Structural elucidation of two intricate polycyclic polyprenylated acylphloroglucinols using quantum chemical calculations and their hypoglycemic activities

Li, Qingqing; Yang, Shuang; Teng, Haida; Li, Xueni; Xie, Wenli; Wu, Zhen; Yang, Guangzhong; Xu, Jing; Chen, Yu

doi:10.1016/j.arabjc.2022.104137

Cited by 5 publications

(3 citation statements)

References 16 publications

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“…In this study, we conducted glucose consumption analysis following our previous research. 20 HepG2 cells (1.0 × 10 5 cells/well) were divided into four groups: normal control group (NC), PA-induced model group (MC), metformin hydrochloride (10 μM)-treated group (Met), and different doses of PPAP groups (5 and 10 μM or 2, 4, and 6 μM). All groups, except for the NC group, were cultured with 0.25 mM PA and 30 mM glucose to establish the IR model.…”

Section: Methodsmentioning

confidence: 99%

Garbractin A, a Polycyclic Polyprenylated Acylphloroglucinol with a 4,11-dioxatricyclo[4.4.2.0^1,5]Dodecane Skeleton from Garcinia bracteata Fruits

Yang

et al. 2023

ACS Omega

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Garbractin A (1), a structurally complicated polycyclic polyprenylated acylphloroglucinol (PPAP) with an unprecedented 4,11-dioxatricyclo[4.4.2.01,5] dodecane skeleton, was isolated from the fruits of Garcinia bracteata, along with five new biosynthetic analogues named garcibracteatones A–E (2–6). Their structures containing absolute configurations were revealed using spectroscopic data, the residual dipolar coupling-enhanced NMR approach, and quantum chemical calculations. The antihyperglycemic effect of these PPAPs (1–6) was evaluated using insulin-resistant HepG2 cells (IR-HepG2 cells) induced through palmitic acid (PA). Compounds 1, 3, and 4 were found to significantly promote glucose consumption in the IR-HepG2 cells and, therefore, may hold potential as candidates for treating hyperglycemia.

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Section: Methodsmentioning

confidence: 99%

Garbractin A, a Polycyclic Polyprenylated Acylphloroglucinol with a 4,11-dioxatricyclo[4.4.2.0^1,5]Dodecane Skeleton from Garcinia bracteata Fruits

Yang

et al. 2023

ACS Omega

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“…Their targeting properties are relevant in type 2 diabetes and obesity. Theoretical and experimental structural elucidation of two polyprenylated acylphloroglucinols was reported by Chen et al 109 Characterisation of anti-adipogenic withanolides from the roots of Indian ginseng (Withania somnifera) was reported by Kim et al 110 Ruchirawat et al 111 reported on characterisation of diterpenoids and p-methoxycinnamic acid diol esters from Kaempferia saraburiensis picheans. Li et al 112 characterised secondary metabolites from the fresh leaves of Pinus yunnanensis.…”

Section: Nuclear Shielding Calculation In Natural Productsmentioning

confidence: 99%

Theory and computation of nuclear shielding

2023

Nuclear Magnetic Resonance

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This chapter continues earlier reviews of essential works on theoretical issues of nuclear magnetic shieldings published from 1 January to 31 December 2022. As previously, the chapter concentrates on theoretical calculations of nuclear shielding parameters and/or chemical shifts in case of free molecules in the gas phase and solution, and in some cases in the solid state using a periodic formulation. The nuclear shieldings in solution are mainly calculated using inexpensive polarizable continuum model of solvent (PCM). The use of discrete solvent molecules (in particular water and other polar solvents), which is essential for correct description of hydrogen bonding, is often omitted by numerous authors. Most calculations use a relatively simple and fast, but reliable density functional theory (DFT) combined with gauge-including atomic orbital (GIAO) approach. On the other hand, reports on prediction of nuclear magnetic shielding parameters using high level theoretical methods combined with large and flexible basis sets are not so common due to the enormous computational cost. In addition, correction of raw theoretical nuclear magnetic shieldings due to ro-vibration (zero-point vibration correction, ZPVC) and temperature corrections (TC), as well as implicit and explicit solvent effects and relativistic corrections are not often reported.

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“…However, it is difficult to obtain clear NMR signals or fine single crystals from a large number of compounds, which limits the rapid determination of the stereoconfiguration of MIAs with multiple chiral centers. With the advancement of ECD and nuclear magnetic resonance (NMR) calculation methods, bioactive compound identification based on quantum chemical calculations has become the mainstream approach for the discovery of leading structures [ 8 , 9 , 10 , 11 ].…”

Section: Introductionmentioning

confidence: 99%

Structural Elucidation and Cytotoxic Activity of New Monoterpenoid Indoles from Gelsemium elegans

Song

Liang

et al. 2023

Molecules

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Two new monoterpenoid indole alkaloids, gelselegandines F (1) and G (2), were isolated from the aerial parts of Gelsemium elegans. Their structures were elucidated by means of spectroscopic techniques and quantum chemical calculations. The ECD calculations were conducted at the B3LYP/6-311G(d,p) level and NMR calculations were carried out using the Gauge-Including Atomic Orbitals (GIAO) method. Structurally, the two new compounds possessed rare, cage-like, monoterpenoid indole skeletons. All isolated compounds and the total alkaloids extract were tested for cytotoxicity against four different tumor cell lines. The total alkaloids extract of G. elegans exhibited significant antitumor activity with IC50 values ranging from 32.63 to 82.24 ug/mL. In order to discover anticancer leads from the active extraction, both new indole compounds (1–2) were then screened for cytotoxicity. Interestingly, compound 2 showed moderate cytotoxicity against K562 leukemia cells with an IC50 value of 57.02uM.

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Structural elucidation of two intricate polycyclic polyprenylated acylphloroglucinols using quantum chemical calculations and their hypoglycemic activities

Cited by 5 publications

References 16 publications

Garbractin A, a Polycyclic Polyprenylated Acylphloroglucinol with a 4,11-dioxatricyclo[4.4.2.0^1,5]Dodecane Skeleton from Garcinia bracteata Fruits

Garbractin A, a Polycyclic Polyprenylated Acylphloroglucinol with a 4,11-dioxatricyclo[4.4.2.0^1,5]Dodecane Skeleton from Garcinia bracteata Fruits

Theory and computation of nuclear shielding

Structural Elucidation and Cytotoxic Activity of New Monoterpenoid Indoles from Gelsemium elegans

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Structural elucidation of two intricate polycyclic polyprenylated acylphloroglucinols using quantum chemical calculations and their hypoglycemic activities

Cited by 5 publications

References 16 publications

Garbractin A, a Polycyclic Polyprenylated Acylphloroglucinol with a 4,11-dioxatricyclo[4.4.2.01,5]Dodecane Skeleton from Garcinia bracteata Fruits

Garbractin A, a Polycyclic Polyprenylated Acylphloroglucinol with a 4,11-dioxatricyclo[4.4.2.01,5]Dodecane Skeleton from Garcinia bracteata Fruits

Theory and computation of nuclear shielding

Structural Elucidation and Cytotoxic Activity of New Monoterpenoid Indoles from Gelsemium elegans

Contact Info

Product

Resources

About

Garbractin A, a Polycyclic Polyprenylated Acylphloroglucinol with a 4,11-dioxatricyclo[4.4.2.0^1,5]Dodecane Skeleton from Garcinia bracteata Fruits

Garbractin A, a Polycyclic Polyprenylated Acylphloroglucinol with a 4,11-dioxatricyclo[4.4.2.0^1,5]Dodecane Skeleton from Garcinia bracteata Fruits