Euphopias A–C: Three Rearranged Jatrophane Diterpenoids with Tricyclo[8.3.0.0^2,7]tridecane and Tetracyclo[11.3.0.0^2,10.0^3,7]hexadecane Cores from Euphorbia helioscopia

Abstract

Euphopias A–C (1–3), three rearranged jatrophane-type diterpenoids with tricyclo­[8.3.0.02,7]­tridecane (1 and 2) and tetracyclo­[11.3.0.02,10.03,7]­hexadecane (3) cores, were isolated from Euphorbia helioscopia. Comprehensive spectroscopic analyses, quantum-chemical calculations, and X-ray diffractions were used to identify their structures. Compounds 1–3 could significantly inhibit NLRP3 inflammasome activation and block NLRP3 inflammasome-induced pyroptosis. Additionally, a mechanistic study revealed that 2 could ameliorate mitochondria damage, thereby interrupting NLRP3 inflammasome activation.

Jatrophane Diterpenoids with Kv1.3 Ion Channel Inhibitory Effects from Euphorbia helioscopia

“…Helioscopid A (2), colorless crystals, gave a molecular formula of C 33 H 42 O 10 as determined by its HRESIMS ion peak at m/z 621.2654 [M + Na] + (calcd for C 33 H 42 O 10 Na, 621.2670). The 1 H and 13 C NMR spectra (Table 1) of 2 indicated the presence of one benzoyloxy group and three Table 1. 1 H (500 MHz) and 13 C NMR (125 MHz) Data of Compounds 1−3 in CDCl 3 (J in Hz) no HMBC correlation was found between the carbonyl carbon at δ C 171.3 and any proton from the jatrophane skeleton, the remaining −OAc group could only be placed at the oxygenated quaternary carbon C-15 rather than at C-11.…”

“…The 1 H and 13 C NMR spectra (Table 1) of 2 indicated the presence of one benzoyloxy group and three Table 1. 1 H (500 MHz) and 13 C NMR (125 MHz) Data of Compounds 1−3 in CDCl 3 (J in Hz) no HMBC correlation was found between the carbonyl carbon at δ C 171.3 and any proton from the jatrophane skeleton, the remaining −OAc group could only be placed at the oxygenated quaternary carbon C-15 rather than at C-11. Thus, the planar structure of compound 2 could be established.…”

Metal-Free Intramolecular [3+2] Cycloaddition of γ-Hydroxy Acetylenic Ketones with Alkynes for the Synthesis of Naphtho[1,2-c]furan-5-ones and Its Derivatization via a Selective C(sp2)–H Deuteration Reaction

“…In addition, the reactions of 1h and 1i granted [3+2] cycloaddition products 2h and 2i as well as dehydro Diels–Alder products 2h′ and 2i′ in similar yields. Next, we investigated the reactions of substrates 1j–1n , possessing methoxyl, methyl, and halo substituents on R . They could proceed smoothly and afford the desired naphtho­[1,2- c ]­furanones 2j–2n in moderate to good yields.…”

“…The hydronaphthofuranone and hydronaphthofuran skeletons are the core structures of many important naturally occurring and biologically active substances (Figure ). For example, Rubipodanone B exhibited cytotoxicity and NF-κB inhibitory activity . Rubioncolin B is isolated from the roots of Rubia cotricha .…”

Ecdysteroids from the Aerial Parts of Paris verticillata

“…NMR calculation of 1–2 were calculated with the GIAO method at mPW1PW91/6‐31G*//B3LYP/6‐31G* (in gas phase) and mPW1PW91/6‐31G**//B3LYP/6‐31G* levels (in methanol with PCM model). The shielding constants (including 13 C and 1 H) obtained were directly performed statistical analyses with experimental chemical shifts by using DP4 + probability [19] and ANN‐PRA [20–22] with C−H COSY simulation.…”