Cytotoxic triterpenoid saponins from Thalictrum atriplex
摘要:
Two new cycloartane glycosides, cycloatriosides A and B (1-2), and a new oleanolic acid glycoside, thaliatrioside A (3), along with7known triterpenoids (4-10) were isolated fromThalictrum atriplex. The structures of the new compounds were established as 3-O-beta-D-galactopyranosyl (20S, 24 R)-3 beta,16 beta,25,29-tetrahydroxy-20,24-epoxycycloartane-29-O-beta-D-glucopyranoside (1), 3-O-beta-D-glucopyranosyl-(1 -> 2)-alpha-arabinopyranosyl-3 beta,22 xi,30-trihydroxycycloart-24-en-21-oic acid alpha-L-arabinopyranosyl-(1 -> 6)-beta-D-glucopyranoside (2) and 3-O-[alpha-L-rhamnopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl]-oleanolic acid 28-O-beta-D-glucopyranosyl ester (3) on the basis of extensive NMR and HR-ESI-MS analyses, along with acid hydrolysis. Their cytotoxic activities against human lung cancer cells A549 and human breast cancer cells MDA-MB-231 were evaluated using MTT method. Compound9showed cytotoxicity against MDA-MB-231 cell line with the IC(50)value of 72.53 +/- 1.08 mu M.
New steroidal glycoside 1 was isolated by fractionation of total extracted compounds from rhizomes of Polygonatum verticillatum (Convallariaceae). Chemical transformations, physical constants, and spectral data characterized its structure as (25S)-spirost-5-en-3β-ol 3-O-β-D-glucopyranosyl-(1→3)-[β-Dfucopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside.
Compounds, compositions, and methods for “smart” delivery of a therapeutic, prophylactic or diagnostic agent, such as glucose-mediated delivery of insulin through glucose-sensing insulin derivatives, are provided. The insulin derivatives bind serum albumin or agglomerate in vivo. The insulin derivatives effectively dissociate to release insulin in a hyperglycemic condition, where the complexation of glucose to a glucose-sensing element alters properties of the insulin derivative leading to the dissociation. The compounds, compositions, and methods provide a delivery strategy for both self-regulated and long-term diabetes management.
[EN] INSULIN DERIVATIVES FOR DIABETES TREATMENT<br/>[FR] DÉRIVÉS D'INSULINE POUR LE TRAITEMENT DU DIABÈTE
申请人:MASSACHUSETTS INST TECHNOLOGY
公开号:WO2014093696A2
公开(公告)日:2014-06-19
Compounds, compositions, and methods for "smart" delivery of a therapeutic, prophylactic or diagnostic agent, such as glucose-mediated delivery of insulin through glucose-sensing insulin derivatives, are provided. The insulin derivatives bind serum albumin or agglomerate in vivo. The insulin derivatives effectively dissociate to release insulin in a hyperglycemic condition, where the complexation of glucose to a glucose-sensing element alters properties of the insulin derivative leading to the dissociation. The compounds, compositions, and methods provide a delivery strategy for both self-regulated and long-term diabetes management.
Cytotoxic triterpenoid saponins from <i>Thalictrum atriplex</i>
Two new cycloartane glycosides, cycloatriosides A and B (1-2), and a new oleanolic acid glycoside, thaliatrioside A (3), along with7known triterpenoids (4-10) were isolated fromThalictrum atriplex. The structures of the new compounds were established as 3-O-beta-D-galactopyranosyl (20S, 24 R)-3 beta,16 beta,25,29-tetrahydroxy-20,24-epoxycycloartane-29-O-beta-D-glucopyranoside (1), 3-O-beta-D-glucopyranosyl-(1 -> 2)-alpha-arabinopyranosyl-3 beta,22 xi,30-trihydroxycycloart-24-en-21-oic acid alpha-L-arabinopyranosyl-(1 -> 6)-beta-D-glucopyranoside (2) and 3-O-[alpha-L-rhamnopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl]-oleanolic acid 28-O-beta-D-glucopyranosyl ester (3) on the basis of extensive NMR and HR-ESI-MS analyses, along with acid hydrolysis. Their cytotoxic activities against human lung cancer cells A549 and human breast cancer cells MDA-MB-231 were evaluated using MTT method. Compound9showed cytotoxicity against MDA-MB-231 cell line with the IC(50)value of 72.53 +/- 1.08 mu M.