Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Camellia sinensis
The structure was elucidated in this paperNCBI PubMed ID: 31979166Publication DOI: 10.3390/molecules25030470Journal NLM ID: 100964009Publisher: Basel, Switzerland: MDPI
Correspondence: Guo L <glf533
126.com>; Liu S <liusc
im.ac.cn>; Lin J <linjie
jssnu.edu.cn>; Niu S <niushubin0704
163.com>; Liu L <liul
im.ac.cn>
Institutions: University of Chinese Academy of Sciences, Beijing, China, State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, China, Jiangsu Key Laboratory for Biofunctional Molecules, College of Life Science and Chemistry, Jiangsu Second Normal University, Nanjing, China, School of Biological Medicine, Beijing City University, Beijing, China
Two new xanthone derivatives, pestalotiones A (1) and B (2), one new diphenyl ketone riboside, pestalotione C (7), and one new diphenyl ether, pestalotione D (8), along with five known compounds isosulochrin dehydrate (3), 3,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (4), isosulochrin (5), chloroisosulochrin (6), and pestalotether D (9), were isolated from the crude extract of the plant endophytic fungus Pestalotiopsis theae (N635). The structures of the new compounds were unambiguously deduced by HRESIMS and 1D/2D-NMR spectroscopic data. Compound 6 showed modest cytotoxicity against the HeLa cell line with an IC50 value of 35.2 μM. Compound 9 also showed cytotoxic to the HeLa and MCF-7 cell lines, with IC50 values of 60.8 and 22.6 μM, respectively. Additionally, compounds 1 and 2 exhibited antioxidant activity in scavenging DPPH radical with IC50 values of 54.2 and 59.2 μg/mL, respectively.
structure elucidation, cytotoxicity, Antioxidant, secondary metabolites, Pestalotiopsis theae
Structure type: monomer ; 487.1217 [M+Na]+
C
22H
24O
11Location inside paper: Fig. 1, 7, Table 2
Trivial name: pestalotione C
Compound class: glycoside
Contained glycoepitopes: IEDB_149136
Methods: 13C NMR, 1H NMR, NMR-2D, IR, ESI-MS, biological assays, UV, extraction, optical rotation measurement, CC, RP-HPLC, cell growth, HR-ESI-MS, antioxidant activities, evaporation, VLC, MTS assay
NCBI Taxonomy refs (TaxIDs): 218556Reference(s) to other database(s): GenDB:KF641183
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
5 aDRibf 103.3 73.3 70.7 88.1 63.0
3 Me 56.2
7 Me 52.6
Subst 110.9 163.2 109.0 149.6 109.0 163.2 201.1 22.1 130.6 109.0 161.6 108.2 155.7 130.4 167.7
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15
5 aDRibf 5.56 4.00 3.90 3.96 3.55
3 Me 3.86
7 Me 3.70
Subst - - 6.13 - 6.13 - - 2.20 - 7.17 - 7.03 - - -
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
5 aDRibf 103.3/5.56 73.3/4.00 70.7/3.90 88.1/3.96 63.0/3.55
3 Me 56.2/3.86
7 Me 52.6/3.70
Subst 109.0/6.13 109.0/6.13 22.1/2.20 109.0/7.17 108.2/7.03
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 |
|---|
| 5 | aDRibf | 5.56 | 4.00 | 3.90 | 3.96 | 3.55 | |
| 3 | Me | 3.86 | |
| 7 | Me | 3.70 | |
| | Subst |
|
| 6.13 |
| 6.13 |
|
| 2.20 |
| 7.17 |
| 7.03 |
|
|
|
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 |
|---|
| 5 | aDRibf | 103.3 | 73.3 | 70.7 | 88.1 | 63.0 | |
| 3 | Me | 56.2 | |
| 7 | Me | 52.6 | |
| | Subst | 110.9 | 163.2 | 109.0 | 149.6 | 109.0 | 163.2 | 201.1 | 22.1 | 130.6 | 109.0 | 161.6 | 108.2 | 155.7 | 130.4 | 167.7 |
|
There is only one chemically distinct structure:
Found 
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(later renamed to: Pseudopestalotiopsis theae N635)