Diverse Ring‐seco Limonoids from Munronia unifoliolata and Their Biological Activities

Abstract

Comprehensive Summary Twenty‐two new limonoids, mufolinoids A—V (1—22), including six rings A, B‐seco limonoids (1—6), twelve ring A‐seco limonoids (7—18), four ring‐intact limonoids (19—22), together with thirteen known compounds (23—35) were isolated from Munronia unifoliolata. Their structures including absolute configurations were elucidated by combination of NMR, HR‐MS, single‐crystal X‐ray diffraction and calculations of ECD and NMR technologies. Compounds 24, 25, 33, 34 could be significantly reversed the multidrug resistance of MCF‐7/doxorubicin (DOX) cells, and the reversal fold (RF) was much higher than that of positive drug Verapamil. Compounds 24, 28, and 29 exhibited significant anti‐inflammatory activity with the IC50 values in the range of 17.7—39.4 μmol/L. Furthermore, compound 29 could markedly inhibit the release of IL‐1β by inhibiting the initiation and assembly of NLRP3 inflammasome, which demonstrates the great potential of limonoids as an anti‐inflammatory agent.

Isosteroidal Alkaloids from Fritillaria verticillata Willd. and Their NMR Spectroscopic Characteristics

“…As far as we know, some pro‐inflammatory cytokines, such as TNF‐α, IL‐1β and IL‐17α, play important roles in the pathogenesis of inflammatory diseases. [ 33‐37 ] For example, IL‐1β is produced by activated macrophages as a proprotein, which is an important mediator of the inflammatory response, and is involved in a variety of cellular activities, including cell proliferation, differentiation, and apoptosis. IL‐17α, an important cytokine of T‐helper 17 (TH17) cell subsets, has key roles in extracellular pathogen protection and also stimulates the inflammatory response in autoimmune disorders.…”

Research progress of meliaceous limonoids from 2011 to 2021

“…S1.1-S1.3 †). According to previous studies, these limonoids can be divided into the azadirone-class (A1-A58), cedreloneclass (A59-A99), 97,99,102,105,[110][111][112][113][114][115] havanensin-class (A100-A121), 97,98,108,[116][117][118][119][120][121][122][123][124][125][126][127][128][129][130] trichilin-class (A122-A168), 119,120,122,125,[131][132][133][134][135][136][137][138][139][140] vilasinin-calss (A169-A206) 82,87,122,128,132,[141]…”

“…5), and others (A207-A223). 42,80,82,95,99,102,127,128,146,154 2.2.2 Ring-seco limonoids. Ring A-seco limonoids (B1-B70) were mainly distributed in the genera Toona, 101,103,[155][156][157] Munronia, 78,87,108,128,158 and Aphanamixis.…”

“…42,80,82,95,99,102,127,128,146,154 2.2.2 Ring-seco limonoids. Ring A-seco limonoids (B1-B70) were mainly distributed in the genera Toona, 101,103,[155][156][157] Munronia, 78,87,108,128,158 and Aphanamixis. 47,159,160 A little was found in the genera Aglaia, 161 Guarea, 162 and Dysoxylum 127 (Table S1.4 †).…”

“…They are considered to be produced from ring-intact limonoids by Baeyer-Villiger oxidation (Fig. 6), which has antiin-ammatory, 78,103,128,155 antiTMV, 87,108,142 antimultidrug resis-Ring B-seco limonoids are characteristic components of Toona genus (Table S1. †5).…”