Chemical Constituents of the Deep-Sea-Derived Penicillium citreonigrum MCCC 3A00169 and Their Antiproliferative Effects

Abstract

Six new citreoviridins (citreoviridins J–O, 1–6) and twenty-two known compounds (7–28) were isolated from the deep-sea-derived Penicillium citreonigrum MCCC 3A00169. The structures of the new compounds were determined by spectroscopic methods, including the HRESIMS, NMR, ECD calculations, and dimolybdenum tetraacetate-induced CD (ICD) experiments. Citreoviridins J−O (1–6) are diastereomers of 6,7-epoxycitreoviridin with different chiral centers at C-2–C-7. Pyrenocine A (7), terrein (14), and citreoviridin (20) significantly induced apoptosis for HeLa cells with IC50 values of 5.4 μM, 11.3 μM, and 0.7 μM, respectively. To be specific, pyrenocine A could induce S phase arrest, while terrein and citreoviridin could obviously induce G0-G1 phase arrest. Citreoviridin could inhibit mTOR activity in HeLa cells.

Hepialiamides A–C: Aminated Fusaric Acid Derivatives and Related Metabolites with Anti-Inflammatory Activity from the Deep-Sea-Derived Fungus Samsoniella hepiali W7

“…By comparing the NMR, MS, ECD, and OR data with those reported in the references, 18 previously described components were identified as cordycepin (5) [28], adenosine (6) [29], 3 -deoxyinosine (7) [30], 5 -O-acetyladenosine (8) [31], 5 -acetyl-3 -deoxyadenosine (9) [32], thymidine (10) [33], uridine (11) [34], 5 -O-acetyluridine (12) [35], ergosterol (13) [36], 3β,5α,9α-trihydroxyergosta-7,22-diene-6-one ( 14) [37], 12-acetoxycycloneran-3,7diol (15) [38], dibutyl phthalate ( 16) [39], di-(2-ethylhexyl)phthalate ( 17) [40], oryzasaccharide A (18) [41], D-glucopyranoside, ethyl, 6-acetate (19) [42], 6-O-acetyl-D-glucose (20) [43], walterolactone A (21) [44], and (4R,5S)-5-hydroxyhexan-4-olide (22) [45]. Among them, 16 and 17 were previously described as plasticizers and common contaminants in natural products [46].…”

“…In summary, three new aminated fusaric acid derivatives, hepialiamides A-C (1-3), and one novel hybrid polyketide, hepialide (4), together with 18 known miscellaneous compounds (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22), were isolated from the cultures of the deep-sea-derived fungus Samsoniella hepiali W7 with the aid of GNPS molecular networking. Hepialiamides A-C feature a glycine/alanine unit embedded in the fusaric acid backbone, representing the third examples of naturally occurring fusaric amides, while hepialide features an uncommon isopropenylated pyrrolidone moiety.…”

“…As part of our ongoing exploration of structurally novel and bioactive secondary metabolites from marine microbes [21][22][23][24], we performed a systematic investigation, aided by a GNPS molecular networking approach, on the crude extract of the culture of fungus Samsoniella epialid W7, isolated from the sulfide at a depth of 3073 m in the South Atlantic. Prior to isolation, the GNPS network of the extract revealed a big molecular cluster within which none of the nodes were identified by the internal compound library (Figure 1), indicating a certain possibility of new compounds to be found among these metabolites.…”

Marine natural products

“…Further meroterpenoids were obtained from P. chermesinum ( 644 – 647 ) 218 and P. chrysogenum ( 648 – 650 ), 219 (the latter group via mutation with diethyl sulfate) and indole diterpenoids, paspalines C–D 651 , 652 and paxillines B–D 653 – 655 , 220 N -acetyl- d -glucosamine derivatives 656 , 657 , 221 citreoviridins J–O 658 – 663 , 222 pentacyclic alkaloid 664 , 223 dipeptide 665 (ref. 224) and eremophilane-type sesquiterpenes 666 – 677 (ref.…”

Novel Bioactive Natural Products from Marine-Derived Penicillium Fungi: A Review (2021–2023)

“…BJR-P2 [27]. Citreoviridins J-O (92-97) (Figure 2) belonged to diastereomers of 6,7-epoxycitreoviridin with different chiral centers at C-2-C-7 and were isolated from the deep-sea-sediment-derived P. citreonigrum MCCC 3A00169 [43].…”