Natural Products from Melodinus suaveolens

Antifungal activities and active ingredients of Melodinus suaveolens Champ. ex Benth.[Pubmed: 28714347]

Four Melodinus species with antifungal activity were found in survey of the floral resources, in Shiwan Mountain Natural Reserve, Guangxi Province, China. Crude methanolic extracts of the twigs and leaves of Melodinus suaveolens exhibited potent antifungal activities against the plant pathogenic fungi Colletotrichum musae, Colletotrichum graminicola, Colletotrichum gloeosporioides and Alternaria musae, and the ethyl acetate fraction inhibited these pathogens at rates of 85.37, 91.47, 72.77 and 89.87%, respectively (5 mg/mL). A new compound, (2R, 3S, 5S, 6R)-1-O-methyl- chiro-inositol was isolated from the ethyl acetate fraction, along with 15 known compounds. The antifungal activities of compounds (1-16) were evaluated for the first time. Compound (4) had potent antifungal activity against C. gloeosporioides, C. graminicola and A. musae.

Two new compounds from Melodinus suaveolens.[Pubmed: 27426217]

Two new compounds, 19-hydroxy-melodinine K (1) and melodiside (2), and 25 known compounds were isolated from leaves and twigs of Melodinus suaveolens. Their structures were elucidated based on 1- and 2-D NMR, FTIR, UV and MS spectroscopic data. 19-hydroxy-melodinine K showed cytotoxic activity against MDA-MB-231 breast, BCG-823 gastric, SW480 colon and Hela cancer cells.

Aspidosperma-type Alkaloids from Melodinus suaveolens.[Pubmed: 26996019]

Three new aspidosperma-type alkaloids, 3-oxo-11-hydroxytabersonine (2), 1 1-hydroxytabersonine N-oxide (3) and 11-methoxytabersonine N-oxide (4), along with three known ones were isolated from the twigs and leaves of Melodinus suaveolens. The structures of the new compounds were elucidated by using spectroscopic methods, and circular dichroism experiments. The known compounds were identified by comparing their spectroscopic data with those reported in the literature.

Antibacterial constituents from Melodinus suaveolens.[Pubmed: 25908630]

To investigate the non-alkaloidal chemical constituents of the stems and leaves of Melodinus suaveolens and their antibacterial activities. Compounds were isolated and purified by repeated silica gel, Sephadex LH-20, RP18, and preparative HPLC. Their structures were elucidated by comparison with published spectroscopic data, as well as on the basis of extensive spectroscopic analysis. The antibacterial screening assays were performed by the dilution method. Fourteen compounds were isolated, and identified as lycopersene (1), betulinic aldehyde (2), 3β-acetoxy-22,23,24,25,26,27-hexanordammaran-20-one (3), 3a-acetyl-2, 3, 5-trimethyl-7a-hydroxy-5-(4,8,12-trimethyl-tridecanyl)-1,3a,5,6,7,7a-hexahydro-4-oxainden-1-one (4), 3β-hydroxy-28-norlup-20(29)-ene-17β-hydroperoxide (5), 3β-hydroxy-28-norlup-20(29)-ene-17α-hydroperoxide (6), β-sitosterol (7), 28-nor-urs-12-ene-3β, 17β-diol (8), α-amyrin (9), ergosta-4,6,8(14),22-tetraen-3-one (10), 3β-hydroxy-urs-11-en-28,13β-olide (11), betulin (12), obtusalin (13), and ursolic acid (14). Among the isolates, compounds 1, 2, 6, 8, 10, and 14 showed potent antibacterial activities against the four bacteria. This is the first report of the antibacterial activity of the constituents of Melodinus suaveolens.

Two new alkaloids from Melodinus suaveolens.[Pubmed: 25522534]

Two new Melodinus-type alkaloids, 15β-hydroxy-14,15-dihydroscandine (1) and 14,15-dihydroscandine (2), together with 6 known ones were isolated from Melodinus suaveolens. The structures of the new compounds were identified from spectroscopic (NMR, UV, IR, CD) and mass spectrometric data and Mosher's method. The new compounds exhibited significant, dose-dependent inhibition of the production of lipopolysaccharide (LPS)-induced NO, IL-6 and IL-8 in mice macrophages.

Melosuavines A-H, cytotoxic bisindole alkaloid derivatives from Melodinus suaveolens.[Pubmed: 24274642]

Eight new bisindole alkaloids, melosuavines A-C (1-3), having an aspidosperma-scandine linkage, melosuavines D-F (4-6), possessing an aspidosperma-aspidosperma skeleton, and melosuavines G and H (7 and 8) of the aspidosperma-venalatonine type, tenuicausine (9), and melodinine J (10) were isolated from the twigs and leaves of Melodinus suaveolens. The structures of 1-8 were elucidated by extensive spectroscopic methods, and compounds 9 and 10 were identified by comparison with data in the literature. The relative configuration 9 was determined from the ROESY spectrum, and some NMR signals were reassigned. Compounds 1, 2, 4-6, 8, and 10 exhibited low micromolar cytotoxicity against one or more of five human cancer cell lines.

[Chemical constituents from the twigs and leaves of Melodinus suaveolens].[Pubmed: 24010320]

To investigate the chemical constituents from the twigs and leaves of Melodinus suaveolens.

Melodinines M-U, cytotoxic alkaloids from Melodinus suaveolens.[Pubmed: 22260257]

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.