ABSTRACT
Fourteen new geranyl phenyl ethers (1-14) along with three known compounds (15-17) were isolated from Illicium micranthum, and their structures were elucidated by comprehensive spectroscopic methods. Illimicranins A-H (1-8) were characterized as geranyl vanillin ethers, while 9 and 10 were dimethyl acetal derivatives. Illimicranins I and J (11 and 12) were rare geranyl isoeugenol ethers. Illimicranins K and L (13 and 14) represented the first example of geranyl guaiacylacetone ether and geranyl zingerone ether, respectively. Compounds 1, 2 and 15 exhibited anti-HBV (hepatitis B virus) activity against HBsAg (hepatitis B surface antigen) and HBeAg (hepatitis B e antigen) secretion, and HBV DNA replication.
Subject(s)
Antiviral Agents/pharmacology , Hepatitis B Surface Antigens , Hepatitis B e Antigens , Illicium/chemistry , Phenyl EthersABSTRACT
Three seco-prezizaane-type sesquiterpene lactones, one phenylpropanoid, and two lignans were isolated from the 95% ethanol extract of stems and branches of Illicium ternstroemioides with silica gel column chromatography, ODS column chromatography, and preparative HPLC. Based on the spectral data, they were identified as burmanicumolide D(1), veranisatin A(2), veranisatin B(3), dihydroconiferylalcohol(4), pinoresinol(5),(-)-matairesinol(6), respectively. Among them, compound 1 was a new seco-prezizaane-type sesquiterpene lactone, and 2-6 were obtained from this plant for the first time. None of these compounds display antiviral or cytotoxic activities.
Subject(s)
Antiviral Agents , Illicium , Lactones , Molecular Structure , Phytochemicals , SesquiterpenesABSTRACT
ABSTRACT: Shikimic acid (SA) has witnessed a strong increase in recent years due to the increasing demand of the pharmaceutical and cosmetic industry. The SA is used as a precursor for the synthesis of oseltamivir phosphate (Tamiflu®), a potent viral inhibitor and is extracted from the plant Illicium verum Hook which has a limited availability. This article proposed the use of Urochloa plantaginea (Link.) webster and glyphosate, as an alternative source of SA. U. plantaginea plants with 3 - 4 tillers and 4 - 6 leaves were harvest at 3, 6, 9 and 12 days after application (DAT) of low rates of glyphosate. Samples were dried, extracted, analyzed by HPLC and LC-MS/MS. The maximum SA concentrations were observed at 6 days after glyphosate at 36 g.a.e.ha-1 was applied in plants of U. plantaginea with 4 to 6 leaves. The capability of this annual gramineae to produce elevated SA levels throughout the entire biomass affords its potential for a greater yield on a per hectare basis.
RESUMO: O interesse pelo ácido chiquímico (SA) tem apresentado um forte incremento nos últimos anos devido à crescente demanda da indústria farmacêutica e cosmética. O SA é utilizado como um precursor para a síntese do fosfato de oseltamivir (Tamiflu®), um potente inibidor viral. Este ácido é extraído principalmente da planta Illicium verum Hook. A disponibilidade desta planta é um fator limitante para o crescimento do mercado no futuro próximo. Este artigo propõe Urochloa plantaginea (Link.) webster tratada com sub doses de glifosato, como uma fonte alternativa de SA. Plantas de U. plantaginea com 3 - 4 perfilhos e 4 a 6 folhas foram tratadas com subdoses de glifosato e coletadas aos 0, 3, 6, 9 e 12 dias após sua aplicação (DAT). As amostras foram secas, extraídas e analisadas por HPLC e confirmadas por LC-MS/MS. As concentrações máximas de SA foram observadas aos seis dias após aplicação do glifosato a 36 g.e.a.ha-1 em plantas de U. plantaginea com 4 - 6 folhas. A capacidade anual dessa gramínea para produzir níveis elevados de SA em toda a biomassa, pode ser uma fonte economicamente viável de SA.
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Objective:To evaluate and compare the identification of several DNA barcoding candidate sequences on Illicium difengpi and its fake I. jiadifengpi. Method:Samples from different origins of I. difengpi and I. jiadifengpi, were collect extraction of total DNA,nuclear gene ITS2 sequence,chloroplast rbcL,matK gene sequence were selected for PCR amplification,product purification and sequencing,and CondonCode Aligner V3.7.1 was used to proofread stitching. Result:PCR amplification and sequencing of rbcL sequences of I. difengpi and I. jiadifengpi were not satisfactory. It is assumed that their rbcL sequences were too long with slow evolution,which was unsuitable for interbreeding. The success rate of matK sequencing of I. difengpi and I. jiadifengpi was 0 and 76.8%,which may be because primer standards were different for matK sequences of different groups. The results of PCR amplification and sequencing of ITS2 on I. difengpi and I. jiadifengpi were successful,with the success rate of sequencing was 89.3% and 91.2%. Analysis sequencing results, the total length of ITS2 sequences was 268 bases,and there were 2 variation sites of I. difengpi. The total length of ITS2 sequences was 430 bases,and there were 4 or 3 variation sites of I. jiadifengpi. It shows that ITS2 sequences of I. difengpi and I. jiadifengpi were short and has obvious variability and can be amplify,that ITS2 sequence was better than rbcL and matK sequence in molecular identification of I. difengpi and I. jiadifengpi. Conclusion:DNA barcoding based on ITS2 sequence was a powerful and efficient tool for identification of I. difengpi and its fake I. jiadifengpi.
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Objective: To study the chemical constituents from the twigs and leaves of Illicius majus. Methods: The compounds were isolated by column chromatography over silica gel, Sephadex LH-20, and flash chromatography coupled with preparative HPLC. The structures were elucidated by spectroscopic analysis including ESI-MS, 1D-NMR, and 2D-NMR. The cytotoxic activities were assessed by MTT assay. Results: Compounds 1—14 were isolated from the twigs and leaves of I. majus, and identified as 3′-methoxy-kaempferol-3-O-α-L-rhamnopyranoside (1), quercetin-3-O-arabinoside (2), kaempferol-3-O-arabinoside (3), 8′-oxo-6-hydroxy-dihydrophaseic acid (4), 4-O-methylcedrusin (5), (−)-massoniresinol (6), (7S,8R)-3,3′,5-trimethoxy-4′,7-epoxy- 8,5′-neolignan-4,9,9′-triol (7), vladinol F (8), 2,3-dihydro-2-(4′-α-L-rhamnopyranosyl-3′-methoxyphenyl)-3-hydroxymethyl-7- methoxy-5-benzofuranpropanol (9), quercetin-3-O-α-L-rhamnopyranoside (10), kaempferol-3-O-α-L-rhamnopyranoside (11), vitexin (12), 3,5,7-trihydroxychromone-3-O-glucopyranoside (13), and benzyl alcohol O-β-D-glucopyranoside (14). Compounds 1—14 exhibited the cytotoxic activity against HCT-8, Bel-7402, BGC-823, and A549 with IC50 values of over 10 μmol/L, respectively. Conclusion: Compounds 1—14 are all obtained from I. majus for the first time, and compounds 2, 3, 5, 7, 8, 9, and 14 are obtained from the genus of Illicium for the first time. All compounds show no significant cytotoxic activities against HCT-8, Bel-7402, BGC-823, and A549 cancer cell.
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Illicium henryi Diels is a medicinal and aromatic plant native to China with Chinese name Mancao or Hondu-hui.The name of Mancao was first recorded in the"Classic of Mountains and Rivers"and the earliest documented medicinal function of this plant was found in"Shen Nong′s herbal classic".Its botanical origin includes Illicium lanceolatum A.C. Smith and Illicium henryi Diels while Miscanthus sinensis Anderss(Gramineae)and Tripterygium wilfordii Hook.f. (Celastraceae)were recorded as Mancao by mistake.Mancao is mainly distributed in Henan,Hebei,Sichuan,Zhejiang and Fu-jian Province.All those plants are toxic.In this paper,the name,habitats,origins,the characteristics and effects of Illicium lanceolatum A.C.Smith and Illicium henryi Diels were investigated to correct the origin of the textural records and provide a reference for future research,development and utilization of the medical resources.
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ABSTRACT Equigan is an anabolic steroid that has been developed for veterinary use and derived from endogenous sex hormone testosterone that plays a key role in the development of male reproductive tissue as well as in puberty and spermatogenesis. The current study is aimed to investigate the possible prophylactic effect of star anise extracts (SAE) on the toxicity of rat testes, sexual hormones alternations, sperm count, sperm abnormalities and testicular DNA damage by Equigan. Forty adult male rats were equally divided into four groups (1st Control group, 2nd SAE group, 3rd Equigan and 4th Equigan+SAE group). Food and fluid intakes, relative body weight, potassium, chloride, phosphorous, non-progressive and immotile sperms were significantly increased in Equigan group as compared to control group. In contrast; relative testes weight, sodium, magnesium, total calcium, testosterone, FSH, LH, PRL, sperm count, progressive motility, and viability showed a significant decrease in Equigan group as compared to control groups. The relative weight of epididymis, seminal vesicles, prostates and serum calcium ions didn't change significantly in different studied groups. Co-administration of SAE with Equigan improved the sexual toxicity, electrolyte alternations, sperm count, abnormalities and DNA damage induced by Equigan.
Subject(s)
Animals , Male , Rats , Plant Extracts/analysis , Reproductive Techniques , Illicium/adverse effects , Reproductive Physiological Phenomena , Spermatogenesis/drug effects , Bodily Secretions , DNA Fragmentation/drug effects , Fertility Agents, Male/analysis , Anabolic Agents/pharmacologyABSTRACT
AIM To study the chemical constituents from Illicium brevistylum A.C.Smith and to evaluate their anti-inflammatory activities.METHODS The n-BuOH fraction of 80％ ethanol extract from I.brevistylum was isolated and purified by silica,ODS and Sephadex LH-20,the structures of obtained compounds were identified by spectral data.Then their anti-inflammatory activities were screened.RESULTS Nine compounds were isolated and identified as (7S,8R)-3,3',5-trimethoxy-4',7-epoxy-8,5'-neolignan-4,9,9'-triol (1),methylabieta-8,11,13,15-tetraen-18-oate (2),majusanin A (3),pubeside C (4),(+)-lyoniresinol-3a-O-α-L-rhamnopyranoside (5),junipercomnoside D (6),lyoniside (7),nudiposide (8),rhyncoside A (9).The inhibition rates of compounds 2,6,9 on NF-κB were 47.81％,37.33％,33.37％,respectively.CONCLUSION Compounds 1,5,7-9 are isolated from genus Illicium for the first time,and compounds 2,6,9 exhibit good anti-inflammatory activities.
ABSTRACT
AIM To study the chemical constituents from Illicium brevistylum A.C.Smith and to evaluate their anti-inflammatory activities.METHODS The n-BuOH fraction of 80％ ethanol extract from I.brevistylum was isolated and purified by silica,ODS and Sephadex LH-20,the structures of obtained compounds were identified by spectral data.Then their anti-inflammatory activities were screened.RESULTS Nine compounds were isolated and identified as (7S,8R)-3,3',5-trimethoxy-4',7-epoxy-8,5'-neolignan-4,9,9'-triol (1),methylabieta-8,11,13,15-tetraen-18-oate (2),majusanin A (3),pubeside C (4),(+)-lyoniresinol-3a-O-α-L-rhamnopyranoside (5),junipercomnoside D (6),lyoniside (7),nudiposide (8),rhyncoside A (9).The inhibition rates of compounds 2,6,9 on NF-κB were 47.81％,37.33％,33.37％,respectively.CONCLUSION Compounds 1,5,7-9 are isolated from genus Illicium for the first time,and compounds 2,6,9 exhibit good anti-inflammatory activities.
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Sixteen compounds, including two new natural products (and), were obtained from the twigs of. The structures were elucidated based on NMR, MS, IR data and optical rotation values. Compounds,,anddisplayed moderate antibacterial activities against clinical isolates; compounds,,,andprotected neural cells against oxidative stress; and compoundsandexhibited anti-acetylcholinesterase activity.
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Objective: To study the chemical constituents from the twigs and leaves of Illicius majus. Methods: The compound was isolated by column chromatography over silica gel, Sephadex HL-20, and flash chromatography coupled with preparative HPLC. The structure was elucidated by spectroscopic analysis including HR-ESI-MS, 1D-NMR, and 2D-NMR. The cytotoxic activities were assessed by MTT. Results: A new seco-prezizaane-type sesquiterpenoid named majusatone (1) was isolated from the twigs and leaves of I. majus. Compound 1 exhibited the cytotoxic activity against HCT-8, Bel-7402, BGC-823, and A549 with IC50 values of 42.3, 48.5, 51.1, and 39.9 μmol/L, respectively. Conclusion: Compound 1 is a new special seco-prezizaane-type sesquiterpenoid, and shows no significant cytotoxic activities against HCT-8, Bel-7402, BGC-823, and A549.
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Objective: To study the chemical constituents from the branches and leaves of Illicium micranthum and insecticidal activitives on larvae of Bradysia odoriphaga. Methods: The chemical constituents were isolated and purified by silica gel, and Sephadex LH-20 column chromatography. Their structures were elucidated by physicochemical properties and spectroscopic analyses. The standard contact and stomach bioassay method was used to assess the effects of median lethal dose (LD50) of compound 2 on the demographic parameters of larvae of B. odoriphaga. Results: Five monoterpenoids were isolated from the ethyl acetate layer of methanol extract from the branches and leaves of I. micranthum. Compound 1, (-)-(1R*, 4S*)-1-(hydroxymethyl)-4-isopropylcyclohex-2-ene-1, 4-diol, was a new monoterpenoid and named as illicmicrene A, and the other compounds were identified as (1R, 2R, 4R)-1-methyl-4-(1-methylethyl)-1, 2, 4-cyclohexanetriol (2), 4-hydroxypiperitone (3), olibanumol C (4) and α, α-dimethyl-4-hydroxymethylbenzyl alcohol (5), respectively. Conclusion: Compound 1 is isolated as a new compound and compounds 2-5 are obtained from I. micranthum for the first time. Furthermore, compound 2 shows the insecticidal effects on larvae of B. odoriphaga with LD50 values at 30.4 mg/L after 48 h, at 22.5 mg/L after 72 h.
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OBJECTIVE: To study chemical constituents from the twigs and leaves of Illicius majus Hoot et Thoms. METHODS: The compounds were isolated by column chromatography on silica gel, Sephadex LH-20, and flash chromatography coupled with preparative HPLC. Their structures were elucidated by spectroscopic analysis including IR, NMR, and MS. RESULTS: Six compounds, ie. majusanicol(1), angustanoic acid G(2), 4-hydroxyphenethyl alcohol(3), 4-hydroxybenzoic acid(4), 3-hydroxybenzoic acid(5), and 3, 5-dimethoxy-4-hydroxybenzoic acid(6), were isolated from the twigs and leaves of I. majus. CONCLUSION: Compound 1 is a new abietane-type diterpenoid, and compound 3-6 are isolated from this plant for the first time.
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Objective: To isolate and identify bioactive constituents from the stem barks of Illicium difengpi. Methods: The chemical constituents were isolated and purified by repeated silica gel, Sephadex LH-20, recrystallization, and preparative HPLC techniques. The structures of the compounds were identified on the basis of spectral data including NMR, MS, and IR. Results: Two sesquiterpene lactones, majucin (1) and anisatin (2), two steroids, β-sitosterol (3) and daucosterol (4), three carboxylic acids, 2-ethyldecanoic acid (5), shikimic acid (6), and 3,4-dihydrobenzoic acid (7), and a flavonoid, quercetin (8), were successively isolated from the stem barks of I. difengpi. Conclusion: Apart from compound 3, other seven compounds are reported in this plant for the first time. The results suggested that the current studies on I. difengpi is still far from being well known and therefore more studies need to be done for better understanding of this plant. © 2014 Tianjin Press of Chinese Herbal Medicines.
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Objective: To investigate the chemical constituents from the seeds of Illicium wardii. Methods: The chemical constituents were separated and purified by silica gel, Sephadex LH-20, MCI, etc. Results: Eleven sesquiterpenoids were isolated from the 95% ethanol extract in the seeds of I. wardii. Their structures were elucidated as wardinol C (1), 7, 8-epoxy-1(12)-caryophyllene-9β-ol (2), merrilliortholactone (3), 2α-hydroxyneoanisatin (4), 2, 6-dihydroxyhumlan-9(E)-3(12), 7(13), 9-trien (5), anisatin (6), pseudomajucin (7), 8α-hydroxy-10-deoxycyclomerrillianolide (8), 2α-hydroxyanisatin (9), rel-5-(3S, 8S-dihydroxy-1R, 5S-dimethyl-7-oxa-6-oxobicyclo-[3, 2, 1]-oct-8-yl)-3-methyl-2Z, 4E-pentadienoic acid (10), and phaseic acid (11). Conclusion: Compound 1 is a new one, and the other compounds are isolated from this species for the first time.
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AIM@#To study the chemical constituents of the fruits of Illicium henryi.@*METHOD@#Chromatographic separations on silica gel, Sephadex LH-20 gel and MCI gel were used to isolate the compounds. The structures were elucidated based on extensive spectroscopic data analyses.@*RESULTS@#Seven compounds were obtained and their structures were identified as 10-benzoyl-cycloparvifloralone (1), cycloparvifloralone (2), 2α-hydroxycycloparviforalone (3), henrylactone B (4), merrillianone (5), henrylactone C (6) and 7, 14-ortholactone- 3-hydroxyfloridanolide (7).@*CONCLUSION@#Compound 1 is a new sesquiterpene lactone. The tested compounds showed weak anti-HBV activities on HBV surface antigen (HBsAg) secretion and HBV e antigen (HBeAg) secretion using Hep G2.2.15 cell line.
Subject(s)
Humans , Antiviral Agents , Chemistry , Pharmacology , Fruit , Chemistry , Hep G2 Cells , Hepatitis B virus , Illicium , Chemistry , Molecular Structure , Plant Extracts , Chemistry , Pharmacology , Sesquiterpenes , Chemistry , PharmacologyABSTRACT
Objective: To study the chemical constituents with anti-oxidative activity from the fruits of Illicium micranthum. Methods: DPPH Radical scavenging assay was used for screening the active fractions. The chemical constituents were isolated and purified by various column chromatographic methods such as silica gel and Sephadex LH-20. The structures were identified by physicochemical properties and spectral analyses. Results: The ethyl acetate layer of methanol extract from the fruits of I. micranthum showed anti-oxidative activity, from which 14 compounds were separated. Their structures were identified as gynurenol (1), β-elemol (2), epi-carrisone (3), 6-hydroxy-eudesm-4(14)-ene (4), β-eudesmol (5), trans-eudesmane-4, 11-diol (6), 1R, 2R, 4R-trihydroxy-p-menthane (7), 2-isopropenyl-5-methyl-cyclohexanol (8), (-)-isopulegol (9), 4-isopropenyl-1-methyl-cyclohexanol (10), palmitic acid (11), triacontanoic acid (12), p-hydroxy-benzoic acid (13), and β-daucosterol (14). Conclusion: Except for compound 14, all the other compounds are isolated from the fruits of I. micranthum for the first time, while compounds 1-4, 7, and 8 are isolated from the plants in Illiciaceae family for the first time.
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Objective: To isolate and identify the chemical constituents in the ethanol extract from the barks of Illicium brevistylum. Methods: The barks of I. brevistylum were extracted by 80% ethanol then partitioned by system solvents with different polarity. The ethyl acetate extract was separated on silica gel, Sephadex LH-20, and ODS columns. The isolated compounds were identified by physicochemical properties and spectral analyses. Results: Twelve compounds were isolated and purified from the ethyl acetate extract of I. brevistylum and the structures were identified as quercetin 3-O-β-xylopyranoside (1), quercetin (2), dihydro kaempferol (3), kaempferol (4), wulingzhic acid V (5), catechin (6), 3, 5, 7-trihydroxylchromone-3-O-α-L-arabinopyranoside (7), majucin (8), anislactone B (9), 7-O-acetylanislactone B (10), dunnianolide C (11), and taxifolin-3-O-β-xylopyranoside (12). Conclusion: Compounds 5 and 7 are obtained from the plants in Illiciaceae for the first time and compounds 1, 6, and 8-11 are firstly isolated from I. brevistylum.
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OBJECTIVE: To study the chemical constituents from the fruits oi Illicium lanceolatum. METHODS: The fruits oil. lanceolatumwere extracted with 95% ethanol. The ethanol extract was subjected to silica column, Sephadex LH-20 and MCI chromatography. The isolated compounds were identified on the basis of spectral analyses including MS, H-NMR, and C-NMR. RESULTS: Twelve compounds were isolated, which were characterized as 2, 4-dihydroxy-allylbenzene-2-O-β-D-gluco-pyranoside(1), (+) -catechin (2), quercetin-3-O-β-L-rhamnopyranoside (3), rutin (4), isorhamnetin-3-O-β-D-rutinoside (5), 6-deoxy-1-hydroxy neoanisatin (6), anisatin(7), icariside E3 (8), (75, 8R)-urolignoside (9), 4-hydroxy acid benzoic acid(10), shikimic acid(11) and β-sitosterol(12). CONCLUSION: Compounds 1, 4-6, and 8-10 are obtained from I. lanceolatum for the first time.
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Essential oils are used primarily as natural preservatives, flavourants and fragrances in cosmetic products. Several pharmacopeias possess monographs of plants which are good sources of essential oils, such as Brazilian Pharmacopeia, including Illicium verum Hook. f., Schisandraceae and Rosmarinus offi cinalis. Since determination of Hydrophile-Lipophile Balance (HLB) value of essential oils appears as a critical step for development of emulsions and other semi-solid formulations, evaluation of required HLB values for I. verum and R. offi cinalis essential oils is the aim of this study. They were obtained by hydrodistillation and several emulsions were prepared by changing emulsifiers. The couple sorbitan oleate/polysorbate 20 provided best emulsions and was used at different ratios, at a total blend concentration of 5% w/w. The lowest mean droplet diameters for R. offi cinalis and I. verum emulsions were obtained at HLB 16.5 (97.12 nm) and 16.7 (246.6 nm), respectively. Moreover, emulsions with R. offi cinalis were finer and presented some bluish reflection, characteristic of nanoemulsions. The lowest turbidity value for R. offi cinalis emulsion was also obtained at HLB 16.5 (0.33). Thus, the present study describes for the first time HLB values for R. offi cinalis (16.5) and I. verum (16.7) essential oils, contributing to their physicochemical characterization and technology development of phytopharmaceuticals.