Coumarins

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Jia-you Fang - One of the best experts on this subject based on the ideXlab platform.

  • Coumarin derivatives, but not coumarin itself, cause skin irritation via topical delivery.
    Toxicology Letters, 2014
    Co-Authors: Pei-wen Wang, Yi Yun Hung, Ibrahim A. Aljuffali, Jia-you Fang
    Abstract:

    Abstract Coumarin and its derivatives are widely employed as a fragrance in cosmetics and skin care products. The skin absorption level and possible disruption to the skin by topical application of Coumarins were evaluated in this study. Percutaneous absorption of osthole, daphnoretin, coumarin, byakangelicin, and 7-hydroxycoumarin was assessed in vitro and in vivo. Skin physiology measurements and immunoblotting were utilized as methodologies for validating toxicity. The relationship between structures and permeation/toxicity of Coumarins was elucidated. Both equimolar concentration and saturated solubility in 30% ethanol were used as the applied dose. Osthole with the most lipophilic characteristic demonstrated the greatest skin accumulation, followed by coumarin and 7-hydroxycoumarin. Coumarin was the permeant with the highest flux across the skin. The trend of in vivo deposition was consistent with that of the in vitro profiles. Skin uptake of osthole was 8-fold higher than that of coumarin. Hair follicles played a significant role as a pathway for transport of coumarin according to the examination of follicular accumulation. Osthole and 7-hydroxycoumarin slightly, but significantly, enhanced transepidermal water loss after a consecutive 5-day administration. The immunoblotting profiling verified the role of proliferation in skin damage induced by osthole, byakangelicin, and 7-hydroxycoumarin. The proliferation-related proteins examined in this work included glucose-regulated proteins, cytokeratin, and C-myc. Daphnoretin and coumarin showed a negligible alteration on protein biomarkers. The experimental results suggested that skin irritation caused by Coumarins was mainly derived from the analogs but not from coumarin itself.

  • Coumarin derivatives, but not coumarin itself, cause skin irritation via topical delivery
    Toxicology Letters, 2014
    Co-Authors: Tai Long Pan, Yi Yun Hung, Yann-lii Leu, Ibrahim A. Aljuffali, Pei-wen Wang, Jia-you Fang
    Abstract:

    Coumarin and its derivatives are widely employed as a fragrance in cosmetics and skin care products. The skin absorption level and possible disruption to the skin by topical application of Coumarins were evaluated in this study. Percutaneous absorption of osthole, daphnoretin, coumarin, byakangelicin, and 7-hydroxycoumarin was assessed in vitro and in vivo. Skin physiology measurements and immunoblotting were utilized as methodologies for validating toxicity. The relationship between structures and permeation/toxicity of Coumarins was elucidated. Both equimolar concentration and saturated solubility in 30% ethanol were used as the applied dose. Osthole with the most lipophilic characteristic demonstrated the greatest skin accumulation, followed by coumarin and 7-hydroxycoumarin. Coumarin was the permeant with the highest flux across the skin. The trend of in vivo deposition was consistent with that of the in vitro profiles. Skin uptake of osthole was 8-fold higher than that of coumarin. Hair follicles played a significant role as a pathway for transport of coumarin according to the examination of follicular accumulation. Osthole and 7-hydroxycoumarin slightly, but significantly, enhanced transepidermal water loss after a consecutive 5-day administration. The immunoblotting profiling verified the role of proliferation in skin damage induced by osthole, byakangelicin, and 7-hydroxycoumarin. The proliferation-related proteins examined in this work included glucose-regulated proteins, cytokeratin, and C-myc. Daphnoretin and coumarin showed a negligible alteration on protein biomarkers. The experimental results suggested that skin irritation caused by Coumarins was mainly derived from the analogs but not from coumarin itself. © 2014 Elsevier Ireland Ltd.

Peter E. Brodelius - One of the best experts on this subject based on the ideXlab platform.

  • Sesquiterpene Coumarins
    Phytochemistry Reviews, 2012
    Co-Authors: Anna Gliszczyńska, Peter E. Brodelius
    Abstract:

    Plants have a long history as therapeutic tools in the treatment of human diseases and have been used as a source of medicines for ages. In search of new biologically active natural products, many plants and herbs used in traditional medicine are screened for natural products with pharmacological activity. In this paper, we present a group of natural products, the sesquiterpene Coumarins isolated from plants, and describe their wide range of biological activity. Sesquiterpene Coumarins are found in some plants of the families Apiaceae (Umbelliferae), Asteraceae (Compositae) and Rutaceae. The coumarin moiety is often umbelliferone (7-hydroxycoumarin) but scopoletin (7-hydroxy-6-methoxycoumarin) and isofraxidin (7-hydroxy-6,8-dimethoxycoumarin) are also found. These Coumarins are linked to a C_15 terpene moiety through an ether linkage. Another group of sesquiterpene Coumarins is the prenylated 4-hydroxyCoumarins where the link between the coumarin and the C_15 terpene moiety is a C–C-bond at carbon 3 of the coumarin moiety. Finally, the prenyl-furocoumarin-type sesquiterpenoids are a separate group of sesquiterpene Coumarins based on the suggested biosynthetic pathway. Our relatively limited knowledge on the biosynthesis of sesquiterpene Coumarins is reviewed.

Tai Long Pan - One of the best experts on this subject based on the ideXlab platform.

  • Coumarin derivatives, but not coumarin itself, cause skin irritation via topical delivery
    Toxicology Letters, 2014
    Co-Authors: Tai Long Pan, Yi Yun Hung, Yann-lii Leu, Ibrahim A. Aljuffali, Pei-wen Wang, Jia-you Fang
    Abstract:

    Coumarin and its derivatives are widely employed as a fragrance in cosmetics and skin care products. The skin absorption level and possible disruption to the skin by topical application of Coumarins were evaluated in this study. Percutaneous absorption of osthole, daphnoretin, coumarin, byakangelicin, and 7-hydroxycoumarin was assessed in vitro and in vivo. Skin physiology measurements and immunoblotting were utilized as methodologies for validating toxicity. The relationship between structures and permeation/toxicity of Coumarins was elucidated. Both equimolar concentration and saturated solubility in 30% ethanol were used as the applied dose. Osthole with the most lipophilic characteristic demonstrated the greatest skin accumulation, followed by coumarin and 7-hydroxycoumarin. Coumarin was the permeant with the highest flux across the skin. The trend of in vivo deposition was consistent with that of the in vitro profiles. Skin uptake of osthole was 8-fold higher than that of coumarin. Hair follicles played a significant role as a pathway for transport of coumarin according to the examination of follicular accumulation. Osthole and 7-hydroxycoumarin slightly, but significantly, enhanced transepidermal water loss after a consecutive 5-day administration. The immunoblotting profiling verified the role of proliferation in skin damage induced by osthole, byakangelicin, and 7-hydroxycoumarin. The proliferation-related proteins examined in this work included glucose-regulated proteins, cytokeratin, and C-myc. Daphnoretin and coumarin showed a negligible alteration on protein biomarkers. The experimental results suggested that skin irritation caused by Coumarins was mainly derived from the analogs but not from coumarin itself. © 2014 Elsevier Ireland Ltd.

Pei-wen Wang - One of the best experts on this subject based on the ideXlab platform.

  • Coumarin derivatives, but not coumarin itself, cause skin irritation via topical delivery.
    Toxicology Letters, 2014
    Co-Authors: Pei-wen Wang, Yi Yun Hung, Ibrahim A. Aljuffali, Jia-you Fang
    Abstract:

    Abstract Coumarin and its derivatives are widely employed as a fragrance in cosmetics and skin care products. The skin absorption level and possible disruption to the skin by topical application of Coumarins were evaluated in this study. Percutaneous absorption of osthole, daphnoretin, coumarin, byakangelicin, and 7-hydroxycoumarin was assessed in vitro and in vivo. Skin physiology measurements and immunoblotting were utilized as methodologies for validating toxicity. The relationship between structures and permeation/toxicity of Coumarins was elucidated. Both equimolar concentration and saturated solubility in 30% ethanol were used as the applied dose. Osthole with the most lipophilic characteristic demonstrated the greatest skin accumulation, followed by coumarin and 7-hydroxycoumarin. Coumarin was the permeant with the highest flux across the skin. The trend of in vivo deposition was consistent with that of the in vitro profiles. Skin uptake of osthole was 8-fold higher than that of coumarin. Hair follicles played a significant role as a pathway for transport of coumarin according to the examination of follicular accumulation. Osthole and 7-hydroxycoumarin slightly, but significantly, enhanced transepidermal water loss after a consecutive 5-day administration. The immunoblotting profiling verified the role of proliferation in skin damage induced by osthole, byakangelicin, and 7-hydroxycoumarin. The proliferation-related proteins examined in this work included glucose-regulated proteins, cytokeratin, and C-myc. Daphnoretin and coumarin showed a negligible alteration on protein biomarkers. The experimental results suggested that skin irritation caused by Coumarins was mainly derived from the analogs but not from coumarin itself.

  • Coumarin derivatives, but not coumarin itself, cause skin irritation via topical delivery
    Toxicology Letters, 2014
    Co-Authors: Tai Long Pan, Yi Yun Hung, Yann-lii Leu, Ibrahim A. Aljuffali, Pei-wen Wang, Jia-you Fang
    Abstract:

    Coumarin and its derivatives are widely employed as a fragrance in cosmetics and skin care products. The skin absorption level and possible disruption to the skin by topical application of Coumarins were evaluated in this study. Percutaneous absorption of osthole, daphnoretin, coumarin, byakangelicin, and 7-hydroxycoumarin was assessed in vitro and in vivo. Skin physiology measurements and immunoblotting were utilized as methodologies for validating toxicity. The relationship between structures and permeation/toxicity of Coumarins was elucidated. Both equimolar concentration and saturated solubility in 30% ethanol were used as the applied dose. Osthole with the most lipophilic characteristic demonstrated the greatest skin accumulation, followed by coumarin and 7-hydroxycoumarin. Coumarin was the permeant with the highest flux across the skin. The trend of in vivo deposition was consistent with that of the in vitro profiles. Skin uptake of osthole was 8-fold higher than that of coumarin. Hair follicles played a significant role as a pathway for transport of coumarin according to the examination of follicular accumulation. Osthole and 7-hydroxycoumarin slightly, but significantly, enhanced transepidermal water loss after a consecutive 5-day administration. The immunoblotting profiling verified the role of proliferation in skin damage induced by osthole, byakangelicin, and 7-hydroxycoumarin. The proliferation-related proteins examined in this work included glucose-regulated proteins, cytokeratin, and C-myc. Daphnoretin and coumarin showed a negligible alteration on protein biomarkers. The experimental results suggested that skin irritation caused by Coumarins was mainly derived from the analogs but not from coumarin itself. © 2014 Elsevier Ireland Ltd.

Anna Gliszczyńska - One of the best experts on this subject based on the ideXlab platform.

  • Sesquiterpene Coumarins
    Phytochemistry Reviews, 2012
    Co-Authors: Anna Gliszczyńska, Peter E. Brodelius
    Abstract:

    Plants have a long history as therapeutic tools in the treatment of human diseases and have been used as a source of medicines for ages. In search of new biologically active natural products, many plants and herbs used in traditional medicine are screened for natural products with pharmacological activity. In this paper, we present a group of natural products, the sesquiterpene Coumarins isolated from plants, and describe their wide range of biological activity. Sesquiterpene Coumarins are found in some plants of the families Apiaceae (Umbelliferae), Asteraceae (Compositae) and Rutaceae. The coumarin moiety is often umbelliferone (7-hydroxycoumarin) but scopoletin (7-hydroxy-6-methoxycoumarin) and isofraxidin (7-hydroxy-6,8-dimethoxycoumarin) are also found. These Coumarins are linked to a C_15 terpene moiety through an ether linkage. Another group of sesquiterpene Coumarins is the prenylated 4-hydroxyCoumarins where the link between the coumarin and the C_15 terpene moiety is a C–C-bond at carbon 3 of the coumarin moiety. Finally, the prenyl-furocoumarin-type sesquiterpenoids are a separate group of sesquiterpene Coumarins based on the suggested biosynthetic pathway. Our relatively limited knowledge on the biosynthesis of sesquiterpene Coumarins is reviewed.