Potential Anti‐Inflammatory Activities of Bractelactone and other Compounds Isolated from Fissistigma bracteolatum

Abstract

From the stems of Fissistigma bracteolatum, a novel natural product with an unprecedented skeleton, bractelactone (1), was isolated, together with four known compounds: piperolactam A (2), aristololactam BIII (3), aristololactam BII (4), and fissilandione (5). The structure of 1 was established on the basis of spectroscopic data as (3Z)‐6,7‐dihydroxy‐4‐methoxy‐3‐(phenylmethylidene)‐5‐(3‐phenylpropanoyl)‐1‐benzofuran‐2(3H)‐one. This compound may be derived from a hybrid of a chalcone and a cinnamic acid, or from a degradation product of a dichalcone. Compounds 1, 2, and 5 showed inhibitory effects on NO generation by RAW264.7 macrophages in response to lipopolysaccharide. Compounds 2 and 5 showed inhibitory effects on formyl‐L‐methionyl‐L‐leucyl‐L‐phenylalanine (fMLP)‐induced superoxide anion (O$\rm{_{2}^{{^\cdot} -}}$) generation in human neutrophils.

The First Bis-Retrochalcone fromFissistigma latifolium

“…Assignments were confirmed by 1 H-1 H COSY, HMQC, and HMBC experiments groups located at C-2 and C-5. The above HMBC correlations and the presence of two downfield carbonyl groups in the 13 C NMR spectrum suggested a p-benzoquinone ring rather than an aromatic ring (B ring). Fragment ions in the EI-MS spectrum at m/z 195 and 223 also confirmed that compound 2 belonged to the quinoretrochalcone family.…”

“…IR spectra were measured on an IRprestige-21 spectrophotometer. 1 H NMR (400 MHz, using CDCl 3 as the solvent for measurement), 13 C NMR (100 MHz), HMQC, HMBC, 1 H-1 H COSY, DEPT, and NOESY spectra were recorded with Bruker Avance-400 NMR spectrometers. LREIMS were collected on a JEOL JMS-SX/SX 102A mass spectrometer.…”

“…In this report, the isolation and structural elucidation of two novel compounds, [3-3′]bi-2-hydroxy-4,5,6-trimethoxydihydrochalcone (1) and 4,6-dimethoxy-2,5-quinodihydrochalcone (2) (l " Fig. 1), along with twelve known compounds, aristolactam III a (3) [10], 5,6,7-trimethoxyflavone (4) [11], liriodenine (5), oxocrebanine (6) [4], vanillic acid (7) [12], piperlactam A (8) [13], goniothalactam (9) [1], 2-hydroxy-4,5,6-trimethoxydihydrochalcone (10) [14], benzaldehyde (11) [15], 5-hydroxy-6,7,8-trimethoxyflavone (alnetin) (12) [16], lysicamine (13) [17], and artherospermidine (14) [18], are discussed. The chemical structures of the known compounds were established by comparison with data reported in the literature.…”

Synthesis of 3-Alkylideneisoindolin-1-ones via Sonogashira Cyclocarbonylative Reactions of 2-Ethynylbenzamides

“…In particular, 3-methyleneisoindolin-1-ones have been recognized as nuclei of natural and synthetic compounds such as fumaridine, narceine imide, stigmalactam, magallinesine, chartarlactam L, aristoyagonine, aristolactams, and AKS-186 . These heterocycles have been found to possess antimycobacterial and antifungal activities and antiplatelet , properties, to act as anti-inflammatory − and neuroprotective agents, to inhibit vasoconstriction, , and to show cytotoxic and antitumoral activities. − …”

Zipper-Mode Double C−H Activation: Palladium-Catalyzed Direct Construction of Highly-Fused Heterocyclic Systems

“…Efficient construction of highly fused heterocyclic aromatic ring systems is an important research area in organic synthesis. A number of highly fused aromatic compounds with interesting biological activities have been reported to date, including aristolactams, aporphines, naphthofurans, benzonaphthothiophenes, and benzocarbazoles 5,6 (Figure ). Since synthetic routes to these complex molecules often suffer from lengthy reaction steps of redundancy with a considerable amount of waste, reliable synthetic methods for this class of compounds in direct and atom-economical manners are strongly required.…”