Ecdysteroid Profiles of Two Ajuga species, A. iva and A. remota

Abstract

Phytoecdysteroids are plant analogues of insect moulting hormones and are used by plants to repel or disturb phytophagous insects. They are also active on mammals and present in many plants used in traditional medicine. The Ajuga genus contains several such species, which occur in various pharmacopoeias. We report the isolation and identification of major and minor ecdysteroids present in two Ajuga species, A. iva and A. remota, both of which are used as medicinal plants in Africa. Three minor ecdysteroids (abutasterone, ponasterone A and sidisterone) have been found for the first time in the Ajuga genus.

Chemical Composition, Antioxidant, and Antimicrobial Activities of Leaves of Ajuga Iva

“…Moreover, high levels of campestanol trans -ferulate were found. This is consistent with the general abundance of Ajuga plants in phytoecdysteroids 20-hydroxyecdysone [ 67 , 68 ].…”

Anti-inflammatory neo-Clerodane Diterpenoids from Ajuga pantantha

“…Ajuga Linn., a member of the Labiatae family, comprises approximately 50 species that are primarily dispersed in temperate regions of Eurasia . Several Ajuga species have been employed to treat inflammation and infectious diseases. − Previous phytochemical investigations of this genus of plants resulted in the isolation of diterpenoids, − particularly neo -clerodane diterpenoids, steroids, ,− and iridoids, ,, which displayed extensive biological effects, − such as antibacterial, insect antifeedant, cytotoxic, and vasoconstrictor activities.…”

The minor ecdysteroids from Ajuga turkestanica

“…This is confirmed from HMBC observed with 1 H of 26, 27, 28 methyl signals with the same 13 C NMR signal at 76.4 ppm thus assigned unambiguously to C‐25. Moreover, 1 H‐ and 13 C‐NMR signals of the side‐chain are identical with those of makisterone A, both recorded in D 2 O (Bakrim et al ., ), suggesting that the configuration of the asymmetric centre at C‐24 is equivalent for these two compounds. Thus, the structure was assigned as 25‐hydroxy‐atrotosterone A.…”

“…These elements suggest that a cyclic structure is present in the sidechain, corresponding to a five-membered lactone ring with a double bond between C-22 and C-23, similar to that of sidisterone (Girault et al, 1996). Comparison with 1D and 2D 1 H-and 13 C-NMR data for the side-chain of sidisterone in D 2 O (Bakrim et al, 2014) shows perfect agreement indicating that the compound is 11-hydroxysidisterone and suggesting that the configuration of the asymmetric centre at C-20 is equivalent for these two compounds. figure s8) shows disappearance of the 1 H signal for 22-H and large high frequencies (downfield) shifts of both 23-Ha,b of the side-chain (2.79 ppm) with respect to turkesterone.…”