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A new alkaloid, 2-acetyl-4-methoxyfuro[2,3-b]quinoline (1), and a new benzaldehyde derivative, (2′S)-4-(2′-hydroxy-3′-methyl-3′-butenoxy)benzaldehyde (2), were isolated from the twig of Zanthoxylum rhetsa (Roxb.) DC. along with twenty-six known compounds (3−28). Their structures were determined by spectroscopic analysis (1D and 2D NMR spectroscopy and HRMS analysis) and comparison with data reported in the literature. Thirteen of the known compounds were evaluated for their cytotoxic activities against human cancer cell lines that included MDA-MB-231, SW1353, A549, and HCT116. (±)-8-Acetonyldihydronitidine (15) showed moderate cytotoxicity toward the SW1353 cancer cell line with an IC50 value of 18.90±0.39 µg/mL, and exhibited weak cytotoxic activity against MDA-MB-231, A549 and HCT116 cell lines with IC50 values of 49.86−71.32 µg/mL. [ABSTRACT FROM AUTHOR]

Gonioridleylactam (1), a new compound, is a unique dimeric aristolactam isolated from the EtOAc extract of the twigs of Goniothalamus ridleyi King. The structure of gonioridleylactam (1) consists of two different aristolactams linked together with two methylenedioxy bridges at C–3/C–3′ and C–4/C–4′, generating a ten-membered ring of [1,3,6,8]tetraoxecine. A new natural product, gonioridleyindole (3-hydroxymethyl-1-methyl-1H-benz[f]indole-4,9-dione, 2), together with eight known compounds (3–10) were also isolated from this plant. Their structures were extensively characterized by spectroscopic methods and comparisons were made with the literature. Compounds 1–4, 7, and 9 were evaluated for their α-glucosidase inhibitory activity. Of these, 3,5-demethoxypiperolide (7) displayed the highest α-glucosidase inhibitory activity, with an IC50 value of 1.25 µM. [ABSTRACT FROM AUTHOR]

Comprehensive phytochemical examination from different perspectives using preparative and analytical chromatographic techniques combined with spectroscopic/spectrometric methods of the so-called "yellow twig" Nauclea orientalis (L.) L. (Rubiaceae) led to the identification of 13 tryptamine-derived (=monoterpene-indole) alkaloids. The identified alkaloids comprise strictosamide and four of its glucosidic derivatives, three oxindole derivatives, and five yellow-colored angustine-type aglycones. Qualitative and quantitative HPLC analyses showed the enrichment of strictosamide in all studied organs. Based on these results, we performed metabolomic analyses of monoterpene-indole alkaloids and made a 1H NMR in vitro monitoring of enzymatic deglucosylation of strictosamide. A comparison of the stability of strictosamide and its enantiomer vincoside lactam by theoretical calculations was also performed revealing a slightly higher stability of vincoside lactam. Additionally, we conducted two different anti-feedant assays of strictosamide using larvae of the polyphageous moth Spodoptera littoralis Boisduval. The obtained results indicate that generally two different biosynthetic pathways are most likely responsible for the overall alkaloid composition in this plant. Strictosamide is the key compound in the broader pathway and most likely the source of the identified angustine-type aglycones, which may contribute significantly to the yellow color of the wood. Its cross-organ accumulation makes it likely that strictosamide is not only important as a reservoir for the further biosynthesis, but also acts in the plants' defense strategy. [ABSTRACT FROM AUTHOR]

Subfraction 3A1 (8.0 g) was further subjected on a silica gel column with CHCl SB 3 sb -acetone (5:1) and then purified by Sephadex LH-20 CC (CHCl SB 3 sb -MeOH, 3:2) to afford compounds B 1 b (9.4 mg), B 3 b (20.7 mg), B 5 b (30.3 mg), B 6 b (30.5 mg), B 14 b (10.5 mg), and B 15 b (50.5 mg). Subfraction 3A2 (6 g) was isolated on a silica gel column with petroleum ether-acetone- diethylamine (30:1:1) and CHCl SB 3 sb -MeOH (80:1) and then purified by Sephadex LH-20 CC (CHCl SB 3 sb -MeOH, 3:2) to obtain B 7 b (18.4 mg), B 10 b (27.6 mg), B 12 b (7.4 mg), and B 13 b (6.4 mg). Subfraction 2A (7.20 g) was further separated on an RP-18 column and eluted with 70% aueous MeOH, then on a silica gel column with CHCl SB 3 sb -MeOH (35:1), and purified by Sephadex LH-20 CC (CHCl SB 3 sb -MeOH, 3:2) to produce B 2 b (13.4 mg), B 8 b (8.1 mg), and B 9 b (7.6 mg). Subfraction 3B (3.3 g) was subjected to silica gel column chromatography with petroleum ether-acetone-diethylamine (35:1:1) and then purified by Sephadex LH-20 CC (CHCl SB 3 sb -MeOH, 3:2) to give B 4 b (6.5 mg) and B 11 b (6.7 mg). [Extracted from the article]

• ACG was highly toxic to human cancer cells in comparison to ALK and MeOH extracts. • ACG and MeOH extracts were significantly toxic to the rat cortical neurons. • ALK extract decreased cancer cell viability, but it was not toxic to the neurons. • Aporphine alkaloids were toxic to the neurons according to the statistical analysis. • Liriodenine and norushinsunine were cytotoxic toward all of the tested cancer cells. This study was aimed to evaluate the efficacy and safety of Asimina triloba extracts and its alkaloidal constituents in terms of their cytotoxicity and neurotoxicity towards different cell lines. Six alkaloids (anolobine-9- O - β - d -glucopyranoside, anolobine, norushinsunine, liriodenine, squamolone and coclaurine) were evaluated for their cytotoxic potential in four human solid tumor cell lines (SK-MEL, KB, BT-549, and SK-OV-3). The potential for neurotoxicity was determined using rat cortical neurons. Three extracts, namely a crude methanolic extract, an alkaloid-rich extract, and an acetogenin-rich extract, were also included in the study. The acetogenin-rich extract was the most potent, among all tested extracts, towards SK-MEL, KB, and BT-549 cells with IC 50 values in the range of 0.09–0.11 µg/mL. Also, the same extract was found to be significantly toxic to the neurons at 10 µg/mL. The alkaloid-rich extract also showed cytotoxicity, albeit with lower potency, towards SK-MEL, KB, and BT-549 cell lines with IC 50 values in the range of 1.7–2.6 µg/mL. Out of the six isolated alkaloids, three alkaloids (anolobine-9- O - β -D-glucopyranoside, norushinsunine, and liriodenine) demonstrated cytotoxic activity. Although the alkaloidal extract did not show any toxicity to neurons up to 10 µg/mL, the pure alkaloids were toxic to the neurons in a concentration-dependent manner. In conclusion, this study underlines the contribution of the alkaloidal constituents in the neurotoxicity and cytotoxicity of A. triloba. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of the MeOH-EtOAc (1:1 v/v) soluble fraction partitioned from the MeOH extract of twigs of Uvaria grandiflora Roxb. led to the isolation of six known compounds including aristolactam AII (1), aristolactam BI (2), velutinam (3), griffithinam (4), isoursuline (5), and sinactine (6). Their structures were determined on the basis of spectroscopic analysis and comparison with the literature data. Described in this work is the first report of isoursuline (5), an azafluorene derivative, and sinactine (6), a tetrahydroepiberberine, being isolated from plants in the Uvaria genus. Antioxidant and antimicrobial activities of some isolated compounds were evaluated. Among screened compounds, velutinam (3) showed antioxidant activity in the DPPH radical scavenging assay. [ABSTRACT FROM AUTHOR]

The β-carboline core is the base structure of several biologically active natural and unnatural compounds. Herein, we report the first total synthesis of trigonostemine G, which is a newly isolated natural β-carboline alkaloid from the twigs of Trigonostemon filipes. Synthesis of two structurally close derivatives of trigonostemine G is also reported. Key step of the syntheses involves a nucleophilic addition of 5-{[tert-butyl(dimethyl) silyl]oxy}-1H-indole to 1-formyl-β-carboline building blocks. [ABSTRACT FROM AUTHOR]

The first phytochemical investigation of the twigs of Phaeanthus lucidus Oliv. resulted in the isolation and identification of four undescribed alkaloids, including two aporphine dimers, phaeanthuslucidines A and B, a hybrid of aristolactam-aporphine, phaeanthuslucidine C, and a C– N linked aporphine dimer, phaeanthuslucidine D, together with two known compounds. Their structures were determined by extensive analysis of spectroscopic data, and by comparison of their spectroscopic and physical data with previous reports. Phaeanthuslucidines A–C and bidebiline E were analysed and resolved by chiral HPLC to yield the (R a) and (S a) atropisomers, whose absolute configurations were respectively determined by ECD calculations. Phaeanthuslucidines A and B, bidebiline E, and lanuginosine showed α -glucosidase inhibitory activities with IC 50 values in the range of 6.7–29.2 μM. Moreover, molecular docking simulations of α -glucosidase inhibition of active compounds were studied. Phaeanthuslucidines A−D, undescribed dimeric aporphine alkaloids, and two known aporphine alkaloids were isolated from the twig extract of Phaeanthus lucidus Oliv. Phaeanthuslucidines A and B, bidebiline E, and lanuginosine showed α -glucosidase inhibitory activities with IC 50 values in the range of 6.7–29.2 μM. [Display omitted] • Four undescribed dimeric aporphine alkaloids were isolated from Phaeanthus lucidus. • Phaeanthuslucidine C was a hybrid of aristolactam-aporphine. • Phaeanthuslucidine D had an N -aryl linkage of a dimeric aporphine alkaloid. • Aporphine alkaloid dimers were successful resolved by chiral-phase HPLC. • Four aporphine alkaloids showed significant α -glucosidase inhibitory activities. [ABSTRACT FROM AUTHOR]

The phytochemical investigation on the leaves and twigs of Zanthoxylum dimorphophyllum Hemsl led to the isolation of a new compound 7-(4′ R -hydroxy-3′,7′-dimethyl-2′ E ,6′-octadienyloxy) coumarin (1) and fourteen known compounds, including nine coumarins (2 – 10), one alkaloid (11), three lignans (12 – 14) and one flavone (15). Their structures were elucidated based on extensive spectroscopic methods (NMR, MS, UV, IR and ECD experiments) and comparison with literature data. The chemotaxonomic significance of the isolated compounds has also been discussed. [Display omitted] • 15 compounds were isolated from the leaves and twigs of Zanthoxylum dimorphophyllum. • Compound 1 was a new coumarin. • Compounds 2 , 3 , 5 , 7–10 and 12 were isolated from Z. dimorphophyllum for the first time. • Chemotaxonomic relationships among Z. dimorphophyllum , the genus Zanthoxylum and the family Rutaceae were discussed. [ABSTRACT FROM AUTHOR]

A phytochemical investigation of the twig extract of Trivalvaria costata (Hook.f. & Thomson) I.M.Turner has identified ten undescribed dimeric aporphine alkaloids, trivalcostatines A−J, one undescribed isoquinoline alkaloid, trivalcostaisoquinoline, and four known aporphine alkaloids. Their structures were elucidated by detailed analysis of NMR and HRESITOFMS data. Three of the dimeric aporphine structures were confirmed by single crystal X-ray diffraction analysis. All of the dimeric aporphine alkaloids were isolated as mixtures of atropisomers. Several of them were resolved by chiral-phase HPLC and the absolute configurations of the pure atropisomers were assigned by calculated and experimental ECD analysis. Bidebilines A and B, heteropsine, and urabaine showed α -glucosidase inhibitory activities with IC 50 values in the range of 4.1–11 μM. Ten undescribed dimeric aporphine alkaloids, trivalcostatines A−J, one undescribed isoquinoline alkaloid, trivalcostaisoquinoline, and four known aporphine alkaloids were isolated the twig extract of Trivalvaria costata (Hook.f. & Thomson) I.M.Turner. Four known aporphine alkaloids showed α -glucosidase inhibitory activities with IC 50 values in the range of 4.14–10.9 μM. [Display omitted] • Eleven undescribed alkaloids were isolated from Trivalvaria costata. • Undescribed aporphine alkaloids were dimers and they were atropisomers. • The (R a) and (S a) absolute configuration of atropisomer were determined. • Four aporphine alkaloids showed good α -glucosidase inhibitory activities. • Three x-ray structures of aporphine alkaloids were reported. [ABSTRACT FROM AUTHOR]

Seven undescribed monoterpenoid indole alkaloids, two N (4)-chloromethylation artifacts, and 10 known alkaloids were isolated from the stems and twigs of Strychnos cathayensis. The corresponding structures were elucidated via spectroscopic data interpretation and electronic circular dichroism. The absolute configuration of (17 S)-12-hydroxy-11-methoxydiaboline, the major anomer of 12-hydroxy-11-methoxydiaboline, was characterized by X-ray diffraction analysis for the first time. At an intraperitoneal dose of 30 mg/kg, 12-hydroxy-11-methoxy- N (4)-chloromethyldiaboline and (−)-macusine A exhibited potential analgesic effects with prolongation rates of 99% and 47% for the latency time of hind-paw licking, respectively, compared to the blank control. 12-Hydroxy-11-methoxydiaboline, 12-hydroxy-11-methoxydiaboline N (4)-oxide, retuline N -oxide, and (−)-vincosamide exhibited antiviral activity against Coxsackie virus B3 (CVB3) with IC 50 values of 33.33 μM. [Display omitted] • Seven undescribed indole alkaloids were isolated from Strychnos cathayensis. • The major anomer of 12-hydroxy-11-methoxydiaboline was characterized by X-ray diffraction data. • 12-Hydroxy-11-methoxy- N (4)-chloromethyldiaboline showed potent analgesic activity. [ABSTRACT FROM AUTHOR]

Five new alkaloids ( 1- 5) were isolated from the leaves and twigs of Cephalotaxus lanceolata and C. fortunei var. alpina along with 24 known alkaloids. The new structures were elucidated based on spectroscopic data including 1D and 2D NMR, FTIR, UV and MS. These new alkaloids showed no cytotoxicity to HeLa, SGC-7901 gastric cancer, and A-549 lung cancer cell lines. [ABSTRACT FROM AUTHOR]

The fruits, twigs and leaves of Daphniphyllum oldhamii (Hemsl.) K. Rosenthal, collected from Longshan County, Hunan Province, China, were chemically investigated. Three undescribed daphniphyllum alkaloids, namely longshanoldhamines A‒C, and six known related ones have been isolated from the fruits, whereas two undescribed triterpenoids and one undescribed lignan, along with six known triterpenoids, were found in the twigs and leaves. Their structures were elucidated by extensive spectroscopic analysis, X-ray diffraction analysis and comparison with the reported data. Three undescribed daphniphyllum alkaloids, namely longshanoldhamines A‒C, have been isolated from the fruits of Daphniphyllum oldhamii collected in Hunan Province, China, whereas two undescribed triterpenoids and one undescribed lignan were found from its twigs and leaves. [Display omitted] Three undescribed alkaloids, namely longshanoldhamines A‒C, were isolated from the fruits of Daphniphyllum oldhamii. Two undescribed triterpenoids and one lignan were found from the twigs and leaves of D. oldhamii. The metabolic patterns varied by the geographic locations and plant tissues. [ABSTRACT FROM AUTHOR]

Abstract: Four new compounds, two lignans; lucidenal and lucidanin (1 and 2), one alkaloid (3), and one flavanone (4) together with 26 known compounds (5–30), were isolated from the twigs of Feroniella lucida. The structures of the new compounds were determined on the basis of spectroscopic analyses. Lucidenal 1 showed cytotoxicity against HuCCA-1, A549, MOLT-3 and HepG2 cancer cell lines with IC50 values of 4.27, 9.59, 2.31, and 6.50 μg/mL, respectively. A plausible biosynthetic pathway of 1 was proposed. [Copyright &y& Elsevier]

Abstract: Five carbazole alkaloids, clausenawallines G–K (1–5), along with 12 known alkaloids (6–17) were isolated from the twigs of Clausena wallichii. Their structures were established using spectroscopic methods and the antibacterial activity of compounds 1–5 was evaluated. [Copyright &y& Elsevier]

Three new alkaloids, macrodumines A-C ( 1- 3, resp.), along with ten known analogs, were isolated from the twigs and leaves of Daphniphyllum macropodum. Their structures were elucidated on the basis of spectroscopic methods. The 11-OH configuration of the known alkaloid hydroxydaphgraciline ( 4) was assigned as α for the first time by comparing the NMR data with those of macrodumine C ( 3). [ABSTRACT FROM AUTHOR]

Two unprecedented C,C-linked dimeric indolizidine alkaloids, flueggines A (1) and B (2), were isolated from the twigs and leaves of Flueggea virosa. The structures and absolute configurations were elucidated by means of NMR, single-crystal X-ray diffraction, and CD analyses. Compound 1is the first example of Securinegaalkaloids bearing an isoxazolidine ring, the plausible biogenetic pathway of which is also proposed. Compound 2exhibited growth inhibitory activity against MCF-7 and MDA-MB-231 human breast cancer cells. [ABSTRACT FROM AUTHOR]

Two new securinegatype alkaloids and four known ones were isolated from the twigs and leaves of Flueggea virosa.The structures of the new compounds were elucidated by means of spectroscopic methods UV, IR, HRESIMS, and 1D and 2DNMR, and the absolute configurations were assigned by CD spectra. The structures of the known compounds were identified by comparison of their physical and spectroscopic data with those reported in the literature. [ABSTRACT FROM AUTHOR]

A new triterpenoid alkaloid, buxrugulosamine ( 1), together with four known, ones was isolated from the ethanolic extract of the leaves and twigs of Buxus rugulosa. Their structures were determined by analysis of spectral data or comparing them with authentic samples. [ABSTRACT FROM AUTHOR]

Lucidenal (I), lucidanin (II), alkaloid (III), and flavanone (IV) are isolated from the title twigs. [ABSTRACT FROM AUTHOR]

2 New quinoline alkaloids (I) and (II) are isolated from the twigs and leaves of Melodinus suaveolens along with 6 known alkaloids. [ABSTRACT FROM AUTHOR]