Project description:Graphical abstract Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-013-0007-x and is accessible for authorized users.
Project description:Three new germacrane sesquiterpenes and a new m-menthane monoterpene were isolated together with four known compounds from the pericarp of Illicium lanceolatum, an adulterant to star anise (Illicium verum). All compounds were isolated from Illicium plants for the first time. The absolute stereochemistry of all germacranes and m-menthane was established by a combination of NMR and the modified Mosher's ester method. The biological activity was evaluated on SH-SY5Y neuroblastoma cell line. (1S,5R,7R)-1,5-Dihydroxygermacra-4(15),10(14),11(12)-triene (at 62.5 µM) and (1R,5R,7R)-1,5-dihydroxygermacra-4(15),10(14),11(12)-triene (at 15.6 µM) promoted the proliferation of SH-SY5Y by 36.2% and 45.8%, respectively, after 48 h incubation, indicating potential neurotrophic activity.
Project description:This study aimed at screening the inhibitory activity of Illicium verum extracts against avian reovirus, infectious bursal disease virus (IBDV), Newcastle disease virus (NDV), and infectious laryngotracheitis virus (ILTV). The cytotoxic and antiviral actions of 3 extracts, absolute methanol (100MOH), 50% methanol (50MOH), and aqueous extracts (WA.), were evaluated by MTT assay. The Illicium verum extracts were added to the cultured chick embryo fibroblast (CEF) with tested viruses in three attacks, preinoculation, postinoculation, and simultaneous inoculation. The three extracts showed antiviral inhibitory activity against all tested viruses during simultaneous inoculation and preinoculation except 100MOH and 50MOH that showed no effect against IBDV, thereby suggesting that the extracts have a preventive effect on CEF against viruses. During postinoculation, the extracts exhibited inhibitory effects against NDV and avian reovirus, while no effect against IBDV recorded and only the 100MOH showed an inhibitory effect against ILTV. The initial results of this study suggest that Illicium verum may be a candidate for a natural alternative source for antiviral agents.
Project description:Majucin-type sesquiterpenes from Illicium sp., such as jiadifenolide (2), jiadifenin (3), and (1R,10S)-2-oxo-3,4-dehydroxyneomajucin (4, ODNM), possess a complex caged chemical architecture and remarkable neurotrophic activities. As such, they represent attractive small-molecule leads against various neurodegenerative diseases. We present an efficient, enantioselective, and unified synthesis of 2, 3, and 4 and designed analogues that diverge from tetracyclic key intermediate 7. The synthesis of 7 is highlighted by the use of an enantioselective Robinson annulation reaction (construction of the AB rings), a Pd-mediated carbomethoxylation reaction (construction of the C ring), and a one-pot oxidative reaction cascade (construction of the D ring). Evaluation of the neurotrophic activity of these compounds led to the identification of several highly potent small molecules that significantly enhanced the activity of nerve growth factor (NGF) in PC-12 cells. Moreover, efforts to define the common pharmacophoric motif suggest that substitution at the C-10 center significantly affects bioactivity, while the hemiketal moiety of 2 and 3 and the C-1 substitution might not be critical to the neurotrophic activity.
Project description:In this study, four new lignan glucosides, named difengpiosides A-D (1-4), were isolated from the stem barks of Illicium difengpi, together with seven known compounds 5-11. Their structures were identified on the basis of spectroscopic analyses (1D and 2D NMR, HRESIMS, CD) and a comparison with literature data. All the compounds were evaluated for their inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells.
Project description:Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant biological activities. Herein we report the first chemical synthesis of (+)-pseudoanisatin from the abundant feedstock chemical cedrol (∼$50 USD/kg) in 12 steps using extensive site-selective C(sp3)-H bond functionalization. Significantly, this work represents a novel oxidative strategic template for future approaches to these natural products and their analogs.