The active compounds and AChE inhibitor of the methanol extract of Adonis coerulea maxim against Psoroptes cuniculi.

Adonis coerulea Maxim. presents acaricidal activity in vitro and in vivo, and inhibits AChE and other enzymes activities. However, the active compounds against Psoroptes cuniculi were still unclear. AChE, a common acaricidal and insecticidal target, plays a key role in neural conduction of mites. In this study, using surface plasmon resonance (SPR) technology, AChE was used as a target to capture the compounds from A. coerulea methanol extract (MEAC). After calculating the affinity with molecular docking, the inhibitory effect of compounds against AChE was studied. Results showed that 27 compounds were captured by AChE and identified from MEAC by LC-MS/MS. Among of these compounds, eight compounds presented the high affinity with AChE and high scores in molecular docking assay, especially for silibinin (-12.19 kcal/mol) and vitexin (-11.72 kcal/mol). Further studies showed that although these compounds have the weak cytotoxicity against C6/36 cells, silibinin, quercetin and corilagin could inhibit AChE activity with IC50 values of 40.11 µg/mL, 46.15 µg/mL and 50.98 µg/mL, respectively. These results indicated that silibinin, quercetin and corilagin may be responsible for AChE inhibition which contributes to the acaricidal properties of A coerulea. This study lays the foundation for developing sensitive and sustainability methods for active compound detection from plants.

Multioside, an active ingredient from adonis amurensis, displays anti-cancer activity through autophagosome formation.

BACKGROUND: Adonis amurensis Regel & Radde, commonly found in East Asia, has been traditionally used to treat cardiac insufficiency and edema. Although this plant extract has been shown to regulate cell growth and neovascularization, the anti-cancer mechanism of A. amurensis has not been fully investigated. PURPOSE: In this study, we aimed to examine the anti-cancer activity of A. amurensis and identify its underlying mechanism. METHODS: The growth of cancer cells was evaluated by MTT and hollow fiber assays. A cancer xenograft nude mouse model was used to assess the anti-cancer activities in vivo. Autophagic activity was measured by the detection of autophagosome formation and by performing a monodansylcadaverine (MDC) assay. RESULT: A. amurensis extract showed potent anti-cancer activity both in vitro and in vivo. Importantly, the treatment of cancer cells with A. amurensis extract dramatically increased the formation of autophagosomes and was involved in the activation of multiple signaling components including AKT, ERK, and MAPK. Furthermore, we isolated an active ingredient, Multioside, which exhibited strong anti-cancer activity through autophagy. CONCLUSION: A. amurensis displays anti-cancer activity that is mediated by the activation of autophagy, suggesting that A. amurensis could be a useful therapeutic anti-cancer agent.

Aestivalosides A-L, twelve pregnane glycosides from the seeds of Adonis aestivalis.

Eight adonilide (14,20α-epoxy-3ß,20-dihydroxy-14ß-pregn-5-en-18-oic acid γ-lactone) glycosides, named aestivalosides A-H, and four glycosides of the adonilide derivatives, named aestivalosides I-L, were isolated from the MeOH extract of seeds of Adonis aestivalis. Aestivalosides A-L were previously undescribed compounds, and were structurally characterized using spectroscopic techniques, including two-dimensional NMR, and chemical methods.

The toxicity and the acaricidal mechanism against Psoroptes cuniculi of the methanol extract of Adonis coerulea Maxim.

SCOPE: Adonis coerulea Maxim. is a perennial herbaceous plant that grows in scrub, grassy slope areas, and as traditional medicine it has been used to treat animal acariasis for thousands of years. In this paper, we aimed to study the acute toxicity and cytotoxicity of the methanol extract of A. coerulea (MEAC) in vivo and in vitro for supporting the clinic uses. The acaricidal activity and the mechanism of action against Psoroptes cuniculi were investigated. RESULTS: The results showed that isoorientin, luteolin and apigenin were the primary compounds in MEAC. The toxicity test showed that median lethal dose (LD50) and the 50% inhibitory concentration (IC50) of MEAC were estimated to be more than 5000mg/kg in mice in vivo and more than 50mg/ml against RAW 264.7 and GM00637 cells in the 3-(4, 5-dimethylthiazol-2- yl)-2,5-diphenyltetrazolium bromide (MTT) test. After culturing with MEAC, the activities of superoxide dismutase (SOD), catalase (CAT), malonyldialdehyde (MDA), glutathione-S-transferase (GST), acetylcholinesterase (AChE) and Na+-K+-ATPase of mites were evaluated. Compared with the control group, SOD activity of MEAC-treated group of mites was inhibited, and CAT activity was activated at the preliminary phase but was gradually inhibited over the period of incubation. MDA content reached a peak at 6h and then gradually decreased. However, GST activity in the mites was activated in a dose- and time-dependent manner. AChE and Na+-K+-ATPase activities related to neural conduction, vital functions and the transmembrane ion gradient of the mites were inhibited. CONCLUSION: MEAC is safe in the given doses in both the in vitro and the in vivo tests, can be applied in the clinic and it had good acaricidal activity. The extension of the incubation time in the mites led to dynamic disequilibrium between the production and clearing of superoxide anions, a disruption of the energy metabolism and the transmembrane ion gradient, and the inhibition of motor function. These factors may have resulted in mite death.

Adonis sp., Convallaria sp., Strophanthus sp., Thevetia sp., and Leonurus sp. - Cardiotonic Plants with Known Traditional Use and a Few Preclinical and Clinical Studies.

Plants have been always a fruitful source of active metabolites against many human disorders, where cardiovascular (CV) diseases have been one of the major health problems all over the world. There are some clinically proved medicinal plants with cardioprotective effects such as Crataegus monogyna and C. oxyacantha (hawthorn) from Rosaceae. On the other hand, cardiac glycosides, present in a number of plant species, are wellknown for their cardiotonic activity. However, we encountered such a fact that very less number of studies are available on the source plants; e.g. Adonis vernalis, Convallaria majalis, Strophanthus kombe, Thevetia peruviana, Leonurus cardiaca, etc. Consequently, we herein aimed to cover all available data consisting of in vitro, in vivo, and human studies (if any) on cardiotonic effects of the aforementioned species through a wide literature search using Scopus, Web of Science as well as Pubmed.

Two New Cyototoxic Cardenolides from the Whole Plants of Adonis multiflora Nishikawa & Koki Ito.

A phytochemical investigation of the whole plants of Adonis multiflora Nishikawa & Koki Ito. resulted in the isolation and identification of two new cardenolides--adonioside A (1) and adonioside B (6)--as well as four known cardenolides: tupichinolide (2) oleandrine (3), cryptostigmin II (4), and cymarin (5). Their structures were elucidated on the basis of NMR, MS, and IR spectroscopic analyses. Compounds 1, 2, 5, and 6 showed significant cytotoxicity against six human cancer cell lines (HCT-116, HepG2, HeLa, SK-OV-3, and SK-MEL-5, and SK-BR-3).

Amurensiosides L-P, five new cardenolide glycosides from the roots of Adonis amurensis.

Five new cardenolide glycosides, amurensiosides L-P (1-5), were isolated from the roots of Adonis amurensis. Their structures were determined based on extensive spectroscopic analysis, including two-dimensional (2D) NMR data, and on the results of hydrolytic cleavage. Compounds 1-5 were evaluated for their cytotoxic activities against HL-60 human promyelocytic leukemia and HSC-2 human oral squamous cell carcinoma cell lines.

Acaricidal activity of extracts from Adonis coerulea Maxim. against Psoroptes cuniculi in vitro and in vivo.

The acaricidal activity of Adonis coerulea extracts was investigated against Psoroptes cuniculi. The aqueous, methanol, acetic ether and petroleum ether extracts all showed marked acaricidal activity in vitro. Especially, the acetic ether extract possessed strong toxicity against mites in vitro with LT50 values 0.743 h, 2.730 h, 5.919 h and 22.536 h at concentrations of 500, 250, 125 and 62.5 mg/ml, respectively. At the same time, the acetic ether extract showed the best effectiveness topically to infested rabbits in vivo. After three times treatment, at the day 20, rabbits treated with A. coerulea extract were observed only small scabs or secretions in ear canal, but no mites. These findings suggested that as a potential insecticide, A. coerulea should be studied further to develop active components or a new acaricidal drug.

Elucidation of the pathway to astaxanthin in the flowers of Adonis aestivalis.

A few species in the genus Adonis are the only land plants known to produce the valuable red ketocarotenoid astaxanthin in abundance. Here, we ascertain the pathway that leads from the ß-rings of ß-carotene, a carotenoid ubiquitous in plants, to the 3-hydroxy-4-keto-ß-rings of astaxanthin (3,3'-dihydroxy-ß,ß-carotene-4,4'-dione) in the blood-red flowers of Adonis aestivalis, an ornamental and medicinal plant commonly known as summer pheasant's eye. Two gene products were found to catalyze three distinct reactions, with the first and third reactions of the pathway catalyzed by the same enzyme. The pathway commences with the activation of the number 4 carbon of a ß-ring in a reaction catalyzed by a carotenoid ß-ring 4-dehydrogenase (CBFD), continues with the further dehydrogenation of this carbon to yield a carbonyl in a reaction catalyzed by a carotenoid 4-hydroxy-ß-ring 4-dehydrogenase, and concludes with the addition of an hydroxyl group at the number 3 carbon in a reaction catalyzed by the erstwhile CBFD enzyme. The A. aestivalis pathway is both portable and robust, functioning efficiently in a simple bacterial host. Our elucidation of the pathway to astaxanthin in A. aestivalis provides enabling technology for development of a biological production process and reveals the evolutionary origin of this unusual plant pathway, one unrelated to and distinctly different from those used by bacteria, green algae, and fungi to synthesize astaxanthin.

Occurrence of progesterone and related animal steroids in two higher plants.

Previously, the presence of a wide variety of chemically diverse steroids has been identified in both flora and fauna. Despite the relatively small differences in chemical structures and large differences in physiological function of steroids, new discoveries indicate that plants and animals are more closely related than previously thought. In this regard, the present study gathers supporting evidence for shared phylogenetic roots of structurally similar steroids produced by these two eukaryotic taxa. Definitive proof for the presence of progesterone (3) in a vascular plant, Juglans regia, is provided. Additional evidence is gleaned from the characterization of five new plant steroids from Adonis aleppica: three 3-O-sulfated pregnenolones (6a/ b, 7), a sulfated H-5beta cardenolide, strophanthidin-3-O-sulfate (8), and spirophanthigenin (10), a novel C-18 oxygenated spirocyclic derivative of strophanthidin. The ab initio isolation and structure elucidation (NMR, MS) of these genuine minor plant steroids offers information on preparative metabolomic profiling at the ppm level and provides striking evidence for the conserved structural space of pregnanes and its congeners across the phylogenetic tree.

Amurensiosides A-K, 11 new pregnane glycosides from the roots of Adonis amurensis.

Five new pregnane tetraglycosides, amurensiosides A-E (1-5), two new pregnane hexaglycosides, amurensiosides F (6) and I (9), two new 18-norpregnane hexaglycosides, amurensiosides G (7) and H (8), and two new pregnane octaglycosides, amurensiosides J (10) and K (11), were isolated from the MeOH extract of the roots of Adonis amurensis. The structures of the new compounds were determined on the basis of extensive spectroscopic analysis, including two-dimensional (2D) NMR data, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activity against HSC-2 human oral squamous cell carcinoma cells.