Pregnane glycosides from the bark of Marsdenia cundurango and their cytotoxic activity

Seven new pregnane glycosides (1–7) and eight known compounds (8–15) were isolated from the bark of Marsdenia cundurango (Asclepiadaceae). The structures of 1–7 were determined by spectroscopic analysis, including two-dimension NMR spectroscopy, chemical transformations, and chromatographic analysis of the hydrolyzed products. The isolated compounds 1–15 were evaluated for their cytotoxic activity against HL-60 human leukemia cells, A549 human lung adenocarcinoma cells, and TIG-3 normal human lung cells, including apoptosis-inducing activity of a representative pregnane glycoside in HL-60 cells.

     

Six new furostanol glycosides from Smilax glauco-china and their cytotoxic activity

Six new steroidal saponins, namely glauco-chinaosides A–F, and one known compound were isolated from the tubers of Smilax glauco-china. Their structures were elucidated by a combination of spectroscopic analysis and hydrolysis followed by spectral and chromatographic analysis. Compounds 1–7 were tested in vitro for their cytotoxic activities against four human tumor cell lines (SH-SY5Y, SGC-7901, HCT-116, and Lovo). Compounds 1, 2, and 5 exhibited cytotoxic activity against SGC-7901, with IC₅₀ values of 2.7, 11.5, and 6.8 μM, respectively.     

Two triterpenoid glycosides from the roots of Camellia oleifera and their cytotoxic activity

Two new triterpenoid saponins, oleiferoside N and oleiferoside O, were isolated from the EtOH extract from the roots of Camellia oleifera C. Abel. Their structures were elucidated as 16α-acetoxy-21β,22α-O-diangeloyloxy-23,28-dihydroxyolean-12-ene 3β-O-β-d-xylopyranosyl-(1 → 3)-α-l-arabinopyranosyl-(1 → 3)-β-d-glucuronopyranoside (1), 16α-acetoxy-21β-O-angeloyloxy-23,28-dihydroxy-22α-O-(2-methylbutanoyloxy)olean-12-ene 3β-O-β-d-xylopyranosyl-(1 → 3)-α-l-arabinopyranosyl-(1 → 3)-β-d-glucuronopyranoside (2), on the basis of spectroscopic analyses (IR, ESI-MS, HR-ESI-MS, 1D and 2D NMR) and acid hydrolysis. Both were characterized to be oleanane-type saponins with sugar moieties linked to C-3 of the aglycone. Cytotoxic activities of two saponins were evaluated against four human tumor cell lines (A549, B16, BEL-7402, and MCF-7) by using the MTT in vitro assay. Compounds 1 and 2 showed moderate cytotoxic activities toward the tested cell lines.     

New triterpenoids from Kadsura heteroclita and their cytotoxic activity

Phytochemical investigations of the stem of Kadsura heteroclita (Roxb) Craib (Schizandraceae) resulted in the isolation and structure elucidation of six new triterpenoidal compounds named heteroclitalactones A-E (1-5) as well as heteroclic acid (6) and heteroclitalactone F (7), which was isolated for the first time from a natural source, and the six known compounds schisanlactone E (8), cycloartenone (9), schisandronic acid (10), nigranoic acid (11), changnanic acid (12) and schisanlactone B (13), respectively. The structures of these compounds were characterized by extensive 1D and 2D NMR spectral analyses. The majority of these triterpenoids showed moderate cytotoxic activity against the human tumor cell lines Bel-7402, BGC-823, MCF-7 and HL-60. Among the compounds tested, heteroclitalactone D (4) showed the strongest cytotoxic activity against the HL-60 cells with an IC50 of 6.76 microM.     

New cycloartane glycosides from the rhizomes of Cyperus rotundus and their antidepressant activity

Two new cycloartane glycosides, cyprotusides A (1) and B (2), were isolated from the rhizomes of Cyperus rotundus. Their chemical structures were elucidated on the basis of IR, MS, NMR spectroscopic analyses coupled with chemical degradation. The potential antidepressant activity of the two compounds was evaluated. In the despair mice models, compounds 1 and 2 showed significant antidepressant activity.     

New furostanol saponins from the bulbs of Allium macrostemon Bunge and their cytotoxic activity

Four new furostanol saponins, named as macrostemonoside O, macrostemonoside P, macrostemonoside Q and macrostemonoside R, along with five known compounds, were isolated from the dried bulbs of Allium macrostemon Bunge. The structures of these new compounds were established by the spectral data elucidation (IR, ESIMS, 1D and 2D NMR) as 26-O-beta-D-glucopyranosyl-22-hydroxyl-5beta-furost-25 (27)-ene-3beta, 26-diol-3-O-beta-D-glucopyranosyl (1-->2)-beta-D-galactopyranoside (macrostemonoside O), (25R)-26-O-beta-D-glucopyranosyl-22-hydroxyl-5beta-furost-1beta, 3beta, 26-triol-3- O-beta-D-glucopyranosyl (1-->2)-beta-D-galactopyranoside (macrostemonoside P), (25R)-26-O-beta-D-glucopyranosyl-22-hydroxy-5beta-furost-1alpha, 2beta, 3beta, 26-tetraol-3-O-beta-D-glucopyranosyl (1-->2)-beta-D-galactopyranoside (macrostemonoside Q) and (25R)-26-O-beta-D-glucopyranosyl-22-hydroxyl-5beta-furost-2alpha, 3beta, 26-triol-3-O-beta-D-glucopyranosyl (1-->2) [beta-D-glucopyranosyl (1-->3)]-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside (macrostemonoside R), respectively. Their cytotoxic activities on several cancer cell lines including solid tumor (HepG2, MCF-7, NCI-H460 and SF-268) and drug resistant tumor (R-HepG2) were investigated and five compounds showed diverse cytotoxity to these cancer cell lines which suggest that they might be used as potential leading compounds to cure cancer diseases.     

A new triterpene ester and other chemical constituents from the aerial parts of Anodendron paniculatum and their cytotoxic activity

The aim of the research was to study the active constituents of Anodendron paniculatum Roxb. (Apocynaceae). A new triterpene ester, named anopaniester (1), and cycloartenol (2), ursolic acid (3), esculenic acid (4), bis-(2-ethylhexyl) phthalate (5), desmosterol (6), stigmasterol (7), vaniline (8), and (E)-phytol (9), were isolated from the aerial parts of A. paniculatum. Compounds 3 and 6 showed the significant inhibitory effect (IC₅₀ values ranging from 30.89 ± 3.60 to 44.37 ± 5.40 μg/ml) against tested human cancer cell lines LU-1 and MKN-7. The compounds 1–4, and 6 were isolated from this genus Anodendron for the first time.     

Cycloartane-type triterpene glycosides from Beesia calthaefolia and their anticomplement activity

Two new 9,19-cycloartane triterpenes (1, 2), together with three known compounds (3–5), were isolated from the whole plant of Beesia calthaefolia. Their structures were determined by the application of spectroscopic analyses and chemical methods. Compound 1 showed moderate anticomplement activity similar to that of the positive control (rosmarinic acid), while compounds 3 and 4 showed weak activity. The results suggest that 6′-O-(4″-hydroxy-3″-methoxy-benzoyl)-β-d-glucosyl of 9,19-cycloartane-type triterpenoids could be a structure that is essential for anticomplement activity.     

Flavanone glycosides from Citrus junos and their anti-influenza virus activity

By bioactivity-guided fractionation, a new flavanone triglycoside, naringenin 7-O-(2",6"-di-O-alpha-rhamnopyranosyl)-beta-glucopyranoside (1), as well as hesperetin 7-O-(2", 6"-di-O-alpha-rhamnopyranosyl)-beta-glucopyranoside (2), hesperidin (3) and narirutin (4) have been isolated from the fruits of Citrus junos Tanaka (Rutaceae). In addition, hesperetin 7-O-(2",6"-di-O-alpha-rhamnopyranosyl)-beta-glucopyranoside (2) is reported for the first time from this plant and inhibits the influenza A virus.     

New cytotoxic triterpene acids from aboveground parts of Manihot esculenta from the Suriname rainforest

Two novel triterpene acids, esculentoic acid A ( 1) and B ( 2) as well as the seven known compounds 3 - 9 were isolated from an EtOAc extract of leaves, stems, and twigs of Manihot esculenta by bioassay-guided fractionation for cytotoxic activity. The structures of the two new compounds were established as 3alpha-hydroxytaraxer-14-en-29-oic acid ( 1) and 3-oxotaraxer-14-en-29-oic acid ( 2) on the basis of 1D and 2D NMR spectroscopic data interpretation and chemical conversions. The two new compounds 1 and 2 showed moderate cytotoxicity against the A2780 human ovarian cancer cell line.     

Steroidal saponins from Myriopteron extensum and their cytotoxic activity

Two new steroidal saponins, extensumsides A ( 1) and B ( 2), were isolated from the whole plants of Myriopteron extensum (Wight) K. Schum. Their structures were elucidated as 17 beta-uzarigenin-3- O- beta-glucopyranosyl-(1-->6)- beta-glucopyranosyl-(1-->4)- beta-thevetopyranosyl-(1-->4)- beta-cymaropyranoside ( 1) and 12-(3-methylbut-2-enoyloxy)pregn-5-en-20-one 3- O-[beta-cymaropyranosyl-(1-->4)-beta-cymaropyranosyl-(1-->4)-beta-thevetopyranosyl-(1-->4)-(6- O-sulfo-beta-glucopyranoside)] ( 2) on the basis of chemical and spectral evidence. Extensumside A exhibited significant cytotoxicity against eight cancer cell lines with a mean GI (50) value of 0.346 microg/mL.     

Steroidal saponins from Dioscorea panthaica and their cytotoxic activity

A new steroidal saponin, dioscoreside E (1), and a known compound, protodioscin (2), were isolated from an ethanol extract of the rhizomes of Dioscorea panthaica. The structure of 1 was established as 3-O-[bis-alpha-L-rhamnopyranosyl-(1 --> 2 and 1 --> 4)-beta-D-glucopyranosyl]-26-O-beta-D-glucopyranosyl-20(R)-methoxy-25(R)-furosta-5,22(23)-diene-3beta,26-diol, on the basis of spectral and chemical evidence. Compounds 1 and 2 showed cytotoxic activity against a panel of tumor cell lines.     

The cytotoxic activity of the total alkaloids isolated from different parts of Solanum pseudocapsicum

The total alkaloid fractions of the methanolic extracts of the leaves, ripe fruits, roots, seeds and stem of Solanum pseudocapsicum were subjected to in-vitro cytotoxicity, short-term toxicity and long-term survival studies. All the five fractions exhibited potent activity. The total alkaloid fraction of leaves was found to be the most potent. The HT-29 cell line was the most sensitive to the fractions. The cytotoxic concentration (CTC(50)) values for all these fractions ranged between 0.39-0.91, 0.68-2.8, 0.92-3.56, 4.05-8.2, 3.28-5.65 and 0.95-5.55 microg/ml, respectively for HT-29, RD-228, A-549, HEp-2, B(16)F(10) and Vero cell lines. In short-term toxicity studies, the fractions showed 50% viability at 93-128 microg/ml for DLA cells and 141-189 microg/ml for human lymphocytes. In the long-term survival studies on the cell lines RD-228, HEp-2 and Vero, cells retained their regenerative capacities at concentrations below 8 microg/ml. The total alkaloids of the plant, especially from the leaves merit further investigations to identify the active constituents in animal models.     

Steroidal glycosides from the rhizomes of Anemarrhena asphodeloides and their antiplatelet aggregation activity

Five new steroidal glycosides, timosaponin J ( 1), timosaponin K ( 2), (25 S)-karatavioside C ( 5), timosaponin L ( 6), and (25 S)-officinalisnin-I ( 8), together with eight known steroidal saponins, timosaponin E (1) ( 3), purpureagitosid ( 4), timosaponin BII ( 7), timosaponin B III ( 9), anemarrhenasaponin I ( 10), anemarrhenasaponin III ( 11), anemarrhenasaponin A (2) ( 12), and timosaponin A III ( 13), were isolated from the rhizomes of Anemarrhena asphodeloides. Their structures were elucidated on the basis of spectroscopic and chemical evidence. The aglycones of compounds 1 and 2 are new aglycones. Compounds 1- 13 were evaluated for their platelet aggregation activities, and compound 13 exhibited the strongest inhibitory effect on adenosine diphosphate (ADP)-induced platelet aggregation.     

Chemical constituents from the roots of Tripterygium wilfordii and their cytotoxic activity

In our ongoing search for bioactive constituents, a new sesquiterpene polyol ester, named triptersinine U (1), together with five known triterpenes (2–6) and seven sesquiterpene pyridine alkaloids (7–13), were isolated from the roots of Tripterygium wilfordii Hook. f. Their chemical structures were elucidated using extensive spectroscopic analyses, including 1D and 2D NMR, and HRESIMS, as well as comparison with previously reported data. Cytotoxic activities of all compounds 1–13 were evaluated against six human tumor cell lines (HepG2, Hep3B, Bcap37, U251, MCF-7 and A549) using the MTT in vitro assay. The results showed that triterpenes exhibited moderate cytotoxic activities toward the tested cell lines.     

Steroidal saponins from the rhizomes of Dioscorea bulbifera and their cytotoxic activity

Two new steroidal saponins, diosbulbisides D (1) and E (2), along with five known saponins (3- 7) were isolated from the rhizomes of Dioscorea bulbifera L. Their structures were elucidated on the basis of spectral data. Compounds 6 and 7, two 3- O-trisaccharides of diosgenin spirostanes, showed moderate cytotoxic activity against human hepatocellular carcinoma cells, with IC?? values of 3.89 μM and 7.47 μM on SMMC7721, and 10.87 μM and 19.10 μM on Bel-7402 cell lines, respectively.     

Lignan and phenylpropanoid glycosides from Lancea tibetica and their antitumor activity.

A new lignan glucoside, the first 7,9'-monoepoxyte-trahydrofuran type lignan with the cis-relationship of H-7 and H-8, named tibeticoside (1), as well as ten known compounds have been isolated from the medicinal plant (roots, stems and leaves) Lancea tibetica. The structure of tibeticoside (1) has been elucidated on the basis of chemical and spectral evidence, especially by 2D-NMR (1H-1H COSY, HMQC, HMBC, NOESY). In addition, sylvatesmin (6) exhibited effective antitumor activity on B16 cells.     

Hepatoprotective flavonol glycosides from the aerial parts of Rodgersia podophylla

A new acylated flavonoid, quercetin 3- O-alpha- L-(5"- O-acetyl)-arabinofuranoside ( 1), along with six known flavonoids ( 2 - 7) were isolated from the aerial parts of Rodgersia podophylla. The new flavonoid 1 exhibited 50.1 % hepatoprotective activity at a concentration of 100 microM, and the three known compounds 3, 5 and 6 showed hepatoprotective activities at a concentration of 50 microM (45.7, 50.8 and 57.3 %, respectively) by using the primary cultures of rat hepatocytes injured by H (2)O (2).