{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,30]],"date-time":"2026-03-30T10:16:36Z","timestamp":1774865796412,"version":"3.50.1"},"reference-count":19,"publisher":"Oxford University Press (OUP)","issue":"9","license":[{"start":{"date-parts":[[2014,9,1]],"date-time":"2014-09-01T00:00:00Z","timestamp":1409529600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/academic.oup.com\/journals\/pages\/open_access\/funder_policies\/chorus\/standard_publication_model"}],"funder":[{"name":"Strategic Scholarships for Frontier Research Network"},{"DOI":"10.13039\/501100014795","name":"Center of Excellence for Innovation in Chemistry","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100014795","id-type":"DOI","asserted-by":"crossref"}]},{"name":"Office of the Higher Education Commission, Ministry of Education"},{"DOI":"10.13039\/501100004704","name":"National Research Council of Thailand","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100004704","id-type":"DOI","asserted-by":"crossref"}]},{"DOI":"10.13039\/501100004944","name":"Naresuan University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004944","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2014,9,1]]},"abstract":"<jats:title>Abstract<\/jats:title>\n               <jats:sec>\n                  <jats:title>Objectives<\/jats:title>\n                  <jats:p>Curcuma aeruginosa\u2005Roxb. extract is a 5\u03b1-reductase antagonist that can be used to treat hair loss. We aimed to study the stability of antiandrogenic constituents, germacrone and other sesquiterpene components in the extract.<\/jats:p>\n               <\/jats:sec>\n               <jats:sec>\n                  <jats:title>Methods<\/jats:title>\n                  <jats:p>Germacrone and the extract were analyzed as solid forms or solublized with polyethylene glycol-40 (PEG-40) or methanol using high-performance liquid chromatography and gas chromatography with flame ionization detector. The effects of pH, temperature and light on their stability were studied.<\/jats:p>\n               <\/jats:sec>\n               <jats:sec>\n                  <jats:title>Key findings<\/jats:title>\n                  <jats:p>Degradation of antiandrogenic compounds in C. aeruginosa was highly sensitive to temperature especially pure anhydrous germacrone, which was completely lost within 3 days at 45\u00b0C. Curiously, degradation was slower than as a dried extract. Paradoxically, when solubilized with PEG-40, it was largely intact even after 90 days at 45\u00b0C. The MS spectrum of a major degradation product suggested that it was elemenone probably produced by Cope rearrangement. Two other putative degradation products were germacrone-1,10-epoxide and germacrone-4,5-epoxide suggesting that oxidation of double bonds was an important mechanism. Germacrone stability was unaffected by pH (2.0\u20139.0) but only as dried extract it was slightly degraded by light.<\/jats:p>\n               <\/jats:sec>\n               <jats:sec>\n                  <jats:title>Conclusion<\/jats:title>\n                  <jats:p>Antiandrogenic constituents of C. aeruginosa were instable at high temperature and in solid form. Thus, the extract would be optimately stored as a solution or otherwise as solid form at low temperature.<\/jats:p>\n               <\/jats:sec>","DOI":"10.1111\/jphp.12216","type":"journal-article","created":{"date-parts":[[2014,6,6]],"date-time":"2014-06-06T10:35:05Z","timestamp":1402050905000},"page":"1282-1293","source":"Crossref","is-referenced-by-count":11,"title":["Stability studies of antiandrogenic compounds in <i>Curcuma aeruginosa<\/i>\u2005Roxb. extract"],"prefix":"10.1093","volume":"66","author":[{"given":"Nungruthai","family":"Suphrom","sequence":"first","affiliation":[{"name":"Bioscreening Unit, Department of Pharmaceutical Chemistry and Pharmacognosy, Naresuan University , Phitsanulok,","place":["Thailand"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jukkarin","family":"Srivilai","sequence":"additional","affiliation":[{"name":"Bioscreening Unit, Department of Pharmaceutical Chemistry and Pharmacognosy, Naresuan University , Phitsanulok,","place":["Thailand"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ganniga","family":"Pumthong","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Technology, Naresuan University , Phitsanulok,","place":["Thailand"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nantaka","family":"Khorana","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry and Pharmacognosy, Naresuan University , Phitsanulok,","place":["Thailand"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Neti","family":"Waranuch","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Technology, Naresuan University , Phitsanulok,","place":["Thailand"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nanteetip","family":"Limpeanchob","sequence":"additional","affiliation":[{"name":"Department of Pharmacy Practice, Faculty of Pharmaceutical Sciences and Center of Excellence for Innovation in Chemistry, Naresuan University , Phitsanulok,","place":["Thailand"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kornkanok","family":"Ingkaninan","sequence":"additional","affiliation":[{"name":"Bioscreening Unit, Department of Pharmaceutical Chemistry and Pharmacognosy, Naresuan University , Phitsanulok,","place":["Thailand"]}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"286","published-online":{"date-parts":[[2014,9,1]]},"reference":[{"key":"2024103109164804200_jphp12216-cit-0001","doi-asserted-by":"crossref","first-page":"433","DOI":"10.1016\/j.jep.2008.10.022","article-title":"Uterine relaxant effects of Curcuma aeruginosa Roxb. rhizome extracts","volume":"121","author":"Thaina","year":"2009","journal-title":"J Ethnopharmacol"},{"key":"2024103109164804200_jphp12216-cit-0002","first-page":"999","article-title":"Investigation the antinociceptive, antipyretic and antiinflammatory activities of Curcuma aeruginosa Roxb. extracts in experimental animals","volume":"28","author":"Reanmongkol","year":"2006","journal-title":"Songklanakarin J Sci Technol"},{"key":"2024103109164804200_jphp12216-cit-0003","first-page":"162","article-title":"Pharmacognostic evaluation of Curcuma aeurigenosa Roxb","volume":"12","author":"Srivastava","year":"2006","journal-title":"Nat Prod Sci"},{"key":"2024103109164804200_jphp12216-cit-0004","volume-title":"Mai-Tet-Muang-Thai: Medicinal Characteristic of Foreign and Thai Traditional Medicine","author":"Pongbunrod","year":"1979"},{"key":"2024103109164804200_jphp12216-cit-0005","doi-asserted-by":"crossref","first-page":"6","DOI":"10.1002\/ptr.2650090103","article-title":"Screening of Indonesian plant extracts for anti-human immunodeficiency virus-type 1 (HIV-1) activity","volume":"9","author":"Otake","year":"1995","journal-title":"Phytother Res"},{"key":"2024103109164804200_jphp12216-cit-0006","doi-asserted-by":"crossref","first-page":"1337","DOI":"10.1021\/jf00020a008","article-title":"Antioxidant activity of tropical ginger extracts and analysis of the contained curcuminoids","volume":"40","author":"Jitoe","year":"1992","journal-title":"J Agric Food Chem"},{"key":"2024103109164804200_jphp12216-cit-0007","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1016\/j.phymed.2003.06.006","article-title":"Platelet-activating factor (PAF) receptor-binding antagonist activity of Malaysian medicinal plants","volume":"12","author":"Jantan","year":"2005","journal-title":"Phytomedicine"},{"key":"2024103109164804200_jphp12216-cit-0008","doi-asserted-by":"crossref","first-page":"385","DOI":"10.3109\/09546634.2011.568470","article-title":"Curcuma aeruginosa, a novel botanically derived 5alpha-reductase inhibitor in the treatment of male-pattern baldness: a multicenter, randomized, double-blind, placebo-controlled study","volume":"23","author":"Pumthong","year":"2011","journal-title":"J Dermatol Treat"},{"key":"2024103109164804200_jphp12216-cit-0009","doi-asserted-by":"crossref","first-page":"864","DOI":"10.1016\/j.fitote.2012.03.017","article-title":"Anti-androgenic effect of sesquiterpenes isolated from the rhizomes of Curcuma aeruginosa Roxb","volume":"83","author":"Suphrom","year":"2012","journal-title":"Fitoterapia"},{"key":"2024103109164804200_jphp12216-cit-0010","doi-asserted-by":"crossref","first-page":"200","DOI":"10.1208\/pt0804105","article-title":"The solution and solid state stability and excipient compatibility of parthenolide in feverfew","volume":"8","author":"Jin","year":"2007","journal-title":"AAPS PharmSciTech"},{"key":"2024103109164804200_jphp12216-cit-0011","doi-asserted-by":"crossref","first-page":"1174","DOI":"10.1139\/v89-177","article-title":"Thermal instability of germacrone: implications for gas chromatographic analysis of thermally unstable analytes","volume":"67","author":"Reichardt","year":"1989","journal-title":"Can J Chem"},{"key":"2024103109164804200_jphp12216-cit-0012","doi-asserted-by":"crossref","first-page":"73","DOI":"10.1016\/j.jpba.2006.06.014","article-title":"Optimization of GC\u2013MS conditions based on resolution and stability of analytes for simultaneous determination of nine sesquiterpenoids in three species of Curcuma rhizomes","volume":"43","author":"Yang","year":"2007","journal-title":"J Pharm Biomed Anal"},{"key":"2024103109164804200_jphp12216-cit-0013","doi-asserted-by":"crossref","first-page":"5145","DOI":"10.1016\/j.tet.2009.04.062","article-title":"(\u2212)-trans-\u03b2-Elemene and related compounds: occurrence, synthesis, and anticancer activity","volume":"65","author":"Adio","year":"2009","journal-title":"Tetrahedron"},{"key":"2024103109164804200_jphp12216-cit-0014","doi-asserted-by":"crossref","first-page":"440","DOI":"10.1016\/j.jpba.2006.07.024","article-title":"Analysis of volatile components of Curcuma sichuanensis X. X. Chen by gas chromatography-mass spectrometry","volume":"43","author":"Zhou","year":"2007","journal-title":"J Pharm Biomed Anal"},{"key":"2024103109164804200_jphp12216-cit-0015","volume-title":"Chemicals Constituents from the Rhizomes of Curcuma Zedoaria (Christm.) Rosc. and the Stems of Citrus Medica Linn","author":"Pomkeua","year":"2010"},{"key":"2024103109164804200_jphp12216-cit-0016","doi-asserted-by":"crossref","first-page":"2059","DOI":"10.1248\/cpb.32.2059","article-title":"The absolute stereostructure of (4S,5S)-(+)-germacrone 4,5-epoxide from zedoariae rhizoma cultivated in Yukushima island","volume":"32","author":"Yoshihara","year":"1984","journal-title":"Chem Pharm Bull"},{"key":"2024103109164804200_jphp12216-cit-0017","doi-asserted-by":"crossref","first-page":"1381","DOI":"10.1104\/pp.117.4.1381","article-title":"(+)-Germacrene A biosynthesis","volume":"117","author":"de Kraker","year":"1998","journal-title":"Plant Physiol"},{"key":"2024103109164804200_jphp12216-cit-0018","doi-asserted-by":"crossref","first-page":"1533","DOI":"10.1016\/j.tet.2008.11.050","article-title":"Germacrenes A\u2013E and related compounds: thermal, photochemical and acid induced transannular cyclizations","volume":"65","author":"Adio","year":"2009","journal-title":"Tetrahedron"},{"key":"2024103109164804200_jphp12216-cit-0019","doi-asserted-by":"crossref","first-page":"7733","DOI":"10.1016\/j.tet.2007.04.037","article-title":"Conformational analysis of (+)-germacrene A by variable-temperature NMR and NOE spectroscopy","volume":"63","author":"Faraldos","year":"2007","journal-title":"Tetrahedron"}],"container-title":["Journal of Pharmacy and Pharmacology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1111%2Fjphp.12216","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1111%2Fjphp.12216","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/academic.oup.com\/jpp\/article-pdf\/66\/9\/1282\/60252879\/jphp12216.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/academic.oup.com\/jpp\/article-pdf\/66\/9\/1282\/60252879\/jphp12216.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,10,31]],"date-time":"2024-10-31T09:25:10Z","timestamp":1730366710000},"score":1,"resource":{"primary":{"URL":"https:\/\/academic.oup.com\/jpp\/article\/66\/9\/1282\/6128009"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,9,1]]},"references-count":19,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2014,9,1]]},"published-print":{"date-parts":[[2014,9,1]]}},"URL":"https:\/\/doi.org\/10.1111\/jphp.12216","relation":{},"ISSN":["2042-7158","0022-3573"],"issn-type":[{"value":"2042-7158","type":"electronic"},{"value":"0022-3573","type":"print"}],"subject":[],"published-other":{"date-parts":[[2014,9]]},"published":{"date-parts":[[2014,9,1]]}}}