1.Labdane diterpenes from the rhizomes of Hedychium coronarium.
Chimnoi N1, Pisutjaroenpong S, Ngiwsara L, Dechtrirut D, Chokchaichamnankit D, Khunnawutmanotham N, Mahidol C, Techasakul S. Nat Prod Res. 2008;22(14):1249-56. doi: 10.1080/14786410701726434.
A new labdane diterpenoid, (E)-labda-8(17),12-dien-15,16-olide (1) together with eight known compounds, coronarin D (2), coronarin D methyl ether (3), coronarin D ethyl ether (4), isocoronarin D (5), coronarin B (6), labda-8(17),11,13-trien-15,16-olide (7), (E)-labda-8(17),12-diene-15,16-dial (8) and 16-hydroxylabda-8(17),11,13-trien-15,16-olide (9), are isolated from the rhizomes of Hedychium coronarium. Compounds 2-4, 5 and 9 are isolated as mixtures of C-15, C-14 and C-16 epimers, respectively. Their structures are determined on the basis of their spectroscopic data. The epimeric mixtures of 2 and 3 have not been reported before. Some of them were evaluated for their cytotoxicity.
2.Amomaxins A and B, two unprecedented rearranged labdane norditerpenoids with a nine-membered ring from Amomum maximum.
Yin H1, Luo JG, Shan SM, Wang XB, Luo J, Yang MH, Kong LY. Org Lett. 2013 Apr 5;15(7):1572-5. doi: 10.1021/ol400348a. Epub 2013 Mar 8.
Amomaxins A (1) and B (2), featuring an unprecedented rearranged labdane norditerpene skeleton with a nine-membered ring, along with their biosynthetic related known compound isocoronarin D (3) were isolated from the roots of Amomum maximum. Their structures with absolute configurations were determined by spectroscopic data, CD experimentation, and single-crystal X-ray diffraction. Compound 2 showed an inhibitory effect on nitric oxide (NO) production in lipopolysaccharide-induced RAW264.7 macrophages.
3.Isolation and identification of ingredients inducing cancer cell death from the seeds of Alpinia galanga, a Chinese spice.
Zeng QH1, Lu CL, Zhang XW, Jiang JG. Food Funct. 2015 Feb;6(2):431-43. doi: 10.1039/c4fo00709c.
This study was carried out to isolate ingredients from the seeds of a Chinese spice (Alpinia galangal) and to evaluate their cytotoxic activity on cancer cell lines. Isolation and purification of the phytochemical constituents were conducted using silica gel, Sephadex LH-20 and ODS columns. After extraction using 95% ethanol, the total extracts were re-extracted, resulting in petroleum ether (PE), ethyl acetate (EA) and water fractions, respectively. Activity tests showed that the EA fraction exhibited obvious (p < 0.05) protective effects on H2O2 damaged PC-12 cells at 20 μg mL(-1), and showed much higher (p < 0.05) cytotoxic activity on cancer cell lines than other fractions. Five compounds, 1'-S-1'-acetoxyeugenol acetate (I), 1'-S-1'-acetoxychavicol acetate (II), 2-propenal, 3-[4-(acetyloxy)-3-methoxyphenyl] (III), isocoronarin D (IV) and caryolane-1, 9β-diol (V), were obtained from the EA fraction and identified by HPLC, UV, MS, and NMR spectroscopic analyses.
4.Labdane diterpenes from the aerial parts of Curcuma comosa enhance fetal hemoglobin production in an erythroid cell line.
Chokchaisiri R1, Chaneiam N, Svasti S, Fucharoen S, Vadolas J, Suksamrarn A. J Nat Prod. 2010 Apr 23;73(4):724-8. doi: 10.1021/np900568k.
Three new labdane diterpenes, curcucomosins A-C (1-3), four known labdane diterpenes, 4-7, and a known diarylheptanoid, 8, were isolated from the aerial parts of Curcuma comosa. The structures of the new diterpenes were elucidated by spectroscopic data analysis. The fetal hemoglobin (Hb F) induction potency of the isolated compounds was examined using a K562 reporter cell line harboring the enhanced green fluorescence protein (EGFP) gene under the control of a (G)gamma-globin promoter. Compound 6, isocoronarin D, exhibited the highest Hb F induction effect of 1.6-fold at 20 microM.