A new cucurbitane - type triterpenoid from the bark of Elaeocarpus hygrophilus Kurz.

A new cucurbitacin, 3ß-(ß-D-glucopyranosyloxy)-5ß,6ß:16α,23α-diepoxycucurbit-24-en-11-one or hygrocucurbin A (1), along with two known compounds, including 3ß-(ß-D-glucopyranosyloxy)-16α,23α-epoxycucurbita-5,24-dien-11-one (2) and (+)-lyoniresinol (3), were isolated from the bark of Elaeocarpus hygrophilus. Their chemical structures were elucidated by spectroscopic NMR, HR-IDA- TOF-MS analysis, and by comparison with the spectral data of corresponding compounds in the literature. Two cucurbitacins (1) and (2) were evaluated for their α-glucosidase inhibitory activity and cytotoxic against KB, MCF-7, Hep G2, and A549 cancer cell lines. For the α-glucosidase inhibitory activity, compound 1 showed an equivalent effect (IC50 197.4 ± 4.1 µM) compared to the acarbose, a positive control (IC50 208.5 ± 4.7 µM). And for the cytotoxicity, 2 was inactive while 1 was slightly sensitive against KB cells (IC50 233.3 ± 2.5 µM).

Spermacosides a and B, two new triterpenoid saponins from Spermacoce ocymoides burm.f.

Two new triterpenoid saponins, named spermacosides A-B (1 - 2), together with two known oleanane-type triterpenoid saponins, 3-O-ß-D-xylopyranosyl-(1→3)-ß-D-glucopyranosylbayogenin (3) and 3-O-ß-D-glucopyranosylbayogenin (4), were isolated from the ethyl acetate extract of Spermacoce ocymoides Burm.f. in a phytochemical investigation. Their chemical structures were elucidated by spectroscopic data analysis (1D and 2D NMR, and HR-ESI-MS), as well as comparison with reported data. All these compounds were evaluated for inhibiting nitric oxide production in lipopolysaccharide-stimulated RAW 264.7 cells. Among them, 1 showed a slight effect with an IC50 value of 108.65 ± 7.91 µM, and compounds 2-4 were inactive.

Comtrifosides A and B, two new triterpenoid saponins from the leaves of Combretum trifoliatum.

The phytochemical composition of the Combretum trifoliatum leaves was studied for the first time. Two new triterpenoid saponins, named comtrifoside A (1) and comtrifoside B (2), together with two other saponins (3-4) were purified by variously chromatographic techniques. For the first time, compound 3 was informed from the Combretum genus, as well as all of the isolated compounds (1-4) were reported from C. trifoliatum. The chemical structures of them were clearly characterised using extensive UV-VIS, IR, HRMS-ESI, and NMR experimental data. The in vitro anti-inflammatory activities of 1 & 2 were examined against NO overproduction in LPS activation of RAW264.7.

Jasminanthoside - a new pregnane-steroid from Jasminanthes tuyetanhiae.

A new pregnane steroid, jasminanthoside (1), together with three known compounds, telosmoside A7 (2), syringaresinol (3), and methyl 6-deoxy-3-O-methyl-ß-D-allopyranosyl-(1→4)-ß-D-oleandropyranoside (4) were isolated from the ethyl acetate extract of Jasminanthes tuyetanhiae roots collected in Vietnam. Their chemical structures were elucidated by NMR and MS spectroscopic data analysis along with the comparison of their data with the published ones in the literature. Although 4 was a known compound, its full NMR data were reported for the first time. All isolated compounds, evaluated for their α-glucosidase inhibition, showed activities stronger than the positive control acarbose. Among them, 1 was the best with the IC50 value of 7.41 ± 0.59 µM.

Two new halogenated sesquiterpene lactones from Palisada intermedia.

Two new sesquiterpene lactones, laurenolide A (1) and laurenolide B (2), along with six known compounds, palmitic acid (3), (R,R)-hexahydrofarnesyl acetone (4), trans-phytol acetate (5), cholesterol (6), cholesteryl acetate (7), cholesteryl heptadecanoate (8) were isolated from Palisada intermedia. The chemical structures of all compounds were elucidated by 1D and 2D-NMR spectroscopy and HR-ESI-MS analysis as well as compared with data in the literature. The petroleum ether, chloroform, ethyl acetate, methanol extracts and compounds 1, 2 were tested for the inhibition of two cancer cell lines MCF-7, NCI-H460 and they showed weak or none activities.

Hedyocoronins A and B: two new oleanane saponins from the aerial parts of Hedyotis coronaria.

Two new oleanane saponins, hedyocoronin A (1) and hedyocoronin B (2), were isolated from the aerial parts of Hedyotis coronaria (Kurz) Craib, Rubiaceae, collected at Da Oai district, Lam Dong province in Vietnam. Their chemical structures were elucidated by HR-MS, 1D and 2D-NMR spectra, along with the comparison with those reported in the literature. Compounds 1 and 2 showed weak cytotoxicity against KB and HeLa-S3 cancer cell lines with IC50 values of more than 54 µM.

Nepetifoliol - a new glutinane-triterpenoid from Leonotis nepetifolia.

A new glutinane-triterpenoid, nepetifoliol (1), together with two known compounds, dymacrin D (2), and (+)-ar-tumerone (3) were isolated from the n-hexane extract of the aerial parts of Leonotis nepetifolia. Their chemical structures were elucidated by spectroscopic data analysis as well as the comparison of their NMR data with the ones published in the literatures. A putative biosynthetic pathway for the formation of the new compound (anti-diaxial-5,6-diol) (1) from the precursor triterpene glutinol was proposed. Compounds (2), (3) and some previously reported ones, isolated from this extract, including 5α-stigmasta-22-ene-3-one (4), friedelin (5), chrysophanol (6), physcion (7), and 4'-O-methylalpinumisoflavone (8) were evaluated for their α-glucosidase inhibition. Among tested compounds, 3 and 6 showed good activities with their IC50 values of 5.3 ± 0.2 and 4.9 ± 0.3 µg/mL, respectively, comparing to the positive control, acarbose (IC50 127.7 ± 0.2 µg/mL).

A new resorcinol derivative from the bark of Aegiceras floridum (Primulaceae).

Chemical investigation of the Vietnamese plant Aegiceras floridum Roem. & Schult. (Primulaceae) led to the isolation of the new compound 3-methoxy-5-nonylphenol (1) along with five known ones 2,8,10-trihydroxy-6H-benzo[c]chromen-6-one (2), 2-hydroxy-5-methoxy-3-nonylbenzo-1,4-quinone (3), 5-(3-hydroxypropyl)-7-methoxy-3-(methylbenzofuran-2-yl)-3-methoxyphenol (4), 2,8-dihydroxy-7-methoxy-3,9-diundecyldibenzofuran-1,4-dione (5) and 10-hydroxy-4-methoxy-2,11-diundecylgomphilactone (6). The structures were elucidated by analysis of their HRESIMS and NMR data as well as the comparison of their NMR data with those reported in the literature. The cytotoxic activity of selected isolated compounds against some cancer cell lines such as human epithelial carcinoma (HeLa), human lung cancer (NCI-H460), liver hepatocellular carcinoma (HepG2), human breast cancer (MCF-7), and acute T cell leukemia (Jurkat) was evaluated. Among them, 3 showed moderate activities against MCF-7 with an IC50 of 17.77 µM and NCI-H460 with an IC50 of 25.02 µM. The result of DPPH radical scavenging activity assay indicated that compounds 2-4 and 6 revealed weak antioxidant activity.

A new triterpenoid saponin from Glinus oppositifolius.

From the ethanol extract of Glinus oppositifolius, collected at Phu Yen province, Viet Nam, one new triterpenoid saponin (1) and four known compounds (2-5) were isolated. By means of NMR and HR-ESI-MS analyses, their structure was elucidated as 3-O-(ß-D-xylopyranosyl-(1→3)-ß-D-xylopyranosyl)spergulagenin A or glinusopposide V (1), glinusopposide L (2), spergulin B (3), vitexin (4) and astralagin (5). Two compounds (1-2) showed weak inhibitory activity against α-glucosidase.

A new depsidone from the lichen Usnea ceratina Arch.

Chemical investigation of the lichen Usnea ceratina Arch led to the isolation of five depsidones, including one new compound ceratinalone (1) along with four known compounds bailesidone (2), stictic acid (3), 8'-O-methylstictic acid (4) and 8'-O-ethylstictic acid (5). The structures were determined by analysis of their MS and NMR data as well as by comparison with literature values. Compounds 1 and 4 were evaluated the cytotoxic activity against HeLa (human epithelial carcinoma), NCI-H460 (human lung cancer), HepG2 (liver hepatocellular carcinoma), and MCF-7 (human breast cancer) cell lines, showing the moderate activity.

Telosmoside A21, a new steroid glycoside from the roots of Jasminanthes tuyetanhiae.

A new glycoside, telosmoside A21 (1) and two known compounds, telosmoside A6 (2) and telosmoside A1 (3), were isolated from the roots of Jasminanthes tuyetanhiae. The structure of compound 1 was identified from its spectroscopic data and by comparison with the literature.

Three new diphenyl ethers from the lichen Parmotrema praesorediosum (Nyl.) Hale (Parmeliaceae).

Three new diphenyl ethers, named praesorethers E, F and G (1, 2 and 3), were isolated from the lichen Parmotrema praesorediosum. Their chemical structures were elucidated on the basis of extensively spectroscopic analysis including HR-ESI-MS and NMR as well as comparison with previously published data. These compounds were evaluated for the cytotoxicity against three human cancer cell lines (HeLa, NCI-H460 and MCF-7) using SRB assay. As results, 1 and 2 exhibited weak cytotoxic activity against three tested cancer cell lines with the inhibitive percentage of 64-79.9% at the concentration of 100 µg/mL while 3 was inactive.

Three new phenolic compounds from the lichen Ramalina peruviana Ach. (Ramalinaceae).

Three new phenolic compounds, peruvinides A-C were isolated from the lichen Ramalina peruviana Ach. (Ramalinaceae). Their structures were unambiguously determined by extensive spectroscopic analyses and comparison with literature data. Peruvinides A and B bearing unusual moieties were found for the first time among lichen metabolites.

Usneaceratins A and B, two new secondary metabolites from the lichen Usnea ceratina.

Two new compounds, comprising one dibenzofuran, named usneaceratin A (1), and one phenolic acid, named usneaceratin B (2), together with one known dibenzofuran, isousnic acid (3), and two known phenolics, orsellinic acid (4) and methyl orsellinate (5) were clarified from the lichen Usnea ceratina using variously chromatographic methods. Their structures were testified by comprehensive HR-ESI-MS, and NMR spectroscopic analysis, and comparison with published data. Their α-glucosidase inhibitory activity of all compounds was measured. Usneaceratin B (2) possessed better inhibition against α-glucosidase enzyme (IC50 value of 41.8 µM) than the standard drug acarbose (IC50 value of 214.50 µM).

Two new phenolic compounds from the Vietnamese lichen Parmotrema tinctorum.

Chemical investigation of the lichen Parmotrema tinctorum (Nyl.) Hale led to the isolation of two new phenolic compounds, 2-ethylhexyl orsellinate (1) and tinctorinone (2). The structures were determined by analysis of their MS and NMR data as well as by comparison with literature data. The 2-ethylhexyl ester group of 2-ethylhexyl orsellinate is uncommon among lichen metabolites. Tinctorinone revealed strong inhibition towards α-glucosidase.

Synthesis and cytotoxic evaluation of usnic acid benzylidene derivatives as potential anticancer agents.

A series of usnic acid benzylidene derivatives (groups I-V) were designed, synthesized and evaluated for their anticancer activity in the search for potentially new anticancer agents. Compounds 1a, 5b, 2b, 2e and 2f exhibited the most potent cytotoxcity against K562 cell line with IC50 values of 10.0 ± 3.6, 5.6 ± 0.4, 8.8 ± 1.0, 4.5 ± 0.1 and 8.4 ± 0.4 µM, respectively. It is noteworthy that compound 2e displayed potent cytotoxicity against K562 cells without any cytotoxic effect on HEK293 normal cell line.

Further terpenoids from Euphorbia tirucalli.

The phytochemical investigation of Euphorbia tirucalli L. (Euphorbiaceae) yielded four new compounds, including a rare cadalene-type sesquiterpene (tirucadalenone), two tirucallane triterpenoids, euphorol L and euphorol M, with the latter being described as an epimeric mixture, and a euphane triterpene, namely, euphorol N, together with 7 known compounds. Their structures and absolute configurations were elucidated from analysis of 1D (1H, J-modulated 13C) and 2D NMR (HSQC, HMBC and NOESY), high-resolution mass spectrometry (HRESIMS), optical rotation, and GIAO NMR shift calculation followed by CP3 analysis, along with comparison with literature reports. All these compounds were tested for cytotoxicity against K562, MCF-7 and/or and HepG2 tumor cell lines. Only tirucadalenone displayed a mild cytotoxic activity.

DP4-Assisted Structure Elucidation of Isodemethylchodatin, a New Norlichexanthone Derivative Meager in H-Atoms, from the Lichen Parmotrema tsavoense.

A phytochemical investigation of the foliose lichen Parmotrema tsavoense (Krog and Swinscow) Krog and Swinscow (Parmeliaceae) resulted in the isolation of a new trichlorinated xanthone, isodemethylchodatin. The structure elucidation of this new norlichexanthone derivative proved tricky owing to proton deficiency, and to the lack of NMR data of closely related analogues. The structure of this compound was determined based on an integrated interpretation of 13C-NMR chemical shifts, MS spectra, and DP4-based computational chemistry was also performed to provide an independent and unambiguous validation of the determined structure. Isodemethylchodatin represents the first chlorinated lichexanthone/norlichexanthone derivative bearing a methoxy group at C-5.

Two new triterpenoids from the roots of Phyllanthus emblica.

Two new triterpenes, the seco-friedelane type secofriedelanophyllemblicine and the ursane-derived saponin ursophyllemblicoside were isolated from the roots of the edible fruit-producing Phyllanthus emblica. Their structures were unambiguously elucidated using extensive 1D and 2D NMR analyses, high resolution mass spectrometry and single-crystal X-ray crystallographic analyses along with comparison with literature data. Secofriedelanophyllemblicine represents the first 3,4-secofriedelane bearing a carboxylic acid group substituent at C-20. Ursophyllemblicoside, incorporating the rare 21α hydroxyursolic acid as a sapogenol represents the first example of saponin comprising this aglycone. Secofriedelanophyllemblicine displayed a moderate cytotoxicity against K562 and HepG2 cancer cell lines.