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Pawinee Piyachaturawat - One of the best experts on this subject based on the ideXlab platform.
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selective estrogen receptor modulator serm like activities of Diarylheptanoid a phytoestrogen from curcuma comosa in breast cancer cells pre osteoblast cells and rat uterine tissues
Journal of Agricultural and Food Chemistry, 2017Co-Authors: Natthakan Thongon, Patoomratana Tuchinda, Kanoknetr Suksen, Arthit Chairoungdua, Apichart Suksamrarn, Nittaya Boonmuen, Patsorn Wichit, Wipawee Winuthayanon, Pawinee PiyachaturawatAbstract:Diarylheptanoids from Curcuma comosa, of the Zingiberaceae family, exhibit diverse estrogenic activities. In this study we investigated the estrogenic activity of a major hydroxyl Diarylheptanoid, 7-(3,4 -dihydroxyphenyl)-5-hydroxy-1-phenyl-(1E)-1-heptene (compound 092) isolated from C. comosa. The compound elicited different transcriptional activities of estrogen agonist at low concentrations (0.1–1 μM) and antagonist at high concentrations (10–50 μM) using luciferase reporter gene assay in HEK-293T cells. In human breast cancer (MCF-7) cells, compound 092 showed an anti-estrogenic activity by down-regulating ERα-signaling and suppressing estrogen-responsive genes, whereas it attenuated the uterotrophic effect of estrogen in immature ovariectomized rats. Of note, compound 092 promoted mouse pre-osteoblastic (MC3T3-E1) cell differentiation and the related bone markers, indicating its positive osteogenic effect. Our findings highlight a new, nonsteroidal, estrogen agonist/antagonist of catechol diarylhepta...
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protective effects of a Diarylheptanoid from curcuma comosa against hydrogen peroxide induced astroglial cell death
Planta Medica, 2016Co-Authors: Jaturavit Vattanarongkup, Patoomratana Tuchinda, Pawinee Piyachaturawat, Pimtip Sanvarinda, Yupin Sanvarinda, Nattinee JantaratnotaiAbstract:Oxidative stress is one of the major mechanisms causing neuronal and astroglial cell death in various neurological disorders such as Alzheimerʼs disease, Parkinsonʼs disease, and brain ischemia. Two Diarylheptanoids, (3 R )-1,7-diphenyl-(4 E ,6 E )-4,6-heptadien-3-ol (ASPP 049) and (3 S )-7-(3,4-dihydroxyphenyl)-1-phenyl-(1 E )-1-hepten-3-ol (ASPP 092), isolated from Curcuma comosa were investigated for cytoprotective effects on C6 astroglial cells using hydrogen peroxide (H 2 O 2 ) exposure as a model of oxidative stress. ASPP 092 demonstrated free radical scavenging activity comparable to that of vitamin C, while ASPP 049 showed no antioxidant activity. Treatment with H 2 O 2 at 400 µM for 12 h caused 79 % C6 astroglial cell death which was significantly reduced to 37 % by pretreatment with ASPP 092 (5 µM). In addition, ASPP 092 attenuated the increase in reactive oxygen species production and the decrease in total glutathione level induced by H 2 O 2 . The mechanism of ASPP 092 protection against H 2 O 2 -induced apoptotic signaling appeared to involve prevention of increase in the level of phosphorylated p53 and the Bax/Bcl-2 ratio as well as cleaved caspase-3. These findings provide new evidence that the Diarylheptanoid ASPP 092 from C. comosa possesses antiapoptotic properties and could be further developed as a potential treatment for oxidative stress-related neuronal diseases.
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Induction of apoptosis in murine leukemia by Diarylheptanoids from Curcuma comosa Roxb.
Cell Biology and Toxicology, 2011Co-Authors: Surawat Jariyawat, Thanapol Thammapratip, Kanoknetr Suksen, Podchanart Wanitchakool, Jintapat Nateewattana, Arthit Chairoungdua, Apichart Suksamrarn, Pawinee PiyachaturawatAbstract:Diarylheptanoids, isolated from the rhizome of Curcuma comosa Roxb., have several biological activities including anti-oxidant and anti-inflammation. The present study investigated the effect of five Diarylheptanoids isolated from C. comosa rhizome on the proliferation of murine P388 leukemic cells. Compound-092, (3 S )-1-(3,4-dihydroxyphenyl)-7-phenyl-(6 E )-6-hepten-3-ol, bearing a catechol moiety, was the most potent Diarylheptanoid (IC_50 of 4 μM) in inhibiting P388 leukemic cell viability by causing DNA breakage and inducing apoptosis. Apoptotic cell death was characterized by the presence of chromatin condensation, formation of apoptotic bodies, DNA fragmentation, and externalization of plasma membrane phosphatidylserine. This compound increased caspase-3 activity about fivefold above the untreated control, decreased the intracellular reduced glutathione level, and impaired mitochondrial transmembrane potential. In the presence of Cu(II) ion, the compound exhibited a pro-oxidant activity causing DNA strand breakage and enhancing the anti-proliferative activity. The results provide evidence for the pro-oxidant activity of the Diarylheptanoid bearing a catechol moiety in the induction of apoptosis in murine P388 leukemia.
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Diarylheptanoid phytoestrogens isolated from the medicinal plant curcuma comosa biologic actions in vitro and in vivo indicate estrogen receptor dependent mechanisms
Environmental Health Perspectives, 2009Co-Authors: Wipawee Winuthayanon, Apichart Suksamrarn, Pawinee Piyachaturawat, Mathurose Ponglikitmongkol, Yukitomo Arao, Sylvia C Hewitt, Kenneth S KorachAbstract:Medicinal herbal products have traditionally been used as home remedies for treatment of many diseases for centuries (Rodriguez-Fragoso et al. 2008). Although many have promising therapeutic potential, in general there is a lack of rigorous controlled scientific testing, and little information is available regarding appropriate patient use or adverse effects. Biosafety and efficacy are major public concerns, particularly in developing countries, which are still establishing biosafety policies. However, the extensive traditional uses of nonapproved herbal medicines, as well as environmental exposures, result in a possible risk of both acute and chronic toxicities. Chronic forms of toxicities such as carcinogenicity, mutagenicity, and hepatotoxicity have been reported (Pak et al. 2004). In addition, some specific patient groups may have more of a health risk (e.g., pregnant or nursing mothers and the elderly). Herbal medicines may also interfere with the efficacy of conventional medicines through herb–drug interactions (Tomlinson et al. 2000). Many herbs that have traditionally been reported to have estrogen-like activity are potentially abortifacient (Sylvestre et al. 2006), which may affect certain groups of individuals. Phytoestrogens, plant-derived nonsteroidal polyphenolic compounds, are present in soybeans, clover, and oilseeds. Isoflavones, lignans, coumestans, resorcylic acid lactones, and stilbenes are known phyto estrogens (Knight and Eden 1996). Isoflavones, such as genistein, apigenin, and kaempferol, have stronger binding affinity for estrogen receptor (ER) β than for ERα (Kuiper et al. 1998). However, the transcriptional activity of phytoestrogens such as genistein, daidzein, apigenin, naringenin, kaempferol, and coumestrol can be mediated by either ERα or ERβ (Harris et al. 2005). In addition, the stilbene resveratrol, a phytoestrogen from grapes, induced the estrogen-regulated gene progesterone receptor (PR) in MCF-7 (human breast cancer) cells in a dose-dependent manner (Gehm et al. 1997). These estrogen-like activities of phytoestrogens have been demonstrated to have beneficial roles in prevention of several diseases, including cardiovascular diseases, osteoporosis, cancers, and menopausal symptoms (Usui 2006). However, phytoestrogen had no significant effect on hot flashes in women (Huntley and Ernst 2004). Therefore, the search for novel phytoestrogens as an alternative treatment is still a subject of high interest for postmenopausal women. Diarylheptanoids consist of two aromatic rings linked by a linear seven-carbon aliphatic chain. The first naturally occurring Diarylheptanoid, curcumin, a yellow dye of the Curcuma species, was reported in the early 1800s (Keseru and Nogradi 1995). Diarylheptanoids have been reported to have a variety of therapeutic actions in vitro such as inhibition of platelet aggregation (Doug et al. 1998), antioxidation (Yao et al. 2007), antiinflammation (Sodsai et al. 2007), and antitumor-promoting effects (Chun et al. 1999; Lee et al. 1998). Because Curcuma comosa Roxb., an indigenous medicine, has estrogen-like activity (Piyachaturawat et al. 1995a, 1995b) and has been extensively used among menopausal women, it is essential to characterize its biological action to avoid any risk that may occur from chronic consumption or environmental exposures. Recently, Diarylheptanoids isolated from C. comosa have also been reported to exhibit estrogenic activity both in vitro (Suksamrarn et al. 2008) and in vivo (Winuthayanon et al. 2009) and are useful for nutraceutical health promotion and hormone replacement therapy. The reported high content of Diarylheptanoids in C. comosa (Suksamrarn et al. 2008) provided this plant species as an attractive source of novel phytoestrogens. However, the precise mechanisms of the estrogenic action of Diarylheptanoids have not yet been identified. The Diarylheptanoids (3S)-1,7-diphenyl-(6E)-6-hepten-3-ol (D1), 1,7-diphenyl-(6E)-6-hepten-3-one (D2), and (3R)-1,7-diphenyl-(4E,6E)-4,6-heptadien-3-ol (D3; Figure 1), the major components of C. comosa, exhibited high estrogenic activity (Suksamrarn et al. 2008). In the present study we aimed to characterize the estrogenic activity of these potent naturally occurring Diarylheptanoids in vivo and determine their mechanism of action on ERs in vitro by using well-characterized and appropriate experimental model systems. Figure 1 Structure of the Diarylheptanoids (3S)-1,7-diphenyl-(6E)-6-hepten-3-ol (D1), 1,7-diphenyl-(6E)-6-hepten-3-one (D2), and (3R- ) 1,7-diphenyl-(4E,6E)-4,6-heptadien-3-ol (D3), purified compounds isolated from rhizome (Suksamrarn et al. 2008).
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Diarylheptanoid phytoestrogens isolated from the medicinal plant curcuma comosa biologic actions in vitro and in vivo indicate estrogen receptor dependent mechanisms
Environmental Health Perspectives, 2009Co-Authors: Wipawee Winuthayanon, Apichart Suksamrarn, Pawinee Piyachaturawat, Mathurose Ponglikitmongkol, Yukitomo Arao, Sylvia C Hewitt, Kenneth S KorachAbstract:Medicinal herbal products have traditionally been used as home remedies for treatment of many diseases for centuries (Rodriguez-Fragoso et al. 2008). Although many have promising therapeutic potential, in general there is a lack of rigorous controlled scientific testing, and little information is available regarding appropriate patient use or adverse effects. Biosafety and efficacy are major public concerns, particularly in developing countries, which are still establishing biosafety policies. However, the extensive traditional uses of nonapproved herbal medicines, as well as environmental exposures, result in a possible risk of both acute and chronic toxicities. Chronic forms of toxicities such as carcinogenicity, mutagenicity, and hepatotoxicity have been reported (Pak et al. 2004). In addition, some specific patient groups may have more of a health risk (e.g., pregnant or nursing mothers and the elderly). Herbal medicines may also interfere with the efficacy of conventional medicines through herb–drug interactions (Tomlinson et al. 2000). Many herbs that have traditionally been reported to have estrogen-like activity are potentially abortifacient (Sylvestre et al. 2006), which may affect certain groups of individuals. Phytoestrogens, plant-derived nonsteroidal polyphenolic compounds, are present in soybeans, clover, and oilseeds. Isoflavones, lignans, coumestans, resorcylic acid lactones, and stilbenes are known phyto estrogens (Knight and Eden 1996). Isoflavones, such as genistein, apigenin, and kaempferol, have stronger binding affinity for estrogen receptor (ER) β than for ERα (Kuiper et al. 1998). However, the transcriptional activity of phytoestrogens such as genistein, daidzein, apigenin, naringenin, kaempferol, and coumestrol can be mediated by either ERα or ERβ (Harris et al. 2005). In addition, the stilbene resveratrol, a phytoestrogen from grapes, induced the estrogen-regulated gene progesterone receptor (PR) in MCF-7 (human breast cancer) cells in a dose-dependent manner (Gehm et al. 1997). These estrogen-like activities of phytoestrogens have been demonstrated to have beneficial roles in prevention of several diseases, including cardiovascular diseases, osteoporosis, cancers, and menopausal symptoms (Usui 2006). However, phytoestrogen had no significant effect on hot flashes in women (Huntley and Ernst 2004). Therefore, the search for novel phytoestrogens as an alternative treatment is still a subject of high interest for postmenopausal women. Diarylheptanoids consist of two aromatic rings linked by a linear seven-carbon aliphatic chain. The first naturally occurring Diarylheptanoid, curcumin, a yellow dye of the Curcuma species, was reported in the early 1800s (Keseru and Nogradi 1995). Diarylheptanoids have been reported to have a variety of therapeutic actions in vitro such as inhibition of platelet aggregation (Doug et al. 1998), antioxidation (Yao et al. 2007), antiinflammation (Sodsai et al. 2007), and antitumor-promoting effects (Chun et al. 1999; Lee et al. 1998). Because Curcuma comosa Roxb., an indigenous medicine, has estrogen-like activity (Piyachaturawat et al. 1995a, 1995b) and has been extensively used among menopausal women, it is essential to characterize its biological action to avoid any risk that may occur from chronic consumption or environmental exposures. Recently, Diarylheptanoids isolated from C. comosa have also been reported to exhibit estrogenic activity both in vitro (Suksamrarn et al. 2008) and in vivo (Winuthayanon et al. 2009) and are useful for nutraceutical health promotion and hormone replacement therapy. The reported high content of Diarylheptanoids in C. comosa (Suksamrarn et al. 2008) provided this plant species as an attractive source of novel phytoestrogens. However, the precise mechanisms of the estrogenic action of Diarylheptanoids have not yet been identified. The Diarylheptanoids (3S)-1,7-diphenyl-(6E)-6-hepten-3-ol (D1), 1,7-diphenyl-(6E)-6-hepten-3-one (D2), and (3R)-1,7-diphenyl-(4E,6E)-4,6-heptadien-3-ol (D3; Figure 1), the major components of C. comosa, exhibited high estrogenic activity (Suksamrarn et al. 2008). In the present study we aimed to characterize the estrogenic activity of these potent naturally occurring Diarylheptanoids in vivo and determine their mechanism of action on ERs in vitro by using well-characterized and appropriate experimental model systems. Figure 1 Structure of the Diarylheptanoids (3S)-1,7-diphenyl-(6E)-6-hepten-3-ol (D1), 1,7-diphenyl-(6E)-6-hepten-3-one (D2), and (3R- ) 1,7-diphenyl-(4E,6E)-4,6-heptadien-3-ol (D3), purified compounds isolated from rhizome (Suksamrarn et al. 2008).
Apichart Suksamrarn - One of the best experts on this subject based on the ideXlab platform.
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selective estrogen receptor modulator serm like activities of Diarylheptanoid a phytoestrogen from curcuma comosa in breast cancer cells pre osteoblast cells and rat uterine tissues
Journal of Agricultural and Food Chemistry, 2017Co-Authors: Natthakan Thongon, Patoomratana Tuchinda, Kanoknetr Suksen, Arthit Chairoungdua, Apichart Suksamrarn, Nittaya Boonmuen, Patsorn Wichit, Wipawee Winuthayanon, Pawinee PiyachaturawatAbstract:Diarylheptanoids from Curcuma comosa, of the Zingiberaceae family, exhibit diverse estrogenic activities. In this study we investigated the estrogenic activity of a major hydroxyl Diarylheptanoid, 7-(3,4 -dihydroxyphenyl)-5-hydroxy-1-phenyl-(1E)-1-heptene (compound 092) isolated from C. comosa. The compound elicited different transcriptional activities of estrogen agonist at low concentrations (0.1–1 μM) and antagonist at high concentrations (10–50 μM) using luciferase reporter gene assay in HEK-293T cells. In human breast cancer (MCF-7) cells, compound 092 showed an anti-estrogenic activity by down-regulating ERα-signaling and suppressing estrogen-responsive genes, whereas it attenuated the uterotrophic effect of estrogen in immature ovariectomized rats. Of note, compound 092 promoted mouse pre-osteoblastic (MC3T3-E1) cell differentiation and the related bone markers, indicating its positive osteogenic effect. Our findings highlight a new, nonsteroidal, estrogen agonist/antagonist of catechol diarylhepta...
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natural Diarylheptanoid compounds from curcuma comosa roxb promote differentiation of mouse myoblasts c2c12 cells selectively via er alpha receptors
Medicinal Chemistry Research, 2017Co-Authors: Chittipong Tipbunjong, Apichart Suksamrarn, Yindee Kitiyanant, Ganyapong Chaturapanich, Nilubon Sornkaew, Narisorn Kitiyanant, Karyn A Esser, Chumpol PholpramoolAbstract:Diarylheptanoids exhibit numerous biological activities and have been used as traditional medicine in Asian countries. However, their effects on myogenesis are still unknown. This study determined the effects of eight different Diarylheptanoid compounds including 1,7-diphenyl-(6E)-6-hepten-3-one (compound 1) and its analogs (compounds 2–8) isolated and purified from Curcuma comosa Roxb. on mouse myoblasts (C2C12 cells) proliferation and differentiation. All compounds (10−9–10−5 M) were non-toxic to C2C12 cells, and had no anti-oxidant activity except (3S)-1-(3,4–dihydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol (compound 8), which showed higher activity compared to that of ascorbic acid. Additionally, this compound (10−8 M) effectively prevented the toxic effect of H2O2 on C2C12 cells. Proliferation of C2C12 cells was significantly increased by all compounds except compound 1 and (3R)-1,7-diphenyl-(4E,6E)-4,6-heptadien-3-ol (compound 4), whereas differentiation of myoblasts was enhanced by all compounds. The effect on proliferation was not blocked by ICI 182,780, but this blocker completely inhibited the effects of Diarylheptanoids on differentiation. In addition, silencing the transcription of oestrogen receptor α (ERα), but not estrogen receptor β (ERβ), completely abolished the enhancement of differentiation. Together, the results indicate that Diarylheptanoids enhance proliferation of C2C12 cells by a non-estrogenic mechanism, but induce differentiation selectively via ERα. These compounds may have potential for further development as therapeutic agents for treatment of muscle injury and/or diseases.
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Diarylheptanoid from curcuma comosa roxb suppresses rankl induced osteoclast differentiation by decreasing nfatc1 and c fos expression via mapk pathway
European Journal of Pharmacology, 2016Co-Authors: Supatta Chawalitpong, Apichart Suksamrarn, Nilubon Sornkaew, Tanapat PalagaAbstract:Abstract Osteoporosis is caused by a functional imbalance between osteoblasts and osteoclasts. The increased activation of osteoclasts that is a hallmark of osteoporosis results in the progressive loss of bone mass and therefore in an increased susceptibility to bone fractures. Diarylheptanoids are a group of phytoestrogens that have been isolated from a number of plant species, including the rhizomes of Curcuma comosa Roxb. In this study, the effect of one of Diarylheptanoids, (3S)-1-(3,4-dihydroxyphenyl)-3-hydroxy-7-phenyl-(6E)-6-heptene (DHPH), was investigated for anti-inflammatory and anti-osteoclastogenic activity. DHPH significantly inhibited nitric oxide production in RAW264.7 cell line following their activation by lipopolysaccharide and interferon-γ, with no cytotoxicity. In primary mouse bone-marrow-derived macrophage precursors, DHPH suppressed osteoclastogenesis induced by receptor activator of nuclear factor-κB (RANK) ligand at an inhibitory concentration 50 of 325±1.37 nM. DHPH treatment delayed and reduced the expression of master regulators of osteoclast differentiation, NFATc1 and c-Fos. Consistent with this result, the mRNA level of cathepsin K, associated with osteoclast differentiation, was decreased whereas the reduction in the mRNA of irf8, a negative regulator of osteoclast differentiation, was similar to that measured in the vehicle-treated control cells. DHPH reduced the phosphorylation of p38 MAPK, ERK (p44/42). Furthermore, DHPH suppressed the bone absorption activity of osteoclasts and enhanced osteoblast differentiation. Taken together, DHPH interrupts the immediate downstream signaling cascade of RANK and interferes with osteoclast differentiation and its function while enhances osteoblast differentiation. These results demonstrate the potential of this Diarylheptanoid as a new therapeutic agent in osteoporosis.
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Induction of apoptosis in murine leukemia by Diarylheptanoids from Curcuma comosa Roxb.
Cell Biology and Toxicology, 2011Co-Authors: Surawat Jariyawat, Thanapol Thammapratip, Kanoknetr Suksen, Podchanart Wanitchakool, Jintapat Nateewattana, Arthit Chairoungdua, Apichart Suksamrarn, Pawinee PiyachaturawatAbstract:Diarylheptanoids, isolated from the rhizome of Curcuma comosa Roxb., have several biological activities including anti-oxidant and anti-inflammation. The present study investigated the effect of five Diarylheptanoids isolated from C. comosa rhizome on the proliferation of murine P388 leukemic cells. Compound-092, (3 S )-1-(3,4-dihydroxyphenyl)-7-phenyl-(6 E )-6-hepten-3-ol, bearing a catechol moiety, was the most potent Diarylheptanoid (IC_50 of 4 μM) in inhibiting P388 leukemic cell viability by causing DNA breakage and inducing apoptosis. Apoptotic cell death was characterized by the presence of chromatin condensation, formation of apoptotic bodies, DNA fragmentation, and externalization of plasma membrane phosphatidylserine. This compound increased caspase-3 activity about fivefold above the untreated control, decreased the intracellular reduced glutathione level, and impaired mitochondrial transmembrane potential. In the presence of Cu(II) ion, the compound exhibited a pro-oxidant activity causing DNA strand breakage and enhancing the anti-proliferative activity. The results provide evidence for the pro-oxidant activity of the Diarylheptanoid bearing a catechol moiety in the induction of apoptosis in murine P388 leukemia.
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Diarylheptanoid phytoestrogens isolated from the medicinal plant curcuma comosa biologic actions in vitro and in vivo indicate estrogen receptor dependent mechanisms
Environmental Health Perspectives, 2009Co-Authors: Wipawee Winuthayanon, Apichart Suksamrarn, Pawinee Piyachaturawat, Mathurose Ponglikitmongkol, Yukitomo Arao, Sylvia C Hewitt, Kenneth S KorachAbstract:Medicinal herbal products have traditionally been used as home remedies for treatment of many diseases for centuries (Rodriguez-Fragoso et al. 2008). Although many have promising therapeutic potential, in general there is a lack of rigorous controlled scientific testing, and little information is available regarding appropriate patient use or adverse effects. Biosafety and efficacy are major public concerns, particularly in developing countries, which are still establishing biosafety policies. However, the extensive traditional uses of nonapproved herbal medicines, as well as environmental exposures, result in a possible risk of both acute and chronic toxicities. Chronic forms of toxicities such as carcinogenicity, mutagenicity, and hepatotoxicity have been reported (Pak et al. 2004). In addition, some specific patient groups may have more of a health risk (e.g., pregnant or nursing mothers and the elderly). Herbal medicines may also interfere with the efficacy of conventional medicines through herb–drug interactions (Tomlinson et al. 2000). Many herbs that have traditionally been reported to have estrogen-like activity are potentially abortifacient (Sylvestre et al. 2006), which may affect certain groups of individuals. Phytoestrogens, plant-derived nonsteroidal polyphenolic compounds, are present in soybeans, clover, and oilseeds. Isoflavones, lignans, coumestans, resorcylic acid lactones, and stilbenes are known phyto estrogens (Knight and Eden 1996). Isoflavones, such as genistein, apigenin, and kaempferol, have stronger binding affinity for estrogen receptor (ER) β than for ERα (Kuiper et al. 1998). However, the transcriptional activity of phytoestrogens such as genistein, daidzein, apigenin, naringenin, kaempferol, and coumestrol can be mediated by either ERα or ERβ (Harris et al. 2005). In addition, the stilbene resveratrol, a phytoestrogen from grapes, induced the estrogen-regulated gene progesterone receptor (PR) in MCF-7 (human breast cancer) cells in a dose-dependent manner (Gehm et al. 1997). These estrogen-like activities of phytoestrogens have been demonstrated to have beneficial roles in prevention of several diseases, including cardiovascular diseases, osteoporosis, cancers, and menopausal symptoms (Usui 2006). However, phytoestrogen had no significant effect on hot flashes in women (Huntley and Ernst 2004). Therefore, the search for novel phytoestrogens as an alternative treatment is still a subject of high interest for postmenopausal women. Diarylheptanoids consist of two aromatic rings linked by a linear seven-carbon aliphatic chain. The first naturally occurring Diarylheptanoid, curcumin, a yellow dye of the Curcuma species, was reported in the early 1800s (Keseru and Nogradi 1995). Diarylheptanoids have been reported to have a variety of therapeutic actions in vitro such as inhibition of platelet aggregation (Doug et al. 1998), antioxidation (Yao et al. 2007), antiinflammation (Sodsai et al. 2007), and antitumor-promoting effects (Chun et al. 1999; Lee et al. 1998). Because Curcuma comosa Roxb., an indigenous medicine, has estrogen-like activity (Piyachaturawat et al. 1995a, 1995b) and has been extensively used among menopausal women, it is essential to characterize its biological action to avoid any risk that may occur from chronic consumption or environmental exposures. Recently, Diarylheptanoids isolated from C. comosa have also been reported to exhibit estrogenic activity both in vitro (Suksamrarn et al. 2008) and in vivo (Winuthayanon et al. 2009) and are useful for nutraceutical health promotion and hormone replacement therapy. The reported high content of Diarylheptanoids in C. comosa (Suksamrarn et al. 2008) provided this plant species as an attractive source of novel phytoestrogens. However, the precise mechanisms of the estrogenic action of Diarylheptanoids have not yet been identified. The Diarylheptanoids (3S)-1,7-diphenyl-(6E)-6-hepten-3-ol (D1), 1,7-diphenyl-(6E)-6-hepten-3-one (D2), and (3R)-1,7-diphenyl-(4E,6E)-4,6-heptadien-3-ol (D3; Figure 1), the major components of C. comosa, exhibited high estrogenic activity (Suksamrarn et al. 2008). In the present study we aimed to characterize the estrogenic activity of these potent naturally occurring Diarylheptanoids in vivo and determine their mechanism of action on ERs in vitro by using well-characterized and appropriate experimental model systems. Figure 1 Structure of the Diarylheptanoids (3S)-1,7-diphenyl-(6E)-6-hepten-3-ol (D1), 1,7-diphenyl-(6E)-6-hepten-3-one (D2), and (3R- ) 1,7-diphenyl-(4E,6E)-4,6-heptadien-3-ol (D3), purified compounds isolated from rhizome (Suksamrarn et al. 2008).
Wipawee Winuthayanon - One of the best experts on this subject based on the ideXlab platform.
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selective estrogen receptor modulator serm like activities of Diarylheptanoid a phytoestrogen from curcuma comosa in breast cancer cells pre osteoblast cells and rat uterine tissues
Journal of Agricultural and Food Chemistry, 2017Co-Authors: Natthakan Thongon, Patoomratana Tuchinda, Kanoknetr Suksen, Arthit Chairoungdua, Apichart Suksamrarn, Nittaya Boonmuen, Patsorn Wichit, Wipawee Winuthayanon, Pawinee PiyachaturawatAbstract:Diarylheptanoids from Curcuma comosa, of the Zingiberaceae family, exhibit diverse estrogenic activities. In this study we investigated the estrogenic activity of a major hydroxyl Diarylheptanoid, 7-(3,4 -dihydroxyphenyl)-5-hydroxy-1-phenyl-(1E)-1-heptene (compound 092) isolated from C. comosa. The compound elicited different transcriptional activities of estrogen agonist at low concentrations (0.1–1 μM) and antagonist at high concentrations (10–50 μM) using luciferase reporter gene assay in HEK-293T cells. In human breast cancer (MCF-7) cells, compound 092 showed an anti-estrogenic activity by down-regulating ERα-signaling and suppressing estrogen-responsive genes, whereas it attenuated the uterotrophic effect of estrogen in immature ovariectomized rats. Of note, compound 092 promoted mouse pre-osteoblastic (MC3T3-E1) cell differentiation and the related bone markers, indicating its positive osteogenic effect. Our findings highlight a new, nonsteroidal, estrogen agonist/antagonist of catechol diarylhepta...
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Diarylheptanoid phytoestrogens isolated from the medicinal plant curcuma comosa biologic actions in vitro and in vivo indicate estrogen receptor dependent mechanisms
Environmental Health Perspectives, 2009Co-Authors: Wipawee Winuthayanon, Apichart Suksamrarn, Pawinee Piyachaturawat, Mathurose Ponglikitmongkol, Yukitomo Arao, Sylvia C Hewitt, Kenneth S KorachAbstract:Medicinal herbal products have traditionally been used as home remedies for treatment of many diseases for centuries (Rodriguez-Fragoso et al. 2008). Although many have promising therapeutic potential, in general there is a lack of rigorous controlled scientific testing, and little information is available regarding appropriate patient use or adverse effects. Biosafety and efficacy are major public concerns, particularly in developing countries, which are still establishing biosafety policies. However, the extensive traditional uses of nonapproved herbal medicines, as well as environmental exposures, result in a possible risk of both acute and chronic toxicities. Chronic forms of toxicities such as carcinogenicity, mutagenicity, and hepatotoxicity have been reported (Pak et al. 2004). In addition, some specific patient groups may have more of a health risk (e.g., pregnant or nursing mothers and the elderly). Herbal medicines may also interfere with the efficacy of conventional medicines through herb–drug interactions (Tomlinson et al. 2000). Many herbs that have traditionally been reported to have estrogen-like activity are potentially abortifacient (Sylvestre et al. 2006), which may affect certain groups of individuals. Phytoestrogens, plant-derived nonsteroidal polyphenolic compounds, are present in soybeans, clover, and oilseeds. Isoflavones, lignans, coumestans, resorcylic acid lactones, and stilbenes are known phyto estrogens (Knight and Eden 1996). Isoflavones, such as genistein, apigenin, and kaempferol, have stronger binding affinity for estrogen receptor (ER) β than for ERα (Kuiper et al. 1998). However, the transcriptional activity of phytoestrogens such as genistein, daidzein, apigenin, naringenin, kaempferol, and coumestrol can be mediated by either ERα or ERβ (Harris et al. 2005). In addition, the stilbene resveratrol, a phytoestrogen from grapes, induced the estrogen-regulated gene progesterone receptor (PR) in MCF-7 (human breast cancer) cells in a dose-dependent manner (Gehm et al. 1997). These estrogen-like activities of phytoestrogens have been demonstrated to have beneficial roles in prevention of several diseases, including cardiovascular diseases, osteoporosis, cancers, and menopausal symptoms (Usui 2006). However, phytoestrogen had no significant effect on hot flashes in women (Huntley and Ernst 2004). Therefore, the search for novel phytoestrogens as an alternative treatment is still a subject of high interest for postmenopausal women. Diarylheptanoids consist of two aromatic rings linked by a linear seven-carbon aliphatic chain. The first naturally occurring Diarylheptanoid, curcumin, a yellow dye of the Curcuma species, was reported in the early 1800s (Keseru and Nogradi 1995). Diarylheptanoids have been reported to have a variety of therapeutic actions in vitro such as inhibition of platelet aggregation (Doug et al. 1998), antioxidation (Yao et al. 2007), antiinflammation (Sodsai et al. 2007), and antitumor-promoting effects (Chun et al. 1999; Lee et al. 1998). Because Curcuma comosa Roxb., an indigenous medicine, has estrogen-like activity (Piyachaturawat et al. 1995a, 1995b) and has been extensively used among menopausal women, it is essential to characterize its biological action to avoid any risk that may occur from chronic consumption or environmental exposures. Recently, Diarylheptanoids isolated from C. comosa have also been reported to exhibit estrogenic activity both in vitro (Suksamrarn et al. 2008) and in vivo (Winuthayanon et al. 2009) and are useful for nutraceutical health promotion and hormone replacement therapy. The reported high content of Diarylheptanoids in C. comosa (Suksamrarn et al. 2008) provided this plant species as an attractive source of novel phytoestrogens. However, the precise mechanisms of the estrogenic action of Diarylheptanoids have not yet been identified. The Diarylheptanoids (3S)-1,7-diphenyl-(6E)-6-hepten-3-ol (D1), 1,7-diphenyl-(6E)-6-hepten-3-one (D2), and (3R)-1,7-diphenyl-(4E,6E)-4,6-heptadien-3-ol (D3; Figure 1), the major components of C. comosa, exhibited high estrogenic activity (Suksamrarn et al. 2008). In the present study we aimed to characterize the estrogenic activity of these potent naturally occurring Diarylheptanoids in vivo and determine their mechanism of action on ERs in vitro by using well-characterized and appropriate experimental model systems. Figure 1 Structure of the Diarylheptanoids (3S)-1,7-diphenyl-(6E)-6-hepten-3-ol (D1), 1,7-diphenyl-(6E)-6-hepten-3-one (D2), and (3R- ) 1,7-diphenyl-(4E,6E)-4,6-heptadien-3-ol (D3), purified compounds isolated from rhizome (Suksamrarn et al. 2008).
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Diarylheptanoid phytoestrogens isolated from the medicinal plant curcuma comosa biologic actions in vitro and in vivo indicate estrogen receptor dependent mechanisms
Environmental Health Perspectives, 2009Co-Authors: Wipawee Winuthayanon, Apichart Suksamrarn, Pawinee Piyachaturawat, Mathurose Ponglikitmongkol, Yukitomo Arao, Sylvia C Hewitt, Kenneth S KorachAbstract:Medicinal herbal products have traditionally been used as home remedies for treatment of many diseases for centuries (Rodriguez-Fragoso et al. 2008). Although many have promising therapeutic potential, in general there is a lack of rigorous controlled scientific testing, and little information is available regarding appropriate patient use or adverse effects. Biosafety and efficacy are major public concerns, particularly in developing countries, which are still establishing biosafety policies. However, the extensive traditional uses of nonapproved herbal medicines, as well as environmental exposures, result in a possible risk of both acute and chronic toxicities. Chronic forms of toxicities such as carcinogenicity, mutagenicity, and hepatotoxicity have been reported (Pak et al. 2004). In addition, some specific patient groups may have more of a health risk (e.g., pregnant or nursing mothers and the elderly). Herbal medicines may also interfere with the efficacy of conventional medicines through herb–drug interactions (Tomlinson et al. 2000). Many herbs that have traditionally been reported to have estrogen-like activity are potentially abortifacient (Sylvestre et al. 2006), which may affect certain groups of individuals. Phytoestrogens, plant-derived nonsteroidal polyphenolic compounds, are present in soybeans, clover, and oilseeds. Isoflavones, lignans, coumestans, resorcylic acid lactones, and stilbenes are known phyto estrogens (Knight and Eden 1996). Isoflavones, such as genistein, apigenin, and kaempferol, have stronger binding affinity for estrogen receptor (ER) β than for ERα (Kuiper et al. 1998). However, the transcriptional activity of phytoestrogens such as genistein, daidzein, apigenin, naringenin, kaempferol, and coumestrol can be mediated by either ERα or ERβ (Harris et al. 2005). In addition, the stilbene resveratrol, a phytoestrogen from grapes, induced the estrogen-regulated gene progesterone receptor (PR) in MCF-7 (human breast cancer) cells in a dose-dependent manner (Gehm et al. 1997). These estrogen-like activities of phytoestrogens have been demonstrated to have beneficial roles in prevention of several diseases, including cardiovascular diseases, osteoporosis, cancers, and menopausal symptoms (Usui 2006). However, phytoestrogen had no significant effect on hot flashes in women (Huntley and Ernst 2004). Therefore, the search for novel phytoestrogens as an alternative treatment is still a subject of high interest for postmenopausal women. Diarylheptanoids consist of two aromatic rings linked by a linear seven-carbon aliphatic chain. The first naturally occurring Diarylheptanoid, curcumin, a yellow dye of the Curcuma species, was reported in the early 1800s (Keseru and Nogradi 1995). Diarylheptanoids have been reported to have a variety of therapeutic actions in vitro such as inhibition of platelet aggregation (Doug et al. 1998), antioxidation (Yao et al. 2007), antiinflammation (Sodsai et al. 2007), and antitumor-promoting effects (Chun et al. 1999; Lee et al. 1998). Because Curcuma comosa Roxb., an indigenous medicine, has estrogen-like activity (Piyachaturawat et al. 1995a, 1995b) and has been extensively used among menopausal women, it is essential to characterize its biological action to avoid any risk that may occur from chronic consumption or environmental exposures. Recently, Diarylheptanoids isolated from C. comosa have also been reported to exhibit estrogenic activity both in vitro (Suksamrarn et al. 2008) and in vivo (Winuthayanon et al. 2009) and are useful for nutraceutical health promotion and hormone replacement therapy. The reported high content of Diarylheptanoids in C. comosa (Suksamrarn et al. 2008) provided this plant species as an attractive source of novel phytoestrogens. However, the precise mechanisms of the estrogenic action of Diarylheptanoids have not yet been identified. The Diarylheptanoids (3S)-1,7-diphenyl-(6E)-6-hepten-3-ol (D1), 1,7-diphenyl-(6E)-6-hepten-3-one (D2), and (3R)-1,7-diphenyl-(4E,6E)-4,6-heptadien-3-ol (D3; Figure 1), the major components of C. comosa, exhibited high estrogenic activity (Suksamrarn et al. 2008). In the present study we aimed to characterize the estrogenic activity of these potent naturally occurring Diarylheptanoids in vivo and determine their mechanism of action on ERs in vitro by using well-characterized and appropriate experimental model systems. Figure 1 Structure of the Diarylheptanoids (3S)-1,7-diphenyl-(6E)-6-hepten-3-ol (D1), 1,7-diphenyl-(6E)-6-hepten-3-one (D2), and (3R- ) 1,7-diphenyl-(4E,6E)-4,6-heptadien-3-ol (D3), purified compounds isolated from rhizome (Suksamrarn et al. 2008).
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Estrogenic Activity of Diarylheptanoids from Curcuma comosa Roxb. Requires Metabolic Activation
Journal of agricultural and food chemistry, 2009Co-Authors: Wipawee Winuthayanon, Kanoknetr Suksen, Apichart Suksamrarn, Mathurose Ponglikitmongkol, Chuenchit Boonchird, Aporn Chuncharunee, Pawinee PiyachaturawatAbstract:Curcuma comosa Roxb. has traditionally been used as a dietary supplement for health promotion in peri- and postmenopausal women in Thailand. We investigated the estrogenic activity of 7 naturally occurring Diarylheptanoids from the extracts of C. comosa both in vitro and in vivo. A yeast recombinant system containing human estrogen receptor α, coactivator TIF2 and a β-galactosidase reporter gene was used to determine estrogenic activity of Diarylheptanoids metabolically activated with rat liver S9-fraction prior to the assay. The most potent compound was (3R)-1,7-diphenyl-(4E,6E)-4,6-heptadien-3-ol, with a relative potency of 4% compared to 17β-estradiol. The metabolic activation of Diarylheptanoids markedly enhanced their efficiency. The chemical structure required for estrogenic activity of Diarylheptanoids was the presence of a keto group at C3 and absence of hydroxyl moiety in ring B. Only Diarylheptanoids showing full estrogenic efficiency in vitro were able to elicit uterotrophic activity of in imma...
David R Gang - One of the best experts on this subject based on the ideXlab platform.
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Characterization and identification of Diarylheptanoids in ginger (Zingiber officinale Rosc.) using high-performance liquid chromatography/electrospray ionization mass spectrometry.
Rapid communications in mass spectrometry : RCM, 2007Co-Authors: Hongliang Jiang, Barbara N Timmermann, David R GangAbstract:In our continuing investigation of Diarylheptanoids in Zingiberaceae plants using liquid chromatography/electrospray ionization mass spectrometry (LC/ESI-MS/MS), 26 Diarylheptanoids were identified from fresh ginger rhizome. Of the 26 compounds, 15 Diarylheptanoids appear to be new compounds. In addition, the majority of these compounds (18) were acetylated, which is different from our investigation of Diarylheptanoids from turmeric, another member of the Zingiberaceae, which did not possess any acetylated Diarylheptanoids. In all, five distinct groups (homologous series) of Diarylheptanoids were found in extracts from ginger rhizome. These groups were differentiated by structural differences on the heptane skeletons, whereas homologs within each group differed by substitution patterns on the aromatic rings. Diagnostic fragmentation behavior in (+)- and (-)ESI-MS/MS analyses for each group of homologs, as well as information regarding polarity obtained from retention time data, allowed us to classify compounds by group and identify them based on key structural features.
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use of liquid chromatography electrospray ionization tandem mass spectrometry to identify Diarylheptanoids in turmeric curcuma longa l rhizome
Journal of Chromatography A, 2006Co-Authors: Hongliang Jiang, Barbara N Timmermann, David R GangAbstract:LC-ESI-MS/MS coupled to DAD analysis was used as an on-line tool for identification of Diarylheptanoids in fresh turmeric rhizome extracts. Based on their mass spectra, from both negative and positive mode LC-ESI-MS/MS analysis, and supported by their DAD spectra, 19 Diarylheptanoids were identified. Among these 19 compounds, curcumin, demethoxycurcumin, and bisdemethoxycurcumin were identified by comparing their chromatographic and spectral data with those of authentic standard compounds. The other Diarylheptanoid compounds were identified or tentatively identified based on comparison to the three curcuminoids and each other. Twelve of the identified Diarylheptanoids have not been previously reported from turmeric and six of these are new compounds.
Masayuki Yoshikawa - One of the best experts on this subject based on the ideXlab platform.
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Diarylheptanoids with inhibitory effects on melanogenesis from the rhizomes of curcuma comosa in b16 melanoma cells
Bioorganic & Medicinal Chemistry Letters, 2013Co-Authors: Takahiro Matsumoto, Masayuki Yoshikawa, Seikou Nakamura, Souichi Nakashima, Katsuyoshi Fujimoto, Tomoe Ohta, Azumi Morita, Rie Yasui, Eri Kashiwazaki, Hisashi MatsudaAbstract:Abstract The methanolic extract from the dried rhizomes of Curcuma comosa cultivated in Thailand was found to inhibit melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the methanolic extract, three new Diarylheptanoids, diarylcomosols I–III, were isolated together with 12 known Diarylheptanoids. Their chemical structures were elucidated on the basis of chemical and physicochemical evidence. The Diarylheptanoids inhibited melanogenesis, and several structural requirements of the active constituents for the inhibition were clarified. In particular, (3 R )-1,7-bis(4-hydroxyphenyl)-(6 E )-6-hepten-3-ol exhibited stronger inhibitory effect [IC 50 = 0.36 μM] without inducing cytotoxicity. The biological effect was much stronger than that of a reference compound, arbutin [IC 50 = 174 μM]. We conclude that Diarylheptanoid analogs are promising therapeutic agents for the treatment of skin disorders.
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structures of new cyclic Diarylheptanoids and inhibitors of nitric oxide production from japanese folk medicine acer nikoense
Journal of Natural Products, 2003Co-Authors: Toshio Morikawa, Iwao Toguchida, Hisashi Matsuda, Masayuki YoshikawaAbstract:Three new cyclic Diarylheptanoids, acerosides B1 and B2 and aceroketoside, were isolated together with 20 known compounds from a Japanese folk medicine, the stem bark of Acer nikoense. The absolute stereostructures of the new compounds were determined on the basis of chemical and physicochemical evidence. In addition, the principal Diarylheptanoid constituents were found to exhibit inhibitory activity on nitric oxide production in lipopolysaccharide-activated macrophages.
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inhibitors of nitric oxide production from the bark of myrica rubra structures of new biphenyl type Diarylheptanoid glycosides and taraxerane type triterpene
Bioorganic & Medicinal Chemistry, 2002Co-Authors: Jing Tao, Toshio Morikawa, Iwao Toguchida, Shin Ando, Hisashi Matsuda, Masayuki YoshikawaAbstract:Abstract Three new biphenyl type Diarylheptanoid glycosides, myricanol 11-O-β- d -glucopyranoside, myricanone 5-O-β- d -glucopyranoside, and neomyricanone 5-O-β- d -glucopyranoside, and a new taraxerane type triterpene, myricetrione, were isolated from the bark of Chinese Myrica rubra. Their structures were elucidated on the basis of chemical and physicochemical evidence. Biphenyl type Diarylheptanoids, triterpene, and their polyphenols showed potent inhibitory effects on nitric oxide production in lipopolysaccharide-activated macrophages. Furthermore, Diarylheptanoids, myricanol and myricanone, were found to inhibit induction of inducible nitric oxide synthase.
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bioactive constituents of chinese natural medicines vii inhibitors of degranulation in rbl 2h3 cells and absolute stereostructures of three new Diarylheptanoid glycosides from the bark of myrica rubra
Chemical & Pharmaceutical Bulletin, 2002Co-Authors: Hisashi Matsuda, Jing Tao, Toshio Morikawa, Kazuho Ueda, Masayuki YoshikawaAbstract:Three new Diarylheptanoid glycosides, named (+)-S-myricanol 5-0-beta-D-glucopyranoside, myricanene A 5-O-alpha-L-arabinofuranosyl(1-->6)-beta-D-glucopyranoside, and myricanene B 5-0-alpha-L-arabinofuranosyl(1-->6)-beta-D-glucopyranoside, were isolated from the bark of Chinese Myrica rubra, together with twenty known compounds. The absolute stereostructures of the new Diarylheptanoid glycosides were elucidated on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method. The inhibitory effects of isolated constituents on the release of beta-hexosaminidase from RBL-2H3 cells were examined, and several Diarylheptanoids, myricanol, (+)-S-myricanol, myricanone, and myricanenes A and B, and a flavonol, myricetin, were found to show the inhibitory activity.
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stomachic principles in ginger ii pungent and anti ulcer effects of low polar constituents isolated from ginger the dried rhizoma of zingiber officinale roscoe cultivated in taiwan the absolute stereostructure of a new Diarylheptanoid
Yakugaku Zasshi-journal of The Pharmaceutical Society of Japan, 1992Co-Authors: Johji Yamahara, Shoko Hatakeyama, Kumiko Taniguchi, Meri Kawamura, Masayuki YoshikawaAbstract:By using the effects on HCl/ethanol-induced gastric lesions in rats, beta-sesquiphellandrene (2), beta-bisabolene (3), ar-curcumene (4) and 6-shogaol (5) were isolated as anti-ulcer active principles in ginger, the dried rhizoma of Zingiber officinale Roscoe (Shokyo in Japanese) which was cultivated in Taiwan, together with nine known compounds and a new Diarylheptanoid. The absolute stereostructure of the Diarylheptanoid was characterized as (3S,5S)-dihydroxy 1-(4'-hydroxy-3',5'-dimethoxyphenyl)-7-(4''-hydrox y-3''-methoxyphenyl)heptane (15) on the basis of chemical and spectroscopic evidence which included the application of the benzoate chirality method. The pungent effects of several constituents isolated from ginger were examined.