Stelleralides D–J and Anti-HIV Daphnane Diterpenes from Stellera chamaejasme

Abstract

Bioassay-guided fractionation of a petroleum ether extract of the roots of Stellera chamaejasme led to the isolation of seven new (stelleralides D–J, 1–7) and 12 known (8–19) daphnane diterpenoids. The structures and relative configurations of 1–7 were established on the basis of extensive spectroscopic analysis, including HRESIMS and comprehensive NMR techniques. All isolates were evaluated for anti-HIV activity in MT4 cells. All compounds tested, except 2, showed anti-HIV activity, and, especially, five 1α-alkyldaphnane diterpenoids (3, 4, 5, 10, and 11) exhibited extremely potent anti-HIV activity, with EC50 values of 0.06–1.1 nM and selectivity index values of more than 10 000.

Extract of Stellera Chamaejasme L. Inhibits the Progression of Hepatocellular Carcinoma by Regulating miR-134-5p and JAK1/STAT3 Pathway

“…ESC is widely utilized in traditional Chinese medicine and confirmed to possess antibacterial, 24 antivirus, 25 and antitumors activities. 6,7 To explore the effects of ESC on HCC progression, the authors first detected its cytotoxicity to HCC cells and found that ESC inhibited cell proliferation in a dose-and time-dependent manner, and cell sur-vival rate had a sharp downtrend at 20 lg/mL ESC.…”

Natural Products Research in China From 2015 to 2016

“…Seven novel daphnane diterpenoids, stelleralides D–J, were obtained from the roots of Stellera chamaejasme (Baotou, Inner Mongolia, China). Stelleralides F ( 413 ), G ( 414 ), and H ( 415 ) exhibited anti-HIV activities with EC 50 values of 0.93, 0.73, and 0.98 nM and SI values of >10,000, much more potent than zidovudine (EC 50 32 nM, SI ≥ 116) (Yan et al, 2015a ). Seven filicinic acid-based meroterpenoids comprised 6/6/11, 6/6/7/5, or 6/6/10 ring systems were obtained from Hypericum japonicum .…”

Diterpenoids of terrestrial origin

“…Molecular modeling and advanced NMR methods have been used in locating esters in the jatrophanes of Euphorbia amydaloides. 180 192 Daphne genkwa (Thymelaeaceae), 193 Gnidia polycephela (Thymelaeaceae), 194 and Stellera chamaejasme (Thymelaeaceae) 195 whilst some more tigliane (phorbol) esters with cytotoxic and anti-viral activity were obtained from Croton tiglium (Euphorbiaceae), 196,197 Daphne aurantica, 198 and Stillingia lineata (Euphorbiaceae). 199 The anti-viral activity of these compounds (e.g.…”