Ya-Ping Liu

A cage-monoterpene indole alkaloid from Alstonia scholaris.

An unprecedented cage-like alkaloid, scholarisine A was isolated from the leaves of Alstonia scholaris and its structure determined on the basis of 1D and 2D NMR, FTIR, UV, and high-resolution mass spectroscopic data. This alkaloid might be derived from picrinine via oxygenation, rearrangement, and lactonization.

Melodinines A-G, monoterpenoid indole alkaloids from Melodinus henryi.

Nineteen monoterpenoid indole alkaloids including seven new ones, melodinines A-G (1-7), were isolated from Melodinus henryi. The structures of the new compounds were elucidated using spectroscopic methods, and the structure of compound 4 was confirmed by single-crystal X-ray diffraction analysis. The known compounds were identified by comparing their spectroscopic data with those reported in the literature. All of the compounds were evaluated for cytotoxic activity against five human cancer cell lines, and compound 11 exhibited cytotoxicity against HL-60, SMMC-7721, A-549, and SK-BR-3 cells with IC50 values of 2.0, 16.8, 25.9, and 24.7 microM, respectively.

Melotenine A, a Cytotoxic Monoterpenoid Indole Alkaloid from Melodinus tenuicaudatus

Melotenine A (1), an unprecedented skeleton with a 6/5/5/6/7 pentacyclic rearranged ring system, was isolated from Melodinus tenuicaudatus. The structure was elucidated by means of spectroscopic methods and further confirmed by the single-crystal X-ray diffraction analysis. A possible biogenesis was also proposed. Melotenine A exhibited potential inhibition against five human cancer cell lines.

Cytotoxic indole alkaloids from Melodinus tenuicaudatus.

Four new bisindole alkaloids, melodinines H-K (1-4), a new monomer, melodinine L (5), and 11 known alkaloids were isolated from Melodinus tenuicaudatus. The structures of 1-5 were elucidated by extensive spectroscopic methods, and the known compounds were identified by comparison with data in the literature. All of the compounds were evaluated for their cytotoxicity against five human cancer cell lines. Alkaloids 1, 3, and 4 and the known compound 11-methoxytabersonine (8) exhibited inhibitory effects, with IC(50) values comparable to those of cisplatin and vinorelbine.

Monoterpenoid indole alkaloids from Alstonia yunnanensis.

Eight new monoterpenoid indole alkaloids, alstoyunines A-H (1-8), along with 17 known analogues, were isolated from Alstonia yunnanensis. The structures of the new alkaloids were established by means of extensive spectroscopic methods. Alstoyunines C (3), E (5), and F (6) showed selective inhibition of Cox-2 (>75%). Alstoyunine F (6) showed weak cytotoxicity against the human myeloid leukemia HL-60 (IC50 = 3.89 microM) and hepatocellular carcinoma SMMC-7721 (IC50 = 21.73 microM) cell lines.

Melohenines A and B, Two Unprecedented Alkaloids from Melodinus henryi

A phytochemical study on Melodinus henryi has led to the isolation of two novel alkaloids, melohenines A (1), a monoterpenoid indole alkaloid with additional skeletal carbons arranged compactly in eight rings, and melohenine B (2), an alkaloid with an unprecedented 6/9/6/6 tetracyclic ring system regarded as a key intermediate from indole to quinoline alkaloids. Their structures were elucidated by means of spectroscopic methods and further confirmed by X-ray diffraction analysis.

Melodinines M-U, Cytotoxic Alkaloids from Melodinus suaveolens

Nine new alkaloids, melodinines M-U (1-9), and 11 known alkaloids were isolated from Melodinus suaveolens. The new structures were elucidated by extensive NMR and mass spectroscopic analyses and comparison to known compounds. All compounds were evaluated for their cytotoxicity against five human cancer cell lines. Compounds 6, 11, and 16 showed significant cytotoxicity.

Psychotripine: A New Trimeric Pyrroloindoline Derivative from Psychotria pilifera

Psychotripine, a trimeric pyrroloindoline derivative with an unprecedented hendecacyclic system bearing a hexahydro-1,3,5-triazine unit, was isolated from the leaves of Psychotria pilifera. The structure was elucidated on the basis of spectroscopic and quantum theory. A possible biogenesis was also postulated.

Inhibition of enterovirus 71 replication by chrysosplenetin and penduletin

In recent years, enterovirus 71 (EV71) infections have caused an increasing epidemic in young children, accompanying with more severe nervous system disease and more deaths. Unfortunately, there is no specific medication for it so far. Here we investigated the anti-EV71 activity of chrysosplenetin and penduletin, two o-methylated flavonols isolated from the leaves of Laggera pterodonta. These two compounds were found to have strong activity in vitro against EV71 with low cytotoxicity. In the cytopathic effect (CPE) inhibition assays, both plaque reduction assay and virus yield inhibition assay, the compounds showed a similar 50% inhibitory concentration (IC(50)) value of about 0.20 μM. The selectivity indices (SI) of chrysosplenetin and penduletin were 107.5 and 655.6 in African green monkey kidney (Vero) cells, and 69.5 and 200.5 in human rhabdomyosarcoma (RD) cells, accordingly. The preliminary mechanism analysis indicates that they function not through blocking virus entry or inactivating virus directly but inhibiting viral RNA replication. In the time-of-addition assay, both compounds inhibited progeny virus production and RNA replication by nearly 100% when introduced within 4h post infection. In addition to EV71, both compounds inhibited several other human enteroviruses with similar efficacy. These findings provide a significant lead for the discovery of anti-EV71 drug.

Picrinine-type Alkaloids from the Leaves of Alstonia scholaris

AIM: To investigate the chemical constituents of Yunnan local medicinal plants Alstonia scholaris. METHODS: Silica gel column chromatography was used to isolate the constituents, and spectroscopic techniques (NMR, IR, UV and MS) were used for structural elucidation. RESULTS: Four picrinine-type monoterpenoid indole alkaloids, 5β-methoxyaspidophylline (1), picrinine (2), picralinal (3) and 5-methoxystrictamine (4) were obtained from the leaves of Alstonia scholaris. CONCLUSION: Compound 1 is a new monoterpenoid indole alkaloid.