Calosides A-F, Cardenolides from Calotropis gigantea and Their Cytotoxic Activity.

Phytochemical analysis of the roots of Calotropis gigantea led to the isolation of six new cardenolide glycosides, calosides A-F (1-6), and five known cardenolides (7-11). The structures of 1-6 were elucidated based on NMR and ECD spectroscopic data interpretation. Caloside D (4) is the first naturally occurring example of a cardenolide containing a C-8/C-19 oxygen bridge. In turn, calosides E (5) and F (6) represent the first naturally occurring 3-epi-cannogenol diglycosides having potent cytotoxicity against the PANC-1 cell line (IC50, 0.081 and 0.070 µM, respectively) and HeLa (IC50, both 0.17 µM) cells, under normoglycemic conditions.

Phytochemical and cytotoxic studies on the leaves of Calotropis gigantea.

A new lignan, 9'-methoxypinoresinol (1), and two new glycosylated 5-hydroxymethylfurfurals, calofurfuralside A (2), and calofurfuralside B (3), together with nine known compounds (4-12) have been isolated from the active fractions, CHCl3 (IC50, 0.32µgmL-1) and EtOAc (IC50, 0.55µgmL-1) fractions of the leaves of Calotropis gigantea. Their structures were elucidated based on NMR and MS data. Among the isolated compounds, compounds 1 and 9 exhibited potent cytotoxicity against PANC-1 human pancreatic cancer cell line under the normoglycemic condition with IC50 values of 3.7 and 3.3µM, respectively. 9'-Methoxypinoresinol (1) significantly inhibited the colony formation of PANC-1 cells in a concentration-dependent manner.

Quinoliniumolate and 2H-1,2,3-Triazole Derivatives from the Stems of Paramignya trimera and Their α-Glucosidase Inhibitory Activities: In Vitro and in Silico Studies.

From a CHCl3-soluble extract of the stems of Paramignya trimera, two new alkaloids, (E)-2-(prop-1-enyl)-N-methylquinolinium-4-olate (1) and (R)-2-ethylhexyl 2H-1,2,3-triazole-4-carboxylate (2), were isolated. Their structures were elucidated based on the spectroscopic data interpretation. Compound 2 possesses α-glucosidase inhibitory activity, with an IC50 value of 137.9 µM. Molecular docking studies of 1 and 2 with human maltase-glucoamylase (MGAM) were performed for the first time; thus, the 2,3-diH+-1H-1,2,3-triazolium cation (2i) showed good interactions with both MGAM-N (2QMJ) and -C (3TOP) terminal subunits.

Lignans from the Roots of Taxus wallichiana and Their α-Glucosidase Inhibitory Activities.

From an EtOAc-soluble extract of the roots of Taxus wallichiana, six new (1-6) and 11 known lignans were isolated. The structures of the new compounds were elucidated based on interpretation of spectroscopic data. (+)-7'-epi-Tsugacetal (1) is a rare aryltetralin-type lignan having a cis-orientation of H-7' and H-8'. Compounds 3-6 were identified as the first naturally occurring tetrahydrofuranoid lignans having a cis-orientation of H-7 and H-8. All tested compounds were found to possess α-glucosidase inhibitory activity, with formosanol (9) showing the most potent effect with an IC50 value of 35.3 µM.

Artocarmins G-M, Prenylated 4-Chromenones from the Stems of Artocarpus rigida and Their Tyrosinase Inhibitory Activities.

Phytochemical analysis of an EtOAc extract of the stems of Artocarpus rigida led to the identification of seven new prenylated 4-chromenones, artocarmins G-M (1-7), and nine known compounds (8-17). Their structures were identified based on physical data analysis. In the tyrosinase inhibitory activity test, norartocarpetin (8) displayed the strongest effect, with an IC50 value of 0.023 µM.

A new ß-carboline-type alkaloid from the flowers of Calotropis gigantea (L.) W.T.Aiton.

In our antioxidant screening of some Vietnamese plant extracts, the CHCl3-soluble fraction from Calotropis gigantea (L.) W.T.Aiton flowers showed moderate DPPH free radical scavenging activity with an IC50 value of 55.8 µg/mL. Thus, a further phytochemical study was carried out to obtain five alkaloids, including a new ß-carboline-type alkaloid, caloside H (1). These known compounds were identified as 5-hydroxy-(2-methoxymethyl)pyridine (2), nicotinic acid (3), p-(acetylamino)phenol (4), and thymine (5). These structures were determined based on the NMR spectroscopic analysis. In antioxidant assay, caloside H at concentration of 100 µM showed DPPH radical scavenging capacity with a percentage of inhibition of 40.2%. In addition, a plausible biosynthetic pathway for the formation of caloside H was proposed based on the Schiff base formation and Mannich-like reaction.

A new 7',9-epoxylignan from the stems of Salacia chinensis.

Bioactivity-guided isolation of the CHCl3-soluble fraction of the stems of Salacia chinensis L. (Celastraceae) was carried out to obtain a new 7',9-epoxylignan (1) and three 7,9':7',9-diepoxylignans (2-4). The absolute configuration of 1 was elucidated based on NMR and ECD spectroscopic data interpretation. All isolated lignans showed intermediate α-glucosidase inhibitory activity with the IC50 values ranging from 28.5 to 85.6 µM.

Diarylalkanoids as Potent Tyrosinase Inhibitors from the Stems of Semecarpus caudata.

From a CHCl3-soluble extract of the stems of Semecarpus caudata (Anacardiaceae), two new diarylalkanoids, semedienone (1) and semetrienone (2), were isolated. Their structures were elucidated based on NMR spectroscopic data interpretation. These compounds possess strong tyrosinase inhibitory activity with the IC50 values of 0.033 and 0.11 µM, respectively. Docking studies of 1 and 2 with oxy-tyrosinase were carried out to analyze their interactions. Accordingly, semedienone (1) showed good interactions with the peroxide group and amino acid residues. The biosynthesis of the isolated diarylalkanoids was proposed.

A new cytotoxic cardenolide from the roots of Calotropis gigantea.

Bioactivity-guided isolation of the CHCl3-soluble fraction of the roots of Calotropis gigantea was carried out to obtain a new cardenolide glycoside, caloside G. Its absolute structure was elucidated based on NMR and ECD spectroscopic data interpretation. Caloside G showed noteworthy cytotoxicity against the PANC-1 human pancreatic and HeLa human cervical carcinoma cell lines, with the submicromolar IC50 values of 0.038 and 0.09 µM, respectively.

Tyrosinase Inhibitors from the Stems of Streblus Ilicifolius.

Two new stilbene derivatives, named strebluses C and D, were isolated from the EtOAc-soluble fraction of the stems of Streblus ilicifolius (Moraceae). Its absolute configuration was elucidated based on NMR spectroscopic data interpretation and optical rotation calculation. Streblus C possesses strong tyrosinase inhibitory activity with an IC50 value of 0.01 µM. Docking studies of 1 and 2 with oxy-tyrosinase were carried out to analyze their interactions. The analysis of the docked poses confirmed that 1 showed better binding affinity for oxy-tyrosinase than that of 2.

Panduratins Q-Y, dimeric metabolites from Boesenbergia rotunda and their antiausterity activities against the PANC-1 human pancreatic cancer cell line.

A methanolic extract of the rhizomes of Boesenbergia rotunda showed potent preferential cytotoxicity against PANC-1 human pancreatic cancer cells under nutrient deficiency conditions with a PC50 value of 6.6 µg/mL. Bioactivity-guided phytochemical investigation of the rhizomes of B. rotunda led to the isolation of nine undescribed dimeric metabolites, panduratins Q-Y. Their structures were elucidated based on NMR, MS, and ECD spectroscopic data interpretation. Panduratins Q-S and U-W exhibited potent cytotoxicity towards PANC-1 cell line with the PC50 values ranging from 0.8 to 6.3 µM. Panduratin W, which possessed a cyclohexenylchalcone-linked flavanone skeleton, showed the most cytotoxicity with a PC50 value of 0.8 µM under nutrient-deprived medium.

A new lactam 28-norlimonoid from the leaves of Azadirachta indica A. Juss. (Meliaceae).

From an EtOAc-soluble fraction of the leaves of Azadirachta indica, one new lactam 28-norlimonoid named nimbandiolactam-21 (1), together with 2 known limonoids (2 and 3) were isolated. Their relative structures were elucidated based on NMR spectroscopic analysis. Nimbandiolactone-23 (2) showed the most potent α-glucosidase inhibitory activity, with an IC50 value of 38.7 µM. Compound 1 represents the first naturally occurring example of a 28-norlimonoid having the lactam moiety. The plausible biosynthetic pathway for the formation of lactam moiety in 1 was proposed.

A new dimeric alkylresorcinol from the stem barks of Swintonia floribunda (Anacardiaceae).

From an EtOAc-soluble fraction of the stem barks of Swintonia floribunda (Anacardiaceae), one new dimeric alkylresorcinol named integracin E (1), together with 4 known compounds (2-5) were isolated. Their chemical structures were elucidated based on the spectroscopic data interpretation. The absolute configuration of 1 was determined by the specific rotation analysis of its acid-catalyzed hydrolysis product. Compound 1 showed potent tyrosinase inhibitory activity with an IC50 value of 48.2 µM.

A new bischromanone from the stems of Semecarpus caudata.

From an CHCl3-soluble fraction of the stems of Semecarpus caudata, one new bischromanone named semecarpanone (1), together with 5 known flavonoids (2-6) were isolated. Their structures were elucidated based on interpretation of spectroscopic data. The stereo-configuration of 1 was identified based on the calculated and experimental coupling constants. Compounds 4-6 showed potent tyrosinase inhibitory activity with the IC50 values ranging from 15.0 to 76.3 µM.