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Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)

The structure was elucidated in this paper
NCBI PubMed ID: 30735051
Publication DOI: 10.1021/acs.orglett.8b04042
Journal NLM ID: 100890393
Publisher: American Chemical Society
Correspondence: Chooi YH <yitheng.chooi

uwa.edu.au>; Piggott AM <andrew.piggott

mq.edu.au>
Institutions: Department of Molecular Sciences, Macquarie University, Sydney, Australia, School of Molecular Sciences, The University of Western Australia, Perth, Australia, Microbial Screening Technologies Pty. Ltd., Smithfield, Australia, Commonwealth Scientific and Industrial Research Organisation, North Ryde, Australia

The burnettramic acids are a new class of antibiotics from an Australian fungus Aspergillus burnettii. The rare bolaamphiphilic scaffold consists of β-D-mannose linked to a pyrrolizidinedione unit via a 26-carbon chain. The most abundant metabolite displayed potent in vitro antifungal activity. Comparative genomics identified the hybrid PKS-NRPS bua gene cluster, which was verified by heterologous pathway reconstitution in Aspergillus nidulans.

secondary metabolites, Aspergillus burnettii, pyrrolizidinediones

Structure type: monomer ; 768.4898 [M-H]-
C₄₁H₇₁NO₁₂
Location inside paper: Fig. 1, 1, supplementary materials, Table S6
The structure in this paper was incorrect:

Original structure from CSDB record 50386

← originally published structure

Show legend

Trivial name: burnettramic acid A
Compound class: glycoside
Contained glycoepitopes: IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72

Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, biological assays, UV, extraction, RP-HPLC, cell growth, antibacterial assay, HR-ESI-MS, cytotoxicity assay, gene expression, antifungal activity test, BLAST, LC-DAD-MS, antiparasitic assay
Biological activity: compound exhibited both antibacterial and antifungal activities, with especially potent activity against Candida albicans and Saccharomyces cerevisiae (IC50 0.5 and 0.2 μg/mL, respectively), comparable to amphotericin B. Compound also showed modest cytotoxicity against murine myeloma (NS-1) cells (IC50 13.8 μg/mL) but only minor activity against the nontumorigenic neonatal foreskin fibroblasts (NFF) at 100 μg/mL, indicative of a good therapeutic index
Enzymes that release or process the structure: BuaA, BuaC, BuaF, BuaG, BuaB, ketosynthase, malonyl-CoA transferase, dehydratase, methyltransferase, enoyl reductase, ketoreductase, acyl carrier protein
Biosynthesis and genetic data: biochemical and genetic data

Related record ID(s): 50385, 50387, 50388
NCBI Taxonomy refs (TaxIDs): 2508778
Reference(s) to other database(s): GenDB:MK425157
Show glycosyltransferases

NMR conditions: in DMSO-d6 at 298 K [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	C19	C20	C21	C22	C23	C24	C25	C26	C27	C28	C29	C30	C31	C32	C33	C34	C35
34	bDManp	100.2	70.6	73.7	67.2	77.5	61.4
	Subst	?	?	190.8	32.8	16.9	40.2	30.0	19.4	36.11	26.2	28.8-29.2	28.8-29.2	28.5	28.8-29.2	28.8-29.2	28.8-29.2	32.0	131.5	127.2	40.6	69.9	36.6	21.5	37.4	69.6	37.2	25.3	25.6	29.3	68.4	194.8	?	36.17	72.1	52.5


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	H24	H25	H26	H27	H28	H29	H30	H31	H32	H33	H34	H35
34	bDManp	4.32	3.60	3.23	3.27	2.99	3.43-3.67
	Subst	-	-	-	3.62	1.04	1.35-1.43	1.36	0.81	1.03-1.26	1.16-1.25	1.14-1.31	1.14-1.31	1.21	1.14-1.31	1.14-1.31	1.14-1.31	1.93	5.35	5.39	2.01	3.37	1.20-1.33	1.20-1.46	1.21-1.29	3.33	1.24-1.30	1.23-1.34	1.27	1.49	3.39-3.74	-	4.22	1.59-1.92	4.47	2.96-3.76


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	C19/H19	C20/H20	C21/H21	C22/H22	C23/H23	C24/H24	C25/H25	C26/H26	C27/H27	C28/H28	C29/H29	C30/H30	C31/H31	C32/H32	C33/H33	C34/H34	C35/H35
34	bDManp	100.2/4.32	70.6/3.60	73.7/3.23	67.2/3.27	77.5/2.99	61.4/3.43-3.67
	Subst				32.8/3.62	16.9/1.04	40.2/1.35-1.43	30.0/1.36	19.4/0.81	36.11/1.03-1.26	26.2/1.16-1.25	28.8-29.2/1.14-1.31	28.8-29.2/1.14-1.31	28.5/1.21	28.8-29.2/1.14-1.31	28.8-29.2/1.14-1.31	28.8-29.2/1.14-1.31	32.0/1.93	131.5/5.35	127.2/5.39	40.6/2.01	69.9/3.37	36.6/1.20-1.33	21.5/1.20-1.46	37.4/1.21-1.29	69.6/3.33	37.2/1.24-1.30	25.3/1.23-1.34	25.6/1.27	29.3/1.49	68.4/3.39-3.74		?/4.22	36.17/1.59-1.92	72.1/4.47	52.5/2.96-3.76

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	H24	H25	H26	H27	H28	H29	H30	H31	H32	H33	H34	H35
34	bDManp	4.32	3.60	3.23	3.27	2.99	3.43 3.67
	Subst				3.62	1.04	1.35 1.43	1.36	0.81	1.03 1.26	1.16 1.25	1.14 1.31	1.14 1.31	1.21	1.14 1.31	1.14 1.31	1.14 1.31	1.93	5.35	5.39	2.01	3.37	1.20 1.33	1.20 1.46	1.21 1.29	3.33	1.24 1.30	1.23 1.34	1.27	1.49	3.39 3.74		4.22	1.59 1.92	4.47	2.96 3.76

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	C22	C23	C24	C25	C26	C27	C28	C29	C30	C31	C32	C33	C34	C35
34	bDManp	100.2	70.6	73.7	67.2	77.5	61.4
	Subst	?	?	190.8	32.8	16.9	40.2	30.0	19.4	36.11	26.2	28.8 29.2	28.8 29.2	28.5	28.8 29.2	28.8 29.2	28.8 29.2	32.0	131.5	127.2	40.6	69.9	36.6	21.5	37.4	69.6	37.2	25.3	25.6	29.3	68.4	194.8	?	36.17	72.1	52.5

The spectrum also has 3 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

$C[C@@H](C[C@H](C)CCCCCCC/C=C/C[C@H](O)CCC[C@H](O)CCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)/C(O)=C1\C(=O)[C@H]2C[C@@H](O)CN2C1=O$

SVG MW SMILES 3D mol Ionize

uwa.edu.au>; Piggott AM <andrew.piggott

secondary metabolites, Aspergillus burnettii, pyrrolizidinediones

Structure type: monomer ; 768.4898 [M-H]-
C₄₁H₇₁NO₁₂
Location inside paper: Fig. 1, 2, supplementary materials, Table S7
Trivial name: burnettramic acid B
Compound class: glycoside
Contained glycoepitopes: IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72

Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, biological assays, UV, extraction, RP-HPLC, cell growth, antibacterial assay, HR-ESI-MS, cytotoxicity assay, gene expression, antifungal activity test, BLAST, LC-DAD-MS, antiparasitic assay
Biological activity: compound exhibited reduced antimicrobial and cytotoxic activities in comparison with burnettramic acid A, most noteworthy being the loss of activity against Staphylococcus aureus
Enzymes that release or process the structure: BuaA, BuaC, BuaF, BuaG, BuaB, ketosynthase, malonyl-CoA transferase, dehydratase, methyltransferase, enoyl reductase, ketoreductase, acyl carrier protein
Biosynthesis and genetic data: biochemical and genetic data

Related record ID(s): 50386
NCBI Taxonomy refs (TaxIDs): 2508778
Reference(s) to other database(s): GenDB:MK425157
Show glycosyltransferases

NMR conditions: in DMSO-d6 at 298 K [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	C19	C20	C21	C22	C23	C24	C25	C26	C27	C28	C29	C30	C31	C32	C33	C34	C35
34	bDManp	100.2	70.6	73.7	67.2	77.5	61.4
	Subst	?	?	192.5	33.8	16.9	40.2	30.0	19.4	36.11	26.2	28.8-29.2	28.8-29.2	28.5	28.8-29.2	28.8-29.2	28.8-29.2	32.0	131.5	127.2	40.6	69.9	36.6	21.5	37.4	69.6	37.2	25.3	25.6	29.3	68.4	?	?	35.5	71.1	53.4


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	H24	H25	H26	H27	H28	H29	H30	H31	H32	H33	H34	H35
34	bDManp	4.32	3.60	3.23	3.27	2.99	3.43-3.67
	Subst	-	-	-	3.64	1.04	1.35-1.43	1.36	0.81	1.03-1.26	1.16-1.25	1.14-1.31	1.14-1.31	1.21	1.14-1.31	1.14-1.31	1.14-1.31	1.93	5.35	5.39	2.01	3.37	1.20-1.33	1.20-1.46	1.21-1.29	3.33	1.24-1.30	1.23-1.34	1.27	1.49	3.39-3.74	-	4.05	1.58-2.18	4.30	3.08-3.59


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	C19/H19	C20/H20	C21/H21	C22/H22	C23/H23	C24/H24	C25/H25	C26/H26	C27/H27	C28/H28	C29/H29	C30/H30	C31/H31	C32/H32	C33/H33	C34/H34	C35/H35
34	bDManp	100.2/4.32	70.6/3.60	73.7/3.23	67.2/3.27	77.5/2.99	61.4/3.43-3.67
	Subst				33.8/3.64	16.9/1.04	40.2/1.35-1.43	30.0/1.36	19.4/0.81	36.11/1.03-1.26	26.2/1.16-1.25	28.8-29.2/1.14-1.31	28.8-29.2/1.14-1.31	28.5/1.21	28.8-29.2/1.14-1.31	28.8-29.2/1.14-1.31	28.8-29.2/1.14-1.31	32.0/1.93	131.5/5.35	127.2/5.39	40.6/2.01	69.9/3.37	36.6/1.20-1.33	21.5/1.20-1.46	37.4/1.21-1.29	69.6/3.33	37.2/1.24-1.30	25.3/1.23-1.34	25.6/1.27	29.3/1.49	68.4/3.39-3.74		?/4.05	35.5/1.58-2.18	71.1/4.30	53.4/3.08-3.59

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	H24	H25	H26	H27	H28	H29	H30	H31	H32	H33	H34	H35
34	bDManp	4.32	3.60	3.23	3.27	2.99	3.43 3.67
	Subst				3.64	1.04	1.35 1.43	1.36	0.81	1.03 1.26	1.16 1.25	1.14 1.31	1.14 1.31	1.21	1.14 1.31	1.14 1.31	1.14 1.31	1.93	5.35	5.39	2.01	3.37	1.20 1.33	1.20 1.46	1.21 1.29	3.33	1.24 1.30	1.23 1.34	1.27	1.49	3.39 3.74		4.05	1.58 2.18	4.30	3.08 3.59

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	C22	C23	C24	C25	C26	C27	C28	C29	C30	C31	C32	C33	C34	C35
34	bDManp	100.2	70.6	73.7	67.2	77.5	61.4
	Subst	?	?	192.5	33.8	16.9	40.2	30.0	19.4	36.11	26.2	28.8 29.2	28.8 29.2	28.5	28.8 29.2	28.8 29.2	28.8 29.2	32.0	131.5	127.2	40.6	69.9	36.6	21.5	37.4	69.6	37.2	25.3	25.6	29.3	68.4	?	?	35.5	71.1	53.4

The spectrum also has 4 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

CC(CCCCCCCCCC=CCC(O)CCCC(O)CCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)CC(C)C(O)=C1C(=O)[C@H]2C[C@@H](O)CN2C1=O

SVG MW SMILES 3D mol Ionize