Metabolites and novel compounds with anti-microbial or antiaging activities from Cordyceps fumosorosea

Abstract

High-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) analysis revealed that there are 20 main components in spores and mycelia extract of Cordyceps fumosorosea strain RCEF 6672 including mannitol (1), uridine (2), adenine (3). N6-(2-hydroxyethyl)-adenosine (4). N6-(2-hydroxyethylacetate)-adenosine (5), fumosoroseanoside A (6) and B (7), ovalicin-4α-alcohol (8), 1-linoleoyl-sn-glycero-3-phosphocholine (9) and its isomer (10), fumosoroseain A (11) and its isomer (12), 5 non-ribosomal peptides (13 to 17) and 3 fatty acids (18 to 20). The compounds 5, 6, 7, 9 and 11 were prepared with preparative and semi-preparative HPLC and identified with 1D and 2D NMR. Compounds 4 and 5 were the first time identified from C. fumosorosea. Compounds 6, 7 and 11 are novel compounds. Compounds 6 and 7 showed antibacterial and antifungal activities, and 11 showed antiaging activity. All the secondary metabolites (4 to 8 and 11 to 17) have strong bioactivities indicating that the metabolites have pharmaceutical development potentiality. Graphical Abstract

Chemical Constituents From the Marine Microalgae Thraustochytrium pachydermum

“…The known compounds were determined to be ergosta-7,22-diene-3 β ,5 α- diol ( 2 ), 5 cerevisterol ( 3 ), 8 (22 E ,24 S) -5 α ,6 α -epoxy-ergosta-8(9),22-diene-3 β ,7 α -diol ( 4 ), ergosterol ( 5 ), 9 5 α ,8 α -epidioxyergosta-6,22-diene-3 β -ol ( 6 ), 7 linoleic acid ( 7 ), 10 4-((9 Z ,12 Z )-octadeca-9,12-dienoyloxy)butanoic acid ( 8 ), 11 1-linoleoyl-sn-glycero-3-phosphocholine ( 9 ), 12 cibotiglycerol ( 10 ), 13 gingerglycolipid B ( 11 ), 14 oleic acid ( 12 ), 15 4-((9Z)-octadec-9-enoyloxy)butanoic acid ( 13 ), 16 (2 S )-1- O -(9 Z )-octadec-9-enoyl)-3- O -(6-sulfo-D-quinovopyranosyl)glycerol ( 14 ), 17 6′- O -linoleylsucrose ( 15 ), 18 gingerglycolipid C ( 16 ), 14 and ( S )-3-stearoyl- sn -glycerol ( 17 ) 19 by comparing their NMR data with those reported in the literature (Figure 2).…”

Metabolites and Their Bioactivities from the Genus Cordyceps

“…At experimental doses of 10–30 μg, compounds 53 and 54 exhibited excellent ( p < 0.05) antibacterial and antifungal activity compared to the negative control group. In a range of concentrations from 100 μM to 400 μM, compound 55 could lengthen the life of nematodes; at 200 μM, it showed optimal activity ( p < 0.05), and the average life of the nematodes was lengthened by 11.3% [ 47 ]. The structures of 41 – 56 are shown in Figure 4 .…”

Phytochemical Profiling, Isolation, and Pharmacological Applications of Bioactive Compounds from Insects of the Family Blattidae Together with Related Drug Development

“…Finally, the chemical shift of the active hydrogen on the hydroxyl group in the typical structure of polyols is affected by the conditions (concentration, temperature, solvent) in 1 HNMR, and the chemical shift will change in a range of 0.5-5.5 ppm with a blunt peak. The heavy water exchange method can identify the absorption peak of active hydrogen because the peak of active hydrogen disappears after adding deuterated water [104].…”

“…The data obtained from the LC-MS for each part (extract of brain, hemolymph, or muscle lysates) contained over 160 peaks for water-soluble and over 170 peaks for methanol-extracted lysates, which contained 2,5dihydroxy-4′-methoxy-flavanone ( 18), 2-ethyl-2-methoxypentanoic acid, 7-(isopropoxy)- Finally, the chemical shift of the active hydrogen on the hydroxyl group in the typical structure of polyols is affected by the conditions (concentration, temperature, solvent) in 1 HNMR, and the chemical shift will change in a range of 0.5-5.5 ppm with a blunt peak. The heavy water exchange method can identify the absorption peak of active hydrogen because the peak of active hydrogen disappears after adding deuterated water [104].…”