Isolation of cytotoxic daphnane-type and tigliane-type diterpenoids from <i>Daphne genkwa</i> using MetGem software

Mi, Si-Hui; Duan, Zhi-Kang; Wang, Yujue; Dong, Shu-Hui; Zhao, Peng; Yao, Guo-Dong; Liu, Qingbo; Lin, Bin; Song, Shao‐Jiang; Huang, Xiao‐Xiao

doi:10.1039/d2nj05276h

Cited by 6 publications

(3 citation statements)

References 40 publications

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“…Therefore, the development of efficient and practical total/semi-synthetic methods and further exploration of plant resources are eagerly awaited. Recently, target isolation using LC-tandem mass spectrometry and the molecular network has improved the efficiency of these diterpenoids [ 22 , 42 , 107 – 109 ]. It is hoped that further dereplication using LC–MS and molecular network strategies will lead to the discovery of new compounds with even more attractive chemical structures and biological activities.…”

Section: Discussionmentioning

confidence: 99%

Tigliane and daphnane diterpenoids from Thymelaeaceae family: chemistry, biological activity, and potential in drug discovery

Otsuki

2023

J Nat Med

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Tigliane and daphnane diterpenoids are characteristically distributed in plants of the Thymelaeaceae family as well as the Euphorbiaceae family and are structurally diverse due to the presence of polyoxygenated functionalities in the polycyclic skeleton. These diterpenoids are known as toxic components, while they have been shown to exhibit a wide variety of biological activities, such as anti-cancer, anti-HIV, and analgesic activity, and are attracting attention in the field of natural product drug discovery. This review focuses on naturally occurring tigliane and daphnane diterpenoids from plants of the Thymelaeaceae family and provides an overview of their chemical structure, distribution, isolation, structure determination, chemical synthesis, and biological activities, with a prime focus on the recent findings.

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Section: Discussionmentioning

confidence: 99%

Tigliane and daphnane diterpenoids from Thymelaeaceae family: chemistry, biological activity, and potential in drug discovery

Otsuki

2023

J Nat Med

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“…[29][30][31][32] In general, conformational analyses were carried out via random searching in CONFLEX software using the MMFF94 force field, and all structures were optimized at the B3LYP/ 6-31G(d) level in the Gaussian 09 software. [33][34][35] In the ECD calculations, the conformers with Boltzmann-population of over 5 % were chosen and initially optimized at the PBE0/6-311 + + G(2d,p)//B3LYP/6-31G(d) level using the PCM model in MeOH solution. The Boltzmann-averaged ECD curves of these conformers were generated using the SpecDis 1.51 software.…”

Section: Calculations Detailsmentioning

confidence: 99%

Four Pairs of Neuroprotective Aryldihydronaphthalene‐Type Lignanamide Enantiomers from the Herbs of Solanum lyratum

Mi,

Chang,

Zhang

et al. 2023

Chemistry & Biodiversity

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Four pairs of aryldihydronapthalene‐type lignanamide enantiomers were isolated from Solanum lyratum (Solanaceae). The enantiomeric separation was accomplished by chiral‐phase HPLC, and five undescribed compounds were elucidated. Analysis by various spectroscopy and ECD calculations, the structures of undescribed compounds were illuminated. The neuroprotective effects of all compounds were evaluated using H2O2‐induced human neuroblastoma SH‐SY5Y cells and AchE inhibition activity. Among them, compound 4a exhibited remarkable neuroprotective effects at high concentrations of 25 and 50 μmol/L comparable to Trolox. Compound 1a showed the highest AchE inhibition with the IC50 value of 3.06 ± 2.40 μmol/L. Molecular docking of the three active compounds was performed and the linkage between the compounds and the active site of AchE was elucidated.

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“…Daphne species (Thymelaeaceae) are renowned as significant medicinal plants and serve as a valuable source of anti-inflammatory and anti-tumor leading compounds. 1–5 Sesquiterpenes have been discovered as a typical component from the genus Daphne , such as Daphne aurantiaca , 6–9 Daphne genkwa , 10–14 Daphne oleoides , 15 Daphne papyracea , 16 Daphne tangutica , 17 and Daphne holosericea. 18 Structurally diverse sesquiterpenes also represent extensive pharmacological activities, including antioxidant, 19 anti-inflammatory, 20,21 anti-HIV, 22 and cytotoxicity.…”

Section: Introductionmentioning

confidence: 99%

Nine undescribed sesquiterpenoids from the aerial parts of Daphne penicillata: cyclooxygenase-2 inhibition, molecular docking, and molecular dynamics studies

Zhao,

Xin,

et al. 2023

New J. Chem.

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Isolation of cytotoxic daphnane-type and tigliane-type diterpenoids from Daphne genkwa using MetGem software

Abstract: To discover diterpenoids that naturally possess chemical weapons against cancer, the biological and chemical diversity of the flower buds of Daphne genkwa Sieb. et Zucc was investigated. Guided by LC-MS/MS...

Cited by 6 publications

References 40 publications

Tigliane and daphnane diterpenoids from Thymelaeaceae family: chemistry, biological activity, and potential in drug discovery

Tigliane and daphnane diterpenoids from Thymelaeaceae family: chemistry, biological activity, and potential in drug discovery

Four Pairs of Neuroprotective Aryldihydronaphthalene‐Type Lignanamide Enantiomers from the Herbs of Solanum lyratum

Nine undescribed sesquiterpenoids from the aerial parts of Daphne penicillata: cyclooxygenase-2 inhibition, molecular docking, and molecular dynamics studies

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