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Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)

The structure was elucidated in this paper
NCBI PubMed ID: 33387642
Publication DOI: 10.1016/j.fitote.2020.104823
Journal NLM ID: 16930290R
Publisher: Elsevier
Correspondence: Guang-Ying Chen <chgying123

163.com>
Institutions: Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158, China, Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, China, State Key Laboratory of Quality Study of Traditional Chinese Medicine, Macau University of Science and Technology, China

Four new cyclohexene derivatives cladoscyclitols A-D (1-4) and one new ribofuranose phenol derivative 4-O-α-D-ribofuranose-2-pentyl-3-phemethylol (5) were obtained from the EtOAC extract of the mangrove-derived endophytic fungus Cladosporium sp. JJM22. The structures were elucidated by extensive NMR and MS analysis, while the absolute configurations of the stereogenic carbons were established based on quantum-chemical electronic circular dichroism calculations or comparison of the optical rotations with those of related compounds. Compounds 2 and 5 displayed potent inhibitory activity against α-glucosidase with the IC50 values of 2.95 and 2.05 μM, respectively.

Ceriops tagal, Cladosporium sp., ribofuranose phenol, cyclohexene derivatives

Structure type: monomer ; 349.1624 [M+Na]+
Location inside paper: Fig. 5, table 2, compound 5
Trivial name: ribofuranose phenol derivative
Contained glycoepitopes: IEDB_149136

Methods: 13C NMR, 1H NMR, NMR-2D, IR, HPLC, extraction, optical rotation measurement, fermentation, HR-ESI-MS, antibacterial assay, taxonomy studies, ECD, silica gel chromatography, identification, α-glucosidase activity

NCBI Taxonomy refs (TaxIDs): 5498
Show glycosyltransferases

NMR conditions: in CD3OD at 298 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12
4	aDRibf	101.9	73.7	71.5	88.2	63.3
	Subst	157.4	143.9	129.7	124.4	129.5	113.8	34.0	32.9	33.0	23.6	14.4	57.0


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12
4	aDRibf	5.71	4.21	4.11	4.16	3.66
	Subst	-	-	-	6.84	7.16	7.03	2.71	1.33	1.57	1.37	0.91	4.69-4.75


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
4	aDRibf	101.9/5.71	73.7/4.21	71.5/4.11	88.2/4.16	63.3/3.66
	Subst				124.4/6.84	129.5/7.16	113.8/7.03	34.0/2.71	32.9/1.33	33.0/1.57	23.6/1.37	14.4/0.91	57.0/4.69-4.75

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12
4	aDRibf	5.71	4.21	4.11	4.16	3.66
	Subst				6.84	7.16	7.03	2.71	1.33	1.57	1.37	0.91	4.69 4.75

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12
4	aDRibf	101.9	73.7	71.5	88.2	63.3
	Subst	157.4	143.9	129.7	124.4	129.5	113.8	34.0	32.9	33.0	23.6	14.4	57.0

There is only one chemically distinct structure:

CCCCCc1c(CO)cccc1O[C@H]1O[C@H](CO)[C@@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)

The structure was elucidated in this paper
NCBI PubMed ID: 35186411
Publication DOI: 10.1080/21501203.2021.1964630
Journal NLM ID: 101523848
Publisher: Abingdon, Oxon: Taylor & Francis
Correspondence: Wen-Bing Yin <yinwb

im.ac.cn>
Institutions: State Key Laboratory Of Mycology, Institute Of Microbiology, Chinese Academy Of Sciences, Beijing, Republic of China, University Of Chinese Academy Of Sciences, Beijing, Republic of China

Two new sesquiterpenoids, 1-2, together with three known compounds, were isolated from Trichoderma hypoxylon. Among the known compounds, compound 4 was isolated as naturally occurring compound for the first time. The structures of these new compounds were characterized by HR-ESI-MS and spectroscopic methods including 1D and 2D NMR. The absolute configurations of 1-2 were assigned by electronic circular dichroism (ECD) calculations.

glycoside, fungi, Trichoderma, rearranged cuparane, sesquiterpenes

Structure type: monomer ; 395.1995 [M+H]+
C₂₁H₃₁O₇
Location inside paper: Fig. 1, table 1, compound 2, Fig. 3, 6b ((1S,4R)
Trivial name: cuparane sesquiterpene glycoside, dunnianoside B
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, NMR-2D, IR, acid hydrolysis, HPLC, extraction, optical rotation measurement, fermentation, HR-ESI-MS, ECD, silica gel chromatography, identification
Comments, role: NMR temperature was not specified; NMR checked.

NCBI Taxonomy refs (TaxIDs): 1888172
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
4	aDGlcp	101.0	73.6	74.8	71.9	74.6	62.9
	Subst	48.5	54.4	222.3	39.1	75.5	142.2	127.8	129.8	137.0	129.8	127.8	22.7	18.9	27.0	20.9


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15
4	aDGlcp	5.30	3.43	3.66	3.29	3.66	3.69-3.86
	Subst	-	-	-	4.60	2.03-3.20	-	7.30	7.17	-	7.17	7.30	0.67	1.17	1.39	2.32


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
4	aDGlcp	101.0/5.30	73.6/3.43	74.8/3.66	71.9/3.29	74.6/3.66	62.9/3.69-3.86
	Subst				39.1/4.60	75.5/2.03-3.20		127.8/7.30	129.8/7.17		129.8/7.17	127.8/7.30	22.7/0.67	18.9/1.17	27.0/1.39	20.9/2.32

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15
4	aDGlcp	5.30	3.43	3.66	3.29	3.66	3.69 3.86
	Subst				4.60	2.03 3.20		7.30	7.17		7.17	7.30	0.67	1.17	1.39	2.32

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15
4	aDGlcp	101.0	73.6	74.8	71.9	74.6	62.9
	Subst	48.5	54.4	222.3	39.1	75.5	142.2	127.8	129.8	137.0	129.8	127.8	22.7	18.9	27.0	20.9

There is only one chemically distinct structure:

Cc1ccc([C@]2(C)C[C@@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(=O)C2(C)C)cc1

SVG MW SMILES 3D mol Ionize