Saponins from the seeds of Mimusops laurifolia.

Nine saponins were isolated from the seeds of Mimusops laurifolia. Their structures were established using one- and two-dimensional NMR spectroscopy and mass spectrometry. Three of them are identified as: 3-O-(beta-d-apiofuranosyl-(1-->3)-beta-d-glucuronopyranosyl)-28-O-(alpha-l-rhamnopyranosyl-(1-->3)-beta-d-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-arabinopyranosyl)-16alpha-hydroxyprotobassic acid, 3-O-(beta-d-glucopyranosyl-(1-->3)-beta-d-glucopyranosyl)-28-O-(alpha-l-rhamnopyranosyl-(1-->3)-beta-d-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-arabinopyranosyl)-16alpha-hydroxyprotobassic acid and 3-O-(beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranosyl)-28-O-(alpha-l-rhamnopyranosyl-(1-->3)-beta-d-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-arabinopyranosyl)-16alpha-hydroxyprotobassic acid.

Saponins and acylated saponins from Dizygotheca kerchoveana.

Four new triterpenoid saponins were isolated from the leaves and stem of branches of Dizygotheca kerchoveana along with seven known ones. The new saponins were respectively characterized as 3-O-[beta-D-glucopyranosyl-(1-->3)]-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl echinocystic acid, 3-O-[beta-D-glucopyranosyl-(1-->3)]-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl echinocystic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester, 3-O-[beta-D-3-O-trans-p-coumaroyl-glucopyranosyl-(1-->3)]-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl echinocystic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester and 3-O-[beta-d-3-O-cis-p-coumaroyl-glucopyranosyl-(1-->3)]-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl echinocystic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester. Their structures were elucidated by 1D and 2D NMR experiments, FAB-MS as well as chemical means.

New steroidal saponins from Agave lophantha Schiede and their pharmacological evaluation.

The structures of one new monodesmosidic spirostanoside and one new bisdesmosidic furanostanol glycoside isolated from leaves of Agave lophantha Schiede have been determined by means of spectroscopic and chemical methods as (25R)-5 beta-spirostan-3 beta-ol-3-O-(beta-D-apiofuranosyl(1-->4)beta-D -glucopyranosyl(1-->3)[beta-D-glucopyranosyl(1-->2)]beta-D -galactopyranoside) and 26-O-beta-D-glucopyranosyl(25R)-5 beta-furost-20(22)-ene-3 beta, 26-diol-3-O-(beta-D-xylopyranosyl(1-->3)-[beta-D-glucopyranosyl(1--2)] beta-D-galactopyranoside), respectively. The 1H and 13C NMR resonances of the two compounds were assigned by NMR (1H, 13C, HOHAHA, 1H-1H COSY, HMQC, HMBC, NOE difference) studies. The pharmacological activities of the saponin containing fraction are discussed.

Triterpenoid saponins from Oreopanax guatemalensis.

Seven oleanane-type saponins were isolated from the leaves and stems of Oreopanax guatemalensis, together with ten known saponins of lupane and oleanane types. The new saponins were respectively characterized as 3-O-alpha-L-arabinopyranosyl echinocystic acid 28-O-[alpha- L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester, 3-O-beta-D-glucopyranosyl 3beta-hydroxy olean-11,13(18)-dien-28-oic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta- D-glucopyranosyl]ester, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl]3beta-hydroxy olean-11,13(18)-dien-28-oic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl]3beta, 23 dihydroxy olean-18-en-28-oic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-6-O-acetyl glucopyranosyl-(1-->6)-beta-D-glucopyranosyl]ester, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl] hederagenin 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-[beta-D-xylopyranosyl-(1-->2 )-]beta-D-glucopyranosyl]ester, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl]hederagenin 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-[beta-D-glucopyranosyl-(1-->2)-]beta-D-glucopyranosyl] ester and 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl] hederagenin 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-[alpha-L-arabinofuranosyl-(1-->2)]-beta-D-glucopyranosyl] ester. The structures were determined by spectral analyses. The NMR assignments were made by means of HOHAHA, 1H-1H COSY, HMQC, HMBC spectra and NOE difference studies.

Further saponins from Fagonia cretica.

Three triterpenoid saponins including two new ones were isolated and identified from the aerial parts of Fagonia cretica. The new saponins were characterized as 3-O-[beta-D-xylopyranosyl(1-->2)alpha-L-arabinopyranosyl]27-hydroxyoleanolic acid 28-O-[beta-D-glucopyranosyl(1-->6)beta-D-glucopyranosyl]ester and 3 beta-O-[beta-D-xylopyranosyl(1-->2)alpha-L-arabinopyranosyl] olean-12-en-27-al-28-oic acid 28-O-[beta-D-glucopyranosyl(1-->6)beta-D-glycopyranosyl] ester. The structures were determined by spectral analyses. The NMR assignments were made by means of HOHAHA, 1H-1H COSY, HMQC, HMBC spectra and NOE studies.

Saponins from Fagonia glutinosa.

Twelve triterpenoid saponins, including six new, were isolated and identified from the aerial parts of Fagonia glutinosa. The new saponins were characterised as 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-glucopyranosyl(1-->3)]-alpha-L - arabinopyranosyl-27-hydroxy oleanolic acid 28-O-beta-D-glucopyranosyl ester, 3-O-[beta-D-glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl ursolic acid, 3-O-alpha-L-arabinopyranosyl ursolic acid 28-O-beta-D-glucopyranosyl ester, 3-O-[beta-D-xylopyranosyl(1-->2)][beta- D-glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl ursolic acid, 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D- glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl ursolic acid 28-O-beta-D-glucopyranosyl ester and 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-glucopyranosyl(1-->3)]-alpha-L - arabinopyranosyl-27-hydroxy ursolic acid 28-O-beta-D-glucopyranosyl ester. The structures of the saponins were established by spectral and chemical evidences. The assignments of the NMR signals were performed by means of HOHAHA, 1H-1H COSY, ROE, HMQC and HMBC experiments.

Triterpenoid saponins from Fagonia cretica.

Four new triterpenoid saponins were isolated and identified from the aerial parts of Fagonia cretica. They were characterized as 3-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl] hederagenin 28-O-beta-D-glucopyranosyl ester, 3-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl] oleanolic acid 28-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] ester, 3-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl] 27-hydroxy oleanolic acid 28-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] ester and 3beta-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl] olean-12-en-27-al-28-oic acid 28-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] ester. The structures of the saponins were assigned by spectral analyses (FABMS, 1H, 13C NMR, 1H-1H COSY, TOCSY, HMQC and HMBC spectra) and NOE experiments. To the best of our knowledge the genin 3beta hydroxy olean-12-en-27-al-28-oic acid is new.

Saponins from Fagonia arabica.

Seven new triterpenoid saponins were isolated and identified from the aerial parts of Fagonia arabica. They were characterized as 3-O-beta-D-xylopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->3)]-alpha-L- arabinopyranosyl oleanolic acid 28-O-beta-D-glucopyranoside, 3-O-beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->3)]-alpha-L- arabino pyranosyl oleanolic acid 28-O-beta-D-glucopyranoside, 3-O-beta-D-xylopyranosyl(1-->2)-[beta-D-glucopyranosyl (1-->3)]-alpha- L-arabinopyranosyl oleanolic acid, 3-O-beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->3)]-alpha-L- arabino pyranosyl oleanolic acid, 3-O-beta-D-xylopyranosyl(1-->2)-[beta-D-glucopyranosyl (1-->3)]-alpha-L-arabinopyranosyl 27-hydroxyoleanolic acid, 28-O-beta-D-glucopyranoside, 3-O-beta-D-xylopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->3)]-alpha-L- arabinopyranosyl ursolic acid 28-O-beta-D-glucopyranoside and 3-O-beta-D-xylopyranosyl (1-->2)-[beta-D-glucopyranosyl (1-->3)-alpha-L-arabinopyranosyl 27-hydroxyursolic acid 28-O-beta-D-glucopyranoside. The structures of the saponins were established by analyses of their 1H and 13C NMR spectra with the aid of 2D experiments. The two genins, 27-hydroxyoleanolic acid and 27-ursolic acid, are new.