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• Sixteen compounds were isolated from the EtOAc extract of C. excavata fruits. • Nine compounds (1, 3, 5, 6, 8 – 10, 15 , and 16) were isolated from C. excavata for the first time. • The absolute configuration of the bioactive limonoids 15 and 16 were confirmed by the X-ray crystallography using Cu Kα radiation. • Compounds 7 (auraptene) and 14 (safrole) showed a moderate glucose uptake with ratios of 1.38-fold and 1.41-fold, respectively. • The cytotoxicity of auraptene 7, 8 , and 10 against lung cancer A549, RAW 264.7 cells, and colorectal cancer SW480 are reported for the first time in this study. Phytochemical investigation of the fruit extract of Clausena excavata Burm. f. resulted in the isolation and identification of 16 compounds, including seven coumarins (1 – 7), four phenylpropanoids (8 – 10 and 14), two benzaldehyde derivatives (11 and 12), one carbazole alkaloid (13), and two limonoids (15 and 16). Of these, nine compounds (1, 3, 5, 6, 8 – 10, 15 , and 16) were isolated from C. excavata for the first time. The absolute configuration of limonoids 15 and 16 was established by X-ray diffraction analysis using Cu Kα radiation. Some isolated compounds were evaluated for their in vitro cytotoxicity against three human cancer cell lines, namely lung cancer A549, colorectal cancer SW480, leukemic K562 cells as well as glucose uptake, glucose consumption, and antibacterial activity against Staphylococcus aureus (SA) and methicillin-resistant Staphylococcus aureus (MRSA). Compounds 7 (auraptene) and 14 (safrole) showed moderate glucose uptake with ratios of 1.38-fold and 1.41-fold compared to the positive control (metformin, 2.25-fold). Compound 7 (auraptene) also exhibited weak cytotoxicity against lung cancer A549, colorectal cancer SW480, and leukemic K562 cells with IC 50 values of 77.2, 157.3, and 105.3 µM, respectively, while compounds 8 ((E)-piperonylprop-2-enal) and 10 (ethyl p -coumarate) exhibited weak cytotoxicity against RAW 264.7 cells and colorectal cancer SW480 cells with IC 50 values of 234.9 and 219.5 μM, respectively. Compounds 1, 3, 7 , and 14 – 16 showed a MIC of >512 µg/mL revealing them to be inactive. : [Display omitted] [ABSTRACT FROM AUTHOR]

This article discusses the cytotoxic and antibacterial activities of chemical constituents found in the EtOAc extract of Uvaria hamiltonii twigs. The Uvaria genus has been traditionally used in medicine to treat malaria symptoms, fever, and stomach disorders. The study isolated 15 known compounds from the twig extract and tested their cytotoxicity and antibacterial activity. Some of the compounds showed potential in inhibiting cancer cell growth and exhibited antibacterial activity against certain strains. The article provides detailed information about the isolated compounds, including their physical properties and nuclear magnetic resonance (NMR) spectra. The research was supported by the Thailand Science Research and Innovation and conducted at Mae Fah Luang University. [Extracted from the article]

Kaempferia parviflora (Black ginger) is used widely in medical fields as an anti-microorganism and anti-inflammation. In this study, the aim was to evaluate the in vitro and in vivo anti-acne efficacy of black ginger extract. The results indicate that the methanol and ethanol extracts showed the highest total phenolic contents, without a significant difference, whereas the n-hexane extract showed the highest total flavonoid content. Nine flavones were detected using UPLC−QTOF−MS, and the ethyl acetate extract showed the highest amount of 5,7-dimethoxyflavone (DMF) according to HPLC. Antibacterial activity against Staphylococcus aureus, S. epidermidis, and Cutibacterium acnes was observed. All the extracts showed antimicrobial activity against C. acnes, revealing MICs in the range of 0.015 to 0.030 mg/mL, whereas the ethyl acetate extract inhibited the growth of S. epidermidis with a MIC of 3.84 mg/mL. In addition, the ethyl acetate extract showed the highest activity regarding nitric oxide inhibition (IC50 = 12.59 ± 0.35 µg/mL). The ethyl acetate extract was shown to be safe regarding cell viability at 0.1 mg/mL. The anti-acne efficacy was evaluated on volunteers. The volunteers were treated in two groups: one administered a 0.02% ethyl acetate extract gel-cream (n = 9) and one administered a placebo (n = 9) for 6 weeks. The group treated with the gel-cream containing the extract showed 36.52 and 52.20% decreases in acne severity index (ASI) after 4 and 6 weeks, respectively, and 18.19 and 18.54% decreases in erythema, respectively. The results suggest that K. parviflora could be a potent active ingredient in anti-inflammatory and anti-acne products. [ABSTRACT FROM AUTHOR]

This work was the first investigation of the essential oil composition of Goniothalamus tortilipetalus M.R.Hend. The aim of this study is to investigate the essential oil composition extracted from different parts of Goniothalamus tortilipetalus M.R.Hend., including flowers, leaves, and twigs, and to evaluate their antioxidant and antibacterial activities. The Clevenger apparatus was used for hydrodistillation to prepare the essential oils. The essential oils were investigated using gas chromatography–mass spectrometry (GC-MS). The three major compounds of the flowers were bicyclogermacrene (15.81%), selin-11-en-4-α-ol (14.68%), and E-caryophyllene (7.02%), whereas the leaves were p-cymene (39.57%), ascaridole (9.39%), and α-copaene (9.12%). In the case of the twigs, α-copaene (10.34%), selin-11-en-4-α-ol (8.85%), and p-cymene (7.76%) were the major compounds. The flower essential oil showed antioxidant activities with IC50 values of 725.21 µg/mL and 123.06 µg/mL for DPPH and ABTS assays, respectively. The flower essential oil also displayed antibacterial activity against Bacillus subtilis, Staphylococcus aureus, Micrococcus luteus, Salmonella typhimurium, and Shigella flexneri, with the same MIC value of 640 µg/mL. [ABSTRACT FROM AUTHOR]

Chemical investigation of the mycelia of the pathogenic fungus Curvularia sp. which was isolated from a leaf of Dactyloctenium aegyptium (crowfoot grass), resulted in the isolation of a new compound, curvulariahawadride (5), along with five known compounds (1–4, and 6). Their structures were determined on the basis of spectroscopic data, including 1D and 2D NMR and HRESIMS. The absolute configuration of 5 was established from experimental and calculated electronic circular dichroism (ECD). Compounds 1, 3, and 5 showed nitric oxide (NO) production inhibitory activity with IC50 values of 53.7, 32.8, and 12.8 µM, respectively. Compounds 2 and 4 showed significant cytotoxicity against lung cancer A549, colorectal cancer SW480, and leukemic K562 cells with an IC50 ranging value of 11.73 to 17.59 µM. [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]

Phytochemical investigations of the twig and leaf extracts of Uvaria dac Pierre ex Finet & Gagnep. resulted in the isolation and identification of five new highly oxygenated cyclohexenes, uvaridacols M − Q (1 – 3 , 5 , and 6), and six known compounds (4 and 7 – 11). All new structures were elucidated by spectroscopic methods and HRESITOFMS data. The absolute configuration of 1 , 5 , and 6 was confirmed by single X-ray diffraction analysis with Cu Kα radiation. In contrast, other compounds were established by comparing their specific rotation and ECD spectra with those of known compounds. Some of the isolated compounds with sufficient quantity were evaluated for their α-glucosidase inhibitory activity. Of these, (−)-1,6-desoxypipoxide (10) showed α-glucosidase inhibitory activity with an IC 50 value of 28.6 μM. The in silico molecular docking of active compounds was also studied. Phytochemical investigations of the twig and leaf extracts of Uvaria dac Pierre ex Finet & Gagnep. resulted in the isolation and identification of five new highly oxygenated cyclohexenes and six known compounds. Some of the isolated compounds with sufficient quantity were evaluated for their α-glucosidase inhibitory activity. Of these, (−)-1,6-desoxypipoxide (10) showed α-glucosidase inhibitory activities with an IC 50 value of 28.6 μM. [Display omitted] • Five new oxygenated cyclohexenes were isolated from Uvaria dac. • The absolute configuration of uvaridacol M, P, Q were confirmed by single X-ray diffraction analysis with Cu Kα radiation. • Oxygenated cyclohexenes containing a cinnamoyl moiety, such as uvaridacols N and P first reported here. • 1,6-Desoxypipoxide showed α -glucosidase inhibitory activity. • 1,6-Desoxypipoxide was docked into α -glucosidase (PDB ID: 2QMJ) in silico molecular docking. [ABSTRACT FROM AUTHOR]

Three previously undescribed aporphine alkaloids, phaeanthuslucidines E–G, one previously undescribed naphthoquinone derivative, phaeanthusnaphthoquinone, and three known compounds were isolated from an EtOAc extract of the leaves of Phaeanthus lucidus Oliv. The structures of all previously undescribed compounds were established through extensive spectroscopic investigations and high-resolution mass spectroscopy. The 6a R configuration of phaeanthuslucidines E–G was assigned by comparing their ECD spectra and specific rotation values with the reported known compounds. Some isolated compounds were evaluated for their α -glucosidase inhibitory activity. Among these compounds, phaeanthuslucidine E showed the highest α -glucosidase inhibitory activity with an IC 50 value of 17.9 ± 0.4 μM. The molecular docking of phaeanthuslucidine E was further studied. Three undescribed N -benzoyl aporphine alkaloids, phaeanthuslucidines E–G, and a previously undescribed naphthoquinone derivative, phaeanthusnaphthoquinone, were isolated from the leaves of Phaeanthus lucidus Oliv. Phaeanthuslucidine E showed good α -glucosidase inhibitory activity. [Display omitted] • Three undescribed N -benzoyl aporphine alkaloids were isolated. • A previously undescribed naphthoquinone derivative was isolated. • Phaeanthuslucidine E showed good α -glucosidase inhibitory activity. • The molecular docking of phaeanthuslucidine E was investigated. [ABSTRACT FROM AUTHOR]

The phytochemical investigation of the fruit and leaf extracts of Maclura cochinchinensis (Lour.) Corner (Moraceae) resulted in the isolation and identification of four undescribed isoflavones (macluracochinones A-D) and one undescribed flavone (macluracochinone E), together with 24 known compounds. The structures of the undescribed compounds were elucidated using nuclear magnetic resonance (NMR) and high-resolution electrospray ionization time-of-flight mass spectrometry (HRESITOFMS) experiments. Gancaonin M, lupiwighteone, lupalbigenin, warangalone, auriculatin, and millexatin F displayed good antibacterial activities against Gram-positive bacteria with MIC values in the range of 1–8 μg/mL. Lupalbigenin showed strong activities against methicillin-resistant Staphylococcus aureus (MRSA) and S. aureus with the same MIC value of 1 μg/mL. [Display omitted] • Five undescribed flavonoids were isolated from Maclura cochinchinensis. • Flavonoids are the major compounds of M. cochinchinensis. • Five compounds showed good antibacterial activity against Gram-positive bacteria. • Lupalbigenin showed strong activities against MRSA and S. aureus. [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]

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]

Phytochemical investigations of the leaf and pod extracts of Millettia brandisiana Kurz led to the isolation and identification of four previously undescribed rotenoids, (–)-(6a S ,12a S)-millettiabrandisins A–C and (–)-(6a S ,12a S)-6-deoxyclitoriacetal, two previously undescribed isoflavones, millettiabrandisins D and E, and 20 known compounds. The structures of previously undescribed compounds were determined on the basis of NMR and MS data. The absolute configurations of (–)-(6a S ,12a S)-millettiabrandisins A–C were determined from the comparison of their experimental and calculated ECD spectra. (–)-(6a R ,12a R)-12a-Hydroxy-α-toxicarol was also confirmed by X-ray crystallographic data. Some isolated compounds were evaluated for their cytotoxicity against three cancer cell lines, including lung cancer (A549), colorectal cancer (SW480), and leukemic cells (K562). Of these, α-toxicarol displayed the best cytotoxicity against lung cancer (A549) and leukemic cells (K562) with the IC 50 values of 104.4 and 67.5 μM, respectively. 6″,6″-Dimethylchromene-[2″,3″:7,8]-flavone showed the highest cytotoxicity against colorectal cancer (SW480) with an IC 50 value of 97.2 μM. Four undescribed rotenoids and two undescribed isoflavones, along with twenty known compounds, were isolated from the leaf and pod extracts of Millettia brandisiana Kurz. The cytotoxicity against lung cancer (A549), colorectal cancer (SW480), and leukemic cells (K562) were evaluated. [Display omitted] • Six previously undescribed compounds were isolated from M. brandisiana. • The absolute configuration of rotenoids were determined by ECD spectra. • All rotenoids isolated from this plant were single enantiomers. • The cytotoxicities against three cancer cell lines were evaluated. • The x-ray structure of (–)-(6a R ,12a R)-12a-hydroxy-α-toxicarol was reported. [ABSTRACT FROM AUTHOR]