Jicheng Shu

Two new pterosin dimers from Pteris mutifida Poir

Two new C₁₄ pterosin dimers, which are a pair of isomers named as bimutipterosins A (1) and B (2), were isolated from the whole plant of Pteris multifida. Their structures have been elucidated on the basis of NMR and MS data. From a biogenetic point of view, these compounds including a cyclobutane basic core should be considered as a [2+2] dimerization product of dehydropterosin Q, which was a known compound and also isolated from this plant. This novel type of pterosin dimer was reported here for the first time. Compounds 1 and 2 showed cytotoxicity against HL 60 cell line (human leukemia) with the IC₅₀ values of 12.8 and 26.6 μM, respectively.

A new alkaloid from the fruit of Nandina domestica Thunb.

A new steroidal alkaloid, (20S,22R,24R)-24-ethyl-3-oxocholest-4-en-22-amino, named as nandsterine (1), together with 10 known alkaloids, palmatine (2), O-methylbulbocapnine (3), nantenine (4), dehydronantenine (5), glaucine (6), didehydroglaucine (7), dehydrocorydaline (8), jatrorrhizine (9), magnoflorine (10) and berberine (11), was isolated from the fruit of Nandina domestica Thunb. Their structures were elucidated by using spectroscopic methods as well as by comparing with the published data. Compound 1 was a new class of steroidal alkaloid isolated from the family Berberidaceae, meanwhile compounds 2, 3, 6–8 and 10 were obtained from N. domestica for the first time. Compound 1 exhibited cytotoxicity against HL-60 cells (human leukaemia) with IC50 values of 52.1 μM.

A novel phloroglucinol and two new phenolic glycosides from Psidium littorale

Abstract One novel phloroglucinol, psidosone A (1), and two new phenolic glycosides, psidoside A (2), and psidoside B (3), together with nine known phenol compounds (4–12), were isolated from the fruits of Psidium littorale Raddi. Their structures were elucidated using data obtained from MS, 1H and 13C NMR spectra, and correlation experiments (HMQC and HMBC), as well as by comparison with published data.

Three new abietane-type diterpene glycosides from the roots of Tripterygium wilfordii

Three new abietane-type diterpene glycosides named as tripterycoside A (1), tripterycoside B (2), tripterycoside C (3), along with two known ones, 11-O-β-d-glucopyranosyl-neotritophenolide (4), wilfordoside A (5), and nine other known compounds, 5-hydroxymethylmellein (6),1,2-bis-(3-methoxy-4-hydroxyphenyl)-1,3-propanediol (7), leptolepisol C (8), icariol A2 (9), tripfordine A (10), 16α-hydroxy-ent-kauran-19-oic acid (11),wilforine (12), wilfordine (13), 3-acetyloleanolic acid (14),were isolated from the roots of Tripterygium wilfordii. Their structures have been elucidated on the basis of NMR and MS data. To the best of our knowledge, abietane-type diterpene glycosides were rarely reported natural products, especially abietane-type diterpene glycoside containing 7-oxo group (compound 3) was reported here for the first time. Furthermore, compounds 6, 7, 8 and 14 were isolated from this plant for the first time. Compounds 1-5 showed statistically significant inhibitory effects on IL-1β secretion in LPS-induced rat primary synovial fibroblasts at 10μM.

New Benzophenone and Diphenylmethane Glycosides from Psidium littorale

The methanol extract from the fresh leaves of P. littorale was subjected to various column chromatography. This resulted in the isolation of four benzophenone glycoside derivatives: one new benzophenone glycoside, 2,6-dihydroxy-3-methyl-4-O-β-D-glucopyranosyl-benzophenone (1), one new diphenylmethane glycoside, 2,6-dihydroxy-3-methyl-4-O-(6″-O-galloyl-β-D-glucopyranosyl)-diphenylmethane (2), along with two known benzophenones, 2,6-dihydroxy-4-O-β-D-glucopyranosyl-benzophenone (3) and 2,6-dihydroxy-3-methyl-4-O-(6″-O-galloyl-β-D-glucopyranosyl)-benzophenone (4). Their structures were elucidated using data obtained from FAB-MS, 1H, and 13C NMR spectra and correlation experiments (HMQC and HMBC), as well as by comparison with published data. The activity of compounds 1–4 against five fungal species was investigated: the antimicrobial activity of all isolated compounds increased with concentration and varied according to the following rank: 1 ≥ 4 > 3 > 2, thereby showing some structure–activity relationships.

Three new flavonoid glycosides from Smilax glabra and their anti-inflammatory activity

Abstract Three new flavonoid glycosides, 2(S)-5-hydroxy-6,8-dimethoxyflavonone-7-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranoside (1), 5-hydroxy-3,8-dimethoxyflavone-7-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranoside (2) and 3,7-dihydroxy-8-methoxyflavone-6-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranoside (3), together with five known flavonoids (4–8) were isolated from the roots of Smilax glabra Roxb. Their structures were elucidated on the basis of chemical and spectral evidence, as well as by comparison with literature data. Three new flavonoids were subjected to evaluate anti-inflammatory activity. Compounds 1–3 inhibited the NF κB induction by 32.2, 55.8 and 61.7%, respectively.

Distinguishing Smilax glabra and Smilax china rhizomes by flow-injection mass spectrometry combined with principal component analysis

Abstract Flow-injection mass spectrometry (FIMS) coupled with a chemometric method is proposed in this study to profile and distinguish between rhizomes of Smilax glabra (S. glabra) and Smilax china (S. china). The proposed method employed an electrospray-time-of-flight MS. The MS fingerprints were analyzed using principal component analysis (PCA) and orthogonal partial least squares discriminant analysis (OPLS-DA) with the aid of SIMCA software. Findings showed that the two kinds of samples perfectly fell into their own classes. Further predictive study showed desirable predictability and the tested samples were successfully and reliably identified. The study demonstrated that the proposed method could serve as a powerful tool for distinguishing between S. glabra and S. china.

New furostanol saponins with anti-inflammatory and cytotoxic activities from the rhizomes of Smilax davidiana

HIGHLIGHTSSeven new furostanol glycosides were isolated from the ethanol extract of Smilax davidiana.The structures of new compounds were determined on the basis of NMR spectroscopy and HR‐ESI‐MS.Compounds 3, 5 and 7 were found to have modest anti‐inflammatory effects.Davidianoside F (6) showed activity against MCF‐7 and HELA cell lines. ABSTRACT Seven new furostanol saponins have been isolated from the rhizomes of Smilax davidiana. Their structures were established by 2D NMR spectroscopic techniques (1H,1H‐COSY, NOESY, HSQC and HMBC), mass spectrometry and comparison with the literature. The isolated compounds were subjected to evaluate anti‐inflammatory and cytotoxic activities in vitro. Compounds 3, 5 and 7 were found to have modest anti‐inflammatory effects through suppression of IL‐1&bgr; production and promote the expression of IL‐10 in LPS‐stimulated RAW 264.7 cells. Davidianoside F (6) showed activity against MCF‐7 and HELA cell lines at the concentration of 10.2 &mgr;M and 4.3 &mgr;M, respectively.

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

Abstract 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.