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Seven undescribed lavandulyl benzophenones garcimultiflorones K – Q, and fourteen known compounds were isolated from the CHCl 3 soluble fraction of 95% EtOH extract of Garcinia multiflora branches. Their structures and absolute configurations were determined by spectroscopic techniques including NMR spectroscopy, MS analysis, and ECD calculations. Seven isolated compounds expect for garcimultiflorone L and garcimultiflorone O exhibited cytotoxic activities in vitro against five cancer cell lines (HL-60, A549, SMMC-7721, MCF-7, and SW480). It is worth mentioning that garcimultiflorone Q exhibited most significant cytotoxicities against five cancer cell lines with IC 50 values ranging from 3.07–12.56 μM. [ABSTRACT FROM AUTHOR]

Garcinia oblongifolia Champ. ex Benth. (Clusiaceae) is a well-known medicinal plant from southern China, with edible fruits. However, the phytochemistry and bioactivity of the different plant parts of G. oblongifolia have not been studied extensively. Comparative metabolic profiling and bioactivities of the leaf, branch, and fruit of G. oblongifolia were investigated. A total of 40 compounds such as biflavonoids, xanthones, and benzophenones were identified using UPLC-QTOF-MS and MS E , including 15 compounds reported for the first time from this species. Heatmap analyses found that benzophenones, xanthones, and biflavonoids were predominately found in branches, with benzophenones present in relatively high concentrations in all three plant parts. Xanthones were found to have limited distribution in fruit while biflavonoids were present at only low levels in leaves. In addition, the cytotoxic (MCF-7 breast cancer cell line) and antioxidant (ABTS and DPPH chemical tests) activities of the crude extracts of G. oblongifolia indicate that the branch extract exhibits greater bioactivity than either the leaf or the fruit extracts. Orthogonal partial least squares discriminate analysis was used to find 12 marker compounds, mainly xanthones, from the branches, including well-known antioxidants and cytotoxic agents. These G. oblongifolia results revealed that the variation in metabolite profiles can be correlated to the differences in bioactivity of the three plant parts investigated. This UPLC-QTOF-MS strategy can be useful to identify bioactive constituents expressed differentially in the various plant parts of a single species. [ABSTRACT FROM AUTHOR]

Twenty-five amide alkaloids ( 1 – 25 ) from Piper boehmeriifolium and 10 synthetic amide alkaloid derivatives ( 39 – 48 ) were evaluated for antiproliferative activity against eight human tumor cell lines, including chemosensitive and multidrug-resistant (MDR) cell lines. The results suggested tumor type-selectivity. 1-[7-(3,4,5-Trimethoxyphenyl)heptanoyl]piperidine ( 46 ) exhibited the best inhibitory activity (IC 50 = 4.94 μM) against the P-glycoprotein (P-gp)-overexpressing KBvin MDR sub-line, while it and all other tested compounds, except 9 , were inactive (IC 50 >40 μM) against MDA-MB-231 and SK-BR-3. Structure–activity relationships (SARs) indicated that (i) 3,4,5-trimethoxy phenyl substitution is critical for selectivity against KBvin, (ii) the 4-methoxy group in this pattern is crucial for antiproliferative activity, (iii) double bonds in the side chain are not needed for activity, and (iv), in arylalkenylacyl amide alkaloids, replacement of an isobutylamino group with pyrrolidin-1-yl or piperidin-1-yl significantly improved activity. Further study on Piper amides is warranted, particularly whether side chain length affects the ability to overcome the MDR cancer phenotype. [ABSTRACT FROM AUTHOR]

Highlights: [•] Five phenylphenalenones and two diarylheptanoids were isolated from Musa itinerans. [•] A putative biosynthetic pathway to the phenylphenalenone-related heterodimer is proposed. [•] Two of the phenylphenalenones exhibited weak cytotoxic effects against a human lung adenocarcinoma cell line. [Copyright &y& Elsevier]

A novel pyrrolidine alkaloid, (2R*,3S*,5S*)-N,2-dimethyl-3-hydroxy-5-(10-phenyldecyl)pyrrolidine (1), and 17 known compounds were isolated fromArisaema franchetianumEngl. (Araceae) tubers. The 17 compounds were bergenin (2), emodin (3), caffeic acid (4), nobiletin (5), 3-O-β-d-galactopyranosyl-hederagenin 28-O-β-d-xylopyranosyl(1 → 6)-β-d-galactopyranosyl ester (6), coniferin (7), qingyangshengenin (8), methylconiferin (9), syringaresinol 4′-O-β-d-glucopyranoside (10), gagaminine (11), perlolyrine (12), (S)-1-(1′-hydroxyethyl)-β-carboline (13), 1-(β-carboline-1-yl)-3,4,5-trihydroxy-1-pentanone (14), 1-methoxycarbonyl-β-carboline (15), indolo[2,3-α]carbazole (16), 4-hydroxycinnamic acid methyl ester (17), and methyl 4-[2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethyl] ferulate (18). The inhibitory activities of compound1and itsN-methyl derivative (1a) against porcine respiratory and reproductive syndrome virus (PRRSV), human leukemic K562 cells, and human breast cancer MCF-7 cells were evaluated. Compounds1[50% inhibited concentration (IC50) = 12.5 ± 0.6 μM] and1a(IC50 = 15.7 ± 0.9 μM) were cytotoxic against K562 cells. Compound1aalso had a weak effect on PRRSV with an IC50value of 31.9 ± 6.0 μM [selectivity index (SI) = 18.7]. [ABSTRACT FROM PUBLISHER]

• Chemical composition and bioactivity of Acer truncatum seeds were investigated. • Oil yield, fatty acids and nervonic acid content varied greatly among locations. • Fifteen compounds from the seed residue were putatively identified in A. truncatum. • Seed residue showed cytotoxicity in human cancer cells and anti-AChE activity. • Prioritize Inner Mongolia samples for further study and product development. Acer truncatum , an ornamental, medicinal, and edible plant, is a tree endemic to China and now widely cultivated throughout Asia, North America, and Europe. It has been developed as an industrial crop from its traditional use as a substitute for tea. The oil from its seeds is rich in unsaturated fatty acids (FA), especially in nervonic acid (NA). However, studies on the chemical components and bioactivities of the seeds are limited, and comparative studies of seeds collected from different locations are even more limited. Therefore, A. truncatum seeds were collected from 12 different locations in China to investigate the chemical composition, cytotoxicity, and acetylcholinesterase (AChE) inhibition of A. truncatum seed oil (ATO) and Acer seed residue extracts (ASR). The oil yields varied about five-fold among different locations from 7.27% to 35.05%. Nine fatty acids were identified and relatively quantified, and myristic acid, linoleic acid, oleic acid, and a NA isomer [C24:1(15 E)] were the dominant fatty acids. The NA isomer has not been reported previously in A. truncatum , and NA levels ranged from 0.66 to 14.86 mg/μL of ATO. This is the first GC–MS study to focus on the FA differences of A. truncatum collected from different locations. Using UPLC-QTOF-MS analysis, 15 compounds were putatively identified from ASR, including N -acetyl-D-tryptophan, nonanedioic acid, 10 E -heptadecenoic acid, pregnanolone, phosphatidylglycerol (34:2), and phosphatidylinositol (34:1), which have not been reported in Acer prior to this study. The flavonoids miscanthoside and isovitexin/vitexine were also newly identified in A. truncatum. Furthermore, five samples each of ATO and ASR were selected to estimate the cytotoxic activities against four human tumor cell lines (A-549, SMMC-7721, MCF-7, and SW-480) and the AChE inhibitory activity. All ASR were cytotoxic on all tested cells and exhibited higher inhibitory activity than ATO at 100 μg/mL. ASR exhibited stronger cytotoxicity on SMMC-7721 with IC 50 from 29.46 to 52.55 μg/mL. Similarly, the ASR exhibited higher AChE inhibitory activity than the ATO. All ASR significantly inhibited AChE activity, and the inhibition rates were close to 90% at 20 μg/mL. The IC 50 values for the ASR ranged from 0.124 to 0.232 μg/mL. Overall, the results of this study indicate that ATO is abundant in FAs and NA, but the contents of ATO varies by location. ASR are rich in bioactive components with cytotoxic and AChE inhibitory activities. These findings suggest that ATO and ASR could be a promising resource in the nutraceutical and pharmaceutical fields. [ABSTRACT FROM AUTHOR]