Illicium Simonsii Research Articles

The complete chloroplast genome of Illicium simonsii Maxim. (Illiciaceae), a species with important medicinal properties

Illicium simonsii Maxim (1888) is a medicinal species of the genus Illicium in the Illiciaceae family. It is commonly used to cure gastro-frigid vomiting, cystic hernia, gas pains in the chest, and scabies as folk medicine. To utilize its resources efficiently, the complete chloroplast genome of I. simonsii was sequenced, assembled, and annotated by using high-throughput sequencing data. The complete chloroplast genome was 143,038 bp in length, with a large single-copy region (LSC) of 101,094 bp, a short single-copy region (SSC) of 20,070 bp, and a pair of inverted repeats (IRs) of 21,874 bp. A total of 113 genes were annotated, including 79 protein-coding genes, 30 tRNA genes, and four rRNA genes. The phylogenetic tree exhibited that I. simonsii and Illicium burmanicum form a sister group, and were nested in the monophyletic clade of the Illicium genus.

Fire resistance of 15 main economic tree species in Liangshan Prefecture, Sichuan, China.

Liangshan Prefecture is one of the three major forest areas in Sichuan Province and one of the three major disaster areas of forest fire. We measured the physicochemical properties and combustion performances of different organs (leaves and branches) of 15 main economic tree species in Liangshan, and analyzed the bioecology characteristics, silviculture characteristics and value characteristics of different tree species. We investigated the fire resistance of different tree species to screen out fire-resistant species suitable for economic forest development in Liangshan Prefecture, and improve the biological fire prevention ability. The seven physicochemical properties and combustion performances indices of 15 tree species showed significant differences. Except for crude ash and lignin, the weights of moisture content, caloric value, ignition point, crude fat, and crude fibre of leaves were higher than those of branches. Crude fibre index of leaves (9.6%) and the crude ash index of branches (9.9%) were the highest weight indices of the two organs, respectively. Based on the fire resistance, we divided all the species into three classes, i.e., class Ⅰ (excellent fire-resistance trees) Juglans regia and Morus alba; class Ⅱ (better fire-resistant trees) Sapium sebiferum, Mangifera indica, Phyllanthus emblica, Eriobotrya japonica, Ligustrum lucidum, Castanea mollissima, and Punica granatum; class Ⅲ (poor fire-resistant trees) Pinus armandii, Illicium simonsii, Morella rubra, Sapindus mukorossi, Olea europaea and Camellia oleifera. J. regia and M. alba had fireproof solid performance and could be used as the preferred species for fireproof economic forest in Liangshan region. It was suggested that to use class Ⅰ to Ⅱ fire-resistant tree species built the main fireproof isolated forest belt, and pay attention to fire prevention after planting class Ⅲ tree species in a large area.

High resolution melting of chloroplast mini-barcode in star anise (Illicium verum) authentication

Star anise (Illicium verum), dubbed the ‘King of Spices’, is one of the most popular spices widely used in cuisine, cosmetics and herbal medicine. However, recent surveys have found that commercial products occasionally replace star anise with some toxic lookalike species. To address this problem, we applied a high resolution melting of chloroplast mini-barcode method to distinguish star anise from poisonous adulterants. We sequenced the complete chloroplast genomes of four reported adulterant species (i.e., Illicium lanceolatum, Illicium simonsii, Illicium henryi and Illicium brevistylum). We carried out a comparative analysis between these species and the published chloroplast genome of star anise. Although the chloroplast genomes are conserved among Illicium species, we found some divergent hotspot regions that can potentially exploit high resolution DNA mini-barcodes for species authentication. Subsequently, we used high resolution melting (HRM) assay to generate standard melting profiles of these mini-barcodes for these species. The melting data showed that the mini-barcodes derived from two divergence regions (i.e., atpF–atpH and ndhF–rpl32) have high resolution for species discrimination and could clearly distinguish star anise from four tested adulterants. We applied these two mini-barcodes to check twelve commercial products alleged or labelled as “star anise”, which were purchased from China traditional markets and internet shops. The HRM curves of eleven samples are clustered with the reference star anise with confidence higher than 95%, indicating that these products contain the correct species as declared. We also found one toxic adulterant, as its melting curve clustered with Illicium simonsii. We conclude that DNA mini-barcode derived from divergent hotspot region of chloroplast genome combined with HRM analysis is an effective and rapid strategy to discriminate star anise from its toxic lookalike adulterants.

Chemical constituents from the fruits of Illicium simonsii and their antiviral activity and neuroprotective effect

One undescribed diterpenoid illisimonone A, four undescribed sesquiterpenes named (±)-simonones A, simonterpenoids A and B, and two undescribed lignans, illisimonins A and B, along with five known compounds were isolated from the fruits of Illicium simonsii. Their structures were elucidated by extensive spectroscopic data. The absolute configuration of illisimonone A was determined by single-crystal X-ray diffraction analysis. Illisimonone A showed potential antiviral activity against the Coxsackie B3 virus, with an IC50 value of 3.70 μM. Illisimonin B and henrylactone A showed potential neuroprotective effects against oxygen-glucose deprivation induced cell injury in SK-N-SH cells, with survival rates of 57.6%, 58.0%, respectively.

Sesquiterpenes and Monoterpenes from the Leaves and Stems of Illicium simonsii and Their Antibacterial Activity.

Two undescribed ether derivatives of sesquiterpenes, 1-ethoxycaryolane-1, 9β-diol (1) and 2-ethoxyclovane-2β, 9α-diol (3), and one new monoterpene glycoside, p-menthane-1α,2α,8-triol-4-O-β-D-glucoside (5), were obtained, together with eight known compounds from the stems and leaves of I. simonsii. Their structures were elucidated by spectroscopic methods. Compounds 1–11 were evaluated for their potency against Staphylococcus aureus and clinical methicillin-resistant S. aureus (MRSA). Among them, compound 3 was weakly active against S. aureus (MIC = 128 μg/mL), and compounds 6 and 7 exhibited good antibacterial activity against S. aureus and MRSA (MICs = 2–8 µg/mL). A primary mechanism study revealed that compounds 6 and 7 could kill bacteria by destroying bacterial cell membranes. Moreover, compounds 6 and 7 were not susceptible to drug resistance development.

Synthesis of Illisimonin a Skeleton by Intramolecular Diels–Alder Reaction of Ortho-Benzoquinones and Biomimetic Skeletal Rearrangement of Allo-Cedranes

Illisimonin A is a new sesquiterpene isolated from Illicium simonsii, and it possesses a novel 5/5/5/5/5 pentacyclic skeleton. The tricyclic skeleton of illisimonin A, tricyclo[5.2.1.01,5]decane, is presumed to be biosynthesized from allo-cedranes via a skeletal rearrangement. Herein, we report the concise synthesis of highly oxidized allo-cedranes by an intramolecular Diels–Alder reaction using ortho-benzoquinones and demonstrate the biomimetic transformation of allo-cedranes by a retro-Claisen/aldol pathway.

Triphenyl-sesquineolignan analogues derived from Illicium simonsii Maxim exhibit potent antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) by disrupting bacterial membranes

Infections caused by clinical methicillin-resistant Staphylococcus aureus (MRSA) are a serious public problem. Triphenyl-sesquineolignans from Illicium genus possess antibacterial activity, but few researches have reported their antibacterial spectrums, structure–activity relationships (SARs) and antibacterial mechanism. In this study, three triphenyl-sesquineolignans, dunnianol (1), macranthol (2) and isodunnianol (3) were isolated from the stems and leaves of I. simonsii Maxim, and seven dunnianol derivatives were prepared through esterification, etherification and halogenation reactions. Among all triphenyl-sesquineolignan analogues, compound 6 showed the best antibacterial activity against four Gram-positive bacteria (MICs = 1–2 µg/mL) and ten clinical MRSA strains (MICs = 2–8 µg/mL), and also exhibited characteristics of killing MRSA more rapidly than tigecycline. Meanwhile, compound 6 did not only show a low probability of drug resistance development, but also exhibited relatively low hemolysis, and good stability in 50% plasma. Further mechanism studies revealed that 6 could kill bacterial strains by disrupting bacterial membranes. These results suggested that 6 may be developed into a new antibacterial candidate for combating MRSA infections.

Discovery, Synthesis, and Biological Evaluation of Dunnianol-Based Mannich Bases against Methicillin-Resistant Staphylococcus aureus (MRSA)

Dunnianol, a natural sesqui-neoligan derived from the leaves and stems of Illicium simonsii Maxim, has been found to possess moderate antibacterial activity. To improve the antibacterial activity and solubility of dunnianol, a series of dunnianol-based Mannich bases were prepared and evaluated for their antibacterial activities. The most promising compound, 5a', exhibited excellent antibacterial activity against Staphylococcus aureus and clinically isolated methicillin-resistant Staphylococcus aureus (MRSA) with MIC values of 1 to 2 μg/mL. Structure-activity relationships indicated that the introduction of (dimethylamino)methyl at the ortho position of the phenolic hydroxyl group of dunnianol could obtain a more active compound. A mechanism study revealed that 5a' killed MRSA more rapidly than did vancomycin by disrupting the cell membrane. Moreover, 5a' was not susceptible to drug resistance development and also showed low toxicity and good antibacterial efficacy in vivo. These results indicate that the dunnianol-based Mannich base 5a' could be a promising antibiotic candidate for further research.

Anti-Inflammatory Effect of Simonsinol on Lipopolysaccharide Stimulated RAW264.7 Cells through Inactivation of NF-κB Signaling Pathway.

Simonsinol is a natural sesqui-neolignan firstly isolated from the bark of Illicium simonsii. In this study, the anti-inflammatory activity of simonsinol was investigated with a lipopolysaccharide (LPS)-stimulated murine macrophages RAW264.7 cells model. The results demonstrated that simonsinol could antagonize the effect of LPS on morphological changes of RAW264.7 cells, and decrease the production of nitric oxide (NO), tumor necrosis factor α (TNF-α), and interleukin 6 (IL-6) in LPS-stimulated RAW264.7 cells, as determined by Griess assay and enzyme-linked immunosorbent assay (ELISA). Furthermore, simonsinol could downregulate transcription of inducible nitric oxide synthase (iNOS), TNF-α, and IL-6 as measured by reverse transcription polymerase chain reaction (RT-PCR), and inhibit phosphorylation of the alpha inhibitor of NF-κB (IκBα) as assayed by Western blot. In conclusion, these data demonstrate that simonsinol could inhibit inflammation response in LPS-stimulated RAW264.7 cells through the inactivation of the nuclear transcription factor kappa-B (NF-κB) signaling pathway.

Total Synthesis and Structure Revision of (-)-Illisimonin A, a Neuroprotective Sesquiterpenoid from the Fruits of Illicium simonsii.

Illisimonin A was isolated from Illicium simonsii and has a previously unreported tricyclic carbon framework. It displayed neuroprotective effects against oxygen-glucose deprivation-induced cell injury in SH-SY5Y cells. It incorporates a highly strained trans-pentalene ring system. We report the first synthesis of (±)-illisimonin A. Notable steps in the route include a 1,3-dioxa-2-silacyclohexene templated Diels-Alder cycloaddition and type-3 semipinacol rearrangement to generate the trans-pentalene. The final step is an iron-catalyzed C-H oxidation. The synthetic route is robust, with 94 mg of racemic material prepared in a single pass. Resolving an intermediate enabled the synthesis of natural (-)-illisimonin A. The absolute configuration of (-)-illisimonin A was revised to 1S,4S,5S,6S,7R,9R,10R based on the X-ray structure of a heavy-atom analogue.

Sesquiterpenes from the fruits of Illicium Simonsii maxim

A new allo-cedrane sesquiterpene glycoside (1) and nine known compounds (2–10) were isolated from the ethanol extract of the fruit of Illicium simonii Maxim. Their structures were elucidated by spectroscopic methods, including 1D-, 2D-NMR, and HRESIMS. The absolute configuration of compound 1 was confirmed by CD experiments. Among them, compounds 1, 4, 5, and 7 displayed moderate anti-inflammatory activities by use of an in vitro bioassay.

Sesquiterpenoids and lignans from the fruits of Illicium simonsii Maxim

Twenty-two known compounds were isolated from the 95% alcohol extract of the fruits of Illicium simonsii Maxim, including seven sesquiterpenoids (16–22) and fifteen lignans (1–15). In the present research, compounds 3 ((7S,8R,8′S)-3,3′-dimethoxy-4,4′,9-trihydroxy-7,9′-epoxylignan-7′-one), 4 ((−)-(7′S,8S,8′R)-4,4′-dihydroxy-3,3′,5,5′-tetramethoxy-7′,9-epoxylignan-9′-ol-7-one), 5 ((+)-8-hydroxypinoresinol), 6 ((+)-8-hydroxymedioresinol), 8 ((2R,3R)-2β-(4″-hydroxy-3″-methoxybenzyl)-3α-(4′-hydroxy-3′-methoxybenzyl)-γ-butyrolactone 2-O-(β-D-glucopyranoside), 12 ((+)-8-methoxyisolariciresinol), 13 (α-conidendrin), 14 (boehmenan) and 15 (7R,8R,7′E-7′,8′-didehydro-4,7,9,9′- tetrahydroxy-3-methoxy-8-O-4′-neolignan) were reported from the Illicium genus for the first time, and compounds 1 (simulanol), 7 ((+)-secoisolariciresinol monoglucoside), 10 ((+)-9-O-β-D-glucopyranosyl lyoniresinol), 11 ((+)-isolariciresinol), 18 (neoanisatin), 19 (veranisatin A), 20 (4,5-d2-8′-oxo-dihydrophaseic acid) and 22 (Oligandrumin A) were firstly isolated from the plant. Their structures were elucidated on the basis of NMR spectroscopic and mass spectrometric data. Moreover, the chemotaxonomic significance of the isolated compounds is discussed.

Neolignan and phenylpropanoid compounds from the fruits of Illicium simonsii Maxim

One new sesqui-neolignan compound, namely, sesqui-illisimonan A (1), one new neolignan, illisimonan A (2), and one new phenylpropanoid compound, illisimoid A (3) were isolated from the fruits of Illicium simonsii Maxim. The structures and absolute configurations of these compounds were determined by extensive spectroscopic, including NMR, circular dichroism and calculated electronic circular dichroism methods. The antioxidant activities of compounds 1–3 were also evaluated. Vitamin E was selected as the positive control (IC50 = 49.73 ± 0.88 μM). Compounds 1 and 2 exhibited in vitro antioxidant activity with an IC50 value of 55.76 ± 1.30 and 59.36 ± 0.50 μM, respectively. However, the compound 3 didn’t show obvious antioxidant activity.

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A personal selection of 32 recent papers is presented covering various aspects of current developments in bioorganic chemistry and novel natural products such as illisimonin A from Illicium simonsii.

Pharmacologic Effect of Miao Medicine Illicium simonsii Maxim. on Collagen-Induced Arthritis in Rats.

Objectives To study the pharmacologic effect and mechanism of action of Miao medicine Illicium simonsii Maxim. (ISM) in treating rheumatoid arthritis. Methods Sixty rats were randomly divided to six groups: normal control (normal), collagen-induced arthritis (CIA) model (model), CIA + tripterygium glycosides (TG), CIA + ISM high dose oral (ISM-H), CIA + ISM low-dose oral (ISM-L), and CIA + ISM topical application (ISM-T). The treatment doses were selected based on published reports and folk medicine practice. The outcome measurements included paw swelling, joint pathology, organ index, blood count, T helper 17 (Th17) cell count, and interleukin-6 (IL-6) level. Results Compared to the CIA model group, all treatment groups showed a significant reduction in paw swelling, blood vessel pathology, Th17 cell count, and IL-6 levels (p < 0.05 or p < 0.01). All treatment groups showed alleviated foot swelling and lower total number of white blood cells, and these effects were observed earlier with oral ISM than topical ISM. The effect of ISM was weaker than that of TG. In addition, less organ damage was observed with topical ISM than oral ISM but better than TG. Conclusions These results suggest that, by downregulating Th17 cells, ISM inhibits the production of Il-6, thereby alleviating the proliferation of endothelial and rheumatoid-like cells and leukocytosis in CIA rats, ultimately eliminating foot swelling.

Illisimonin A, a Caged Sesquiterpenoid with a Tricyclo[5.2.1.01,6]decane Skeleton from the Fruits of Illicium simonsii.

Illisimonin A, an unprecedented sesquiterpenoid with a tricyclo[5.2.1.01,6]decane skeleton, was isolated from the fruits of Illicium simonsii. The structure and absolute configuration of 1 were determined using extensive spectroscopic evidence and electronic circular dichroism (ECD) calculations. It was determined that 1 possesses a caged 2-oxatricyclo[3,3,0,14,7]nonane ring system fused to a five-membered carbocyclic ring and a five-membered lactone ring. A plausible biogenetic pathway for 1 was proposed, and 1 showed neuroprotective effects against oxygen-glucose deprivation (OGD)-induced cell injury in SH-SY5Y cells with an EC50 value of 27.72 μM.

Sesquineolignans and Terpene-Sesquineolignans: Anti-Acetylcholinesterase Constituents from Illicium simonsii

Chemical investigation of the aerial parts of Illicium simonsii resulted in the isolation of nine new compounds, simonsols A-E (1-5), simonsins A-B (7-8), terpene-sesquineolignans, clovanedunnianol (9), and p-menthadunnianol (10). Compound 5 was equilibrated with 7 as an inseparable mixture. The structures were elucidated by extensive NMR and MS analysis. Compounds 9, 10, and the mixture of 5 and 7 moderately inhibited acetylcholinesterase with IC50 values of 4.58 µM, 6.55 µM, and 10.34 µM, respectively.

Terriera angularis sp. nov. on Illicium simonsii from China

Terriera angularis, a new species of Terriera that develops on leaves of Illicium simonsii, was collected from Shennongjia forestry region of Hubei Province, China. Description, illustration, and comments are given for this fungus. The type collection is deposited in the Reference Collection of Forest Fungi of Anhui Agricultural University, China (AAUF).

Sesquiterpenes and lignans from the fruits of Illicium simonsii and their cytotoxicities

AimTo study the constituents and bioactivity of Illicium simonsii. MethodsCompounds were isolated by a combination of chromatographic materials, silica gel, ODS, and Sephadex LH-20, and finally purified by preparative HPLC. Their structures were elucidated on the basis of spectroscopic methods, and they were evaluated for their cytotoxic activities by the MTT method. ResultsSeven compounds were obtained and were identified as veranisatin F (1), anisatin (2), (1S)-minwanenone (3), honokiol (4), macranthol (5), (+-pinoresinol (6), and matairesinol (7). ConclusionCompound 1 is a new seco-prezizaane-type sesquiterpene, while compounds 6 and 7 were isolated from Illicium simonsii for the first time. Compounds 2 and 3 showed strong inhibitory activities against the growth of NCI-H460 and SMMC-7721 cells comparable to 5-fluorouracil, and compound 7 to a lesser extent; the other isolates showed no cytotoxicity.

Two New Phenylpropanoid Derivatives and Other Constituents from Illicium simonsii Active Against Oral Microbial Organisms

Two New Phenylpropanoid Derivatives and Other Constituents from Illicium simonsii Active Against Oral Microbial Organisms