{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,11,2]],"date-time":"2026-11-02T17:56:21Z","timestamp":1793642181931,"version":"4.5.1"},"reference-count":37,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2020,1,9]],"date-time":"2020-01-09T00:00:00Z","timestamp":1578528000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Gifu University (COC project)","award":["COC project H30"],"award-info":[{"award-number":["COC project H30"]}]},{"name":"The Japanese Foundation for Applied Enzymology","award":["H30"],"award-info":[{"award-number":["H30"]}]},{"name":"The Ogawa Science and Technology Foundation","award":["H30"],"award-info":[{"award-number":["H30"]}]},{"name":"The Koshiyama Research Grant","award":["H30 R1"],"award-info":[{"award-number":["H30 R1"]}]},{"name":"Gifu City","award":["R1-2"],"award-info":[{"award-number":["R1-2"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Foods"],"abstract":"<jats:p>Background: Ent-11\u03b1-hydroxy-15-oxo-kaur-16-en-19-oic acid (11\u03b1OH-KA) is a multifunctional biochemical found in some ferns, Pteris semipinnata, and its congeneric species. Although a number of therapeutic applications of 11\u03b1OH-KA have been proposed (e.g., anti-cancer, anti-inflammation, and skin whitening), the content of 11\u03b1OH-KA in these ferns is not high. Adenostemma lavenia (L.) O. Kuntze, an Asteraceae, has also been reported to contain 11\u03b1OH-KA. The decoction (hot water extract) of whole plants of A. lavenia is used as a folk remedy for inflammatory disorders, such as hepatitis and pneumonia, suggesting that 11\u03b1OH-KA may be the ingredient responsible for the medicinal properties of this plant. Methods: The anti-melanogenic activities of the water extracts of A. lavenia leaves and Pteris dispar Kunze (a cognate of P. semipinnata) leaves were compared in mouse B16F10 melanoma cells. The amount of 11\u03b1OH-KA was measured by using liquid chromatography spectrometry. C57BL\/6J mice were treated with the water extract of A. lavenia leaf, and the blood concentration of 11\u03b1OH-KA was measured. The in vivo efficacy of the water extract of A. lavenia leaf was evaluated according to tis anti-melanogenic activity by monitoring hair color. Results: Although both the extracts (A. lavenia and P. dispar Kunze) showed high anti-melanogenic activities, only A. lavenia contained a high amount of 11\u03b1OH-KA, approximately 2.5% of the dry leaf weight. 11\u03b1OH-KA can be purified from A. lavenia leaves in two steps: water extraction followed by chloroform distribution. The treatment of mice with the water extract of A. lavenia leaf suppresses pigmentation in their hairs. Conclusions: Despite the small number of mice examined, the present preliminary result of the suppressed hair pigmentation suggests that the water extract of A. lavenia leaf and the ingredient that is possibly responsible for this\u201411\u03b1OH-KA\u2014are new materials for oral cosmetics. The results may also be helpful in the future development of functional foods and methods to treat patients suffering from hyperpigmentation disorders, such as melasma.<\/jats:p>","DOI":"10.3390\/foods9010073","type":"journal-article","created":{"date-parts":[[2020,1,10]],"date-time":"2020-01-10T04:06:51Z","timestamp":1578629211000},"page":"73","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["The High Content of Ent-11\u03b1-hydroxy-15-oxo-kaur- 16-en-19-oic Acid in Adenostemma lavenia (L.) O. Kuntze Leaf Extract: With Preliminary in Vivo Assays"],"prefix":"10.3390","volume":"9","author":[{"given":"Akie","family":"Hamamoto","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ryosuke","family":"Isogai","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miwa","family":"Maeda","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masumi","family":"Hayazaki","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Eito","family":"Horiyama","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2273-1643","authenticated-orcid":false,"given":"Shigeo","family":"Takashima","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1496-2177","authenticated-orcid":false,"given":"Mamoru","family":"Koketsu","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1815-2964","authenticated-orcid":false,"given":"Hiroshi","family":"Takemori","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,1,9]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"607","DOI":"10.1016\/j.foodchem.2017.08.002","article-title":"A major daidzin metabolite 7,8,4\u2019-trihydroxyisoflavone found in the plasma of soybean extract-fed rats attenuates monocyte-endothelial cell adhesion","volume":"240","author":"Lee","year":"2018","journal-title":"Food Chem."},{"key":"ref_2","first-page":"541","article-title":"Effects of antitumor compounds isolated from Pteris semipinnata L on DNA topoisomerases and cell cycle of HL-60 cells","volume":"20","author":"Li","year":"1999","journal-title":"Zhongguo Yao Li Xue Bao"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"484","DOI":"10.1248\/cpb.59.484","article-title":"Pterisolic acids A-F, new ent-kaurane diterpenoids from the fern Pteris semipinnata","volume":"59","author":"Wang","year":"2011","journal-title":"Chem. 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