Characteristic guaiane sesquiterpenes from Daphne penicillata and ECD/NMR-based assignment of C-1 configuration

Abstract

A novel C17 homo-guaiane sesquiterpene (1) and twenty-nine new guaiane-type sesquiterpenes (5−18, 23−25, 27-30, 33−40), along with ten known analogues were isolated from Daphne penicillate. Compound 1 may be derived...

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

“…The detailed ECD and NMR calculation processes have been described in previous reports. 24,25,[30][31][32]…”

“…[24][25][26] Our previous study on this herb has also resulted in the identification of a variety of novel sesquiterpenes, including one unique caged tetracyclic sesquiterpene (daphnenoid A), 24 two unprecedented 5/5 fused spirocyclic sesquiterpenes (daphnenoids B-C), 24 and a series of guaiane-type sesquiterpene derivatives. 25 Not only their unusual structures and potential biological activities but also the challenges of their total synthesis to complete these contiguous chiral centers have attracted wide attention from chemical researchers. [27][28][29] In our efforts to discover more novel and bioactive sesquiterpenes, 11 diverse sesquiterpenes, including six undescribed carotene sesquiterpenes (1)(2)(3)(4)(5)(6) and three undescribed rearranged guaiane sesquiterpenes with rare 5/6/5 tricyclic systems (7)(8)(9) were obtained from Daphne penicillata.…”

“…23 Daphne penicillata Rehd., a previously little-studied species, is mainly distributed in the Sichuan province of China. 24–26 Our previous study on this herb has also resulted in the identification of a variety of novel sesquiterpenes, including one unique caged tetracyclic sesquiterpene (daphnenoid A), 24 two unprecedented 5/5 fused spirocyclic sesquiterpenes (daphnenoids B-C), 24 and a series of guaiane-type sesquiterpene derivatives. 25 Not only their unusual structures and potential biological activities but also the challenges of their total synthesis to complete these contiguous chiral centers have attracted wide attention from chemical researchers.…”

Rapid screening of unprecedented sesquiterpenes with distinctive ring skeletons from Daphne aurantiaca employing an integrated strategy

“…As the major bioactive components of the genus Daphne, these compounds usually exhibit diverse biological properties, especially cholinesterase (ChE) inhibitory, neuroprotective, and anti-neuroinflammatory activities. [1][2][3] Rearrangement, oxidative cleavage, and aldol condensation occurring spontaneously at multiple sites of the structure typically, operated by the energy derived from the enzymatic catalysis of spontaneous reactions, immensely increase the structural diversity of natural guaiane-type sesquiterpenoids. [4][5][6][7][8] The unusual rearranged and highly oxygenated structural features make us take a fresh look at efficient strategies for precision mining of novel skeletal structures with promising pharmacological activities.…”

Discovery of the Caged-Vibsane Norditerpenoids with Unprecedented Chemical Architectures and Exploration of Their Various Acid Tolerances

“…As a consequence of the continuous investigation on Viburnum odoratissimum , four unique VibDs, cyclovibsanones A–D sharing the same molecular weight, were target-isolated by GNPS-guided separation (Figure B and Figure S1). − Although ≤113 VibDs with diverse structures have been identified so far, 1 – 3 represent the first examples of VibDs featuring unique [5.4.1.0 5,9 ]­dodecane cores. − Their structures were identified via multiple spectroscopic analyses, quantum chemical calculations, and one emerging machine learning method, ML- J DP4, combined with MAE ΔΔδ methods. , In addition, epimers 1 and 2 were discovered to possess acid stability dissimilarities during nuclear magnetic resonance (NMR) experiments. Compound 2 was found to be readily converted to 5 , while 1 was relatively stable.…”