Anti-Neuroinflammatory Components from Clausena lenis Drake.

Clausena lenis Drake (C. lenis) is a folk medicinal herb to treat influenza, colds, bronchitis, and malaria. The 95% and 50% ethanol extract of C. lenis showed significant nitric oxide (NO) inhibition activity in BV-2 microglial cells stimulated by lipopolysaccharide (LPS). Bio-guided isolation of the active extract afforded five new compounds, including a chlorine-containing furoquinoline racemate, (±)-claulenine A (1), an amide alkaloid, claulenine B (2), a prenylated coumarin, claulenin A (3), a furocoumarin glucoside, clauleside A (4), and a multi-prenylated p-hydroxybenzaldehyde, claulenin B (5), along with 33 known ones. Their structures were determined via spectroscopic methods, and the absolute configurations of new compounds were assigned via the electronic circular dichroism (ECD) calculations and single-crystal X-ray diffraction analysis. Compounds 2, 23, 27, 28, 33, and 34 showed potent anti-neuroinflammatory effects on LPS-induced NO production in BV-2 microglial cells, with IC50 values in the range of 17.6-40.9 µM. The possible mechanism was deduced to interact with iNOS through molecular docking.

Three new coumarins and a new coumarin glycoside from Micromelum integerrimum.

Three new coumarins, integmarins A-C (1-3), and a new coumarin glycoside, integmaside A (4) were isolated from the leaves and stems of Micromelum integerrimum. Their structures were elucidated on the basis of 1D and 2D NMR and MS data, and their absolute configurations were assigned according to the ECD data of the in situ formed transition metal complexes and comparison of experimental and calculated ECD data. Compounds 1 and 2 are two rare coumarins with butyl and propyl moieties at the C-6 position; compound 3 is a novel coumarin with a highly oxidized prenyl group, and compound 4 is a rare bisdihydrofuranocoumarin glycoside.

Carbazole alkaloids with potential cytotoxic activities targeted on PCK2 protein from Murraya microphylla.

From the 95% aqueous ethanol extract of Murraya microphylla, five pairs of new carbazole alkaloid enantiomers, (+/-)-microphylines N-R (1a/1b-5a/5b), were isolated, together with 20 known carbazole alkaloids. The structures of the new compounds were determined by the HRMS and NMR spectroscopic data, along with the calculated electronic circular dichroism (ECD) and Mo2(AcO)4-induced CD data. The known compound (+)-mahanine (21) showed significant cytotoxicities against Du145, HepG2, HeLa, and HCT-116 cell lines, and its possible mechanism was deduced to target on phosphoenolpyruvate carboxykinase 2 (PCK2) protein via surface plasmon resonance (SPR) and molecular docking.

A new prenylated coumarin diglycoside with insulin-release promoting activity from Clausena dunniana.

A new prenylated coumarin diglycoside, 6-prenylcoumarin-7-O-ß-D-apiofuranosyl-(1→6)-ß-D-glucopyranoside (1) and five known flavonoid glycosides (2-6) were isolated from the leaves and stems of Clausena dunniana. The structures of these isolates were elucidated based on comprehensive MS, UV, IR, and NMR spectroscopic data analysis and comparison with the data reported in literature. Compounds 2-6 are obtained from the title plant for the first time. All these isolates were evaluated for their insulin-release promoting effects, and compounds 1, 2, and 4 exhibited significant activities (2.0 to 3.3-fold higher in comparison with the control, p < 0.01) at 40 µM.[Formula: see text].

Isolation and structure characterization of cytotoxic alkaloids from Micromelum integerrimum.

Ten undescribed alkaloids, named integerrines A-J, including one racemic heterodimer of carbazole and indole, two racemic, two scalemic, and one enantiomerically enriched biscarbazoles, two aldoximes, and one racemic pyrrolone, were isolated from the dried leaves and stems of Micromelum integerrimum. The racemic or scalemic compounds were resolved using chiral-phase HPLC and their configurations were determined by comparison of experimental and calculated ECD data. Four compounds exhibited moderate to weak cytotoxicities against HepG2, HTC-116, HeLa, and PANC-1 cell lines, with IC50 values of 14.1-67.5 µM.

Terpenoids from Resina Commiphora Regulating Lipid Metabolism via Activating PPARα and CPT1 Expression.

Commiphoranoids A-E (1-5), five novel sesquiterpenoids, dinorditerpenoids, and heterodimers with unprecedented carbon skeletons, were isolated from Resina Commiphora. The structure of 1 was secured by X-ray crystallography. Compound 4 represents the first example of C38 terpenoids, whereas 5 is a C30 terpenoid formed by two types of sesquiterpenoids. These metabolites possess lipid regulatory activities via activating PPARα and CPT1.

Commipholactam A, a cytotoxic sesquiterpenoidal lactam from Resina Commiphora.

Diverse terpenoids including a novel sesquiterpenoidal lactam, commipholactam A (1), and a structurally related new cadinane sesquiterpenoid, commiphorane H (2), a new eudesmane sesquiterpenoid, commiphorane I (4), a new guaiane sesquiterpenoid, commiphorane J (5), and two new nor-abietane diterpenoids, commiphoranes K1 and K2 (6 and 7) along with two known terpenoids (3 and 8), were isolated from Resina Commiphora. Their structures with absolute configurations were characterized by spectroscopic methods and calculated electronic circular dichroism (ECD). Notably, commipholactam A represents the first example of cadinane sesquiterpene alkaloids isolated from Resina Commiphora. Biological assessment toward human cancer cells showed that the IC50 values of 1 against HepG2 and A549 cells were 21.73 µM and 128.50 µM, respectively.