Arteperoxides A–C, tris-normonoterpene–sesquiterpene conjugates with peroxide-bridges from Artemisia judaica exhibiting antiosteoclastogenic activity. (February 2023)

• Record Type: Journal Article
• Authors: El-Desoky, Ahmed H.; Asano, Toshifumi; Maeyama, Yuka; Kato, Hikaru; Hitora, Yuki; Goto, Eishu; Kotani, Shunsuke; Nakajima, Makoto; Tsukamoto, Sachiko
• Is Part Of: Phytochemistry. Volume 206(2023)
• Publication Date: 2023-02
• Subjects: Artemisia judaica L. -- Asteraceae -- Terpenoid -- Peroxide -- Antiosteoclastogenesis; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2022.113548
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Antiosteoclastogenic-guided screening was conducted with 120 extracts of the medicinal plants collected in Egypt that led to the selection of Artemisia judaica L. (Asteraceae). Three undescribed davanone-related terpenoids, arteperoxides A–C, were isolated from the extract with two known derivatives, hydroxydavanone and davana acid. Structural analysis revealed that arteperoxides A–C were tris -normonoterpene–sesquiterpene conjugates with peroxide bridges. Although davanone derivatives with peroxides, such as a hydroperoxyl and peroxyhemiketal groups, have been isolated from Artemisia species, arteperoxides A–C are the first variations observed to contain peroxide bridges between two terpene-derived units. The absolute configurations of arteperoxides A and B were studied based on their spectroscopic data compared with those of the semisynthetic analogs that have ether linkages. The natural and synthetic compounds were tested for the antiosteoclastogenic activity, and arteperoxide C and hydroxydavanone were more potent than other compounds at 20 μM. Graphical abstract: Image 1 Highlights: Antiosteoclastogenic-bioguided screening of 120 medicinal plant extracts. Artemisia judaica L. (Asteraceae) demonstrated the most potent activity. Three undescribed davanone-related terpenoids, arteperoxides A–C, were isolated. Peroxide-bridged containing structures.