Bicyclo [6.3.0] Undecane Sesquiterpenoids: Structures, Biological Activities, and Syntheses

Qin, Guo-Fei; Liang, Hongbao; Liu, Wenxiu; Zhu, Feng; Li, Pinglin; Li, Guoqiang; Yao, Jingchun

doi:10.3390/molecules24213912

Cited by 10 publications

(2 citation statements)

References 65 publications

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“…The n-hexane fraction (PCHF) had the lowest value (DPPH = 58.09 ± 1.54, and ABTS = 113.41 ± 1.06). The higher values of antioxidant activities of methanolic extract also correlated with the antioxidant compounds (1,2,4,8,9,10,11,16,17,19,23,25,26,27,30,31,42,43,44,47,51, from Table 2), which constituted 67.86% of non-polar compounds of the total extract (Table 2); however, the highest phenolic contents also contributed to the higher antioxidant activities of PCME [90]. Moreover, the radical scavenging effect of PCHF was also significant, which may be due to the presence of many compounds ( 3) possessing antioxidant activities, as proven by many pieces of researches (Table 3).…”

Section: Biological Activities 221 Antioxidant Activitiesmentioning

confidence: 79%

Comprehensive Phytochemical Profiling, Biological Activities, and Molecular Docking Studies of Pleurospermum candollei: An Insight into Potential for Natural Products Development

et al. 2022

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The purpose of this study was to find the biological propensities of the vegetable plant Pleurospermum candollei by investigating its phytochemical profile and biological activities. Phytochemical analysis was done by spectroscopic methods to investigate the amount of total polyphenols, and biological evaluation was done by the different antioxidant, enzyme inhibitory (tyrosinase, α-amylase, and α-glucosidase), thrombolytic, and antibacterial activities. The highest amount of total phenolic and flavonoid contents was observed in methanolic extract (240.69 ± 2.94 mg GAE/g and 167.59 ± 3.47 mg QE/g); the fractions showed comparatively less quantity (57.02 ± 1.31 to 144.02 ± 2.11 mg GAE/g, and 48.21 ± 0.75 to 96.58 ± 2.30 mg QE/g). The effect of these bioactive contents was also related to biological activities. GCMS analysis led to the identification of bioactive compounds with different biological effects from methanolic extract (antioxidant; 55.07%, antimicrobial; 56.41%), while the identified compounds from the n-hexane fraction with antioxidant properties constituted 67.86%, and those with antimicrobial effects constituted 82.95%; however, the synergetic effect of polyphenols may also have contributed to the highest value of biological activities of methanolic extract. Molecular docking was also performed to understand the relationship of identified secondary metabolites with enzyme-inhibitory activities. The thrombolytic activity was also significant (40.18 ± 1.80 to 57.15 ± 1.10 % clot lysis) in comparison with streptokinase (78.5 ± 1.53 to 82.34 ± 1.25% clot lysis). Methanolic extract also showed good activity against Gram-positive strains of bacteria, and the highest activity was observed against Bacillus subtilis. The findings of this study will improve our knowledge of phytochemistry, and biological activities of P. candollei, which seems to be a ray of hope to design formulations of natural products for the improvement of health and prevention of chronic diseases; however, further research may address the development of novel drugs for use in pharmaceuticals.

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Section: Biological Activities 221 Antioxidant Activitiesmentioning

confidence: 79%

Comprehensive Phytochemical Profiling, Biological Activities, and Molecular Docking Studies of Pleurospermum candollei: An Insight into Potential for Natural Products Development

et al. 2022

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“…Compounds 3-5 can be assigned to the asteriscanes according to their characteristic four methyl groups on the five-eight-membered ring system [9].…”

Section: Resultsmentioning

confidence: 99%

Heimionones A–E, New Sesquiterpenoids Produced by Heimiomyces sp., a Basidiomycete Collected in Africa

et al. 2023

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With heimionones A–E (1–5), five new terpenoids were isolated from submerged cultures of Heimiomyces sp. in addition to the previously described compounds hispidin, hypholomin B, and heimiomycins A and B. Planar structures of the metabolites were elucidated by 1D and 2D NMR in addition to HRESIMS data. While ROESY data assigned relative configurations, absolute configurations were determined by the synthesis of MTPA esters of 1, 3, and 5. The [6.3.0] undecane core structure of compounds 3–5 is of the asteriscane-type, however, the scaffold of 1 and 2 with their bicyclo [5.3.0] decane core and germinal methyl substitution is, to our knowledge, unprecedented. Together with several new compounds that were previously isolated from solid cultures of this strain, Heimiomyces sp. showed an exceptionally high chemical diversity of its secondary metabolite profile.

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(4+3) Cycloadditions of Allylic and Related Cations

Harmata,

Tu,

Clark

2024

Organic Reactions

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The reaction of allylic cations with 1,3‐dienes is formally equivalent to the Diels–Alder reaction but leads to seven‐membered rings. An allylic cation contains 2 pi electrons, and is thus precisely analogous to an alkene and, like the latter, can function as a dienophile. The substituent at the central carbon of the allylic cation serves to terminate the reaction. Most often, this substituent is an oxyanion or a silyl ether, but other groups have been used. These (4+3) cycloadditions can proceed via mechanisms that range from stepwise to concerted. Diastereoselectivity, regioselectivity, and enantioselectivity have all been achieved, though there are still opportunities for the development of new reactions in this area. Asymmetric catalysis and enzymatic catalysis of such reactions is in its infancy. More recent advances center on cations that are related to benzylic cations but involve electron rich heterocycles such as furans, indoles, thiophenes and related structures. This chapter covers advances in (4+3) cycloadditions of allylic and related cations from 1997 to 2017, with supplemental references added to bring the work up to date through 2023. It illustrates both the growth in technical progress and theoretical understanding of this reaction during that time.

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Bicyclo [6.3.0] Undecane Sesquiterpenoids: Structures, Biological Activities, and Syntheses

Cited by 10 publications

References 65 publications

Comprehensive Phytochemical Profiling, Biological Activities, and Molecular Docking Studies of Pleurospermum candollei: An Insight into Potential for Natural Products Development

Comprehensive Phytochemical Profiling, Biological Activities, and Molecular Docking Studies of Pleurospermum candollei: An Insight into Potential for Natural Products Development

Heimionones A–E, New Sesquiterpenoids Produced by Heimiomyces sp., a Basidiomycete Collected in Africa

(4+3) Cycloadditions of Allylic and Related Cations

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