14,15-Secopregnane-type C 21 -steriosides from the roots of Cynanchum stauntonii

14,15-Secopregnane-Type Glycosides with 5α:9α-Peroxy and Δ6,8(14)-diene Linkages from the Roots of Cynanchum stauntonii

“…This finding provided evidence supporting the application of C. stauntonii in some traditional medicine systems to treat inflammations [ 3 , 13 , 14 ]. Following the isolation and identification of several steroidal glycosides from the roots of C. stauntonii sharing the first reported aglycones of 8α:14α,14:16,15:20,18:20-tetraepoxy-14,15-secopregn-6-ene-3β,5α,9α-triol or its 5α:9α-peroxy bridge structure [ 3 ], our ongoing searches for new steroids in the same subjects lead to the isolation of three new steroidal glycoside, stauntosides UA, UA 1 , and UA 2 ( 1 – 3 ) ( Figure 1 ). Structural identification affirmed that stauntosides UA, UA 1 , and UA 2 shared an aglycone of 3β-hydroxy-5α:9α-peroxy-14:16,15:20,18:20-triepoxy-14,15-secopregnane-6, 8(14)-diene, similar to, but somewhat different from the aforementioned first reported aglycones.…”

“…The natural resource of this class of steroids is very affluent in the plant world, with both sugar-free and glycosidated pregnane-type steroids having been isolated by many researchers through phytochemical methods. In addition to the usual four-ring C 21 -pregnane-type skeleton, there are also several unusual skeletons, such as the 8,14-seco-C 21 -pregnane-type, 14,15-seco-C 21 -pregnane-type, and 13,14:14,15-diseco-C 21 -pregnane-type skeletons, all of these usual and unusual skeletons possessing multiple stereogenic centers and other structural diversities [ 1 , 2 , 3 ]. It is well known that the Cynanchum species of the Asclepiadaceae family are very rich in C 21 -steroids, with the unusual 14,15-seco-C 21 -pregnane-type and 13,14:14,15-diseco-C 21 -pregnane-type skeletons being most often discovered in previous investigations [ 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 ].…”

“…Schltr. ex Levl., a perennial medicinal herb naturally growing in the south-central region of China, showed anti-inflammatory activity [ 3 ]. This finding provided evidence supporting the application of C. stauntonii in some traditional medicine systems to treat inflammations [ 3 , 13 , 14 ].…”

“…ex Levl., a perennial medicinal herb naturally growing in the south-central region of China, showed anti-inflammatory activity [ 3 ]. This finding provided evidence supporting the application of C. stauntonii in some traditional medicine systems to treat inflammations [ 3 , 13 , 14 ]. Following the isolation and identification of several steroidal glycosides from the roots of C. stauntonii sharing the first reported aglycones of 8α:14α,14:16,15:20,18:20-tetraepoxy-14,15-secopregn-6-ene-3β,5α,9α-triol or its 5α:9α-peroxy bridge structure [ 3 ], our ongoing searches for new steroids in the same subjects lead to the isolation of three new steroidal glycoside, stauntosides UA, UA 1 , and UA 2 ( 1 – 3 ) ( Figure 1 ).…”

New Immunomodulating Polyhydroxypregnane Glycosides from the Roots of Cynanchum otophyllum C.K.Schneid.

“…The existence of one β-cymaropyranoside (δ(C) 34.3 C-2''), one α-cymaropyranoside (δ(C) 32.4 C-2'''') and one αdiginopyranoside (δ(C) 31.6 C-2''') unit was confirmed by co-TLC of the acid hydrolysate with the standard sugars and comparison of its spectroscopic data with those in the literatures. [11,17] The sugar sequence of 1 was revealed by the HMBCs of H…”