Dictyoptesterols A–C, ∆22-24-oxo cholestane-type sterols with potent PTP1B inhibitory activity from the brown alga Dictyopteris undulata Holmes

Yang, Fei; Zhang, Liangwei; Feng, Mei-Tang; Liu, Aihong; Li, Jia; Zhao, Tiansheng; Lai, Xiaoping; Wang, Bin; Guo, Yue‐Wei; Mao, Shui-Chun

doi:10.1016/j.fitote.2018.09.001

Cited by 12 publications

(5 citation statements)

References 24 publications

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“…The recombinant PTP1B catalytic domain was expressed and purified according to the methodology as previously reported. − The enzymatic activities of the PTP1B catalytic domain were determined at 30 °C by monitoring the hydrolysis of p NPP. Dephosphorylation of p NPP generated the product p NP, which was monitored at an absorbance of 405 nm with an EnVision multilabel plate reader (Perkin–Elmer Life Sciences, Boston, MA, USA).…”

Section: Methodsmentioning

confidence: 99%

Rearranged Diels–Alder Adducts and Prenylated Flavonoids as Potential PTP1B Inhibitors from Morus nigra

Wang

Jiang³

et al. 2021

J. Nat. Prod.

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Two novel rearranged Diels−Alder adducts, morunigrines A (1) and B (2), and four new prenylated flavonoids, morunigrols A−D (3−6), were isolated from the twigs of Morus nigra, together with four known prenylated phenolic compounds, including two flavonoids (7 and 8) and two 2-arylbenzofurans (9 and 10). Morunigrines A (1) and B (2) are a novel class of Diels− Alder adducts with unprecedented carbon skeletons featuring a rearranged chalcone−stilbene/2-arylbenzofuran core decorated with a unique methylbiphenyl moiety. The structures of the new compounds were assigned by analysis of spectroscopic data. The absolute configuration of compound 6 was determined by the measurement of specific rotation. A plausible biogenetic pathway for 1 and 2 is also proposed. Compounds 1 and 2 exhibited more potent protein tyrosine phosphatase 1B inhibitory activity with IC 50 values of 1.8 ± 0.2 and 1.3 ± 0.3 μM, respectively, than that of the positive control oleanolic acid (IC 50 , 2.5 ± 0.1 μM).

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Section: Methodsmentioning

confidence: 99%

Rearranged Diels–Alder Adducts and Prenylated Flavonoids as Potential PTP1B Inhibitors from Morus nigra

Wang

Jiang³

et al. 2021

J. Nat. Prod.

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“…This genus has been proved to be an outstanding source of structurally diverse secondary metabolites [19]. Several sesquiterpenes, steroids, sulfated polysaccharides, disulphides, C11-hydrocarbons (sex pheromones) and halogenated compounds are reported from Dictyopteris species with potent biological activities [20][21][22][23][24][25][26][27].…”

Section: Introductionmentioning

confidence: 99%

α-Glucosidase Inhibition and Molecular Docking Studies of Natural Brominated Metabolites from Marine Macro Brown Alga Dictyopteris hoytii

et al. 2019

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Bioassay guided isolation of the methanolic extract of marine macro brown alga Dictyopteris hoytii afforded one new metabolite (ethyl methyl 2-bromobenzene 1,4-dioate, 1), one new natural metabolite (diethyl-2-bromobenzene 1,4-dioate, 2) along with six known metabolites (3–8) reported for the first time from this source. The structure elucidation of all these compounds was achieved by extensive spectroscopic techniques including 1D (1H and 13C) and 2D (NOESY, COSY, HMBC and HSQC) NMR and mass spectrometry and comparison of the spectral data of known compounds with those reported in literature. The in vitro α-glucosidase inhibition studies confirmed compound 7 to be the most active against α-glucosidase enzyme with IC50 value of 30.5 ± 0.41 μM. Compounds 2 and 3 demonstrated good inhibition with IC50 values of 234.2 ± 4.18 and 289.4 ± 4.91 μM, respectively, while compounds 1, 5, and 6 showed moderate to low inhibition. Furthermore, the molecular docking studies of the active compounds were performed to examine their mode of inhibition in the binding site of the α-glucosidase enzyme.

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“…The relative configuration of 1 was consistent with previously reported naturally occurring steroids. 12 , 13 To establish the absolute configuration at C-3, C-15, and C-24, the modified Mosher’s method was applied. 14 According to a convenient Mosher ester procedure carried out in NMR tubes, the corresponding ( R )- and ( S )-MTPA esters ( 1r and 1s ) of 1 were prepared by treatment with ( S )-MTPA-Cl and ( R )-MTPA-Cl, respectively.…”

Section: Resultsmentioning

confidence: 99%

Structure Elucidation and Biosynthesis of Nannosterols A and B, Myxobacterial Sterols from Nannocystis sp. MNa10993

et al. 2023

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Myxobacteria represent an underinvestigated source of chemically diverse and biologically active secondary metabolites. Here, we report the discovery, isolation, structure elucidation, and biological evaluation of two new bacterial sterols, termed nannosterols A and B (1, 2), from the terrestrial myxobacterium Nannocystis sp. (MNa10993). Nannosterols feature a cholestanol core with numerous modifications including a secondary alcohol at position C-15, a terminal vicinal diol side chain at C-24−C-25 (1, 2), and a hydroxy group at the angular methyl group at C-18 (2), which is unprecedented for bacterial sterols. Another rare chemical feature of bacterial triterpenoids is a ketone group at position C-7, which is also displayed by 1 and 2. The combined exploration based on myxobacterial high-resolution secondary metabolome data and genomic in silico investigations exposed the nannosterols as frequently produced sterols within the myxobacterial suborder of Nannocystineae. The discovery of the nannosterols provides insights into the biosynthesis of these new myxobacterial sterols, with implications in understanding the evolution of sterol production by prokaryotes.

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Dictyoptesterols A–C, ∆22-24-oxo cholestane-type sterols with potent PTP1B inhibitory activity from the brown alga Dictyopteris undulata Holmes

Cited by 12 publications

References 24 publications

Rearranged Diels–Alder Adducts and Prenylated Flavonoids as Potential PTP1B Inhibitors from Morus nigra

Rearranged Diels–Alder Adducts and Prenylated Flavonoids as Potential PTP1B Inhibitors from Morus nigra

α-Glucosidase Inhibition and Molecular Docking Studies of Natural Brominated Metabolites from Marine Macro Brown Alga Dictyopteris hoytii

Structure Elucidation and Biosynthesis of Nannosterols A and B, Myxobacterial Sterols from Nannocystis sp. MNa10993

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