{"data":{"id":"10.6084/m9.figshare.c.2112845.v1","type":"dois","attributes":{"doi":"10.6084/m9.figshare.c.2112845.v1","prefix":"10.6084","suffix":"m9.figshare.c.2112845.v1","identifiers":[],"alternateIdentifiers":[],"creators":[{"name":"Li, Jun","givenName":"Jun","familyName":"Li","affiliation":[],"nameIdentifiers":[]},{"name":"Li, Jianzu","givenName":"Jianzu","familyName":"Li","affiliation":[],"nameIdentifiers":[]},{"name":"Xu, Yuan","givenName":"Yuan","familyName":"Xu","affiliation":[],"nameIdentifiers":[]},{"name":"Wang, Yunjie","givenName":"Yunjie","familyName":"Wang","affiliation":[],"nameIdentifiers":[]},{"name":"Zhang, Luyong","givenName":"Luyong","familyName":"Zhang","affiliation":[],"nameIdentifiers":[]},{"name":"Ding, Li","givenName":"Li","familyName":"Ding","affiliation":[],"nameIdentifiers":[]},{"name":"Xuan, Yining","givenName":"Yining","familyName":"Xuan","affiliation":[],"nameIdentifiers":[]},{"name":"Pang, Tao","givenName":"Tao","familyName":"Pang","affiliation":[],"nameIdentifiers":[]},{"name":"Lin, Hansen","givenName":"Hansen","familyName":"Lin","affiliation":[],"nameIdentifiers":[]}],"titles":[{"title":"Asymmetric synthesis and biological activities of natural product (+)-balasubramide and its derivatives"}],"publisher":"Taylor \u0026 Francis","container":{},"publicationYear":2015,"subjects":[{"subject":"Biochemistry"},{"subject":"Cell Biology"},{"subject":"Neuroscience"},{"subject":"Pharmacology"},{"subject":"Biotechnology"},{"subject":"Evolutionary Biology"},{"subject":"FOS: Biological sciences","schemeUri":"http://www.oecd.org/science/inno/38235147.pdf","subjectScheme":"Fields of Science and Technology (FOS)"},{"subject":"Chemical Sciences not elsewhere classified"},{"subject":"Ecology"},{"subject":"Immunology"},{"subject":"FOS: Clinical medicine","schemeUri":"http://www.oecd.org/science/inno/38235147.pdf","subjectScheme":"Fields of Science and Technology (FOS)"}],"contributors":[],"dates":[{"date":"2015-12-05","dateType":"Created"},{"date":"2019-08-19","dateType":"Updated"},{"date":"2015","dateType":"Issued"}],"language":null,"types":{"ris":"GEN","bibtex":"misc","citeproc":"article","schemaOrg":"Collection","resourceType":"Collection","resourceTypeGeneral":"Collection"},"relatedIdentifiers":[{"relationType":"IsIdenticalTo","relatedIdentifier":"10.6084/m9.figshare.c.2112845","relatedIdentifierType":"DOI"}],"relatedItems":[],"sizes":[],"formats":[],"version":null,"rightsList":[{"rights":"Creative Commons Attribution 4.0 International","rightsUri":"https://creativecommons.org/licenses/by/4.0/legalcode","schemeUri":"https://spdx.org/licenses/","rightsIdentifier":"cc-by-4.0","rightsIdentifierScheme":"SPDX"}],"descriptions":[{"description":"The natural product (+)-balasubramide (\u003cb\u003e3j\u003c/b\u003e) and its derivatives (\u003cb\u003e3a–3i\u003c/b\u003e) were synthesized using a two-step asymmetric synthesis, and the biological activities of \u003cb\u003e3a–3j\u003c/b\u003e were determined \u003ci\u003ein vitro\u003c/i\u003e. Methyl (2S,3R)-(+)-3-phenyloxirane-2-carboxylate (\u003cb\u003e1h\u003c/b\u003e), the asymmetric synthesis of which was described in a previous paper, was selected as the starting material. Compounds \u003cb\u003e3a–3j\u003c/b\u003e were evaluated for their neuroprotective, antioxidative, and anti-neuroinflammatory effects. (+)-Balasubramide and its derivatives with different electronegative groups in the 6-phenyl ring produced little neuroprotection and antioxidation, but induced potent anti-neuroinflammatory effects in BV-2 microglial cells (with the exception of \u003cb\u003e3g)\u003c/b\u003e. Compound \u003cb\u003e3c\u003c/b\u003e, with a trifluoromethyl group in its 6-phenyl ring, was a particularly potent anti-neuroinflammatory agent. These results demonstrated that the electronegativity of the 6-phenyl ring of (+)-balasubramide is an important determinant of its inhibitory effect on neuroinflammation. More electronegative substituents result in more potent anti-neuroinflammatory effects. Moreover, cytotoxicity assays indicated no significant effects of the tested compounds.","descriptionType":"Abstract"}],"geoLocations":[],"fundingReferences":[],"xml":"PD94bWwgdmVyc2lvbj0iMS4wIiBlbmNvZGluZz0iVVRGLTgiPz4KPHJlc291cmNlIHhtbG5zPSJodHRwOi8vZGF0YWNpdGUub3JnL3NjaGVtYS9rZXJuZWwtNCIgeG1sbnM6eHNpPSJodHRwOi8vd3d3LnczLm9yZy8yMDAxL1hNTFNjaGVtYS1pbnN0YW5jZSIgeHNpOnNjaGVtYUxvY2F0aW9uPSJodHRwOi8vZGF0YWNpdGUub3JnL3NjaGVtYS9rZXJuZWwtNCBodHRwOi8vc2NoZW1hLmRhdGFjaXRlLm9yZy9tZXRhL2tlcm5lbC00LjQvbWV0YWRhdGEueHNkIj4KICA8aWRlbnRpZmllciBpZGVudGlmaWVyVHlwZT0iRE9JIj4xMC42MDg0L005LkZJR1NIQVJFLkMuMjExMjg0NS5WMTwvaWRlbnRpZmllcj4KICA8Y3JlYXRvcnM+CiAgICA8Y3JlYXRvcj4KICAgICAgPGNyZWF0b3JOYW1lPkp1biBMaTwvY3JlYXRvck5hbWU+CiAgICAgIDxnaXZlbk5hbWU+SnVuPC9naXZlbk5hbWU+CiAgICAgIDxmYW1pbHlOYW1lPkxpPC9mYW1pbHlOYW1lPgogICAgPC9jcmVhdG9yPgogICAgPGNyZWF0b3I+CiAgICAgIDxjcmVhdG9yTmFtZT5KaWFuenUgTGk8L2NyZWF0b3JOYW1lPgogICAgICA8Z2l2ZW5OYW1lPkppYW56dTwvZ2l2ZW5OYW1lPgogICAgICA8ZmFtaWx5TmFtZT5MaTwvZmFtaWx5TmFtZT4KICAgIDwvY3JlYXRvcj4KICAgIDxjcmVhdG9yPgogICAgICA8Y3JlYXRvck5hbWU+WXVhbiBYdTwvY3JlYXRvck5hbWU+CiAgICAgIDxnaXZlbk5hbWU+WXVhbjwvZ2l2ZW5OYW1lPgogICAgICA8ZmFtaWx5TmFtZT5YdTwvZmFtaWx5TmFtZT4KICAgIDwvY3JlYXRvcj4KICAgIDxjcmVhdG9yPgogICAgICA8Y3JlYXRvck5hbWU+WXVuamllIFdhbmc8L2NyZWF0b3JOYW1lPgogICAgICA8Z2l2ZW5OYW1lPll1bmppZTwvZ2l2ZW5OYW1lPgogICAgICA8ZmFtaWx5TmFtZT5XYW5nPC9mYW1pbHlOYW1lPgogICAgPC9jcmVhdG9yPgogICAgPGNyZWF0b3I+CiAgICAgIDxjcmVhdG9yTmFtZT5MdXlvbmcgWmhhbmc8L2NyZWF0b3JOYW1lPgogICAgICA8Z2l2ZW5OYW1lPkx1eW9uZzwvZ2l2ZW5OYW1lPgogICAgICA8ZmFtaWx5TmFtZT5aaGFuZzwvZmFtaWx5TmFtZT4KICAgIDwvY3JlYXRvcj4KICAgIDxjcmVhdG9yPgogICAgICA8Y3JlYXRvck5hbWU+TGkgRGluZzwvY3JlYXRvck5hbWU+CiAgICAgIDxnaXZlbk5hbWU+TGk8L2dpdmVuTmFtZT4KICAgICAgPGZhbWlseU5hbWU+RGluZzwvZmFtaWx5TmFtZT4KICAgIDwvY3JlYXRvcj4KICAgIDxjcmVhdG9yPgogICAgICA8Y3JlYXRvck5hbWU+WWluaW5nIFh1YW48L2NyZWF0b3JOYW1lPgogICAgICA8Z2l2ZW5OYW1lPllpbmluZzwvZ2l2ZW5OYW1lPgogICAgICA8ZmFtaWx5TmFtZT5YdWFuPC9mYW1pbHlOYW1lPgogICAgPC9jcmVhdG9yPgogICAgPGNyZWF0b3I+CiAgICAgIDxjcmVhdG9yTmFtZT5UYW8gUGFuZzwvY3JlYXRvck5hbWU+CiAgICAgIDxnaXZlbk5hbWU+VGFvPC9naXZlbk5hbWU+CiAgICAgIDxmYW1pbHlOYW1lPlBhbmc8L2ZhbWlseU5hbWU+CiAgICA8L2NyZWF0b3I+CiAgICA8Y3JlYXRvcj4KICAgICAgPGNyZWF0b3JOYW1lPkhhbnNlbiBMaW48L2NyZWF0b3JOYW1lPgogICAgICA8Z2l2ZW5OYW1lPkhhbnNlbjwvZ2l2ZW5OYW1lPgogICAgICA8ZmFtaWx5TmFtZT5MaW48L2ZhbWlseU5hbWU+CiAgICA8L2NyZWF0b3I+CiAgPC9jcmVhdG9ycz4KICA8dGl0bGVzPgogICAgPHRpdGxlPkFzeW1tZXRyaWMgc3ludGhlc2lzIGFuZCBiaW9sb2dpY2FsIGFjdGl2aXRpZXMgb2YgbmF0dXJhbCBwcm9kdWN0ICgrKS1iYWxhc3VicmFtaWRlIGFuZCBpdHMgZGVyaXZhdGl2ZXM8L3RpdGxlPgogIDwvdGl0bGVzPgogIDxkZXNjcmlwdGlvbnM+CiAgICA8ZGVzY3JpcHRpb24gZGVzY3JpcHRpb25UeXBlPSJBYnN0cmFjdCI+Jmx0O3AmZ3Q7VGhlIG5hdHVyYWwgcHJvZHVjdCAoKyktYmFsYXN1YnJhbWlkZSAoJmx0O2ImZ3Q7M2ombHQ7L2ImZ3Q7KSBhbmQgaXRzIGRlcml2YXRpdmVzICgmbHQ7YiZndDszYeKAkzNpJmx0Oy9iJmd0Oykgd2VyZSBzeW50aGVzaXplZCB1c2luZyBhIHR3by1zdGVwIGFzeW1tZXRyaWMgc3ludGhlc2lzLCBhbmQgdGhlIGJpb2xvZ2ljYWwgYWN0aXZpdGllcyBvZiAmbHQ7YiZndDszYeKAkzNqJmx0Oy9iJmd0OyB3ZXJlIGRldGVybWluZWQgJmx0O2kmZ3Q7aW4gdml0cm8mbHQ7L2kmZ3Q7LiBNZXRoeWwgKDJTLDNSKS0oKyktMy1waGVueWxveGlyYW5lLTItY2FyYm94eWxhdGUgKCZsdDtiJmd0OzFoJmx0Oy9iJmd0OyksIHRoZSBhc3ltbWV0cmljIHN5bnRoZXNpcyBvZiB3aGljaCB3YXMgZGVzY3JpYmVkIGluIGEgcHJldmlvdXMgcGFwZXIsIHdhcyBzZWxlY3RlZCBhcyB0aGUgc3RhcnRpbmcgbWF0ZXJpYWwuIENvbXBvdW5kcyAmbHQ7YiZndDszYeKAkzNqJmx0Oy9iJmd0OyB3ZXJlIGV2YWx1YXRlZCBmb3IgdGhlaXIgbmV1cm9wcm90ZWN0aXZlLCBhbnRpb3hpZGF0aXZlLCBhbmQgYW50aS1uZXVyb2luZmxhbW1hdG9yeSBlZmZlY3RzLiAoKyktQmFsYXN1YnJhbWlkZSBhbmQgaXRzIGRlcml2YXRpdmVzIHdpdGggZGlmZmVyZW50IGVsZWN0cm9uZWdhdGl2ZSBncm91cHMgaW4gdGhlIDYtcGhlbnlsIHJpbmcgcHJvZHVjZWQgbGl0dGxlIG5ldXJvcHJvdGVjdGlvbiBhbmQgYW50aW94aWRhdGlvbiwgYnV0IGluZHVjZWQgcG90ZW50IGFudGktbmV1cm9pbmZsYW1tYXRvcnkgZWZmZWN0cyBpbiBCVi0yIG1pY3JvZ2xpYWwgY2VsbHMgKHdpdGggdGhlIGV4Y2VwdGlvbiBvZiAmbHQ7YiZndDszZykmbHQ7L2ImZ3Q7LiBDb21wb3VuZCAmbHQ7YiZndDszYyZsdDsvYiZndDssIHdpdGggYSB0cmlmbHVvcm9tZXRoeWwgZ3JvdXAgaW4gaXRzIDYtcGhlbnlsIHJpbmcsIHdhcyBhIHBhcnRpY3VsYXJseSBwb3RlbnQgYW50aS1uZXVyb2luZmxhbW1hdG9yeSBhZ2VudC4gVGhlc2UgcmVzdWx0cyBkZW1vbnN0cmF0ZWQgdGhhdCB0aGUgZWxlY3Ryb25lZ2F0aXZpdHkgb2YgdGhlIDYtcGhlbnlsIHJpbmcgb2YgKCspLWJhbGFzdWJyYW1pZGUgaXMgYW4gaW1wb3J0YW50IGRldGVybWluYW50IG9mIGl0cyBpbmhpYml0b3J5IGVmZmVjdCBvbiBuZXVyb2luZmxhbW1hdGlvbi4gTW9yZSBlbGVjdHJvbmVnYXRpdmUgc3Vic3RpdHVlbnRzIHJlc3VsdCBpbiBtb3JlIHBvdGVudCBhbnRpLW5ldXJvaW5mbGFtbWF0b3J5IGVmZmVjdHMuIE1vcmVvdmVyLCBjeXRvdG94aWNpdHkgYXNzYXlzIGluZGljYXRlZCBubyBzaWduaWZpY2FudCBlZmZlY3RzIG9mIHRoZSB0ZXN0ZWQgY29tcG91bmRzLiZsdDsvcCZndDs8L2Rlc2NyaXB0aW9uPgogIDwvZGVzY3JpcHRpb25zPgogIDxzdWJqZWN0cz4KICAgIDxzdWJqZWN0PkJpb2NoZW1pc3RyeTwvc3ViamVjdD4KICAgIDxzdWJqZWN0PkNlbGwgQmlvbG9neTwvc3ViamVjdD4KICAgIDxzdWJqZWN0Pk5ldXJvc2NpZW5jZTwvc3ViamVjdD4KICAgIDxzdWJqZWN0PlBoYXJtYWNvbG9neTwvc3ViamVjdD4KICAgIDxzdWJqZWN0PkJpb3RlY2hub2xvZ3k8L3N1YmplY3Q+CiAgICA8c3ViamVjdD5Fdm9sdXRpb25hcnkgQmlvbG9neTwvc3ViamVjdD4KICAgIDxzdWJqZWN0PkNoZW1pY2FsIFNjaWVuY2VzIG5vdCBlbHNld2hlcmUgY2xhc3NpZmllZDwvc3ViamVjdD4KICAgIDxzdWJqZWN0PkVjb2xvZ3k8L3N1YmplY3Q+CiAgICA8c3ViamVjdD5JbW11bm9sb2d5PC9zdWJqZWN0PgogIDwvc3ViamVjdHM+CiAgPHB1Ymxpc2hlcj5UYXlsb3IgJmFtcDsgRnJhbmNpczwvcHVibGlzaGVyPgogIDxwdWJsa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