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Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)

The structure was elucidated in this paper
NCBI PubMed ID: 36109198
Publication DOI: 10.1021/acs.jafc.2c05703
Journal NLM ID: 0374755
Publisher: American Chemical Society
Correspondence: J. Li <lijing356

mail.sysu.edu.cn>
Institutions: School of Marine Sciences, Sun Yat-sen University, Zhuhai 519082, P.R. China, Key Laboratory for Biobased Materials and Energy of Ministry of Education, College of Materials and Energy, South China Agricultural University, Guangzhou, China, Guangdong Provincial Key Laboratory of Marine Resources and Coastal Engineering, Zhuhai 519082, China

Five new carotane sesquiterpenoids (asperalacids A-E (1-5)), one new tricyclic sesquiterpenoid (4-hydroxy-5(6)-dihydroterrecyclic acid A (6)), and two known analogues (7-8) were obtained from a seagrass-derived fungus Aspergillus alabamensis, which was speculated to be a phytopathogenic fungus, isolated from the necrotic leaves of Enhalus acoroides. The structures of 1-6 were established by a combination of spectroscopic methods, including comprehensive NMR analysis, mass spectrometry, conformational analysis, NMR computational methods, and ECD calculations. Compound 4, with higher inhibitory activity on wheat (Triticum aestivum L.) root and shoot elongation than the positive control terbutryn, a broad-spectrum systemic herbicide, is a new natural plant growth inhibitor. Compound 5, belonging to the rare glycosylated sesquiterpenoid class, represents the first example of glycosylated carotane sesquiterpenoid whose sugar moiety was identified as α-D-glucose. Compounds 1-4 and 6 displayed weak to potent antimicrobial activity against the plant pathogenic fungi Fusarium oxysporum, Fusarium graminearum, and Penicillium italicum and the Gram-positive bacteria Bacillus subtilis and Staphylococcus aureus.

antimicrobial activity, phytopathogenic fungus, Aspergillus alabamensis, carotane sesquiterpenoid, Enhalus acoroides, phytotoxic activity

Structure type: monomer ; 411.2025 [M-H]-
C₂₁H₃₂O₈
Location inside paper: p. 12066, Fig. 1, table 2, compound 5
Trivial name: asperalacid E
Compound class: carotane sesquiterpenoid
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, HPLC, UV, extraction, optical rotation measurement, CD, column chromatography, fermentation, antibacterial assay, HR-ESI-MS, phytotoxicity assay
Comments, role: NMR temperature was not specified

NCBI Taxonomy refs (TaxIDs): 657433
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
12	aDGlcp	98.9	73.7	75.2	71.8	73.7	62.0
	Subst	40.9	29.2	144.5	59.7	25.8	28.4	136.3	142.7	42.0	42.6	124.6	71.5	17.0	171.8	19.4


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15
12	aDGlcp	4.76	3.39	3.66	3.31	3.60	3.72-3.80
	Subst	1.42-1.53	2.37-2.46	-	2.35	1.36-2.42	2.05-3.04	-	7.09	2.21-2.40	-	-	4.02-4.12	1.84	-	0.75


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
12	aDGlcp	98.9/4.76	73.7/3.39	75.2/3.66	71.8/3.31	73.7/3.60	62.0/3.72-3.80
	Subst	40.9/1.42-1.53	29.2/2.37-2.46		59.7/2.35	25.8/1.36-2.42	28.4/2.05-3.04		142.7/7.09	42.0/2.21-2.40			71.5/4.02-4.12	17.0/1.84		19.4/0.75

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15
12	aDGlcp	4.76	3.39	3.66	3.31	3.60	3.72 3.80
	Subst	1.42 1.53	2.37 2.46		2.35	1.36 2.42	2.05 3.04		7.09	2.21 2.40			4.02 4.12	1.84		0.75

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15
12	aDGlcp	98.9	73.7	75.2	71.8	73.7	62.0
	Subst	40.9	29.2	144.5	59.7	25.8	28.4	136.3	142.7	42.0	42.6	124.6	71.5	17.0	171.8	19.4

There is only one chemically distinct structure:

C/C(CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=C1/CC[C@]2(C)CC=C(C(=O)O)CC[C@@H]12

SVG MW SMILES 3D mol Ionize