Two new meroterpenoids and two new monoterpenoids from the deep sea-derived fungus Penicillium sp. YPGA11

Cheng, Zhongbin; Xu, Wei; Wang, Yanyan; Bai, Shangyuan; Liu, Lijun; Luo, Zengwei; Yuan, Wangjun; Li, Qin

doi:10.1016/j.fitote.2018.12.022

Cited by 38 publications

(28 citation statements)

References 22 publications

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“…Andrastone A ( 1 ) and 16-epi-citreohybriddione A ( 2 ) are two meroterpenoids biosynthesized from a sesquiterpene and a tetraketide. In fact, compounds possessing the same scaffold are rarely found in nature, including citreohybridones A and B (Kosemura et al, 1991b), Andrastins A–D (Shiomi et al, 1996; Uchida et al, 1996), atlantinones A and B (Wang et al, 2010), citreohybriddiones A–C (Kosemura, 2003), citreohybridones A–G and J–L (Kosemura, 2002), citreohybridonol (Oezkaya et al, 2018), 3-deacetylcitreohybridonol (Gao et al, 2012), 15-deacetylated citreohybridone E (Cheng et al, 2019), isocitreohybridones A–C and H–J (Kosemura, 2002, 2003), and isopenicins A–C (Tang et al, 2019). Among them, 18 possess a lactone moiety at the C-23 position.…”

Section: Resultsmentioning

confidence: 99%

Andrastone A From the Deep-Sea-Derived Fungus Penicillium allii-sativi Acts as an Inducer of Caspase and RXRα-Dependent Apoptosis

et al. 2019

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Two new (1, 2) and one known (3) meroterpenoids were isolated from the deep-sea-derived fungus Penicillium allii-sativi. The relative structures of new compounds were determined on the basis of an extensive analysis of the NMR and MS data, and the absolute configurations were established by ECD calculations. Andrastone A (1) is a rare andrastin bearing an unusual cyclopentan-1,3-dione. It shows a selectively antiproliferative effect against HepG2 tumor cells with an IC50 value of 7.8 μM. Mechanism study showed that apoptosis via Caspase and RXRα pathways are responsible for the inhibitory effect.

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Section: Resultsmentioning

confidence: 99%

Andrastone A From the Deep-Sea-Derived Fungus Penicillium allii-sativi Acts as an Inducer of Caspase and RXRα-Dependent Apoptosis

et al. 2019

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“…The andrastin-type meroterpenoids derived from 5-dimethylorsellinic acid (DMOA) and farnesyl diphosphate (FPP) via a mixed polyketide-terpenoid pathway are characterized by a five-methyl substituted ent-5 α ,14 β -androstane skeleton (6,6,6,5-tetracarbocyclic skeleton) [ 3 , 4 ]. Since citreohybridones A and B were isolated in 1991, over 30 analogues have been isolated and characterized [ 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 ]. Many andrastin-type meroterpenoids have shown potent cyotoxic, antifeedant, and insecticidal activities [ 4 , 8 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

New Andrastin-Type Meroterpenoids from the Marine-Derived Fungus Penicillium sp.

et al. 2021

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Three new andrastin-type meroterpenoids penimeroterpenoids A–C (1–3) together with two known analogs (4 and 5) were isolated from the cultures of the marine-derived Penicillium species (sp.). The structures of the new compounds were elucidated on the basis of 1- and 2-dimensional (1D/2D) Nuclear Magnetic Resonance (NMR) spectroscopic and mass spectrometric analysis. The absolute configurations of 1–3 were determined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Compound 1 showed moderate cytotoxicity against A549, HCT116, and SW480 cell lines.

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“…In our efforts to search for new or bioactive molecules from deep-sea-derived Penicillium or Aspergillus strains [12][13][14][15], chemical examination of Penicillium thomii YPGA3 afforded a new austalide meroterpenoid (1) and seven known analogues (28) ( Figure 1). Compound 1 represented the third example of austalides bearing a phenol hydroxy at C-5 instead of the conserved methoxy in other known analogues.…”

Section: Introductionmentioning

confidence: 99%

Terpenoids from the Deep-Sea-Derived Fungus Penicillium thomii YPGA3 and Their Bioactivities

et al. 2020

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A chemical study of the ethyl acetate (EtOAc) extract from the deep-sea-derived fungus Penicillium thomii YPGA3 led to the isolation of a new austalide meroterpenoid (1) and seven known analogues (2−8), two new labdane-type diterpenoids (9 and 10) and a known derivative (11). The structures of new compounds 1, 9, and 10 were determined by comprehensive analyses via nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data. The absolute configurations of 1, 9, and 10 were determined by comparisons of experimental electronic circular dichroism (ECD) with the calculated ECD spectra. Compound 1 represented the third example of austalides bearing a hydroxyl group at C-5 instead of the conserved methoxy in other known analogues. To our knowledge, diterpenoids belonging to the labdane-type were discovered from species of Penicillium for the first time. Compound 1 showed cytotoxicity toward MDA-MB-468 cells with an IC50 value of 38.9 μM. Compounds 2 and 11 exhibited inhibition against α-glucosidase with IC50 values of 910 and 525 μM, respectively, being more active than the positive control acarbose (1.33 mM).

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Two new meroterpenoids and two new monoterpenoids from the deep sea-derived fungus Penicillium sp. YPGA11

Cited by 38 publications

References 22 publications

Andrastone A From the Deep-Sea-Derived Fungus Penicillium allii-sativi Acts as an Inducer of Caspase and RXRα-Dependent Apoptosis

Andrastone A From the Deep-Sea-Derived Fungus Penicillium allii-sativi Acts as an Inducer of Caspase and RXRα-Dependent Apoptosis

New Andrastin-Type Meroterpenoids from the Marine-Derived Fungus Penicillium sp.

Terpenoids from the Deep-Sea-Derived Fungus Penicillium thomii YPGA3 and Their Bioactivities

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