Illihenin A: An Antiviral Sesquiterpenoid with a Cage-like Tricyclo[6.2.2.0^1,5]dodecane Skeleton from Illicium henryi

Abstract

Illihenin A (1), a novel sesquiterpenoid, was isolated from the roots of Illicium henryi. The structure was determined by spectroscopic analyses, ECD calculation, and single-crystal X-ray diffraction. Compound 1 represents a class of novel 5/7/6 tricyclic sesquiterpenoids featuring a rare cage-like tricyclo[6.2.2.0 1,5 ]dodecane core. A plausible biosynthetic pathway of 1 by rearrangement of allocedrane is proposed. Additionally, 1 showed potent antiviral activity against coxsackievirus B3 with an IC 50 value of 2.87 μM.

Four Highly Oxygenated Sesquiterpenoids from the Fruits of Illicium micranthum Dunn

“…Some species, such as Illicium dunnianum Tutch, I. simonsii Maxim, and I. lanceolatum A. C. Smith, have been used as Chinese fork medicines to treat bleeding, traumatic injuries, and rheumatoid arthritis [2] . In Illicium genus, a series of secondary metabolites have been reported, including monoterpenoids, highly oxygenated sesquiterpenoids, diterpenoids, triterpenoids, lignans, phenylpropanoids, and prenylated C 6 ‐C 3 components [3–9] . Among them, the highly oxygenated sesquiterpenoids including seco‐prezizaane, allo‐cedrane, anislactone, and illicinolide types are the characteristic components of Illicium species and have been reported to display neuroprotective, [6,10,11] neurotrophic, [12,13] neurotoxicity, [14,15] anti‐inflammatory, [16] and antiviral activities [5,17,18] …”

“…[2] In Illicium genus, a series of secondary metabolites have been reported, including monoterpenoids, highly oxygenated sesquiterpenoids, diterpenoids, triterpenoids, lignans, phenylpropanoids, and prenylated C 6 -C 3 components. [3][4][5][6][7][8][9] Among them, the highly oxygenated sesquiterpenoids including secoprezizaane, allo-cedrane, anislactone, and illicinolide types are the characteristic components of Illicium species and have been reported to display neuroprotective, [6,10,11] neurotrophic, [12,13] neurotoxicity, [14,15] anti-inflammatory, [16] and antiviral activities. [5,17,18] Illicium micranthum Dunn, a shrub or small tree, is mainly found in central, southern, and southwestern China.…”

An improved Poisson‐Nernst‐Planck ion channel model and numerical studies on effects of boundary conditions, membrane charges, and bulk concentrations

“…Hence, developing numerical methods becomes essential to search for PNP approximate solutions. So far, different PNP numerical algorithms were developed in the past two decades by using finite difference methods, 10,11 finite element methods, 12,13 a matched interface and boundary method, 14 a finite volume method, 15 a hybrid finite‐difference/finite‐volume method, 16 and a spectral element method, 17 and so forth. Of these numerical methods, the finite element method is the most suitable to handle an irregular molecular surface of an ion channel protein and complicated interface conditions to generate a PNP approximate solution in high accuracy.…”

seco‐Prezizanne Sesquiterpenes and Prenylated C6‐C3 Compounds from the Fruits of Illicium lanceolatum A. C. Smith

“…[2] Chemical studies of Illicium species have led to the isolation of an array of structurally diverse secondary metabolites, such as Illicium sesquiterpenes (including seco-prezi-zaane, anislactone, and allo-cedrane types), prenylated C6-C3 compounds, and neolignans. [3][4][5][6][7][8] The former two classes belong to unique structural types and occur exclusively in Illicium species. These interesting compounds displayed a wide variety of bioactivities, such as neurotoxic, neurotrophic, antiviral, anti-inflammatory, and antimicrobial activities.…”