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

Abstract

Two new seco-prezizaane-type sesquiterpenes, 2β-hydroxy-6-deoxyneoanisatin (1) and 3,4-anhydro-2-oxo-1αhydroxy-6-deoxyneoanisatin (2), and two new prenylated C 6 -C 3 compounds, illilanceofunones A (3) and B (4), were obtained from the fruits of Illicium lanceolatum, along with four known prenylated C 6 -C 3 compounds (5 -8). Their structures were proposed through HR-ESI-MS, 1 H, 13 C, and 2D NMR data interpretation. Moreover, the absolute configuration of 1 and 2 were further assigned by single-crystal X-ray diffraction analysis and electronic circular dichroism (ECD) calculations, respectively. Illihenryipyranol A (6) exhibited neuroprotective activity against MPP + -induced PC12 cell damage in a dose-dependent manner.

Four Highly Oxygenated Sesquiterpenoids from the Fruits of Illicium micranthum Dunn

“…ECD calculation of the optimized conformers were carried out by TDDFT at the PBE1PBE/6‐311++ G (2d, p) level in methanol using PCM model. The calculated ECD spectra of 2–4 were obtained by a SpecDis version 1.62 [8] …”

“…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.…”

“…[22,23] To date, monoterpenoids, [24] highly oxygenated sesquiterpenoids, [20,22,25,26] phenylpropanoids, [20] prenylated C 6 -C 3 compounds have been reported from this species. [21] Following an interest in the discovery of structurally unique and biologically components from I. species, [8,27] phytochemical research on the fruits of I. micranthum led to the isolation of four highly oxygenated sesquiterpenoids, illimicranolides A (1) and B (2), and illicinolides E (3) and F (4), along with one known compound, illicinolide B (5) (Figure 1). Among them, compound 1 was a unique sesquiterpenoid with a 5/5/6/5 fused tetracyclic ring system and was the first seco-prezizaane sesquiterpenoid having a 11,8-γ-lactone ring.…”

Spirocyclohexadienone‐Type Neolignans with Neuroprotective and Neurite Outgrowth Enhancing Activities from Magnolia liliiflora

“…The neuroprotective effect of 1 and 4-6 against corticosterone-induced injury in PC 12 cells were performed according to the reported procedures. [39] PC12 cells purchased from ATCC were cultured in DMEM medium, which contained 10 % FBS with 100 U/mL penicillin and 100 μg/mL streptomycin in a humidified atmosphere at 37 °C with 5 % CO 2 . The logarithmically growing PC12 cells were seeded in 96 well plate with a density of 1 × 10 5 cells/mL per well in 100 μL and incubated for 24 h in the presence or absence of 150 μM corticosterone and test compounds.…”