Propindilactones E−J, Schiartane Nortriterpenoids from Schisandra propinqua var. propinqua

Abstract

Six new nortriterpenoids, propindilatones E-J (1-6), and two known (7, 8) schiartane-type nortriterpenoids were isolated from the stems of Schisandra propinqua var. propinqua. Their structures were elucidated by extensive spectroscopic analyses, and the structure of compound 4 was confirmed through single-crystal X-ray diffraction. The absolute configuration of compounds 1-3 was established using CD methods. Compounds 4-6 were noncytotoxic against K562, A549, and HT-29 human cancer cells.

Asymmetric Total Synthesis of Propindilactone G

“…To complete the total synthesis, we expected that one of the four isomers mentioned above could undergo an OsO 4 -mediated regio-and stereo-selective dihydroxylation, and the resulting intermediate might undergo an intramolecular lactonization to afford the natural product. 1 and its structure has been confirmed by X-ray crystallographic analysis. Thus, as a consequence of our synthetic studies, the structure of (+)-propindilactone G has been revised as compound 1 and the originally proposed structure of propindilactone G has been reassigned as 1b (C17-epi-(+)-propindilactone G) (see Chart 1).…”

Triterpenoids from the Schisandraceae family: an update

“…20 The stereogenic centers in the side chain of propindilactone H (128) were conrmed by X-ray diffraction unambiguously. 43 From a biogenetic point of view, the schiartane skeleton is considered the biogenetic origin of other schinortriterpenoids since it mainly preserves the structural cycloartane core.…”

“…23 Schiglausins D-G (41)(42)(43)(44) and N (78) show weak inhibitory activities against the Farnesoid X receptor at a 25 mM concentrations, with higher than 20% inhibition. 21,35 Furthermore, schiglausins D (41) and N (78) have estrogen receptor beta (ERb) antagonistic activity, with EC 50 values of 25.300 AE 3.100 and 4.680 AE 0.360 mM, respectively.…”

Two New Compounds from Schisandra propinqua var. propinqua

“…propinqua is indigenous in Yunnan Province. Previous chemical investigation into this species has led to the identification of a series of new terpenoids and lignans, such as propindilactones E-O [5, 6], lanopropic acid [7], methylisogomisin O [8], and propindilactones T and U [9]. Our further study on this species, which was collected from Weixi county, Yunnan Province, People’s Republic of China to discover new compounds with interesting bioactivity led to the discovery of a new sesquiterpenoid and a new lignan (Fig.…”