Triterpenoids From Kadsura coccinea With Their Anti-inflammatory and Inhibited Proliferation of Rheumatoid Arthritis-Fibroblastoid Synovial Cells Activities
Yupei Yang, Yuqing Jian, Yongbei Liu, Muhammad Ismail, Qingling Xie, Huanghe Yu, Bin Wang, Bin Li, Caiyun Peng, Bin Liu, Rongyong Man, Wei Wang
Abstract
One new 3,4- seco -17,13-friedo-lanostane triterpenoid heilaohuacid A ( 1 ), one new 3,4- seco -17,14-friedo-lanostane triterpenoid heilaohuacid B ( 2 ), five new 3,4 -seco -lanostane triterpenoids heilaohuacids C-D ( 3–4 ) and heilaohumethylesters A-C ( 7–9 ), one new 3,4- seco -cycloartane triterpenoid heilaohuacid E ( 5 ), and one new intact -lanostane triterpenoid heilaohuacid F ( 6 ), together with twenty-two known analogues ( 10–31 ), were isolated from heilaohu. Their structures were determined using HR-ESI-MS data, 1D and 2D NMR spectra, 13 C NMR calculations, and electronic circular dichroism (ECD) calculations. Heilaohuacids A and B ( 1 and 2 ) contain a 3,4- seco ring A and unprecedented migration of Me-18 from C-13 to C-17 or C-14 to C-18. This type of lanostane triterpenoid derivatives was rarely reported so far. More importantly, all compounds against inflammatory cytokines IL-6 and TNF-α levels on LPS-induced RAW 264.7 macrophages were evaluated, and compounds 4 and 31 significantly inhibited the release level of IL-6 with IC 50 values of 8.15 and 9.86 μM, respectively. Meanwhile, compounds 17, 18, and 31 significantly inhibited proliferation of rheumatoid arthritis-fibroblastoid synovial (RA-FLS) cells in vitro with IC 50 values of 7.52, 8.85, and 7.97 μM, respectively.