Scapiformolactones A-I: germacrane sesquiterpenoids with an unusual Δ3-15,6-lactone moiety from Salvia scapiformis.

Nine germacrane sesquiterpenoids with an unusual Delta(3)-15,6-lactone moiety, scapiformolactones A-I (1-9), and one known seco-germacrane sesquiterpenoid, 3,7,11-trimethyldodeca-1,6,9-triene-3,11-diol (10), were isolated from whole plants of Salvia scapiformis Hance. Their structures were elucidated by spectroscopic methods including HR-ESIMS, IR, UV, NMR, and CD, as well as by quantum mechanical calculations and chemical transformations. Structures of compounds 1-3 were also confirmed by single-crystal X-ray diffraction analysis. Six germacrane 6,15-diol derivatives (11-16) were obtained by chemical transformation. Compounds 1-9 and 11-16 were evaluated for their in vitro immunomodulatory effects on T and B cells, as well as their in vitro cytotoxicity against five human cancer cell lines, HL-60, SMMC-7721, A-549, MCF-7, and SW480. (C) 2013 Elsevier Ltd. All rights reserved.