Terpenoids from Vitex trifolia and their anti-inflammatory activities.

A new diterpenoid glucoside, (3S,5S,6S,8R,9R,10S)-3,6,9-trihydroxy-13(14)-labdean-16,15-olide 3-O-ß-D-glucopyranoside (1), and a new iridoid glucoside, (1S, 5S,6R,9R)-10-O-p-hydroxybenzoyl-5,6ß-dihydroxy iridoid 1-O-ß-D-glucopyranoside (2), along with six known compounds (3-8) were isolated from Vitex trifolia L.. Their structures were elucidated by extensive spectroscopic analysis. All these isolated compounds were evaluated for their inhibitory effects on nitric oxide production in LPS-induced RAW 264.7 macrophages. Compounds 2, 4, 5, and 7 showed moderate inhibitory activities with IC50 values of 90.05, 88.51, 87.26, and 76.06 µM, respectively.

Chemical constituents from Curcuma longa L. and their inhibitory effects of nitric oxide production.

A new bisabolane-type sesquiterpenoid, turmerone Q (1), along with six known compounds (2-7), were isolated from the rhizomes of Curcuma longa L. The structural elucidation of the new compound was conducted using 1H NMR, 13C NMR, HSQC, HMBC and NOESY spectroscopic analyses. The absolute configuration of 1 was elucidated by comparison of the experimental and calculated ECD spectra. The anti-inflammatory effects of 1-7 were evaluated through lipopolysaccharide-induced nitric oxide (NO) production in RAW 264.7 macrophages assays, and compounds 6 and 7 showed potent inhibitory activity against NO production.

Physalins V-IX, 16,24-cyclo-13,14-seco withanolides from Physalis angulata and their antiproliferative and anti-inflammatory activities.

Five new physalins, including a novel 1,10-seco one, physalin V (1), a tricarboxylic acid cycle one, physalin VIII (5), a rare 11,15-cyclo one, physalin IX (6), and two new ones, physalins VI (2) and VII (4) were isolated from stems and leaves of Physalis angulata together with eleven known analogues (3 and 7-16). Their structures were established by MS, IR, UV, and NMR spectroscopic analysis, together with the X-ray diffraction analysis of neophysalin, physalin P (12), and the structure of physalin D1 (3) has been revised here. These isolated compounds were evaluated for their antiproliferative activities against human cancer cells (C4-2B, 22Rv1, 786-O, A-498, ACHN, and A375-S2) and inhibitory effects on nitric oxide production. Compounds 9 and 10 showed antiproliferative activities against all tested human cancer cells with IC50 values of 0.24-3.17 µM. Compounds 1, 3, 4, 9, 10, 13, 14, and 16 exhibited inhibitory activities against NO production. The IC50 values of compounds 9, 10, 13, and 16 were between 0.32 and 4.03 µM, while compounds 1, 3, 4, and 14 had IC50 values of 12.83-34.19 µM. Herein, plausible biosynthetic pathways for rare structures 1 and 6 and structure-activity relationships on the inhibition of NO production for all isolated compounds are discussed.

Stereo- and region-specific biotransformation of physapubescin by four fungal strains.

Biotransformations of physapubescin (1) were performed by four fungal strains-Mucor subtilissimus AS 3.2454, Mucor polymorphosporus AS 3.3443, Aspergillus niger AS 3.795, and Syncephalastrum racemosum AS 3.264. Four metabolites were prepared in the biotransformation process of 1, and their structures were elucidated as 15α-acetoxy-5,6ß:22,26:24,25-triepoxy-26α-hydroxy-3ß-methoxy 4ß-hydroxyergost-1-one (2), 15α-acetoxy-5,6ß:22,26-diepoxy-4ß,24ß,25α,26(α, ß)-tetrahydroxyergost-3ß-methoxy-1-one (3a/3b), 15α-acetoxy-5,6ß:22,26-diepoxy-4ß,24ß,25α,26(α, ß)-tetrahydroxyergost-2-en-1-one (4a/4b), and physapubescin D (5), by spectroscopic data analysis. Among them, metabolites 2 and 3 are new. All of these fungal strains showed the ability to be highly stereo- and region-specific for the bioconversion of substrate (1). Our research provides a reference for the structural derivatization of withanolides or possibly even other natural products.

Constituents from Vitex negundo var. heterophylla and their inhibition of nitric oxide production.

An iridoid glucoside, 10-p-hydroxybenzoyl-6ß-hydroxyiridoid 1-O-ß-D-(6'-O-p-hydroxybenzoyl)-glucopyranoside (1), and a phenol glucoside, 4-hydroxyphenethanol 3-O-ß-D-(6'-O-p-hydroxybenzoyl)-glucopyranoside (2), along with nine known compounds (3-11) were isolated from the dried leaves of Vitex negundo var. heterophylla. Their structures were elucidated by extensive analysis of NMR spectra. All of the isolated compounds were evaluated for their inhibitory effects on nitric oxide production in RAW 264.7 macrophages. Compounds 2 and 3 exhibited obvious inhibitory effects on NO production with IC50 values of 30.76 and 49.89 µM, respectively. Molecular docking studies of compounds 2 and 3 with nitric oxide synthase (NOS) further confirmed the above results.

Antiproliferative and Anti-inflammatory Withanolides from Physalis angulata.

Sixteen new withanolides, physangulatins A-N (1-14) and withaphysalins Y and Z (15 and 16), as well as 12 known analogues, were isolated from the stems and leaves of Physalis angulata L. Their structures were established using extensive spectroscopic data analyses. The absolute configurations of 1 and 9 were assigned via X-ray crystallography. The isolated compounds were tested for their antiproliferative effects against human prostate cancer cells (C4-2B and 22Rvl), human renal carcinoma cells (786-O, A-498, and ACHN), and human melanoma cells (A375-S2), as well as inhibitory effects on NO production induced by LPS in macrophages. Compounds 9, 17, 20, 21, 25, and 27 showed antiproliferative effects against all tested cancer cells, with IC50 values of 0.18-7.43 µM. Compounds 3-5, 9-11, 17, 20-22, 24, 25, and 27 displayed inhibitory effects against NO production, with IC50 values of 1.36-11.59 µM.