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Taxonomic group: bacteria / Actinobacteria (Phylum: Actinobacteria)

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 <shinhj

kiost.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: oligomer ; 733.3804 [M+Na]+
C₃₄H₆₂O₁₃S
Location inside paper: Fig. 1, table 2, compound 2
Trivial name: tsukalipid A
Compound class: trehalose lipid
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_534865,IEDB_742521,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

Related record ID(s): 8427, 8584, 8585, 8586
NCBI Taxonomy refs (TaxIDs): 239498
Show glycosyltransferases

NMR conditions: in CD3OD [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18
1	aDGlcp	95.9	73.0	74.6	71.6	74.2	62.5
2	lXSte	174.6	35.0	25.8	30.3	30.5	30.6	30.8	30.8	30.8	30.8	30.8	30.8	30.8	30.8	30.8	33.1	23.7	14.4
3	Subst	173.1	35.4	29.9	15.4
	aDGlcp	93.0	71.9	74.3	69.6	73.7	61.9


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18
1	aDGlcp	5.10	3.49	3.77	3.35	3.66	3.66-3.70
2	lXSte	-	2.37	1.57	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	0.90
3	Subst	-	2.65	2.73	2.10
	aDGlcp	5.30	4.88	5.51	3.63	4.01	3.81-3.82


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9	C10/H10	C11/H11	C12/H12	C13/H13	C14/H14	C15/H15	C16/H16	C17/H17	C18/H18
1	aDGlcp	95.9/5.10	73.0/3.49	74.6/3.77	71.6/3.35	74.2/3.66	62.5/3.66-3.70
2	lXSte		35.0/2.37	25.8/1.57	30.3/1.30	30.5/1.30	30.6/1.30	30.8/1.30	30.8/1.30	30.8/1.30	30.8/1.30	30.8/1.30	30.8/1.30	30.8/1.30	30.8/1.30	30.8/1.30	33.1/1.30	23.7/1.30	14.4/0.90
3	Subst		35.4/2.65	29.9/2.73	15.4/2.10
	aDGlcp	93.0/5.30	71.9/4.88	74.3/5.51	69.6/3.63	73.7/4.01	61.9/3.81-3.82

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18
1	aDGlcp	5.10	3.49	3.77	3.35	3.66	3.66 3.70
2	lXSte		2.37	1.57	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	0.90
3	Subst		2.65	2.73	2.10
	aDGlcp	5.30	4.88	5.51	3.63	4.01	3.81 3.82

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18
1	aDGlcp	95.9	73.0	74.6	71.6	74.2	62.5
2	lXSte	174.6	35.0	25.8	30.3	30.5	30.6	30.8	30.8	30.8	30.8	30.8	30.8	30.8	30.8	30.8	33.1	23.7	14.4
3	Subst	173.1	35.4	29.9	15.4
	aDGlcp	93.0	71.9	74.3	69.6	73.7	61.9

There is only one chemically distinct structure:

CCCCCCCCCCCCCCCCCC(=O)O[C@@H]1[C@@H](OC(=O)CCSC)[C@H](O)[C@@H](CO)O[C@@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

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

Structure type: oligomer ; 687.3931 [M+Na]+
C₃₄H₆₂O₁₃
Location inside paper: Fig. 1, table 2, compound 3
Trivial name: tsukalipid B
Compound class: trehalose lipid
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_534865,IEDB_742521,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.

Related record ID(s): 8427, 8583, 8585, 8586
NCBI Taxonomy refs (TaxIDs): 239498
Show glycosyltransferases

NMR conditions: in CD3OD [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18
1	aDGlcp	95.9	73.0	74.6	71.6	74.3	62.4
2	lXSte	174.4	34.9	25.9	30.2	30.4	30.5	30.6	30.7	30.8	30.8	30.8	30.8	30.8	30.8	30.8	33.1	23.7	14.4
3	Pp	175.5	28.4	29.5
	aDGlcp	93.0	72.1	73.9	69.6	73.7	62.0


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18
1	aDGlcp	5.10	3.50	3.78	3.34	3.66	3.66-3.71
2	lXSte	-	2.37	1.57	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	0.90
3	Pp	-	2.36	1.12
	aDGlcp	5.30	4.87	5.49	3.63	4.01	3.73-3.82


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9	C10/H10	C11/H11	C12/H12	C13/H13	C14/H14	C15/H15	C16/H16	C17/H17	C18/H18
1	aDGlcp	95.9/5.10	73.0/3.50	74.6/3.78	71.6/3.34	74.3/3.66	62.4/3.66-3.71
2	lXSte		34.9/2.37	25.9/1.57	30.2/1.30	30.4/1.30	30.5/1.30	30.6/1.30	30.7/1.30	30.8/1.30	30.8/1.30	30.8/1.30	30.8/1.30	30.8/1.30	30.8/1.30	30.8/1.30	33.1/1.30	23.7/1.30	14.4/0.90
3	Pp		28.4/2.36	29.5/1.12
	aDGlcp	93.0/5.30	72.1/4.87	73.9/5.49	69.6/3.63	73.7/4.01	62.0/3.73-3.82

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18
1	aDGlcp	5.10	3.50	3.78	3.34	3.66	3.66 3.71
2	lXSte		2.37	1.57	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	1.30	0.90
3	Pp		2.36	1.12
	aDGlcp	5.30	4.87	5.49	3.63	4.01	3.73 3.82

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18
1	aDGlcp	95.9	73.0	74.6	71.6	74.3	62.4
2	lXSte	174.4	34.9	25.9	30.2	30.4	30.5	30.6	30.7	30.8	30.8	30.8	30.8	30.8	30.8	30.8	33.1	23.7	14.4
3	Pp	175.5	28.4	29.5
	aDGlcp	93.0	72.1	73.9	69.6	73.7	62.0

There is only one chemically distinct structure:

CCCCCCCCCCCCCCCCCC(=O)O[C@@H]1[C@@H](OC(=O)CC)[C@H](O)[C@@H](CO)O[C@@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize