Pyranopyran

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Hyunsu Bae - One of the best experts on this subject based on the ideXlab platform.

  • Pyranopyran 1 8 dione an active compound from vitices fructus attenuates cigarette smoke induced lung inflammation in mice
    International Journal of Molecular Sciences, 2017
    Co-Authors: Gihyun Lee, Kyunghwa Jung, Hyunsu Bae
    Abstract:

    Previously, we isolated and identified Pyranopyran-1,8-dione (PPY) from Viticis Fructus, as a bioactive compound possessing anti-inflammatory properties. The present study was aimed to evaluate the preventive benefit of PPY on cigarette-smoke (CS)-induced lung inflammation. C57BL/6 mice were exposed to CS for 2 weeks while PPY was administrated by oral injection 2 h before CS exposure. To validate the anti-inflammatory effects of PPY, the numbers of immune cells in the bronchoalveolar lavage fluid were counted. Proinflammatory cytokines (Tumor necrosis factor-α: TNF-α, IL-6) and keratinocyte chemokine (KC/CXCL1) were also measured. Histopathologic analysis and cellular profiles showed that inflammatory cell infiltrations were significantly decreased in peribronchial and perivascular area by PPY treatment. The alveolar destruction by CS was markedly ameliorated by PPY treatment. In addition, the TNF-α, IL-6, and KC levels were declined in the PPY groups. These observations suggest that PPY has a preventive potential for lung inflammatory diseases.

  • Pyranopyran 1 8 dione an active compound from viticis fructus ameliorates cigarette smoke induced lung inflammatory response in a murine model cam5p 239
    Journal of Immunology, 2014
    Co-Authors: Hyunsu Bae, Kyunghwa Jung, Moochang Hong, Geunhyung Kang, Won Seob Kim, Hyun Seong Kim, Sun Kwang Kim
    Abstract:

    Chronic obstructive pulmonary disease (COPD) is defined as poorly irreversible airflow obstruction due to the inhalation of noxious chemicals and gases, most commonly cigarette smoke (CS). The extract of Viticis Fructus (VF), is widely used as a traditional herbal medicine in various Asian countries for the treatment of migraine pain and allergic diseases. Therefore, we attempt to isolate active compound from VF. After several rounds of activity-guided fractionations, 1H, 8H-Pyrano [3, 4-c] pyran-1, 8-dione (PPY) was isolated. In this study, we hypothesized that PPY, constituent of VF, could suppress CS exposure lung inflammation in mice model. The mice were exposed to 3R4F reference cigarettes for 2 weeks with 6 cigarettes a day. The mice were administered various dose of PPY (1, 2, 10 mg/kg body wt) via an oral administration 2 hr prior to CS exposure. The results of this study indicate cellular profiles and histopathologic analysis demonstrated that peribronchial and perivascular inflammatory cell infiltrates were significantly decreased in the PPY treated groups when compared to the CS exposure group. In summary, the results of this study indicate that PPY has significantly inhibited CS induced lung inflammation. The remarkable anti-inflammatory effects of PPY suggest its therapeutic potential in COPD treatment. Keywords: COPD, 1H, 8H-Pyrano [3, 4-c] pyran-1, 8-dione (PPY), cigarette smoke, IL-6, TNF-α

  • treatment with Pyranopyran 1 8 dione attenuates airway responses in cockroach allergen sensitized asthma in mice
    PLOS ONE, 2014
    Co-Authors: Soojin Park, Kyunghwa Jung, Minsun Park, Joo Hyun Song, You Ah Kim, Hi Jae Cho, Byungil Min, Hyunsu Bae
    Abstract:

    Chronic allergic asthma is characterized by Th2-typed inflammation, and contributes to airway remodeling and the deterioration of lung function. Viticis Fructus (VF) has long been used in China and Korea as a traditional herbal remedy for treating various inflammatory diseases. Previously, we have isolated a novel phytochemical, Pyranopyran-1, 8-dione (PPY), from VF. This study was conducted to evaluate the ability of PPY to prevent airway inflammation and to attenuate airway responses in a cockroach allergen-induced asthma model in mice. The mice sensitized to and challenged with cockroach allergen were treated with oral administration of PPY. The infiltration of total cells, eosinophils and lymphocytes into the BAL fluid was significantly inhibited in cockroach allergen-induced asthma mice treated with PPY (1, 2, or 10 mg/kg). Th2 cytokines and chemokine, such as IL-4, IL-5, IL-13 and eotaxin in BAL fluid were also reduced to normal levels following treatment with PPY. In addition, the levels of IgE were also markedly suppressed after PPY treatment. Histopathological examination demonstrated that PPY substantially inhibited eosinophil infiltration into the airway, goblet cell hyperplasia and smooth muscle hypertrophy. Taken together, these results demonstrate that PPY possesses a potent efficacy on controlling allergic asthma response such as airway inflammation and remodeling.

  • a new compound isolated from vitex rotundifolia linn fil Pyranopyran 1 8 dione suppresses airway epithelial cell inflammatory responses in a murine model of asthma 140 14
    Journal of Immunology, 2009
    Co-Authors: Heekyung Lee, Dongjune Keum, Haejeong Kim, Minkyu Shin, Moochang Hong, Yangseok Kim, Hyunsu Bae
    Abstract:

    The new natural compound, Pyranopyran-1,8-dione (PPD), was isolated from Vitex rotundifolia L. To elucidate the mechanism by which the anti-asthmatic responses of PPD occurred in vitro, A549 cells were stimulated with TNF-¥a, IL-4 and IL-1¥â to induce the expression of chemokines and adhesion molecules involved in eosinophil chemotaxis. PPD treatments reduced the expression of eotaxin, IL-8, IL-16 and VCAM-1 mRNA significantly. Additionally, PPD reduced eotaxin secretion and significantly inhibited eosinophil migration toward A549 medium. In addition, PPD treatment suppressed the phosphorylation of p65 and ERK1/2, suggesting that it can inhibit the MAPK/NF-¥e b pathway. To clarify the anti-inflammatory and antiasthmatic effects of PPD in vivo, mice were sensitized and challenged with OVA and then examined for the following typical asthmatic reactions: an increase in the number of eosinophils in BALF; the presence of Th2 cytokines such as IL-4 and IL-5 in the BALF; the presence of allergen-specific IgE in the serum; and a marked influx of inflammatory cells into the lung. Taken together, our results revealed that PPD exerts profound inhibitory effects on the accumulation of eosinophils into the airways while reducing the levels of IL-4, IL-5, and IL-13 in the BALF.

Kyunghwa Jung - One of the best experts on this subject based on the ideXlab platform.

  • Pyranopyran 1 8 dione an active compound from vitices fructus attenuates cigarette smoke induced lung inflammation in mice
    International Journal of Molecular Sciences, 2017
    Co-Authors: Gihyun Lee, Kyunghwa Jung, Hyunsu Bae
    Abstract:

    Previously, we isolated and identified Pyranopyran-1,8-dione (PPY) from Viticis Fructus, as a bioactive compound possessing anti-inflammatory properties. The present study was aimed to evaluate the preventive benefit of PPY on cigarette-smoke (CS)-induced lung inflammation. C57BL/6 mice were exposed to CS for 2 weeks while PPY was administrated by oral injection 2 h before CS exposure. To validate the anti-inflammatory effects of PPY, the numbers of immune cells in the bronchoalveolar lavage fluid were counted. Proinflammatory cytokines (Tumor necrosis factor-α: TNF-α, IL-6) and keratinocyte chemokine (KC/CXCL1) were also measured. Histopathologic analysis and cellular profiles showed that inflammatory cell infiltrations were significantly decreased in peribronchial and perivascular area by PPY treatment. The alveolar destruction by CS was markedly ameliorated by PPY treatment. In addition, the TNF-α, IL-6, and KC levels were declined in the PPY groups. These observations suggest that PPY has a preventive potential for lung inflammatory diseases.

  • Pyranopyran 1 8 dione an active compound from viticis fructus ameliorates cigarette smoke induced lung inflammatory response in a murine model cam5p 239
    Journal of Immunology, 2014
    Co-Authors: Hyunsu Bae, Kyunghwa Jung, Moochang Hong, Geunhyung Kang, Won Seob Kim, Hyun Seong Kim, Sun Kwang Kim
    Abstract:

    Chronic obstructive pulmonary disease (COPD) is defined as poorly irreversible airflow obstruction due to the inhalation of noxious chemicals and gases, most commonly cigarette smoke (CS). The extract of Viticis Fructus (VF), is widely used as a traditional herbal medicine in various Asian countries for the treatment of migraine pain and allergic diseases. Therefore, we attempt to isolate active compound from VF. After several rounds of activity-guided fractionations, 1H, 8H-Pyrano [3, 4-c] pyran-1, 8-dione (PPY) was isolated. In this study, we hypothesized that PPY, constituent of VF, could suppress CS exposure lung inflammation in mice model. The mice were exposed to 3R4F reference cigarettes for 2 weeks with 6 cigarettes a day. The mice were administered various dose of PPY (1, 2, 10 mg/kg body wt) via an oral administration 2 hr prior to CS exposure. The results of this study indicate cellular profiles and histopathologic analysis demonstrated that peribronchial and perivascular inflammatory cell infiltrates were significantly decreased in the PPY treated groups when compared to the CS exposure group. In summary, the results of this study indicate that PPY has significantly inhibited CS induced lung inflammation. The remarkable anti-inflammatory effects of PPY suggest its therapeutic potential in COPD treatment. Keywords: COPD, 1H, 8H-Pyrano [3, 4-c] pyran-1, 8-dione (PPY), cigarette smoke, IL-6, TNF-α

  • treatment with Pyranopyran 1 8 dione attenuates airway responses in cockroach allergen sensitized asthma in mice
    PLOS ONE, 2014
    Co-Authors: Soojin Park, Kyunghwa Jung, Minsun Park, Joo Hyun Song, You Ah Kim, Hi Jae Cho, Byungil Min, Hyunsu Bae
    Abstract:

    Chronic allergic asthma is characterized by Th2-typed inflammation, and contributes to airway remodeling and the deterioration of lung function. Viticis Fructus (VF) has long been used in China and Korea as a traditional herbal remedy for treating various inflammatory diseases. Previously, we have isolated a novel phytochemical, Pyranopyran-1, 8-dione (PPY), from VF. This study was conducted to evaluate the ability of PPY to prevent airway inflammation and to attenuate airway responses in a cockroach allergen-induced asthma model in mice. The mice sensitized to and challenged with cockroach allergen were treated with oral administration of PPY. The infiltration of total cells, eosinophils and lymphocytes into the BAL fluid was significantly inhibited in cockroach allergen-induced asthma mice treated with PPY (1, 2, or 10 mg/kg). Th2 cytokines and chemokine, such as IL-4, IL-5, IL-13 and eotaxin in BAL fluid were also reduced to normal levels following treatment with PPY. In addition, the levels of IgE were also markedly suppressed after PPY treatment. Histopathological examination demonstrated that PPY substantially inhibited eosinophil infiltration into the airway, goblet cell hyperplasia and smooth muscle hypertrophy. Taken together, these results demonstrate that PPY possesses a potent efficacy on controlling allergic asthma response such as airway inflammation and remodeling.

Tohru Oishi - One of the best experts on this subject based on the ideXlab platform.

  • syntheses and biological activities of the lmno ent lmno and nopqr s ring systems of maitotoxin
    Journal of Organic Chemistry, 2017
    Co-Authors: Hisaaki Onoue, Riho Marubayashi, Erina Ishikawa, Keiichi Konoki, Kohei Torikai, Makoto Ebine, Michio Murata, Tohru Oishi
    Abstract:

    Structure–activity relationship studies of maitotoxin (MTX), a marine natural product produced by an epiphytic dinoflagellate, were conducted using chemically synthesized model compounds corresponding to the partial structures of MTX. Both enantiomers of the LMNO ring system were synthesized via aldol reaction of the LM ring aldehyde and the NO ring ketone. These fragments were derived from a common cis-fused Pyranopyran intermediate prepared through a sequence involving Nozaki–Hiyama–Kishi reaction, intramolecular oxa-Michael addition, and Pummerer rearrangement. The NOPQR(S) ring system, in which the original seven-membered S ring was substituted with a six-membered ring, was also synthesized through the coupling of the QR(S) ring alkyne and the NO ring aldehyde and the construction of the P ring via 1,4-reduction, dehydration, and hydroboration. The inhibitory activities of the synthetic specimens against MTX-induced Ca2+ influx were evaluated. The LMNO ring system and its enantiomer induced 36 and 18%...

  • Syntheses and Biological Activities of the LMNO, ent-LMNO, and NOPQR(S) Ring Systems of Maitotoxin
    2017
    Co-Authors: Hisaaki Onoue, Riho Marubayashi, Erina Ishikawa, Keiichi Konoki, Kohei Torikai, Makoto Ebine, Michio Murata, Tohru Oishi
    Abstract:

    Structure–activity relationship studies of maitotoxin (MTX), a marine natural product produced by an epiphytic dinoflagellate, were conducted using chemically synthesized model compounds corresponding to the partial structures of MTX. Both enantiomers of the LMNO ring system were synthesized via aldol reaction of the LM ring aldehyde and the NO ring ketone. These fragments were derived from a common cis-fused Pyranopyran intermediate prepared through a sequence involving Nozaki–Hiyama–Kishi reaction, intramolecular oxa-Michael addition, and Pummerer rearrangement. The NOPQR­(S) ring system, in which the original seven-membered S ring was substituted with a six-membered ring, was also synthesized through the coupling of the QR­(S) ring alkyne and the NO ring aldehyde and the construction of the P ring via 1,4-reduction, dehydration, and hydroboration. The inhibitory activities of the synthetic specimens against MTX-induced Ca2+ influx were evaluated. The LMNO ring system and its enantiomer induced 36 and 18% inhibition, respectively, at 300 μM, whereas the NOPQR­(S) ring system elicited no inhibitory activity

Sun Kwang Kim - One of the best experts on this subject based on the ideXlab platform.

  • Pyranopyran 1 8 dione an active compound from viticis fructus ameliorates cigarette smoke induced lung inflammatory response in a murine model cam5p 239
    Journal of Immunology, 2014
    Co-Authors: Hyunsu Bae, Kyunghwa Jung, Moochang Hong, Geunhyung Kang, Won Seob Kim, Hyun Seong Kim, Sun Kwang Kim
    Abstract:

    Chronic obstructive pulmonary disease (COPD) is defined as poorly irreversible airflow obstruction due to the inhalation of noxious chemicals and gases, most commonly cigarette smoke (CS). The extract of Viticis Fructus (VF), is widely used as a traditional herbal medicine in various Asian countries for the treatment of migraine pain and allergic diseases. Therefore, we attempt to isolate active compound from VF. After several rounds of activity-guided fractionations, 1H, 8H-Pyrano [3, 4-c] pyran-1, 8-dione (PPY) was isolated. In this study, we hypothesized that PPY, constituent of VF, could suppress CS exposure lung inflammation in mice model. The mice were exposed to 3R4F reference cigarettes for 2 weeks with 6 cigarettes a day. The mice were administered various dose of PPY (1, 2, 10 mg/kg body wt) via an oral administration 2 hr prior to CS exposure. The results of this study indicate cellular profiles and histopathologic analysis demonstrated that peribronchial and perivascular inflammatory cell infiltrates were significantly decreased in the PPY treated groups when compared to the CS exposure group. In summary, the results of this study indicate that PPY has significantly inhibited CS induced lung inflammation. The remarkable anti-inflammatory effects of PPY suggest its therapeutic potential in COPD treatment. Keywords: COPD, 1H, 8H-Pyrano [3, 4-c] pyran-1, 8-dione (PPY), cigarette smoke, IL-6, TNF-α

Hisaaki Onoue - One of the best experts on this subject based on the ideXlab platform.

  • syntheses and biological activities of the lmno ent lmno and nopqr s ring systems of maitotoxin
    Journal of Organic Chemistry, 2017
    Co-Authors: Hisaaki Onoue, Riho Marubayashi, Erina Ishikawa, Keiichi Konoki, Kohei Torikai, Makoto Ebine, Michio Murata, Tohru Oishi
    Abstract:

    Structure–activity relationship studies of maitotoxin (MTX), a marine natural product produced by an epiphytic dinoflagellate, were conducted using chemically synthesized model compounds corresponding to the partial structures of MTX. Both enantiomers of the LMNO ring system were synthesized via aldol reaction of the LM ring aldehyde and the NO ring ketone. These fragments were derived from a common cis-fused Pyranopyran intermediate prepared through a sequence involving Nozaki–Hiyama–Kishi reaction, intramolecular oxa-Michael addition, and Pummerer rearrangement. The NOPQR(S) ring system, in which the original seven-membered S ring was substituted with a six-membered ring, was also synthesized through the coupling of the QR(S) ring alkyne and the NO ring aldehyde and the construction of the P ring via 1,4-reduction, dehydration, and hydroboration. The inhibitory activities of the synthetic specimens against MTX-induced Ca2+ influx were evaluated. The LMNO ring system and its enantiomer induced 36 and 18%...

  • Syntheses and Biological Activities of the LMNO, ent-LMNO, and NOPQR(S) Ring Systems of Maitotoxin
    2017
    Co-Authors: Hisaaki Onoue, Riho Marubayashi, Erina Ishikawa, Keiichi Konoki, Kohei Torikai, Makoto Ebine, Michio Murata, Tohru Oishi
    Abstract:

    Structure–activity relationship studies of maitotoxin (MTX), a marine natural product produced by an epiphytic dinoflagellate, were conducted using chemically synthesized model compounds corresponding to the partial structures of MTX. Both enantiomers of the LMNO ring system were synthesized via aldol reaction of the LM ring aldehyde and the NO ring ketone. These fragments were derived from a common cis-fused Pyranopyran intermediate prepared through a sequence involving Nozaki–Hiyama–Kishi reaction, intramolecular oxa-Michael addition, and Pummerer rearrangement. The NOPQR­(S) ring system, in which the original seven-membered S ring was substituted with a six-membered ring, was also synthesized through the coupling of the QR­(S) ring alkyne and the NO ring aldehyde and the construction of the P ring via 1,4-reduction, dehydration, and hydroboration. The inhibitory activities of the synthetic specimens against MTX-induced Ca2+ influx were evaluated. The LMNO ring system and its enantiomer induced 36 and 18% inhibition, respectively, at 300 μM, whereas the NOPQR­(S) ring system elicited no inhibitory activity