Ecdysteroids of Vitex scabra Stem Bark

Abstract

Two new ecdysteroids, 24-epi-pinnatasterone (1) and scabrasterone (2), together with 11 known ecdysteroids, calonysterone, pterosterone, 24-epi-makisterone A, 20-hydroxyecdysone (3), polypodine B, ajugasterone C, pinnatasterone (4), 11alpha-hydroxyecdysone, 24-epi-abutasterone, 20,26-dihydroxyecdysone, and turkesterone (5), were isolated from the stem bark of Vitex scabra. This plant species contained a very high concentration (1.8%) of 3 and thus provided a good source of this parent ecdysteroid and related rare ecdysteroids. Compounds 1 and 2 exhibited very low moulting activity in the Musca bioassay. The low biological activity of these two ecdysteroids was in agreement with those of other 22-deoxyecdysteroids.

Ecdysteroids from Vitex Species: Distribution and Compilation of Their 13C‐NMR Spectral Data

“…-An extensive literature search was undertaken to identify studies on ecdysteroids in works such as periodicals, data banks such as NAPRALERT (Natural Products Alert) and that at the University of Illinois, Chicago, Chemical (24) [ 2 ] 24-Epimakisterone A (8) [ 8 ] Calonysterone (9) [8] [10] Turkesterone (2) [ 8 ] [ 9 ] 24-Epiabutasterone (11) [ 8 ] Shidasterone (5) [ 8 ] 20,26-Dihydroxyecdysone (19) [11] (24R )-11a,20,24-Trihydroxyecdysone (17) [12] 11a,20,26-Trihydroxyecdysone (15) [12] Canescensterone (4) [ (13) [24] Calonysterone (9) [24] Pterosterone (22) [24] 24-Epimakisterone A (8) [24] 20-Hydroxyecdysone (1) [24] Polypodine B (23) [24] Ajugasterone C (6) [24] Pinnatasterone (3)…”

Ecdysteroids from leaves of Vitex trifolia

“…Ecdysone ( [4] , ¥ δ C of 20-hydroxyecdysone [5] , $ δ C of 20-hydroxyecdysone-2,3-monoacetonide [6] , Ψ δ C of turkesterone [7] , *overlapped signals. [4] .…”

“…All NMR assignments of 2 were confirmed by detailed analyses of HSQC and HMBC spectra, which are in good agreement with those reported in literature. [5] Thus, compound 2 was identified as 20hydroxyecdysone. Previously, this compound was isolated from V. canescens [9] and V. leptobotrys.…”

“…[7] From the above evidence, compound 4 was identified as turkesterone, a compound was also isolated from V. scabra. [5] .…”

Absolute Configuration and Docking Study of Canescensterone, a Potent Phytoecdysteroid, with Non‐Lepidopteran Ecdysteroid Receptor Selectivity

“…[24,27] In the past, differences in chemical shifts were used to identify the configuration at C-24. [28] However, some ecdysteroids show negligible differences in their 13 C chemical shifts even though they represent epimers (e.g., 20,26-dihydroxyecdysone). [29] On the basis of our study we therefore anticipate that by a similar approach to that shown for canescensterone, the configuration at C-24 should be determined unambiguously.…”