Tsukamurella pseudospumae IV19-045. The structures of 1-3 were determined by extensive analysis and comparison of their spectroscopic data with literature values. The absolute configurations of sugar moieties were determined by chemical derivatization followed by LC-MS analysis. Cytotoxicity of 1-3 against six cancer cell lines was evaluated by SRB assay, and 1 showed moderate activity against all the tested cell lines with GI50 values ranging from 8.0 to 10.9 µM.

cytotoxicity, Bacillus, glycosides, marine-derived bacteria, pityriacitrin, trehalose lipid

Structure type: monomer ; 540.1381 [M+Na]+
C₂₇H₂₃N₃O₈
Location inside paper: Fig. 1, table 1, compound 1
Trivial name: pityriacitrin D
Compound class: indole alkaloid
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
 
Methods: 13C NMR, 1H NMR, NMR-2D, IR, acid hydrolysis, HPLC, UV, LC-MS, fermentation, HR-ESI-MS, cytotoxicity assay, isolation
Comments, role: NMR temperature was not specified; pityriacitrin D aglycon (1-(1H-indole-3-carbonyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid)
 
Related record ID(s): 8583, 8584, 8585, 8586
NCBI Taxonomy refs (TaxIDs): 659243
Show glycosyltransferases
 
NMR conditions: in CD3OD        [as TSV]

1H NMR data: Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 3 bDGlcp 5.93 3.76 3.64 3.58 3.58 3.82 3.96     Subst 8.96 8.21 7.34 7.61 7.76 9.62 8.57 7.25 7.25 7.46

13C NMR data: Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 3 bDGlcp 96.7 74.4 78.2 71.2 79.0 62.4     Subst 135.7 139.0 121.1 132.8 124.1 122.2 122.2 130.4 113.9 143.4 138.1 188.4 166.0 140.1 115.9 128.9 122.7 123.4 123.3 112.8 137.5

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