Two new p-coumaroylated sesquiterpenoids from Pilea cavaleriei.

A new p-coumaroylated santalane-type sesquiterpenoid, 8-p-coumaroyl-α-santalene (1), a new p-coumaroylated oplopanane-type sesquiterpenoid, 8-ß-p-coumaroyl-oplopanone (2), and three known p-coumaroylated humulene-type sesquiterpenoids (3-5) were isolated from the ethanol extract of the whole herbs of Pilea cavaleriei. Their structures were elucidated based on the combination of 1D and 2D NMR and HRMS methods. Compound 2 was found to show anti-tuberculosis activity with MIC of 16 µg/ml.

New phenolic glycosides from Pilea cavaleriei.

Five new phenolic glycosides, 2-hydroxy-(2'E)-prenyl benzoate-2,4'-di-O-ß-D-glucopyranoside (1), 2-hydroxy-(2'E)-prenyl benzoate-2-O-α-L-arabinopyranosyl-(1 → 6)-ß-D-glucopyranoside (2), 4-methylphenol-1-O-α-L-rhamnopyranosyl-(1 → 6)-ß-D-glucopyranoside (3), 4-methylphenol-1-O-α-L-arabinopyranosyl-(1 → 6)-ß-D-glucopyranoside (4), and 3,5-dimethoxyphenol-1-O-ß-D-apiofuranosyl-(1 → 2)-ß-D-glucopyranoside (5), together with six known glycosides (6-11), were isolated from the n-BuOH fraction of the EtOH extract of Pilea cavaleriei Levl subsp. cavaleriei. Their structures were elucidated by extensive spectroscopic analysis, including 1D and 2D NMR spectroscopy as well as HR-ESI-MS, and chemical evidences. All these compounds were isolated from the genus Pilea for the first time.

A new triterpenoid and a new glycoside from Pilea cavaleriei.

A new triterpenoid, 11α,12α-epoxy-3ß-hydroxy-24-nor-olean-4(23)-en-28,13ß-olide (1), and a new glycoside, benzyl 2-O-ß-d-apiofuranosyl-(1 â†’ 2)-ß-d-glucopyranosyl benzoate (2), together with eight known triterpenoids (3-10), were isolated from Pilea cavaleriei subsp. cavaleriei. Their structures were established on the basis of spectroscopic analysis including HR-ESI-MS, 1D NMR, and 2D NMR techniques. All compounds showed no anti-hepatitis C virus activity.

[Chemical constituents of Pilea cavaleriei subsp. cavaleriei].

OBJECTIVE: To investigate chemical constituents from folk herb Pilea cavaleriei subsp. cavaleriei. METHOD: The compounds were separated and purified by silica gel, Sephadex LH-20 and the like. The structures were identified by spectral methods such as (1)H, (13)C-NMR and MS. RESULT: Seventeen compounds were isolated and identified as benzoic acid (1), 4-hydroxy benzalde-hyde (2), coumaric acid(3), protocatechuic acid (4), gallic acid (5), 4-hydroxy benzoic acid (6), 3-indole carboxaldehyde (7), 3-indole carbo-xylicacid (8), 4-methyl-(1,2,3) -triazole(9), uracil(10), nicotinamide (11), (2S,E)-N-[2-hydroxy-2-(4-hydroxy phenyl) ethyl] ferulamide (12), (+) -dehydrovomifoliol (13), hentriantane (14), beta-sitosterol (15), palmitic acid (16), daucossterol (17) , respectively. CONCLUSION: All compounds were obtained from the genus for the first time.

Three new p-coumaroylated sesquiterpenoids from Pilea cavaleriei.

Four p-coumaroylated sesquiterpenoids (1-4), including three new ones (1, 2, and 4), were isolated from the whole plants of Pilea cavaleriei. Their structures were established on the basis of comprehensive spectroscopic analysis and comparison with data reported in the literature. Compounds 1-4 were evaluated for their antimycobacterial activities, and 2 and 4 were active against Mycobacterium tuberculosis H37Rv with the MIC values of 19.6 ± 0.19 and 17.4 ± 0.12 µg/mL, respectively.

Chemical constituents from the whole plants of Pilea cavaleriei Levl subsp. cavaleriei.

Three new sesquiterpene glycosides (1-3), three new glycerol glycosides (4-6), two new alkaloids (7-8), together with seven known compounds (9-15) all of which were isolated from the genus Pilea for the first time, were isolated from the whole plants of Pilea cavaleriei Levl subsp. cavaleriei. Their structures were determined by extensive spectroscopic techniques and chemical methods. The cytotoxic activity of the isolated compounds was evaluated against four cancer cell lines, and none of the tested compounds caused a significant reduction of the cell number.