Cytotoxic triterpenoid saponins from the roots of Platycodon grandiflorum

Bioguided fractionation of the ethanol extracts obtained from Platycodon grandiflorum roots led to isolation of two new triterpenoid saponins, characterized as 3-O-beta-D-glucopyranosyl-2beta,12alpha,16alpha,23,24-pentahydroxyoleanane-28(13)-lactone (1) and 3-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-2beta,12alpha,16alpha,23alpha-tetrahydroxyoleanane-28(13)-lactone (2) by 1D- and 2D-NMR and MS techniques, as well as chemical means. Both compounds showed cytotoxic activity against human ECA-109 cells.     

Cytotoxic triterpenoid saponins from Ardisia pusilla

A new triterpenoid saponin,3-O-{β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-ghcopyranosyl-(1→2)]-α-L-arabinopyranosyl }-3β,16α,28α-trihydroxy-1313,28-epoxy-oleanan-30-al(ardipusilloside Ⅲ,1),together with two known sapo-nins,ardisiacrispins A(2)and B(3),were isolated from the whole plants ofArdisia pusilla A.DC.Their structures were elucidated by extensive spectral analysis and chemical evidences.Saponins 1 and 3 exhibited significant cytotoxicity against human glioblastoma U251MG cells.     

Flavonoids from Cephalaria gigantea flowers

Luteolin, quercetin, cinaroside, quercimeritrin, and the new flavonol bioside gigantoside A were isolated from Cephalaria gigantea (Ledeb.) Bobr. (Dipsacaceae) flowers. Spectral properties and chemical transformations established that gigantoside A had the structure quercetin-7-O-[α-L-arabinopyranosyl(1→6)]-β-D-glucopyranoside. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 552–554, November–December, 2006.     

Tirucallane-type triterpenoid saponins from the roots of Sapindus mukorossi

Six new tirucallane-type triterpenoid saponins, sapimukosides E-J (1-6) were isolated from the roots of Sapindus mukorossi GAERTN. Their structures were elucidated by a combination of spectral and chemical analysis.     

New triterpenoid saponins from the roots of Sinocrassula asclepiadea

Five new triterpenoid monodesmosides (sinocrassulosides I-V, 1-5) and six bisdesmosides (sinocrassulosides VI-XI, 6-11), in which 2-11 possess different acyl groups in the glycosidic moieties, were isolated from the roots of Sinocrassula asclepiadea FRANCH. Sinocrassulosides VI (4) and V (5) also contained a novel A-seco aglycone in their structures. All of the structures were determined on the basis of spectroscopic and physicochemical evidence.     

Five new triterpenoid saponins from the roots of Platycodon grandiflorum

Five new triterpenoid saponins, platycoside H [3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], platycoside I [3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], platycoside J [3-O-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], platycoside K [3-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23,24-pentahydroxyolean-12-en-28-oic acid], and platycoside L [3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23,24-pentahydroxyolean-12-en-28 oic acid], and three known triterpenoid saponins, platycoside F, platycoside B, and platycoside C, were isolated from the roots of Platycodon grandiflorum A. DC. Their chemical structures were elucidated on the basis of their spectral data and chemical evidence.     

New A-ring lactone triterpenoid saponins from the roots of Platycodon grandiflorum

Three new A-ring lactone triterpenoid saponins, platycoside M-1 [3-O-beta-D-glucopyranosyl platycogenic acid A lactone], platycoside M-2 [3-O-beta-D-glucopyranosyl platycogenic acid A lactone 28-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], and platycoside M-3 [3-O-beta-D-glucopyranosyl platycogenic acid A lactone 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], were isolated from the roots of Platycodon grandiflorum A. DC. Their chemical structures were elucidated on the basis of their spectral data and chemical evidence.     

New triterpenoid saponins from the roots of Platycodon grandiflorum

Bioassay-directed fractionation of the antiviral active fraction of the roots of Platycodon grandiflorum leads to the isolation of three new triterpenoid saponins, platycosides G1-G3 (1-3), as well as two known saponins, platycodin D3 (4), and platycoside E (5). The structures of the new compounds were elucidated on the basis of their spectral data and chemical evidences. The isolated saponins were tested for their antiviral activities against respiratory syncytial virus (RSV), herpes simplex type 1 virus (HSV-1) and influenza type A virus (Flu A). Compound 4 showed weak anti-RSV activity.     

New triterpenoid saponins from the steaming treated roots of Panax notoginseng

Further phytochemical investigation of the steaming treated roots of Panax notoginseng (Araliaceae) led to the identification of two new dammarane-type triterpenoid saponins, notoginsenoside SP20 (1) and SP21 (2). In addition, a pair of new phenolic glycosides (3a and 3b) was also isolated together with two known compounds. Their structures were elucidated by HRESIMS, 1D- and 2D-NMR spectra. Compounds 1 and 2 showed no in vitro cytotoxicity against five human cancer cell lines (HL-60, SMMC-7712, A-549, MCF-9 and SW480).     

A chemical study of Cephalaria gigantea

Chemistry of Natural Compounds -     

Three new triterpenoid saponins from the roots of Ardisia crenata and their cytotoxic activities

Three new triterpenoid saponins, ardisicrenoside O (1), ardisicrenoside P (2) and ardisicrenoside Q (3) together with three known compounds, 3β,16α-dihydroxy-30-methoxy-28, 30-epoxy-olean-12-en, cyclamiretin A 3-O-β-d-glucopyranosyl-(1→2) -α-l-arabinopyranoside and cyclamiretin A 3-O-β-d-glucopyranosyl-(1→4) -α-l-arabinopyranoside were isolated from the roots of Ardisia crenata Sims. Their structures were determined by one- and two-dimensional NMR techniques, including HSQC, HMBC and TOCSY experiments, as well as acid hydrolysis and GC analysis. All isolates were evaluated for the cytotoxic activities on two human cancer cell lines and compounds 3, 5 and 6 showed significant cytotoxicity.     

Minor triterpenoid saponins from Ardisia crenata

Two minor triterpenoid saponins, ardisicrenoside G [3 beta-O-{alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)- [beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl}-16 alpha,28-dihydroxyolean-12-en-30-oic acid] and ardisicrenoside H [3 beta-O-{beta-D-xylopyranosyl-(1-->2)-beta-D- glucopyranosyl-(1-->4)-[beta-D-glucopyranosyl-(1-->2)]-alpha-L- arabinopyranosyl}-16 alpha,28-dihydroxyolean-12-en-30-oic acid] were isolated from the roots of Ardisia crenata. Structural assignments are based on NMR, MS and chemical reactions.     

New triterpenoid saponins from Stelmatocrypton khasianum

Four new triterpenoid saponins, designated as stelmatotriterpenosides E-H (1-4), together with three known compounds, asterbatanoside B (5), 2alpha,3beta,19alpha,23-tetrahydroxy-olean-12-en-28-oic acid-3-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl ester (6) and 2alpha,3beta,19alpha,23-tetrahydroxy-urs-12-en-28-oic acid-3-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl ester (7), were isolated from the stems of Stelmatocrypton khasianum. On the basis of chemical and spectral evidence, the structures of 1-4 were established as 2alpha,3beta,23-trihydroxy-olean-12-en-28-oic acid-3-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (1), 2alpha,3beta,23-trihydroxy-urs-12-en-28-oic acid-3-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (2), 2alpha,3beta,19alpha-trihydroxy-urs-12-en-28-oic acid-3-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl ester (3), and 2beta,3beta,19alpha-trihydroxy-urs-12-en-24,28-dioic acid-24-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl diester (4).     

Ursane-type triterpenoid saponins from Elsholtzia bodinieri

Investigation of the n-BuOH extract of the aerial parts of Elsholtzia bodinieri led to the isolation of two new ursane-type triterpenoid saponins, bodiniosides O (1) and P (2), along with five known saponins, rotungenoside (3), 3,28-O-bis-β-d-glucopyranosides of 19α-hydroxyarjunolic acid (4), oblonganosides I (5), rotungenic acid 28-O-α-L-rhamnopyranosyl-(1→2)-β-d-glucopyranoside (6), and bodinioside M (7) isolated from the species. The structures of compounds 1 and 2 were characterized by spectroscopic data as well as acid hydrolysis and GC analysis as 3-O-β-d-xylopyranosyl-23-acetoxy-urs-12(13)-en-28-oic acid 28-O-β-d-xylopyranosyl-(1→6)-[β-d-glucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)]-β-d-glucopyranoside and 3-O-β-d-xylopyranosyl-23-hydroxy-urs-12(13)-en-28-oic acid 28-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside. Compounds 1 and 2 exhibited potent anti-HCV activities in vitro with a selective index of 30.63 and 9.08, respectively.     

Two triterpenoid saponins from Neonauclea sessilifolia

From the dried roots of Neonauclea sessilifolia (Rubiaceae), two new triterpenoid saponins, 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-quinovopyranosyl quinovic acid (1) and 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-quinovopyranosyl pyrocincholic acid 28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (2), were isolated, together with five known saponins. The structures of the new saponins were determined by spectroscopic and chemical means.     

Cytotoxic cardenolide and sterols from Calotropis gigantea

The dichloromethane extract from the leaves of Calotropis gigantea Linn. was strongly cytotoxic against non-small cell lung carcinoma (A549), colon carcinoma (HCT 116) and hepatocellular carcinoma (Hep G2), and non toxic to Chinese hamster ovary (AA8). The extract afforded uscharin (1), 3,5,8-trihydroxy-24-methylcholest-6,22-diene (2), a mixture of (24R)-3beta-hydroxy-24-ethylcholest-5-en-7-one (3a) and 6beta-hydroxy-24-ethylcholest-4,22-dien-3-one (3b), and another mixture of (24R)-24-ethylcholest-4-en-3-one (4a) and (24S)-24-ethylcholest-4,22-dien-3-one (4b). Cardenolide 1 exhibited extreme toxicity to A549, HCT 116 and Hep G2 with IC50 values of 0.003 microg/mL, 0.013 microg/mL, and 0.018 microg/mL, respectively, while sample 3 exhibited an IC50 of 1.35 microg/mL, 4.46 microg/mL, and 3.83 microg/mL, respectively.     

Pancreatic lipase-inhibiting triterpenoid saponins from Gypsophila oldhamiana

Three new triterpenoid saponins, gypsosaponins A-C (1-3), were isolated from the roots of Gypsophila oldhamiana (Caryophyllaceae). Their structures were established as 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosyl quillaic acid 28-O-alpha-L-arabinopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (1), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-methyl-beta-D-glucuronopyranosyl gypsogenin 28-O-beta-D-glucopyranosyl-(1-->3)-[beta-D-xylopyranosyl-(1-->4)]-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (2), and 23-O-beta-D-glucopyranosyl gypsogenic acid 28-O-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside (3), on the basis of various spectroscopic analyses and chemical degradations. The biological activities of 1-3 were examined inhibitory activity against pancreatic lipase, which showed inhibition of 58.2%, 99.2% and 50.3% at concentration of 1 mg/ml, respectively.     

Two new triterpenoid saponins from Rhaponticum uniflorum

Two new triterpenoid saponins were isolated from the roots of Rhaponticum uniflorum.Their structures were elucidated as 3-O-[β-D-glucopyranosyl] -ilexolic acid-28-O-[β-D-glucopyranosyl]ester 1 and 3-O-[β-D-glucopyranosyl]-urs-12,19(29)-dien-oic acid-28-O-[β-D-glucopyranosyl]ester 2 mainly by 1D,2D NMR techniques and chemical methods.