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Three new isoprenylated chromones, named harriforatins A−C (1 − 3), along with 13 known compounds (4 − 16) were isolated from the stems of Harrisonia perforata. Their planar structures were elucidated by spectroscopic measurements. The experimental and calculated ECD curves were used to determine their absolute configurations. Most isolated compounds were evaluated for inflammation inhibition against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 macrophages. Only compounds 5 and 6 showed inhibitory effects on NO production, with IC 50 values of 42.8 and 47.0 μM, respectively, that were stronger than that of the positive control, indomethacin (IC 50 = 68.6 μM). [Display omitted] • Three new isoprenylated chromones were isolated from Harrisonia perforata stems. • The structures with absolute configurations were established by extensive spectroscopic methods. • Two compounds showed a significant inhibitory effect on NO production. [ABSTRACT FROM AUTHOR]

• 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]

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 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]

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]

• Thirteen compounds were isolated and identified from Polyathia cinnamomea twigs. • Oxoprotoberberine alkaloids are the major compounds of P. cinnamomea species. • Two compounds were confirmed absolute configuration by X-ray diffraction data. • Six compounds exhibited α -glucosidase inhibitory activity better than acarbose. • (−)-(13a S)-consanguine B exhibited NO inhibitory activity better than indomethacin. The first phytochemical investigation of Polyalthia cinnamomea led to the isolation and identification of two new oxoprotoberberine alkaloids, (−)-(13a S)-polyalthiacinnamines A and B, together with eleven known compounds. The structures of the new compounds were elucidated by extensive spectroscopic methods. The absolute configuration of miliusacunine E and consanguine B was established by X-ray diffraction analysis using Cu Kα radiation and ECD spectra, whereas the absolute configurations of polyalthiacinnamines A and B were established by comparison of their ECD spectra and specific rotations with those of miliusacunine E and consanguine B. Compounds 1 – 4 , 6 , and 8 exhibited α -glucosidase inhibitory activities (IC 50 values ranging from 11.3 to 57.9 µM) better than a positive control (acarbose, IC 50 83.5 μM). Compound 2 also exhibited NO production inhibitory activity with an IC 50 value of 24.4 μM (indomethacin, a positive control, IC 50 = 32.2 μM). [ABSTRACT FROM AUTHOR]