147802-41-3Relevant academic research and scientific papers
Three novel furospirostanol glycosides and a steroidal alkaloid glycoside from the bulbs of Fritillaria camtschatcensis (L.) Ker Gawl., and their cytotoxicity
Iguchi, Tomoki,Kuroda, Minpei,Takayama, Hiroshi,Mimaki, Yoshihiro
, (2021)
Three novel steroidal glycosides (1–3) and a previously described steroidal alkaloid glycoside (4) have been isolated from the bulbs of Fritillaria camtschatcensis (L.) Ker Gawl. (Liliaceae). The structures of novel compounds 1–3 were characterized based on NMR spectroscopy and chemical transformations. Compounds 1–3 are furospirostanol glycosides bearing a (3S)-3-hydroxy-3-methylglutaryl moiety at C-26 in the aglycone. Compounds 1–4 were evaluated in terms of their cytotoxic activities toward HL-60 human promyelocytic leukemia cells, A549 human lung adenocarcinoma cells, and SBC-3 human lung small cell carcinoma cells. Only 4 showed moderate cytotoxicity against HL-60, A549, and SBC-3 cells with IC50 values of 22.9, 13.3, and 11.9 μM, respectively. Compound 4 was found to cause necrotic-like cell death in HL-60 cells.
STEROIDAL SAPONINS FROM THE BULBS OF LILIUM REGALE AND L. HENRYI
Mimaki, Yoshihiro,Sashida, Yutaka,Nakamura, Osamu,Nikaido, Tamotsu,Ohmoto, Taichi
, p. 675 - 682 (1993)
Two new and three known steroidal saponins were isolated from the fresh bulbs of Lilium regale and two known saponins from those of L. henryi.The structures of the new saponins were established by extensive spectral data, hydrolysis and chemical correlation as (25R)-27-O--spirost-5-ene-3β,27-diol 3-O-α-L-rhamnopyranosyl-(1->2)-O-3)>-β-D-glucopyranoside and (25S)-spirost-5-ene-3β,17α,27-triol 3-O-α-L-rhamnopyranosyl-(1->2)-O-2)-O-β-D-glucopyranosyl-(1->4)>-β-D-glucopyranoside.Inhibitory activity of the saponins on cyclic AMP phosphodiesterase was evaluated.Key Word Index - Lilium regale; L. henryi; Liliaceae; bulbs; steroidal saponins; 3-hydroxy-3-methylglutaric acid; cyclic AMP phosphodiesterase; inhibitory activity.
A new reagent for the preparation of chiral HMGA (3-hydroxy-3-methylglutaric acid) esters and amides. Synthesis of (R)- and (S) -β-carboxymethyl-β-methyl-β-lactones by asymmetric desymmetrization of HMGA anhydride
Hashimoto, Kimiko,Kitaguchi, Jun-Ichi,Mizuno, Yasuhiro,Kobayashi, Tadao,Shirahama, Haruhisa
, p. 2275 - 2278 (2007/10/03)
(R)- and (S)-βarboxymethyl-β-methyl-β-lactones, new reagents for the preparation of chiral HMGA (3-hydroxy-3-methylglutaric acid) esters and amides were developed through the asymmetric desymmetrization of HMGA anhydride. The reagent was smoothly reactedwith various alkoxide without racemization to afford the desirable half-esters. On the other hand, the reaction with various amine in refluxing toluene gave a racemic amide. The chiral HMGA amide was prepared using the corresponding methyl ester of the reagent.
