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die wirkung von rohpressaften und rohextrakten aus Ajuga arten auf frasaktivitat und metamorphose von epilachna varivestis muls

The effect of squeezed juices and crude extracts of Ajuga species on feeding activity and metamorphosis of Epilachna varivestis (Col., Coccinellidae)

The effect of fresh, squeezed plant juices and that of crude extracts from dried parts of Ajuga reptans and A. remota on the feeding activity and metamorphosis of Epilachna varivestis was investigated by means of various testing methods.

Squeezed plant juices and crude plant extracts cause a strong antifeedant effect. The causal agents are most probably Ajugarins, at least in case of A. remota. Furthermore, the metamorphosis is strongly influenced by the extracts, leading to high larval and pupal mortalities, the appearance of pupal-adult specimens and of beetles showing more or less deformed wings. The growth-regulating effect is presumedly caused by ecdysoids, primarily ecdysterone.

Zusammenfassung

Die Wirkung von Pressaften aus frischen und von Rohextrakten aus getrockneten Teilen von Ajuga reptans und A. remota auf die Frasaktivitat und Metamorphose von Epilachna varivestis wurde mit Hilfe verschiedener Testmethoden untersucht.

Pressafte und Rohextrakte bewirken eine deutliche Frashemmung, die zumindest bei A. remota wahrscheinlich auf Ajugarine zuruckgefuhrt werden konnen. Auserdem wird die Metamorphose stark beeinflust, was zu hoher Larven- und Puppenmortalitat sowie zur Entstehung sog. pupal-adulter Tiere und zu Kafern mit mehr oder weniger stark deformierten Flugeln fuhrt. Die metamorphosestorende Wirkung ist mit groser Wahrscheinlichkeit auf die in den Ajuga-Arten enthaltenen Ecdysoide, insbesondere das Ecdysteron zuruckzufuhren.

Die Wirkung von Rohpreßsäften und Rohextrakten aus Ajuga‐Arten auf Fraßaktivität und Metamorphose von Epilachna varivestis Muls

The effect of squeezed juices and crude extracts of Ajuga species on feeding activity and metamorphosis of Epilachna varivestis (Col., Coccinellidae)

The effect of fresh, squeezed plant juices and that of crude extracts from dried parts of Ajuga reptans and A. remota on the feeding activity and metamorphosis of Epilachna varivestis was investigated by means of various testing methods.

Squeezed plant juices and crude plant extracts cause a strong antifeedant effect. The causal agents are most probably Ajugarins, at least in case of A. remota. Furthermore, the metamorphosis is strongly influenced by the extracts, leading to high larval and pupal mortalities, the appearance of pupal-adult specimens and of beetles showing more or less deformed wings. The growth-regulating effect is presumedly caused by ecdysoids, primarily ecdysterone.

Zusammenfassung

Die Wirkung von Pressaften aus frischen und von Rohextrakten aus getrockneten Teilen von Ajuga reptans und A. remota auf die Frasaktivitat und Metamorphose von Epilachna varivestis wurde mit Hilfe verschiedener Testmethoden untersucht.

Pressafte und Rohextrakte bewirken eine deutliche Frashemmung, die zumindest bei A. remota wahrscheinlich auf Ajugarine zuruckgefuhrt werden konnen. Auserdem wird die Metamorphose stark beeinflust, was zu hoher Larven- und Puppenmortalitat sowie zur Entstehung sog. pupal-adulter Tiere und zu Kafern mit mehr oder weniger stark deformierten Flugeln fuhrt. Die metamorphosestorende Wirkung ist mit groser Wahrscheinlichkeit auf die in den Ajuga-Arten enthaltenen Ecdysoide, insbesondere das Ecdysteron zuruckzufuhren.

neo clerodane diterpenoids from Ajuga macrosperma var breviflora

Six new naturally occurring Ajugarin-like neo-clerodane diterpenoids, Ajugaflorins A-F, along with six known compounds [the parent Ajugarin I, Ajugalides B and C, Ajugamarin F4, Ajugamacrin E, and Ajugatakasin B] were isolated from A. macrosperma var. breviflora. The structures were elucidated by extensive NMR spectroscopic and MS analyses and comparison with data previously reported.

neo clerodane diterpenoids from Ajuga bracteosa

Different neo-clerodane diterpenoids were isolated from a dichloromethane extract of Ajuga bracteosa depending on the isolation procedure used, owing to the labile nature of these tetrahydrofurofuran derivatives. Under “hydroxyl-free” purification conditions, both clerodin- and dihydroclerodin-type diterpenes were obtained [four new compounds, ajubractins A–D (1–4), along with clerodin (5), 3-epi-caryoptin (6), Ajugapitin (7), 14,15-dihydroclerodin (8), 3-epi-14,15-dihydrocaryoptin (9), ivain II (10), and 14,15-dihydroAjugapitin (11)]. When methanol–water mixtures were used for a C18 reversed-phase prepurification procedure and for semipreparative HPLC, the new ajubractin E (12) was also isolated along with 3 and 8–11, as previously, but 7 was the only tetrahydrofurofuran derivative obtained. Epimeric (15R and 15S) mixtures were obtained instead of 14-hydro-15-hydroxyclerodin derivatives [15-hydroxyajubractin C (13), 14-hydro-15-hydroxyAjugachin A (14), and 14-hydro-15-hydroxyAjugapitin (15)], along with …

new phytoecdysteroids from cultured plants of Ajuga nipponensis makino

An extract from aerial parts of Ajuga nipponensis Makino was examined by high performance liquid chromatography for minor ecdysteroids. Along with the compounds already reported, namely cyasterone, Ajugasterone C, cyasterone 22-acetate and 22-dehydrocyasterone, the presence of three additional bands with the expected ecdysteroid-like UV absorption was observed. The structures of the isolates were unambiguously elucidated based on extensive NMR spectral studies (one and two-dimensional experiments) and pointed out three new phytoecdysteroids. One of the new compounds, 22-dehydrocyasterone 2-glucoside is just the second example of a C-2 glucosyl derivative. The other two compounds displayed hemiacetal functions in the side chain, one unprecedented, and were named Ajugacetalsterone A and B.

Phytoecdysteroids from Ajuga macrosperma var. breviflora roots.

Three new phytoecdysteroids, Ajugacetalsterones C (1) and D (3) and breviflorasterone (2), were isolated from the roots of Ajuga macrosperma var. breviflora along with five known compounds, namely, 20-hydroxyecdysone, cyasterone, makisterone A, 20-hydroxyecdysone 3-acetate, and 20-hydroxyecdysone 2-acetate. The structures of 1-3 were elucidated on the basis of extensive 1D and 2D NMR spectroscopic studies. The new compounds possess acetal oxygen bridges between C-26 and C-20/C-22, or C-26/C-23, or a lactone bridge between C-26 and C-23.

neo-Clerodane diterpenoids from Ajuga: structural elucidation and biological activity

The presence of several types of allelochemicals has been reported from Ajuga , a Labiatae genus comprising more than 40 species of wide distribution in extratropical regions of both hemispheres. The genus is of great medicinal and economic importance and among the biological properties of the secondary metabolites, the antifeedant activity against pest insects appears to be related to the presence of neo -clerodane type diterpenes. This review focuses on the isolation and structural elucidation of this type of compounds from Ajuga species and the hemisynthetic compounds of closely related structure obtained. The reported biological activity of crude extracts and isolated diterpenes will be briefly commented.

New phytoecdysteroids from roots of Ajuga reptans varieties

Abstract Reptansterone ( 8 ), a new C-29 phytoecdysteroid with a δ-lactone in the side chain, was isolated from roots of a green variety of Ajuga reptans . Likewise, other unprecedented members of this polyhydroxysteroid family namely 28- epi -sengosterone ( 9 ), 5,29-dihydroxycapitasterone ( 10 ) 2- and 3-dehydroAjugalactone ( 11 and 12 ) were isolated from A. reptans var. atropurpurea . The structures of all these new compounds were inferred from the corresponding 1 H and 13 C-NMR homo- and heterocorrelations and IR and HPLC-MS(TSP) spectral data.