The elucidation of the structure of thalicoside F, A minor oleanane glycoside from Thalictrum minus L

Natural products from medicinal plants: non-alkaloidal natural constituents of the Thalictrum species

“…Pentacyclic saponins (Table 5) of the Thalictrum genus belong to the oleanane type only. 65 Saponins based on oleanolic acid (Table 6) 49 ; those based on 2a,3b-diacetoxy-30-hydroxyolean-24-en-28-oic acid include a bioside 61 69 ; those based on hederagenin include a tetraoside 62, 57 and a pentaoside 63 57 ; while those based on 11a, 12a-epoxyolean-28,13b-olid include a trioside 64. Free pentacyclic genins have been found in two Thalictrum species, namely oleanolic acid (48) and maslinic acid (49) in T. aquilegifolium 64 and oleanolic acid in T. minus.…”

“…It is worth noting that oleanolic acid is the most widely distributed pentacyclic triterpenoid isolated from plants. 70 The saponins' novelty lies in the structures of the carbohydrate chains. 65 Saponins based on oleanolic acid (Table 6) 49 ; those based on 2a,3b-diacetoxy-30-hydroxyolean-24-en-28-oic acid include a bioside 61 69 ; those based on hederagenin include a tetraoside 62, 57 and a pentaoside 63 57 ; while those based on 11a, 12a-epoxyolean-28,13b-olid include a trioside 64.…”

“…Free pentacyclic genins have been found in two Thalictrum species, namely oleanolic acid (48) and maslinic acid (49) in T. aquilegifolium 64 and oleanolic acid in T. minus. 65 Saponins based on oleanolic acid (Table 6) include a monoside 50, 65 a bioside 51, 65 triosides 52 and 53, 65 tetraosides 54, 66 55, 49 and pentaosides 56-59 49,65,67,68 and 60 49 ; those based on 2a,3b-diacetoxy-30-hydroxyolean-24-en-28-oic acid include a bioside 61 69 ; those based on hederagenin include a tetraoside 62, 57 and a pentaoside 63 57 ; while those based on 11a, 12a-epoxyolean-28,13b-olid include a trioside 64. 70 The saponins' novelty lies in the structures of the carbohydrate chains.…”

“…65 Saponins based on oleanolic acid (Table 6) include a monoside 50, 65 a bioside 51, 65 triosides 52 and 53, 65 tetraosides 54, 66 55, 49 and pentaosides 56-59 49,65,67,68 and 60 49 ; those based on 2a,3b-diacetoxy-30-hydroxyolean-24-en-28-oic acid include a bioside 61 69 ; those based on hederagenin include a tetraoside 62, 57 and a pentaoside 63 57 ; while those based on 11a, 12a-epoxyolean-28,13b-olid include a trioside 64. 70 The saponins' novelty lies in the structures of the carbohydrate chains. Bisdesmosides usually occur among Thalictrum pentacyclic saponins, while tetraosides and pentaosides are widely distributed, having oleanolic acid as the genin.…”

“…It is interesting to note that from 15 oleanane glycosides there are just two whose genins have nontrivial structures: diacyl genin in 61 (T. aquilegifolium) 69 and a derivative of oleanolic acid (64) which possesses a 11a,12a-epoxy ring and 28,13b-clactone ring (T. minus). 70 The carbohydrate part of the pentacyclic glycosides has the following sugars: D-glucose, L-rhamnose, Dxylose and L-arabinose in pyranose form only.…”