Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperNCBI PubMed ID: 31999116Publication DOI: 10.1021/acs.jnatprod.9b01099Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: james-gloer
uiowa.edu
Institutions: Department of Chemistry, UniVersity of Iowa, Iowa City, USA, Texas Therapeutic Institute, The Brown Foundation Institute of Molecular Medicine, University of Texas Health Science Center at Houston, Houston, USA, The Brown Foundation Institute of Molecular Medicine, McGovern Medical School, University of Texas Health Science Center at Houston, Houston, USA
During investigation of the secondary metabolism of four strains of Penicillium arenicola, two new depsides, arenicolins A (1) and B (2), were isolated and characterized. Their structures were established mainly by analysis of NMR and HRMS data and by comparison with known compounds. These depsides incorporate intriguing structural features, including dual alkyl side chains and a C-glycosyl unit, with 1 also containing an acylated 2-hydroxymethyl-4,5,6-trihydroxycyclohexenone moiety. Although the arenicolins were produced by all strains tested, arenicolin A (1) was obtained using only one of five medium compositions employed, while arenicolin B (2) was produced in all media tested. Neither compound showed antibacterial or antifungal activity, but 1 exhibited cytotoxicity toward mammalian cell lines, including colorectal carcinoma (HCT-116), neuroblastoma (IMR-32), and ductal carcinoma (BT-474), with IC50 values of 7.3, 6.0, and 9.7 μM, respectively.
cytotoxicity, anticancer activity, Penicillium arenicola, arenicolins
Structure type: monomer ; 803.3495 [M-H]-
C
41H
56O
16Location inside paper: structure 1, Table 2
Trivial name: arenicolin A
Compound class: С-glycoside
Methods: 13C NMR, 1H NMR, NMR-2D, HPLC, UV, extraction, optical rotation measurement, cell growth, HPLC-MS, HR-ESI-MS, cytotoxicity assay, evaporation, antimicrobial assay, flash chromatography, HPLC-DAD, HPLC-ELSD, ECD
Biological activity: compound decreased cell viability in HCT-116, IMR-32, and BT-474 cell lines in a dose-dependent manner (IC50 values: 7.3, 6.0, and 9.7 μM, respectively). The potency of compound in the tested cancer cell lines compared favorably with that of 5-fluorouracil (5-FU; IC50 values: 6.5 and 5.7 μM in HCT-116 and IMR-32 cells, respectively), a chemotherapeutic agent commonly used for the treatment of breast, colorectal, and pancreatic cancer
Related record ID(s): 50453
NCBI Taxonomy refs (TaxIDs): 168477
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
2,4,5 bD1dGlcp 76.2 73.2 80.0 71.7 82.6 62.7
2,4 Subst 170.8 105.8 164.3 110.9 163.0 112.5 148.1 37.8 33.1 33.0 32.9 30.8 23.7 14.5
2 Subst 169.8 115.3 161.4 109.0 154.6 116.0 148.8 36.1 33.5 32.3 30.4 23.8 31.0 14.5
Subst1 194.0 77.6 71.4 67.2 142.4 140.5 59.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14
2,4,5 bD1dGlcp 4.93 4.01 3.47 3.47 3.40 3.75-3.85
2,4 Subst - - - - - 6.36 - 2.87-2.90 1.64 1.35 1.25 1.29 1.27 0.88
2 Subst - - - 6.66 - 6.62 - 2.86-2.93 1.64 1.29 1.28 1.33 1.34 0.85
Subst1 - 5.94 4.13 4.56 7.07 - 4.26-4.30
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
2,4,5 bD1dGlcp 76.2/4.93 73.2/4.01 80.0/3.47 71.7/3.47 82.6/3.40 62.7/3.75-3.85
2,4 Subst 112.5/6.36 37.8/2.87-2.90 33.1/1.64 33.0/1.35 32.9/1.25 30.8/1.29 23.7/1.27 14.5/0.88
2 Subst 109.0/6.66 116.0/6.62 36.1/2.86-2.93 33.5/1.64 32.3/1.29 30.4/1.28 23.8/1.33 31.0/1.34 14.5/0.85
Subst1 77.6/5.94 71.4/4.13 67.2/4.56 142.4/7.07 59.4/4.26-4.30
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 |
|---|
| 2,4,5 | bD1dGlcp | 4.93 | 4.01 | 3.47 | 3.47 | 3.40 | 3.75
3.85 | |
| 2,4 | Subst |
|
|
|
|
| 6.36 |
| 2.87
2.90 | 1.64 | 1.35 | 1.25 | 1.29 | 1.27 | 0.88 |
| 2 | Subst |
|
|
| 6.66 |
| 6.62 |
| 2.86
2.93 | 1.64 | 1.29 | 1.28 | 1.33 | 1.34 | 0.85 |
| | Subst1 |
| 5.94 | 4.13 | 4.56 | 7.07 |
| 4.26
4.30 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 |
|---|
| 2,4,5 | bD1dGlcp | 76.2 | 73.2 | 80.0 | 71.7 | 82.6 | 62.7 | |
| 2,4 | Subst | 170.8 | 105.8 | 164.3 | 110.9 | 163.0 | 112.5 | 148.1 | 37.8 | 33.1 | 33.0 | 32.9 | 30.8 | 23.7 | 14.5 |
| 2 | Subst | 169.8 | 115.3 | 161.4 | 109.0 | 154.6 | 116.0 | 148.8 | 36.1 | 33.5 | 32.3 | 30.4 | 23.8 | 31.0 | 14.5 |
| | Subst1 | 194.0 | 77.6 | 71.4 | 67.2 | 142.4 | 140.5 | 59.4 | |
|
There is only one chemically distinct structure:
Found 
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(later renamed to: Phialomyces arenicola NRRL 8095)