Amino Acid Conjugated Anthraquinones from the Marine-Derived Fungus Penicillium sp. SCSIO sof101

Abstract

Emodacidamides A-H (1-8), natural products featuring anthraquinone-amino acid conjugates, have been isolated from a marine-derived fungus, Penicillium sp. SCSIO sof101, together with known anthraquinones 9 and 10. The planar structures of 1-8 were elucidated using a combination of NMR spectroscopy and mass spectrometry. The absolute configurations of the amino acid residues were confirmed using Marfey's method and chiral-phase HPLC analyses. Additionally, isolates were evaluated for possible immunomodulatory and cytotoxic activities. Emodacidamides A (1), C (3), D (4), and E (5) inhibited interleukin-2 secretion from Jurkat cells with IC values of 4.1, 5.1, 12, and 5.4 μM, respectively.

Highly Substituted Phenol Derivatives with Nitric Oxide Inhibitory Activities from the Deep-Sea-Derived Fungus Trichobotrys effuse FS524

“…In summary, six new highly substituted phenol derivatives, trieffusols A-F (1-6), along with eleven known analogs (7)(8)(9)(10)(11)(12)(13)(14)(15)(16), were identified from the deep-sea-derived fungus Trichobotrys effuse FS524. Interestingly, trieffusols A and B share an intriguing 6-6/6/6 tetracyclic ring system with the formation of an unprecedented ploy-substituted 9-phenyl-hexahydroxanthone skeleton, which is often encountered as one of the most ubiquitous and intriguing functional moieties in the pharmaceutical drugs but rarely discovered in natural products.…”

“…Over the past decades, the research articles on marine natural products (MNPs) have surged dramatically, bringing about a lot of conspicuous natural products with novel chemical scaffolds and unique biological functional arrays [3][4][5][6][7]. In terms of pharmacological research, secondary metabolites derived from marine fungi are increasingly recognized as important sources of biologically meaningful natural products [8,9]. These MNPs have exhibited a wide range of biological activities such as anti-cancer [10], fungicidal [11], pro-angiogenic [12], anti-lymphangiogenic [13], and osteoclast differentiation inhibitory activities [14].…”

“…During our continuing research for structurally unique and biologically significant NPs from marine fungi [15][16][17], the fungus strain Trichobotrys effuse FS524, isolated from a sediment sample collecting at the South China Sea, attracted our attention, and chemical investigation of the strain resulted in the isolation of six new highly substituted phenol derivatives, trieffusols A-F (1-6), along with eleven known analogues (Figure 1), including phomalone (7) [18], 2,4-dihydroxy-3-(2-hydroxyethyl)-6-methoxyphenyl)-3-hydroxybutan-1-one (8) [18], (E)-1-(2,4-dihydroxy-3-(2-hydroxyethyl)-6-methoxyphenyl)but-2-en-1-one (9) [18], deoxyphomalone (10) [18], phomalichenone A (11) [18], methylindole-3-acetate (12) [19], 3-indole acetic acid (13) [20], 4-methoxyphenylacetic acid (14) [21], papuline (15) [22], and stigmast-4-en-3-one (16) [23]. Furthermore, their structures with absolute configurations were successfully established with the aid of spectroscopic data analyses, single-crystal X-ray diffraction experiments, and ECD calculations.…”

Metabolites of Marine Sediment-Derived Fungi: Actual Trends of Biological Activity Studies

“…SCSIO sof101, in addition to antimicrobial polyketide 50, produced emodacidamides A, C, D, and E (162-165), featuring anthraquinoneamino acid conjugates. Emodacidamides A (162), C (163), D (164), and E (165) inhibited interleukin-2 secretion from Jurkat cells [95].…”

(±)-Peniorthoesters A and B, Two Pairs of Novel Spiro-Orthoester en-antiomers With an Unusual 1,4,6-Trioxaspi-ro[4.5]decane-7-One Unit From Penicillium minioluteum

“…Fungi have historically played an important role in drug discovery. The genus Penicillium has been shown to be a rich source of structurally unique and biologically active secondary metabolites (Meng et al, 2016; Sun et al, 2016; Luo et al, 2017) and many metabolites from Penicillium are clinically used drugs with penicillin as a representative compound. Previous studies on the secondary metabolites of Penicillium minioluteum have resulted in the identification of scores of bioactive metabolites, including isomeric furanones with cytotoxic activities against HeLa cell lines (Tang et al, 2015), sesquiterpene-conjugated amino acids with cytotoxic activities against HepG2 cells (Ngokpol et al, 2015), and hybrid polyketide-terpenoids (Iida et al, 2008).…”