Two New Drimane Sesquiterpenes, Fudecadiones A and B, from the Soil Fungus<i>Penicillium</i>sp. BCC 17468

Pittayakhajonwut, Pattama; Dramae, Aibrahim; Intaraudom, Chakapong; Boonyuen, Nattawut; Nithithanasilp, Sutichai; Rachtawee, Pranee; Laksanacharoen, Pattiyaa

doi:10.1055/s-0030-1250057

Cited by 11 publications

(11 citation statements)

References 10 publications

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“…In summary, two new drimane sesquiterpenes 1 and 2 , six new polyketides 3 – 8 , and 10 known compounds ( 9 – 18 ) were obtained ( Figure 1 ). The known compounds were identified as fudecadione A ( 9 ) [ 6 ], JBIR-138 ( 10 ) [ 6 , 7 ], penioxalicin ( 11 ) [ 8 ], penicichrysogene B ( 12 ) [ 9 ], penitholabene ( 13 ) [ 10 ], penialidin A ( 14 ) [ 11 ], 2,5-dimethyl-7-hydroxychromone ( 15 ) [ 12 ], 3,4-dihydroxybenzeneacetic acid ( 16 ) [ 13 ], BFA seco-acid ( 17 ) [ 14 , 15 ], and ε-caprolactone derivative ( 18 ) [ 16 ] by comparing their MS, NMR, and specific rotation data with those reported.…”

Section: Resultsmentioning

confidence: 99%

New Drimane Sesquiterpenes and Polyketides from Marine-Derived Fungus Penicillium sp. TW58-16 and Their Anti-Inflammatory and α-Glucosidase Inhibitory Effects

Gou¹,

Tian²,

Wei

et al. 2021

Marine Drugs

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Marine fungi-derived natural products represent an excellent reservoir for the discovery of novel lead compounds with biological activities. Here, we report the identification of two new drimane sesquiterpenes (1 and 2) and six new polyketides (3–8), together with 10 known compounds (9–18), from a marine-derived fungus Penicillium sp. TW58-16. The planar structures of these compounds were elucidated by extensive 1D and 2D NMR, which was supported by HR-ESI-MS data. The absolute configurations of these compounds were determined by experimental and calculated electronic circular dichroism (ECD), and their optical rotations compared with those reported. Evaluation of the anti-inflammatory activity of compounds 1–18 revealed that compound 5 significantly inhibited the release of nitric oxide (NO) induced by lipopolysaccharide (LPS) in RAW264.7 cells, correlating with the inhibition of expression of inducible nitric oxide synthase (iNOS). In addition, we revealed that compounds 1, 3–6, 14, 16, and 18 showed strong α-glucosidase inhibitory effects with inhibition rates of 35.4%, 73.2%, 55.6%, 74.4%, 32.0%, 36.9%, 88.0%, and 91.1%, respectively, which were comparable with or even better than that of the positive control, acarbose. Together, our results illustrate the potential of discovering new marine-based therapeutic agents against inflammation and diabetes mellitus.

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Section: Resultsmentioning

confidence: 99%

New Drimane Sesquiterpenes and Polyketides from Marine-Derived Fungus Penicillium sp. TW58-16 and Their Anti-Inflammatory and α-Glucosidase Inhibitory Effects

Gou¹,

Tian²,

Wei

et al. 2021

Marine Drugs

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“…All the trichothecenes contain a sesquiterpenoid ring structure with an epoxide. The epoxide is often responsible for the cytotoxic activity by binding to the 60S ribosomal subunit in eukaryote cells thereby inhibiting protein synthesis [152,153]. Many of the trichothecenes exhibit cytotoxic activity against both fungi and cancer cell lines [154,155,156].…”

Section: Terpenoid-derived Anticancer Compoundsmentioning

confidence: 99%

“…One of the more active compounds of this group is 12′-hydroxyroridin E (Figure 19b), which inhibits leukemia L-1210 with an IC50 value of 0.2 µM [158]. Another trichothecene called anguidine even entered clinical trials against cancer, but did not progress beyond phase II due to a lack of therapeutic efficacy [152,159].…”

Section: Terpenoid-derived Anticancer Compoundsmentioning

confidence: 99%

Anticancer and Antifungal Compounds from Aspergillus, Penicillium and Other Filamentous Fungi

et al. 2013

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“…These values are better than that reported earlier about the IC 50 value of fudecadione A, isolated from Penicillium sp. BCC 17,468 (Pittayakhajonwut et al 2011). The cytotoxic effect of P5 on cancer cells was found to be significantly higher than the positive control (tamoxifen) used in the study.…”

Section: Discussionmentioning

confidence: 73%

Modulation of Bax and Bcl-2 genes by secondary metabolites produced byPenicillium rubensJGIPR9 causes the apoptosis of cancer cell lines

Venkatachalam

Nadumane

2019

Mycology

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Search for an efficient anti-cancer compound of natural origin with well-defined mechanisms of action is an important scientific pursuit today, due to cancer being the second leading cause for the death of affected people. The members of the genus Penicillium are one of the important sources of bioactive compounds. In the present study, Penicillium rubens, isolated from a garden soil in Madurai district of Tamil Nadu, was found to produce a highly promising anti-cancer metabolite. The percentage viabilities of HepG2, HeLa and MCF-7 cancer cells treated with the bioactive fraction (P5) isolated from P. rubens, ranged between 40-50% after 96 h. Apoptosis induction was found to be the major reason for the observed reduction in cancer cell proliferation and cell count which was confirmed by caspase activity, DNA fragmentation, clonogenic assay, cell cycle analysis and LDH assays. The upregulation of proapoptotic Bax, coupled with the downregulation of anti-apoptotic Bcl-2 expressions were confirmed by RT-qPCR and flow cytometry methods. The current study also indicated an upregulation of p53 which further strengthened the apoptogenic property of P5 fraction. Non-toxicity of P5 was demonstrated on normal peripheral lymphocytes. The analysis of P5 fraction through GC-MS indicated the presence of indole-2, 3-(4,4-dimethyl-3-thiosemicarbazone) as one of the major compounds. ARTICLE HISTORY

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Two New Drimane Sesquiterpenes, Fudecadiones A and B, from the Soil FungusPenicilliumsp. BCC 17468

Cited by 11 publications

References 10 publications

New Drimane Sesquiterpenes and Polyketides from Marine-Derived Fungus Penicillium sp. TW58-16 and Their Anti-Inflammatory and α-Glucosidase Inhibitory Effects

New Drimane Sesquiterpenes and Polyketides from Marine-Derived Fungus Penicillium sp. TW58-16 and Their Anti-Inflammatory and α-Glucosidase Inhibitory Effects

Anticancer and Antifungal Compounds from Aspergillus, Penicillium and Other Filamentous Fungi

Modulation of Bax and Bcl-2 genes by secondary metabolites produced byPenicillium rubensJGIPR9 causes the apoptosis of cancer cell lines

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