Humulene

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Igor Jerković - One of the best experts on this subject based on the ideXlab platform.

  • Optimization of supercritical CO2 extraction of Salvia officinalis L. leaves targeted on Oxygenated monoterpenes, α-Humulene, viridiflorol and manool
    The Journal of Supercritical Fluids, 2018
    Co-Authors: Stela Jokić, Maja Molnar, Martina Jakovljević, Krunoslav Aladić, Igor Jerković
    Abstract:

    Abstract Comprehensive approach was applied to optimize the SC-CO2 extraction conditions of Salvia officinalis L. (sage) leaves. Different extraction parameters (pressure, temperature, and CO2 flow rate) were investigated on: the extraction yield; the extracts chemical profile (determined by GC–MS); optimal extraction conditions by response surface methodology (RSM) for targeted most abundant components (oxygenated monoterpenes, α-Humulene, viridiflorol and manool). The pressure exhibited the most significant influence on the yield (0.242–7.361%) and significantly influenced the amount of 1,8-cineole, α-/β-thujone and camphor (within the range 15 or 20 MPa). On the contrast, the highest amount of α-Humulene, viridiflorol and manool was obtained at the lowest pressure (10 MPa). The results showed statistically significant (p

Joao B Calixto - One of the best experts on this subject based on the ideXlab platform.

  • Preventive and therapeutic anti-inflammatory properties of the sesquiterpene α-Humulene in experimental airways allergic inflammation
    British journal of pharmacology, 2009
    Co-Authors: Alexandre De Paula Rogerio, Edinéia L. Andrade, Daniela F. P. Leite, Cláudia P. Figueiredo, Joao B Calixto
    Abstract:

    Background and purpose:  α-Humulene and trans-caryophyllene are plant sesquiterpenes with pronounced anti-inflammatory properties. Here, we evaluated the effects of these compounds in an experimental model of airways allergic inflammation. Experimental approach:  Female BALB/c mice, sensitized to and challenged with ovalbumin received daily α-Humulene or trans-caryophyllene (50 mg·kg−1, orally) or α-Humulene (1 mg·mL−1, by aerosol) as either a preventive (for 22 days) or therapeutic (from the 18th to the 22nd day) treatment. Dexamethasone or budesonide was used as a positive control drug. Inflammation was determined on day 22 post-immunization by leukocyte recruitment, interleukin-5 (IL-5), CCL11, interferon-γ (IFN-γ) and leukotriene (LT)B4 levels in bronchoalveolar lavage fluid (BALF). In addition, transcription factors [nuclear factor κB (NF-κB), activator protein 1 (AP-1)] and P-selectin in lung tissue were measured by immunohistochemistry and mucus secretion by histochemistry. Key results:  Preventive or therapeutic treatments with α-Humulene, but not with trans-caryophyllene, significantly reduced the eosinophil recruitment to the BALF. In addition, α-Humulene recovery INF-γ and reduced the IL-5, CCL11 and LTB4 levels in BALF, as well as the IL-5 production in mediastinal lymph nodes (in vitro assay). Furthermore, α-Humulene decreased the NF-kB and the AP-1 activation, the expression of P-selectin and the increased mucus secretion in the lung. Conclusions and implications:  α-Humulene, given either orally or by aerosol, exhibited marked anti-inflammatory properties in a murine model of airways allergic inflammation, an effect that seemed to be mediated via reduction of inflammatory mediators, adhesion molecule expression and transcription factors activation. This article is part of a themed issue on Mediators and Receptors in the Resolution of Inflammation. To view this issue visit http://www3.interscience.wiley.com/journal/121548564/issueyear?year=2009

  • Pharmacokinetics and Tissue Distribution of the Sesquiterpene α-Humulene in Mice
    Planta medica, 2008
    Co-Authors: Juliana Siqueira Chaves, Paulo César Leal, Luis Pianowisky, Joao B Calixto
    Abstract:

    A quantitative study was undertaken to assess the plasma and tissue levels, tissue distribution and skin (ear) absorption of the sesquiterpene alpha-Humulene, the main active constituent isolated from the plant Cordia verbenacea (Boraginaceae ), after oral, intravenous and topical administration in mice. The alpha-Humulene levels were quantified by GC-MS analysis. The peak alpha-Humulene concentration was achieved 15 min following its oral administration (150 mg/kg). Then, the alpha-Humulene plasma concentration gradually decreased and it was almost undetectable at 2 hours after intravenous administration and 12 hours after oral administration. When the oil of C. verbenacea was given orally (1 g/kg), the peak alpha-Humulene plasma concentration was observed after 30 min, being detectable only up to 2 h. The oral bioavailability of alpha-Humulene was found to be 18 %. The half-lives of alpha-Humulene were very short, 16.8 min after oral administration and 1.8 min after intravenous administration. However, the elimination half-lives were longer, 118.2 min and 55 min, for oral and intravenous routes, respectively. We also assessed the amount of alpha-Humulene in some selected tissues at 0.5 and at 4 h after oral administration. We found a high amount of the compound in the liver, followed by the kidneys, heart, lungs, spleen and brain, 0.5 h after oral administration. Notably, the yield of alpha-Humulene decreased significantly in all analyzed tissues, especially in the liver, 4 h after oral administration. Of note, 30 minutes after topical administration of Acheflan formulations (cream and aerosol) containing 0.5 % of C. verbenacea essential oil, a schedule of treatment that produces marked and similar topical anti-inflammatory activity, the amount of alpha-Humulene absorbed in the ear was very similar (about 2 microg/ear). It is concluded that alpha-Humulene exhibited a rapid onset and relatively good absorption following oral and topical administration. Taken together, these findings further contribute to an explanation of the topical and systemic anti-inflammatory and antinociceptive properties previously reported for the essential oil and for alpha-Humulene obtained from Cordia verbenacea, they also provide support for the clinical studies conducted with the phytomedicine Acheflan.

  • anti inflammatory effects of compounds alpha Humulene and trans caryophyllene isolated from the essential oil of cordia verbenacea
    European Journal of Pharmacology, 2007
    Co-Authors: Elizabeth S Fernandes, Giselle F Passos, Rodrigo Medeiros, Fernanda Marques Da Cunha, Juliano Ferreira, Maria M Campos, Luiz Francisco Pianowski, Joao B Calixto
    Abstract:

    This study evaluated the anti-inflammatory properties of two sesquiterpenes isolated from Cordia verbenacea's essential oil, alpha-Humulene and (-)-trans-caryophyllene. Our results revealed that oral treatment with both compounds displayed marked inhibitory effects in different inflammatory experimental models in mice and rats. alpha-Humulene and (-)-trans-caryophyllene were effective in reducing platelet activating factor-, bradykinin- and ovoalbumin-induced mouse paw oedema, while only alpha-Humulene was able to diminish the oedema formation caused by histamine injection. Also, both compounds had important inhibitory effects on the mouse and rat carrageenan-induced paw oedema. Systemic treatment with alpha-Humulene largely prevented both tumor necrosis factor-alpha (TNFalpha) and interleukin-1beta (IL-1beta) generation in carrageenan-injected rats, whereas (-)-trans-caryophyllene diminished only TNFalpha release. Furthermore, both compounds reduced the production of prostaglandin E(2) (PGE(2)), as well as inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX-2) expression, induced by the intraplantar injection of carrageenan in rats. The anti-inflammatory effects of alpha-Humulene and (-)-trans-caryophyllene were comparable to those observed in dexamethasone-treated animals, used as positive control drug. All these findings indicate that alpha-Humulene and (-)-trans-caryophyllene, derived from the essential oil of C. verbenacea, might represent important tools for the management and/or treatment of inflammatory diseases.

  • Anti-inflammatory effects of compounds alpha-Humulene and (−)-trans-caryophyllene isolated from the essential oil of Cordia verbenacea
    European journal of pharmacology, 2007
    Co-Authors: Elizabeth S Fernandes, Giselle F Passos, Rodrigo Medeiros, Fernanda Marques Da Cunha, Juliano Ferreira, Maria M Campos, Luiz Francisco Pianowski, Joao B Calixto
    Abstract:

    This study evaluated the anti-inflammatory properties of two sesquiterpenes isolated from Cordia verbenacea's essential oil, alpha-Humulene and (-)-trans-caryophyllene. Our results revealed that oral treatment with both compounds displayed marked inhibitory effects in different inflammatory experimental models in mice and rats. alpha-Humulene and (-)-trans-caryophyllene were effective in reducing platelet activating factor-, bradykinin- and ovoalbumin-induced mouse paw oedema, while only alpha-Humulene was able to diminish the oedema formation caused by histamine injection. Also, both compounds had important inhibitory effects on the mouse and rat carrageenan-induced paw oedema. Systemic treatment with alpha-Humulene largely prevented both tumor necrosis factor-alpha (TNFalpha) and interleukin-1beta (IL-1beta) generation in carrageenan-injected rats, whereas (-)-trans-caryophyllene diminished only TNFalpha release. Furthermore, both compounds reduced the production of prostaglandin E(2) (PGE(2)), as well as inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX-2) expression, induced by the intraplantar injection of carrageenan in rats. The anti-inflammatory effects of alpha-Humulene and (-)-trans-caryophyllene were comparable to those observed in dexamethasone-treated animals, used as positive control drug. All these findings indicate that alpha-Humulene and (-)-trans-caryophyllene, derived from the essential oil of C. verbenacea, might represent important tools for the management and/or treatment of inflammatory diseases.

Ryutaro Utsumi - One of the best experts on this subject based on the ideXlab platform.

  • Zingiber zerumbet CYP71BA1 catalyzes the conversion of α-Humulene to 8-hydroxy-α-Humulene in zerumbone biosynthesis
    Cellular and Molecular Life Sciences, 2011
    Co-Authors: Sho Okamoto, Hisashi Harada, Kazuhisa Yamasaki, Norihiko Misawa, Ryutaro Utsumi
    Abstract:

    Plant cytochrome P450s are involved in the biosynthesis of various classes of secondary metabolites. To elucidate the biosynthesis of zerumbone, a sesquiterpenoid with multiple potential anticancer properties, a family of P450 genes expressed in rhizomes of Zingiber zerumbet Smith, were cloned using a PCR-based cloning strategy. After functional expression in yeast, one of these P450s was found to convert α-Humulene into 8-hydroxy-α-Humulene, a proposed intermediate of zerumbone biosynthesis. This P450 has been designated CYP71BA1, a new member of the CYP71 family. CYP71BA1 transcripts were detected almost exclusively in rhizomes and showed a similar expression pattern to ZSS1 transcripts during rhizome development. Coexpression of a gene cluster encoding four enzymes of the mevalonate pathway with CYP71BA1 and ZSS1 in Escherichia coli leads to the production of 8-hydroxy-α-Humulene in the presence of mevalonate, suggesting the possibility of microbial production of this zerumbone intermediate from a relatively simple carbon source by metabolic engineering.

  • Molecular cloning and functional characterization of α-Humulene synthase, a possible key enzyme of zerumbone biosynthesis in shampoo ginger ( Zingiber zerumbet Smith)
    Planta, 2008
    Co-Authors: Sho Okamto, Hisashi Harada, Norihiko Misawa, Kaoru Nakasone, Kyoko Adachi, Satoru Matsuda, Ryutaro Utsumi
    Abstract:

    Shampoo ginger (Zingiber zerumbet Smith) has a high content and large variety of terpenoids in the essential oil of its rhizome. Here, we report on the isolation of a cDNA clone (ZSS1) encoding α-Humulene synthase, a possible key enzyme of zerumbone biosynthesis. This clone contains an open reading frame of 1,644 bp and is predicted to encode a protein of 548 amino acids with a calculated molecular mass of 64.5 kDa. The deduced amino acid sequence shows 34–63% identity with known sesquiterpene synthases of other angiosperm species. Based on exon-intron organization, ZSS1 is classified as the terpene synthase-III (TPS-III) subfamily. When expressed in Escherichia coli, the recombinant enzyme catalyzed the formation of a major product, α-Humulene (95%) and a minor by-product, β-caryophyllene (5%). Introduction of ZSS1 and the foreign mevalonate pathway involved in FPP synthesis into E. coli results in in vivo production of α-Humulene. Transcript of ZSS1 was detected almost exclusively in rhizomes and was up-regulated in both leaves and rhizomes after treatment with methyl jasmonate (MeJA), suggesting its ecological function in shampoo ginger.

Stela Jokić - One of the best experts on this subject based on the ideXlab platform.

  • Optimization of supercritical CO2 extraction of Salvia officinalis L. leaves targeted on Oxygenated monoterpenes, α-Humulene, viridiflorol and manool
    The Journal of Supercritical Fluids, 2018
    Co-Authors: Stela Jokić, Maja Molnar, Martina Jakovljević, Krunoslav Aladić, Igor Jerković
    Abstract:

    Abstract Comprehensive approach was applied to optimize the SC-CO2 extraction conditions of Salvia officinalis L. (sage) leaves. Different extraction parameters (pressure, temperature, and CO2 flow rate) were investigated on: the extraction yield; the extracts chemical profile (determined by GC–MS); optimal extraction conditions by response surface methodology (RSM) for targeted most abundant components (oxygenated monoterpenes, α-Humulene, viridiflorol and manool). The pressure exhibited the most significant influence on the yield (0.242–7.361%) and significantly influenced the amount of 1,8-cineole, α-/β-thujone and camphor (within the range 15 or 20 MPa). On the contrast, the highest amount of α-Humulene, viridiflorol and manool was obtained at the lowest pressure (10 MPa). The results showed statistically significant (p

Krunoslav Aladić - One of the best experts on this subject based on the ideXlab platform.

  • Optimization of supercritical CO2 extraction of Salvia officinalis L. leaves targeted on Oxygenated monoterpenes, α-Humulene, viridiflorol and manool
    The Journal of Supercritical Fluids, 2018
    Co-Authors: Stela Jokić, Maja Molnar, Martina Jakovljević, Krunoslav Aladić, Igor Jerković
    Abstract:

    Abstract Comprehensive approach was applied to optimize the SC-CO2 extraction conditions of Salvia officinalis L. (sage) leaves. Different extraction parameters (pressure, temperature, and CO2 flow rate) were investigated on: the extraction yield; the extracts chemical profile (determined by GC–MS); optimal extraction conditions by response surface methodology (RSM) for targeted most abundant components (oxygenated monoterpenes, α-Humulene, viridiflorol and manool). The pressure exhibited the most significant influence on the yield (0.242–7.361%) and significantly influenced the amount of 1,8-cineole, α-/β-thujone and camphor (within the range 15 or 20 MPa). On the contrast, the highest amount of α-Humulene, viridiflorol and manool was obtained at the lowest pressure (10 MPa). The results showed statistically significant (p