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Two new secondary metabolites isolated from Avena sativa L. (Oat) seedlings and their effects on osteoblast differentiation
[Display omitted] Seedlings of natural crops are valuable sources of pharmacologically active phytochemicals. In this study, we aimed to identify new active secondary metabolites in Avena sativa L. (oat) seedlings. Two new compounds, avenafuranol (1) and diosgenoside (2), along with eight known comp...
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Published in: | Bioorganic & medicinal chemistry letters 2020-07, Vol.30 (14), p.127250-127250, Article 127250 |
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creator | Woo, So-Yeun Lee, Kwang-Sik Shin, Hye-Lim Kim, Shin-Hye Lee, Mi-Ja Young Kim, Hyun Ham, Hyeonmi Lee, Dong-Jin Choi, Sik-Won Seo, Woo Duck |
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Seedlings of natural crops are valuable sources of pharmacologically active phytochemicals. In this study, we aimed to identify new active secondary metabolites in Avena sativa L. (oat) seedlings. Two new compounds, avenafuranol (1) and diosgenoside (2), along with eight known compounds (3–10) were isolated from the A. sativa L. seedlings. Their chemical structures were elucidated via 1D and 2D NMR spectroscopy, high-resolution ESIMS, IR spectroscopy, optical rotation analysis, and comparisons with the reported literature. The effect of each isolated compound on alkaline phosphatase (ALP) activity for osteoblast differentiation induced by bone morphogenetic protein-2 (BMP-2) was investigated using the C2C12 immortal mouse myoblast cell line. Compounds 1, 4, 6, 8, and 9 induced dose-dependent increases in ALP expression relative to ALP expression in cells treated with only BMP-2, and no cytotoxicity was observed. These results suggest that A. sativa L. seedlings are a natural source of compounds that may be useful for preventing bone disorders. |
doi_str_mv | 10.1016/j.bmcl.2020.127250 |
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Seedlings of natural crops are valuable sources of pharmacologically active phytochemicals. In this study, we aimed to identify new active secondary metabolites in Avena sativa L. (oat) seedlings. Two new compounds, avenafuranol (1) and diosgenoside (2), along with eight known compounds (3–10) were isolated from the A. sativa L. seedlings. Their chemical structures were elucidated via 1D and 2D NMR spectroscopy, high-resolution ESIMS, IR spectroscopy, optical rotation analysis, and comparisons with the reported literature. The effect of each isolated compound on alkaline phosphatase (ALP) activity for osteoblast differentiation induced by bone morphogenetic protein-2 (BMP-2) was investigated using the C2C12 immortal mouse myoblast cell line. Compounds 1, 4, 6, 8, and 9 induced dose-dependent increases in ALP expression relative to ALP expression in cells treated with only BMP-2, and no cytotoxicity was observed. These results suggest that A. sativa L. seedlings are a natural source of compounds that may be useful for preventing bone disorders.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2020.127250</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Alkaline phosphatase (ALP) activity ; Avena sativa L ; Oat ; Osteoblast ; Osteoporosis ; Seedlings</subject><ispartof>Bioorganic & medicinal chemistry letters, 2020-07, Vol.30 (14), p.127250-127250, Article 127250</ispartof><rights>2020 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c333t-7cf0dd59fc2a607f8d455f36b41333a95b51b3a797e0794be2a0af154540f93d3</citedby><cites>FETCH-LOGICAL-c333t-7cf0dd59fc2a607f8d455f36b41333a95b51b3a797e0794be2a0af154540f93d3</cites><orcidid>0000-0003-0443-9865 ; 0000-0003-1726-2536 ; 0000-0001-7394-5636</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,27911,27912</link.rule.ids></links><search><creatorcontrib>Woo, So-Yeun</creatorcontrib><creatorcontrib>Lee, Kwang-Sik</creatorcontrib><creatorcontrib>Shin, Hye-Lim</creatorcontrib><creatorcontrib>Kim, Shin-Hye</creatorcontrib><creatorcontrib>Lee, Mi-Ja</creatorcontrib><creatorcontrib>Young Kim, Hyun</creatorcontrib><creatorcontrib>Ham, Hyeonmi</creatorcontrib><creatorcontrib>Lee, Dong-Jin</creatorcontrib><creatorcontrib>Choi, Sik-Won</creatorcontrib><creatorcontrib>Seo, Woo Duck</creatorcontrib><title>Two new secondary metabolites isolated from Avena sativa L. (Oat) seedlings and their effects on osteoblast differentiation</title><title>Bioorganic & medicinal chemistry letters</title><description>[Display omitted]
Seedlings of natural crops are valuable sources of pharmacologically active phytochemicals. In this study, we aimed to identify new active secondary metabolites in Avena sativa L. (oat) seedlings. Two new compounds, avenafuranol (1) and diosgenoside (2), along with eight known compounds (3–10) were isolated from the A. sativa L. seedlings. Their chemical structures were elucidated via 1D and 2D NMR spectroscopy, high-resolution ESIMS, IR spectroscopy, optical rotation analysis, and comparisons with the reported literature. The effect of each isolated compound on alkaline phosphatase (ALP) activity for osteoblast differentiation induced by bone morphogenetic protein-2 (BMP-2) was investigated using the C2C12 immortal mouse myoblast cell line. Compounds 1, 4, 6, 8, and 9 induced dose-dependent increases in ALP expression relative to ALP expression in cells treated with only BMP-2, and no cytotoxicity was observed. These results suggest that A. sativa L. seedlings are a natural source of compounds that may be useful for preventing bone disorders.</description><subject>Alkaline phosphatase (ALP) activity</subject><subject>Avena sativa L</subject><subject>Oat</subject><subject>Osteoblast</subject><subject>Osteoporosis</subject><subject>Seedlings</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kE1LJDEQhsPiwo6uf2BPOeqhZ5N00j0BLyLuBwx4ccFbSCeVNUN3oqk4Iv75zTCe91RQ9T4v1EPIN87WnPHh-249LW5eCybaQoxCsU9kxeUgu14ydUJWTA-s22j58IWcIu4Y45JJuSLv96-ZJnilCC4nb8sbXaDaKc-xAtKIebYVPA0lL_R6D8lStDXuLd2u6cWdrZeNBD_H9BepTZ7WR4iFQgjgKtKcaMYKeZotVupjWxdINbaKnL6Sz8HOCOcf84z8-XF7f_Or2979_H1zve1c3_e1G11g3isdnLADG8PGS6VCP0ySt7vValJ86u2oR2CjlhMIy2zgSirJgu59f0Yujr1PJT-_AFazRHQwzzZBfkEjJBdat9JNi4pj1JWMWCCYpxKXZsVwZg6mzc4cTJuDaXM03aCrIwTtiX2EYtBFSA58LM2C8Tn-D_8HDuaIaQ</recordid><startdate>20200715</startdate><enddate>20200715</enddate><creator>Woo, So-Yeun</creator><creator>Lee, Kwang-Sik</creator><creator>Shin, Hye-Lim</creator><creator>Kim, Shin-Hye</creator><creator>Lee, Mi-Ja</creator><creator>Young Kim, Hyun</creator><creator>Ham, Hyeonmi</creator><creator>Lee, Dong-Jin</creator><creator>Choi, Sik-Won</creator><creator>Seo, Woo Duck</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-0443-9865</orcidid><orcidid>https://orcid.org/0000-0003-1726-2536</orcidid><orcidid>https://orcid.org/0000-0001-7394-5636</orcidid></search><sort><creationdate>20200715</creationdate><title>Two new secondary metabolites isolated from Avena sativa L. (Oat) seedlings and their effects on osteoblast differentiation</title><author>Woo, So-Yeun ; Lee, Kwang-Sik ; Shin, Hye-Lim ; Kim, Shin-Hye ; Lee, Mi-Ja ; Young Kim, Hyun ; Ham, Hyeonmi ; Lee, Dong-Jin ; Choi, Sik-Won ; Seo, Woo Duck</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c333t-7cf0dd59fc2a607f8d455f36b41333a95b51b3a797e0794be2a0af154540f93d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkaline phosphatase (ALP) activity</topic><topic>Avena sativa L</topic><topic>Oat</topic><topic>Osteoblast</topic><topic>Osteoporosis</topic><topic>Seedlings</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Woo, So-Yeun</creatorcontrib><creatorcontrib>Lee, Kwang-Sik</creatorcontrib><creatorcontrib>Shin, Hye-Lim</creatorcontrib><creatorcontrib>Kim, Shin-Hye</creatorcontrib><creatorcontrib>Lee, Mi-Ja</creatorcontrib><creatorcontrib>Young Kim, Hyun</creatorcontrib><creatorcontrib>Ham, Hyeonmi</creatorcontrib><creatorcontrib>Lee, Dong-Jin</creatorcontrib><creatorcontrib>Choi, Sik-Won</creatorcontrib><creatorcontrib>Seo, Woo Duck</creatorcontrib><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Woo, So-Yeun</au><au>Lee, Kwang-Sik</au><au>Shin, Hye-Lim</au><au>Kim, Shin-Hye</au><au>Lee, Mi-Ja</au><au>Young Kim, Hyun</au><au>Ham, Hyeonmi</au><au>Lee, Dong-Jin</au><au>Choi, Sik-Won</au><au>Seo, Woo Duck</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Two new secondary metabolites isolated from Avena sativa L. (Oat) seedlings and their effects on osteoblast differentiation</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><date>2020-07-15</date><risdate>2020</risdate><volume>30</volume><issue>14</issue><spage>127250</spage><epage>127250</epage><pages>127250-127250</pages><artnum>127250</artnum><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
Seedlings of natural crops are valuable sources of pharmacologically active phytochemicals. In this study, we aimed to identify new active secondary metabolites in Avena sativa L. (oat) seedlings. Two new compounds, avenafuranol (1) and diosgenoside (2), along with eight known compounds (3–10) were isolated from the A. sativa L. seedlings. Their chemical structures were elucidated via 1D and 2D NMR spectroscopy, high-resolution ESIMS, IR spectroscopy, optical rotation analysis, and comparisons with the reported literature. The effect of each isolated compound on alkaline phosphatase (ALP) activity for osteoblast differentiation induced by bone morphogenetic protein-2 (BMP-2) was investigated using the C2C12 immortal mouse myoblast cell line. Compounds 1, 4, 6, 8, and 9 induced dose-dependent increases in ALP expression relative to ALP expression in cells treated with only BMP-2, and no cytotoxicity was observed. These results suggest that A. sativa L. seedlings are a natural source of compounds that may be useful for preventing bone disorders.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.bmcl.2020.127250</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0003-0443-9865</orcidid><orcidid>https://orcid.org/0000-0003-1726-2536</orcidid><orcidid>https://orcid.org/0000-0001-7394-5636</orcidid></addata></record> |
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subjects | Alkaline phosphatase (ALP) activity Avena sativa L Oat Osteoblast Osteoporosis Seedlings |
title | Two new secondary metabolites isolated from Avena sativa L. (Oat) seedlings and their effects on osteoblast differentiation |
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