Acetylated glucuronide triterpene bidesmosidic saponins from Symplocos glomerata

Nine new bidesmosidic 3-O-glucuronide oleanane triterpenoid saponins were isolated from the stem bark of Symplocos glomerata King along with two known saponins, salsoloside C and copteroside E, and two major lignans, (-)-pinoresinol and (-)-pinoresinol-4'-O-beta-D-glucopyranoside. The structures of the new saponins were established using one- and two-dimensional NMR spectroscopy and mass spectrometry as, 3-O-[beta-D-xylopyranosyl(1-->4)-[2-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[beta-D-xylopyranosyl(1-->4)-[3-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[beta-D-xylopyranosyl (1-->4)-[2,3-O-diacetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[alpha-L-arabinopyranosyl(1-->4)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[alpha-L-arabinopyranosyl (1-->4)-[2-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[[beta-D-xylopyranosyl (1-->2)]-[beta-D-xylopyranosyl (1-->4)]-[3-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[[beta-D-glucopyranosyl (1-->2)]-[beta-D-xylopyranosyl (1-->4)]-[3-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[[beta-D-glucopyranosyl (1-->2)]-[alpha-L-arabinofuranosyl (1-->4)]-[3-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, and 3beta-O-[beta-D-xylopyranosyl(1-->4)-[2-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-morolic acid. The EtOH and EtOAc extracts of the stem bark showed no cytotoxic activity. At a concentration of 370 microg/ml, the saponin mixture showed haemolytic activity and caused 50% haemolysis of a 10% suspension of sheep erythrocytes.     

Triterpenoid saponins from Fagonia indica.

Two new triterpenoid saponins, 3-O-{[beta-D-glucopyranosyl-(1-->2)]-[alpha-L-arabinopyranosyl-(1- ->3)]- alpha-L-arabinopyranosyl}-ursolic acid-28-O-[beta-D-glucopyranosyl] ester (indicasaponin A), 3-O-{[beta-D-glucopyranosyl-(1-->2)]-[alpha-L-arabinopyranosyl-(1- ->3)]- alpha-L-arabinopyranosyl}-oleanolic acid-28-O-[beta-D-glucopyranosyl] ester (indicasaponin B) and two known triterpenoid saponins, 3-O-[beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl]-ur solic acid-28-O-[beta-D-glucopyranosyl] ester, 3-O-[beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl]-olean olic acid-28-O-[beta-D-glucopyranosyl] ester have been isolated from Fagonia indica. The structures were determined primarily by NMR spectroscopy. The assignment of NMR signals was performed by means of 1H-1H COSY, NOESY, ROESY, TOCSY, HMQC and HMBC experiments.     

Five saponins from the root bark of Aralia elata

Five saponins, 3-O-[beta-D-glucopyranosyl (1-->2)-[beta-D-glucopyranosyl (1-->3)]-beta-D-glucopyranosyl]-oleanolic acid 28-O-beta-D-glucopyranosyl ester (aralia-saponin V), 3-O-[beta-D-glucopyranosyl (1-->2)-[beta-D-glucopyranosyl (1-->3)]-beta-D-glucopyranosyl]-echinocystic acid 28-O-beta-D-glucopyranosyl ester (aralia-saponin VI), 3-O-beta-D-glucopyranosyl (1-->2)-[beta-D-glucopyranosyl (1-->3)]-beta-D-glucopyranosyl]-hederagenin 28-O-beta-D-glucopyranosyl ester (aralia-saponin VII), 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranosyl]-caulophyllogenin 28-O-beta-D-glucopyranosyl ester (aralia-saponin VIII), 3-O-[beta-D-glucopyranosyl (1-->2)-[beta-D-glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl]-hederagenin 28-O-beta-D-glucopyranosyl ester (aralia-saponin IX), were isolated from the root bark of Aralia elata (Miq.) Seem., together with four known compounds. Their structures were determined on the basis of chemical and spectroscopic methods.     

Triterpenoid saponins and sapogenin lactones from Albizia gummifera

The structures of two new monodesmosidic and bisdesmosidic triterpenoid saponins (1 and 2) and the known compound delta 5-stigmasterol-3-O-beta-D-glucopyranoside (3) as well as two new oleanane type triterpene lactone glycosides 4, 5 and a new sapogenin lactone 6 isolated from the stem bark of Albizia gummifera C.A. Smith (Mimosaceae) have been elucidated as 3-O-?beta-D-glucopyranosyl(1-->2)-[alpha-L-arabinopyranosyl(1-->6) ]-beta-D- glucopyranosyl?-oleanolic acid (1), beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl 3-O-?beta-D-glucopyra-nosyl(1-->2)-[alpha-L-arabinopyrano syl(1-->6)]-beta-D- glucopyranosyl?-oleanolate (2), 3 beta-?O-D-glucopyranosyl-(1-->2)-[O-alpha-L-arabinopyranosyl(1-->6 )] beta-D-glucopyranosyloxy?-machaerinic acid gamma-lactone (4), 3 beta-O-beta-D-glucopyranosiduronic acid (1-->2)-beta-D-glucopyranosyloxy]-machaerinic acid gamma-lactone (5), and A-homo-3a-oxa-5 beta-olean-12-en-3-one-28-oic acid (6), respectively. The complete assignment of the 1H and 13C resonances of 1, 2, 4 and 6 and of the peracetate of 5 were achieved by means of 2D-NMR studies.     

Triterpenoid saponins from the stem bark of Elattostachys apetala

Six new triterpenoid saponins have been isolated from the stem bark of Elattostachys apetala together with four known triterpenoid saponins. Three of these new compounds are glycosides of a newly described genin, 29-hydroxyhederagenin (1). On the basis of spectral evidence, the structures of the new saponins were concluded to be alpha-hederin 28-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl] ester (2), sapindoside B 28-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl] ester (3), 3-O-beta-D-xylopyranosyl astrantiasaponin VII (4), 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-glucopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranosyl]-29-hydroxyhederagenin (5), 3-O-[alpha-L-arabinopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->6)]-beta-D-glucopyranosyl]-29-hydroxyhederagenin (6), and 3-O-[beta-D-xylopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-gluco pyranosyl-(1-->6)]-beta-D-glucopyranosyl]-29-hydroxyhederagenin (7).     

Triterpene saponins from Cylicodiscus gabunensis.

Four new saponins were isolated from the alcoholic extract of the bark of Cylicodiscus gabunensis by means of flash chromatography. They were characterized on the basis of spectral and chemical data as 3-O-beta-[alpha-L-arabinopyranosyl (1----2),alpha-L-arabinopyranosyl(1----3),beta-D-glucopyranosyl(1- ---)] maslinic acid-28-[beta-D-glucopyranosyl(1----6),beta-D-glucopyranosyl(1----2),alp ha-L- rhamnopyranosyl(1----)] ester; 3-O-beta-[alpha-L-arabinopyranosyl(1----2),alpha-L-arabinopyran osyl (1----3),beta-D-glucopyranosyl(1----)]maslinic acid-28-[beta-D-glucopyranosyl(1----2),alpha-L-rhamnopyranosyl(1----)] ester, 3-O-beta-[alpha-L-arabinopyranosyl(1----2),alpha-L-arabinopyran osyl (1----3),beta-D-glucopyranosyl(1----)]maslinic acid and 3-O-beta(alpha-L-arabinopyranosyl(1----3),beta-D-glucopyranosyl (1----)] cylicodiscic acid.     

Synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue

The focus of this work was on the synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue. Therefore, 3-O-{[beta-D-glucopyranosyl-(1-->2)]-[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 1 was concisely synthesized by two strategies in 22% and 41% overall yield, respectively, and another congener 3-O-{[beta-D-xylopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 2 was also efficiently prepared in 81% overall yield. The (1)H NMR and (13)C NMR signals of saponin 2 are all consistent with those reported for the natural product.     

Steroidal saponins from Smilax lebrunii.

Two new steroidal saponins, (25 R)-spirostan-3 beta-ol-6-one-3-O-[alpha-L-arabinopyranosyl (1----6)]-beta-D-glucopyranoside and (25 R)-spirostan-3 beta-ol-6-one-3-O-[beta-D-glucopyranosyl(1---4)] [alpha-L-arabinopyranosyl(1----6)]-beta-glucopyranoside, were isolated from the rhizomes of Smilax lebrunii. Their structures have been established by chemical and spectral methods.     

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.     

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 stem bark of Petersianthus macrocarpus.

Two bioactive saponins were isolated from the stem bark of Petersianthus macrocarpus. Their structures were elucidated by chemical degradations and by a combination of 2D NMR techniques and by Californium plasma desorption mass spectrometry. They are 3-O-([beta-D-galactopyranosyl (1-->2)][beta-D-galactopyranosyl (1-->3)]- beta-D-glucuronopyranosyl)-21-O-[3-(3-tigloyloxynilic acid)-4-tigloyloxy- alpha-L-arabinopyranosyl] barringtogenol C and 3-O-([beta-D-galactopyranosyl (1-->2)][beta-D-galactopyranosyl (1-->3)]-beta-D-glucuronopyranosyl)-28-O-alpha-L-rhamnopyranosyl barringtogenol C-21-O-benzoate. The absolute configuration of nilic acid was determined by partial synthesis. 3,3'-Dimethoxy ellagic acid and 3,3'-dimethoxy-4-O-beta-D- glucopyranosyl ellagic acid were also isolated.     

Glucuronide triterpene saponins from Bersama engleriana

Five 3-O-glucuronide triterpene saponins (1-5) were isolated from the stem bark of Bersama engleriana Gurke along with two known saponins, polyscias saponin C and aralia saponin 15, and one major C-glycoside xanthone, mangiferin. The structures of the saponins were established mainly by means of spectroscopic methods (one- and two-dimensional NMR spectroscopy as well as FAB-, HRESI-mass spectrometry) as 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-betulinic acid (1), 3-O-[beta-D-glucopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosyl]-oleanolic acid (2), 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-D-xylopyranosyl-(1-->6)-beta-d-glucopyranosyl]-oleanolic acid (3), 3-O-[beta-D-galactopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl]-oleanolic acid (4), and 3-O-[beta-d-glucopyranosyl-(1-->3)-beta-D-galactopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-d-xylopyranosyl-(1-->6)-beta-D-glucopyranosyl]-oleanolic acid (5).     

Triterpene saponins from the roots of Ampelozizyphus amazonicus.

A new triterpene saponin was isolated from the roots of Ampelozizyphus amazonicus together with the known 3-O-beta-D-glucopyranosyl-20-O-alpha-L-rhamnopyranosyljujubogenin and the known triterpenes melaleucic acid, 3 beta,27 alpha-dihydroxylup-20(29)-en-28 beta-oic acid, betulinic acid, betulin, lupeol. The structure of this saponin was elucidated as 3-O-[beta-D-glucopyranosyl(1----2)alpha-L-arabinopyranosyl]- 20-O-alpha-L-rhamnopyranosyljujubogenin by spectral analysis and chemical transformations.     

27-Nor-triterpenoid glycosides from Mitragyna inermis

From the bark of Mitragyna inermis, two 27-nor-triterpenoid glycosides, named inermiside I (1) and II (2), were isolated and their structures determined based on extensive 2D-NMR and MS spectral analysis as 6-deoxy-beta-D-glucopyranosyl-[3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl]-pyrocincholate and 6-deoxy-beta-D-glucopyranosyl-pyrocincholate, respectively. In addition, the known quinovic acid (6), 3-O-[beta-D-glucopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl]-quinovoic acid (3),beta-D-glucopyranosyl-[3-O-(beta-D-glucopyranosyl)]-quinoviate (4) and cytotoxic 3-O-(beta-D-6-deoxy-glucopyranosyl)-quinovic acid (5) were also isolated.     

Withanolide glycosides from Dunalia australis.

Four new withanolide glycosides, (20R,22R)-O-(3)-[beta-D- xylopyranosyl(1----3), beta-D-xylopyranosyl(1----4)]-beta-D-glucopyranosyl-3 beta,20-dihydroxy-1 alpha-acetoxy-witha-5,24-dienolide, (20R,22R)-O-(3)-[beta-D-xylopyranosyl(1----3), beta-D-glucopyranosyl(1----4)]-beta-D-glucopyranosyl-3 beta,20-dihydroxy-1 alpha-acetoxy-witha-5,24-dienolide, (20R,22R)-O-(3)-[beta-D- glucopyranosyl(1----3), beta-D-glucopyranosyl(1----4)]-beta-D-glucopyranosyl- 3 beta,20-dihydroxy-1 alpha-acetoxy-witha-5,24-dienolide and (20R,22R)-O-(3)-[beta-D-glucopyranosyl(1----3), beta-D- glucopyranosyl(1----4)]-beta-D-glucopyranosyl-3 beta, 12 beta,20-trihydroxy- 1 alpha,acetoxy-witha-5,24-dienolide, named dunawithanines C, D, E and F, respectively, were isolated from Dunalia australis. Their structures were elucidated on the basis of spectral and chemical evidence, especially NMR data of the peracetates.     

In vivo anti-inflammatory activity of saponins from Bupleurum rotundifolium

Seven oleanane-type triterpene saponins were isolated from the methanolic extract of the aerial parts of Bupleurum rotundifolium. They were identified on the basis of their spectral data as 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl]-28-O-[beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl] echinocystic acid (saponin 1), 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->2)-beta-D-fucopyranosyl] 11-methoxy-primulagenin A (saponin 2), rotundioside E (saponin 3), rotundioside F (saponin 4), 3beta-sulfate, 28-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl] ester of primulagenin A (saponin 5), rotundioside C (saponin 6) and 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->2)-beta-D-fucopyranosyl] 11-methoxy-16beta,21alpha,28-trihydroxyolean-12-ene (saponin 7). All these saponins proved to be effective against TPA-induced ear edema in mice. Their ID50 were determined to be 248, 288, 128, 99 and 297 nmol/ear for saponin 1, 2, 3, 4 and 6, respectively. Saponins 3 and 6 were also active on a TPA multiple-dose model of skin chronic inflammation.     

Bioactive flavonoids and saponins from Climacoptera obtusifolia

Two bidesmosidic saponins were isolated from Climacoptera obtusifolia (Chenopodiaceae) and their structures were determined as gypsogenin 3-O-[beta-D-xylopyranosyl-(1-->3)-beta-D-glucopyranoside]-28-O-{beta-D-glucopyranosyl} ester (1) and hederagenin 3-O-[beta-D-xylopyranosyl-(1-->3)-beta-D-glucopyranoside]-28-O-[beta-D-glucopyranosyl} ester (2), by spectroscopic methods. Two known compounds, isorhamnetin 3-O-beta-D-glucopyranoside (3), and isorhamnetin 3-O-[alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (4) were also isolated for the first time from this plant. Compounds 1-4 were tested in various immunomodulatory assays. Compound 2 suppressed (92%) the reactive oxygen species (ROS) production on mononuclear cells in luminol-based chemiluminescence (CL) assay at a higher concentration (50 microg/mL). Compounds 3 and 4 demonstrated a strong inhibition on ROS production in the oxidative burst activity of whole blood, neutrophils, and mononuclear cells. Additionally compounds 3 and 4 also suppressed PHA T-cell proliferation with no cytotoxic effects.     

Xanthone O-glycosides from Polygala tenuifolia

Four xanthone O-glycosides, polygalaxanthones IV-VII were isolated from the roots of Polygala tenuifolia Willd., together with eight known compounds. The structures of the four xanthone O-glycosides were established as 6-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl]-1-hydroxy-3,7-dimethoxyxanthone (polygalaxanthone IV), 6-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl]-1,3-dihydroxy-7-methoxyxanthone (polygalaxanthone V), 6-O-(beta-D-glucopyranosyl)-1,2,3,7-tetramethoxyxanthone (polygalaxanthone VI), and 3-O-[alpha-D-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl]-1,6-dihydroxy-2,7-dimethoxyxanthone (polygalaxanthone VII), respectively, on the basis of analysis of spectroscopic evidence.     

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.     

Triterpenoid glycosides from Bacopa monnieri

Two triterpenoid glycosides have been isolated along with 10 known saponins from Bacopa monnieri. Structures of the compounds have been elucidated as 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl] jujubogenin (1) and 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl] pseudojujubogenin (2) by high resolution NMR spectral data and chemical correlations. Further, the chemical compositions of bacosides A and B have been delineated.