Stelleratenoids A-F, macrocyclic daphnane orthoesters with anti-HIV activity from the roots of Stellera chamaejasme L.

Six undescribed macrocyclic daphnane orthoesters, stelleratenoids A-F (1-6), were isolated from the roots of Stellera chamaejasme L. Their structures were elucidated by extensive spectroscopic analyses, including HRESIMS and NMR spectra. Compound 1 features an unusual terminal double bond at C-2/C-19 in the 1 alpha-alkyldaphnane lactone skeleton. Compounds 2-4 are unique in the presence of different long chain fatty acyl groups. Com-pounds 5 and 6 are unique examples of modified macrocyclic daphnane diterpenoids. All the isolates were evaluated for anti-HIV activity in MT-2 cells. Among them, compounds 1, 5 and 6 exhibited highly potent anti -HIV activity with EC50 values of 66.70, 10.62 and 55.10 nM, respectively, possessing high potential to develop new anti-HIV drugs.

Automated summary

Six undescribed macrocyclic daphnane orthoesters, stelleratenoids A-F (1-6), were obtained from the roots of Stellera chamaejasme L. Their structures were determined using extensive spectroscopic analyses. Compound 1 exhibited an unusual terminal double bond, while compounds 2-4 had different long chain fatty acyl groups and compounds 5 and 6 were modified macrocyclic daphnane diterpenoids. Compounds 1, 5, and 6 showed potent anti-HIV activity, indicating potential for the development of new anti-HIV drugs.