Diterpenoid and triterpenoid glycosides from Clinopodium chinense.

Two new compounds, including a diterpenoid glycoside (1) and a triterpenoid glycoside (6), along with six known compounds were isolated from Clinopodium chinense. The structures of the new compounds were determined on basis of extensive spectral analysis and chemical method. Compounds 1-8 were evaluated for their insulin resistance effect and cytotoxic activity against the A549 and HepG2 cancer cell lines. None of the compounds were cytotoxic (IC50 > 100 µM), while compounds 1-3 and 5 showed the activity of ameliorating insulin resistance in HepG2.

New steroidal alkaloid and furostanol glycosides isolated from Solanum lyratum with cytotoxicity.

Two previously undescribed steroidal compounds, 16, 23-epoxy-22, 26-epimino-cholest-22(N), 23, 25(26)-trien-3ß-ol-3-O-ß-D-glucopyranosyl-(1→2)-ß-D-glucopyranosyl-(1→4)-ß-D-galactopyranoside (1) and 26-O-ß-D-glucopyranosyl-(25R)-5α-furost-20(22)-en-3ß, 26-diol (2), together with 7 known ones including 26-O-ß-D-glucopyranosyl-(25R)-5, 20(22)-dien-furost-3ß, 26-diol (3), (25R)-5-en-spirost-3ß-ol-O-ß-D-glucopyranosyl-(1→4)-[α-L-rhmanopyranosyl-(1→2)]-ß-D-galactopyranoside (4), funkioside D (5), aspidistrin (6), tigogenin-3-O-ß-D-lucotrioside (7), desglucolanatigonin II (8), and degalactotigonin (9), were isolated from Solanum lyratum Thunb. Their cytotoxic activities were tested in two cancer cell lines by MTT method. One of the steroidal glycosides (6) showed significant cytotoxic activity against gastric cancer SGC7901 and liver cancer BEL-7402 cells.

Studies on chemical constituents of Ophiopogon japonicus.

Two new and six known steroidal glucosides were isolated from the tuber of Ophiopogon japonicus. The new steroidal glucosides were established as (20R,25R)-26-O-ß-d-glucopyranosyl-3ß,26-dihydroxycholest-5-en-16,22-dioxo-3-O-α-l-rhamnopyranosyl-(1 â†’ 2)-ß-d-glucopyranoside (1) and 26-O-ß-d-glucopyranosyl-(25R)-furost-5-en-3ß,14α,17α,22α,26-pentaol-3-O-α-l-rhamnopyranosyl-(1 â†’ 2)-ß-d-glucopyranoside (3) on the basis of spectroscopic data as well as chemical evidence.

Chemical constituents from the stems of Gymnema sylvestre.

AIM: To study the chemical constituents of stems of Gymnema sylvestre (Retz.) Schult. METHODS: Chromatographic techniques using silica gel, C18 reversed phase silica gel, and prep-HPLC were used. The structures were elucidated on the basis of MS and spectroscopic analysis (1D and 2D NMR), as well as chemical methods. RESULTS: Seven compounds were isolated and their structures were elucidated as conduritol A (1), stigmasterol (2), lupeol (3), stigmasterol-3-O-ß-D-glucoside (4), the sodium salt of 22α-hydroxy-longispinogenin-3-O-ß-D-glucopyranosyl-(1→3)-ß-D-glu-curono-pyranosyl-28-O-α-L-rhamnopyranoside (5), oleanolic acid-3-O-ß-D-glucopyranosyl-(1→6)-ß-D-glucopyranoside (6), and the sodium salt of 22α-hydroxy-longispinogenin 3-O-ß-D-glucuronopyranosyl-28-O-α-L-rhamnopyranoside (7). The inhibition activities of compounds 1, 5-7 on non-enzymatic glycation of protein in vitro were evaluated. CONCLUSION: Compound 7 is a new triterpenoid saponin. It was shown that compounds 1, 5-7 have weak inhibition activities for non-enzymatic glycation of protein in vitro.

Study on chemical constituents of Cyclocarya paliurus.

A new dammarane triterpenoid glycoside named cyclocarioside J (1) and other three known triterpenoid glycosides were isolated from the leaves of Cyclocarya paliurus. Based on ESI-MS, HR-ESI-MS, (1)H NMR, (13)C NMR, and 2D NMR techniques including (1)H-(1)H COSY, HMBC, HMQC, and NOESY correlations, the structure of cyclocarioside J was elucidated as (20S,24R)-epoxydammarane 3ß,12ß,25-trihydroxy-12-O-ß-d-quinovopyranosyl-3-O-α-l-arabinopyranoside.

A new triterpenoid saponin from Gymnema sylvestre.

Besides four known compounds, a new triterpenoid saponin was isolated from the stems of Gymnema sylvestre. The structure of the new triterpenoid saponin was established as 3ß,16ß,22α-trihydroxy-olean-12-ene 3-O-ß-D-xylopyranosyl-(1 → 6)-ß-D-glucopyranosyl-(1 → 6)-ß-D-glucopyranoside (1) on the basis of 1D and 2D NMR techniques, including COSY, HMBC, HMQC, and NOESY correlations. Four known compounds 2, 3, 4, and 5 were identified on the basis of spectroscopic data.

Two new furostanol saponins from Tribulus terrestris.

Two new furostanol saponins were isolated from the fruits of Tribulus terrestris L. Their structures were established as 26-O-beta-D-glucopyranosyl-(25S)-5alpha-furost-20(22)-en-3beta,26-diol-3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 4)]-beta-D-galactopyranoside (1) and 26-O-beta-D-glucopyranosyl-(25S)-5alpha-furost-20(22)-en-12-one-3beta,26-diol-3-O-beta-D-galactopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 4)-beta-D-galactopyranoside (2) on the basis of spectroscopic data as well as chemical evidence.

[Analysis of fatty acids from the flowers of Trollius chinensis].

OBJECTIVE: To analyze and identify fatty acids from the flowers of Trollius chinensis Bunge. METHODS: To isolate and determine the constituents using GC/MS technique, quantitatively analyze their content by area normalization method. RESULTS: 31 fatty acids and 7 other constituents were isolated and determined. CONCLUSION: The major fatty acids were hexadecanoic (19.85%), (Z,Z)-9,12-octadecadienoic (14.37%), tetradecanoic (13.93%), (Z)-9-octadecenoic (13.00%), dodecanoic (6.79%), 10-hydroxy-hexadecanoic (4.37%) and octadecanoic (3.34%) acids.

A new triterpene hexaglycoside from the bark of Kalopanax septemlobus (Thunb.) Koidz.

The new triterpene glycoside 3-O-beta-D-xylopyranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosylhederagenin 28-O-beta-D-gluco-pyranosyl-(1-->6)-beta-D-glucopyranoside, named septemoside A (1), and the known 3-O-alpha-L-rhamnopyranosyl-(1-->2)-O-alpha-L-arabinopyranoside-28-O-beta-D-glucopyranosyl-(1-->6)-O-beta-D-glucopyranosyl ester of hederagenin (2), were isolated from the bark of Kalopanax septemlobus. The structure elucidation of the compounds was based on spectroscopic evidence, including HRESIMS, 1D and 2D-NMR analysis.

[Determination of ten metal elements in Ziziphora clinopodioides Lam by microwave digestion-FAAS].

Comprehensive utilization of traditional Uighur medicine has been increasingly emphasized, and the relationship between metal elements and traditional Uighur medicine has attracted great attention, so it is quite important to determine the contents of traditional Uighur medicine. The Ziziphora clinopodioides Lam powder was digested with HNO3 by microwave digestion before determination. Ten metal elements in Ziziphora clinopodioides Lam were determined by FAAS. The work conditions, accuracy and precision of the method were studied. The linear correlations of standard curves are good (r = 0.999 0-0.999 8). The recovery (n = 6) is 95%-108%, and the RSD(n = 6) is 0.45%-1.53%. The results showed that there were comparatively rich metal elements, among which are comparatively high calcium, magnesium and potassium in Ziziphora clinopodioides Lam. The method offers traits of low detection limit, high sensitivity, speediness and exactness, and wasapplied to the determination of metal elements in samples with satisfactory results. It provided useful data for discussing the relationship between the content of the metal elements in Ziziphora clinopodioides Lam and clinical application of the Uighur medicine.

Two new steroidal glucosides from Tribulus terrestris L.

Two new furostanol saponins, tribufurosides D (1) and E (2), were isolated from the fruits of Tribulus terrestris L. With the help of chemical and spectral analyses (IR, MS, 1D, and 2D NMR), the structures of the two new furostanol saponins were established as 26-O-beta-d-glucopyranosyl-(25S)-5alpha-furost-12-one-2alpha,3beta,22alpha,26-tetraol-3-O-beta-d-glucopyranosyl-(1 --> 4)-beta-d-galactopyranoside (1) and 26-O-beta-d-glucopyranosyl-(25R)-5alpha-furost-12-one-2alpha,3beta,22alpha,26-tetraol-3-O-beta-d-glucopyranosyl-(1 --> 4)-beta-d-galactopyranoside (2).

A novel triterpenoid saponin from Polygala tenuifolia Willd.

A new triterpenoid saponin, tenuifoside A, was isolated together with three known triterpenoid saponins 2, 3, and 4 from the roots of Polygala tenuifolia Willd. With the help of chemical and spectral analyses (IR, MS, 1D-NMR, and 2D-NMR), the structure of the new saponin was elucidated as 3-O-beta-d-glucopyranosyl presenegenin 28-O-beta-d-xylopyranosyl-(1 --> 3)-beta-d-xylopyranosyl-(1 --> 4)-[beta-D-apiofuranosyl-(1 --> 3)]-alpha-L-rhamnopyranosyl-(1 --> 2)-[4-O-p-methoxycinnamoyl]-[alpha-l-rhamnopyranosyl-(1 --> 3)]-beta-d-fucopyranosyl ester (1). Three known triterpenoid saponins (2-4) were identified on the basis of spectroscopic data.

A new triterpenoid saponin from Albizia julibrissin Durazz.

A new triterpenoid, saponin hehuanoside A, was isolated together with the known triterpenoid saponins 2, 3, and 4 from the stem bark of Albizia julibrissin. With the help of chemical and spectral analyzes (IR, MS, 1D-NMR, and 2D-NMR), the structure of the new triterpenoid saponin was elucidated as 21-O-[(6S)-2-trans-2,6-dimethyl-6-O-beta-d-quinovopyranosyl-2,7-octadienoyl]-3-O-beta-d-xylopyranosyl-(1 --> 2)-beta-d-fucopyranosyl-(1 --> 6)-beta-d-2-deoxy-2-acetamidoglucopyrasyl acacic acid 28-O-alpha-l-arabinofuranosyl-(1 --> 4)-[-beta-d-glucopyranosyl-(1 --> 3)]-alpha-l-rhamnopyranosyl-(1 --> 2)-beta-d-glucopyranosyl ester (1). Three known triterpenoid saponins 2-4 were identified on the basis of spectroscopic data.

Two new furostanol saponins from Tribulus terrestris L.

Two new furostanol saponins, tribufurosides B (1) and C (2), were isolated from the fruits of Tribulus terrestris L. With the help of chemical and spectral analyses (IR, MS, 1D NMR and 2D NMR), the structures of two new furostanol saponins were established as 26-O-beta-d-glucopyranosyl-(25S)-5alpha-furost-20(22)-en-2alpha,3beta,26-triol-3-O-beta-d-galactopyranosyl(1 --> 2)-beta-d-glucopyranosyl(1 --> 2)-beta-d-galactopyranoside (1) and (25S)-5alpha-furost-20(22)-en-12-one-3beta, 26-diol-26-O-beta-d-glucopyranoside (2).

A novel steroidal glycoside, ophiofurospiside A from Ophiopogon japonicus (Thunb.) Ker-Gawl.

A new furospirostanol saponin, ophiofurospiside A (1), was isolated together with the known steroidal glycosides 2, 3, and 4 from the tubers of Ophiopogon japonicus (Thunb.) Ker-Gawl. Using chemical and spectral analyses (IR, MS, 1D NMR, and 2D NMR), the structure of 1 was established as 26-O-beta-d-glucopyranosyl-(22S, 25R)-furospirost-5-ene-3beta, 17alpha, 26-triol-3-O-[alpha-l-rhamnopyranosyl-(1 --> 2)]-[beta-d-xylopyranosyl-(1 --> 4)]-glucopyranoside (1). Three known steroidal saponins 2-4 were identified on the basis of spectroscopic data.

Two new triterpenoid saponins from Pulsatilla cernua (Thunb.) Bercht. et Opiz.

Two new triterpenoid saponins, named cernuaside C and D, have been isolated from Pulsatilla cernua (Thunb.) Bercht. et Opiz. The structures of the two new triterpenoid saponins were elucidated as 3-O-beta-D-xylopyranosyl(1 --> 2)-[alpha-L-rhamnopyranosyl(1 --> 3)]-alpha-L-arabinopyranosyl oleanolic acid 28-alpha-L-rhamnopyranosyl(1 --> 4)-beta-D-glucopyranosyl(1 --> 6)-beta-D-glucopyranoside. (1) and 3-O-alpha-L-arabinopyranosyl (1 --> 3)-alpha-L-rhamnopyranosyl(1 --> 2)-alpha-L-arabinopyranosyl oleanolic acid 28-O-beta-D-glucopyranoside (2) by 1D, 2D-NMR techniques, ESI-MS analysis as well as chemical methods.

[Studeis on the constituents of alkaloids and saponins of ginseng sini tang].

OBJECTIVE: To study the chemical constituents of Ginseng Sini Tang. METHOD: The constituents were identified by physico-chemical properties and spectral analysis. RESULT: The 12 compounds were identified as ginsenoside-Rb1,-Rb2,-Rb3,-Rc,-Rd,-Re,-Rg1,Rg2,Rg3,Rf,Ra1,Ra2. The 10 compounds were identified as benzoylmesaconitine(BM), benzoylaconitine(BA), benzoylhypaconitine(BH), neoline (NL), fuziline (FL), 14-ethyl-talatisamine14-acetyl-talatisamine (AT), 14-benzoylhypaconine-8-linoleate (HAL),14-benzoyldeoxyaconine-8-oleate(HAO), 14-benzoylhypaconine-8-palmitate(HAP), talatisamine(TS). CONCLUSION: All these compounds were obtained from Ginseng Sini Tang for first times.