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Caulophyllum robustum, commonly named Asian blue cohosh, is a perennial herb in the family Berberidaceae. It has traditionally been used for folk medicine in China. We isolated berberine from the leaves, stem, roots, and fruits of C. robustum, and this is the first report on berberine in this species. Transcriptome analysis was conducted for the characterization of berberine biosynthesis genes in C. robustum, in which, all the genes for berberine biosynthesis were identified. From 40,094 transcripts, using gene ontology (GO) analysis, 26,750 transcripts were assigned their functions in the categories of biological process, molecular function, and cellular component. In the analysis of genes expressed in different tissues, the numbers of genes in the categories of intrinsic component of membrane and transferase activity were up-regulated in leaves versus stem. The berberine synthesis genes in C. robustum were characterized by phylogenetic analysis with corresponding genes from other berberine-producing species. The co-existence of genes from different plant families in the deepest branch subclade implies that the differentiation of berberine synthesis genes occurred early in the evolution of berberine-producing plants. Furthermore, the copy number increment of the berberine synthesis genes was detected at the species level. [ABSTRACT FROM AUTHOR]

Two new sesquiterpenoids, flammupin A (1) and flammupin B (2), along with two known compounds, enokipodin C (3) and 5,5'-dibuthoxy-2,2'-bifuran (4) were obtained from Flammulina velutipes, an endophytic fungus isolated from the roots of Caulophyllum robustum Maxim. The structures were elucidated by the combination of HR-ESI-MS, NMR, and ECD analyses. Compound 3 exhibited moderate to potent cytotoxicity against A549, HeLa, and SMMC-7721 cells with IC50 values ranged from 3.69 to 11.84 μM. [ABSTRACT FROM AUTHOR]

Caulophyllum robustum, commonly named Asian blue cohosh, is a perennial herb in the family Berberidaceae. It has traditionally been used for folk medicine in China. We isolated berberine from the leaves, stem, roots, and fruits of C. robustum, and this is the first report on berberine in this species. Transcriptome analysis was conducted for the characterization of berberine biosynthesis genes in C. robustum, in which, all the genes for berberine biosynthesis were identified. From 40,094 transcripts, using gene ontology (GO) analysis, 26,750 transcripts were assigned their functions in the categories of biological process, molecular function, and cellular component. In the analysis of genes expressed in different tissues, the numbers of genes in the categories of intrinsic component of membrane and transferase activity were up-regulated in leaves versus stem. The berberine synthesis genes in C. robustum were characterized by phylogenetic analysis with corresponding genes from other berberine-producing species. The co-existence of genes from different plant families in the deepest branch subclade implies that the differentiation of berberine synthesis genes occurred early in the evolution of berberine-producing plants. Furthermore, the copy number increment of the berberine synthesis genes was detected at the species level.

A UPLC–MS/MS method was developed and validated the determination and pharmacokinetic study of magnoflorine, cauloside C, hederagenin, and oleanolic acid from Caulophyllum robustum. Digoxin was used as the internal standard. The pretreated plasma samples were carried out on a Waters ACQUITYUPLC HSS T3 column at 35 °C with a mobile phase of acetonitrile–water (90:10, v/v) at a flow rate of 0.2 mL/min. This article describes the most simple, sensitive, and validated UPLC–MS/MS method to date for the simultaneous successful determination of four compounds in rat plasma after oral administration of the extract of C. robustum and their pharmacokinetic studies. [ABSTRACT FROM AUTHOR]

Malonyl-triterpene saponins (MTSs) attract scientific attentions because of their structural diversities and valuable bioactivities. However, its thermal instability brings a huge amount of challenges for isolation and purification of this class of compounds. To our best knowledge, there has been no report on isolation and analysis of MTSs from genus Caulophyllum. In this study, a strategy combining data acquisition using an energy-resolved technique and the narrow widow extracted ion chromatograms as data mining method was developed for discovery and identification of MTSs in Caulophyllum robustum hair roots by ultra high liquid chromatography coupled to electrospray ionization Fourier transform mass spectrometry. The method was performed at an independent MS full scan using our bottom-up energies by in-source collision induced dissociations with 0, 25, 50 and 100 eV in both positive and negative modes. Precursor ion as well as fragment ion information was simultaneously collected from four energy-resolved MS spectra in a single run of 18min. The fragmentation pathways of intact deprotonated, protonated and sodium ions of MTSs were proposed for the structural elucidation of Caulophyllum MTSs. A flowchart involving a stepwise procedure based on key fragments from ESI-/ESI+-FT-MS(1, 1) to MS(1, 4) spectra was constructed for the identification of structural elements in the MTSs. As a result, a total of 23 MTSs were discovered and tentatively identified, which had not been reported from Caulophyllum species before. All of these were potentially new compounds. This study provides an excellent example for discovery and identification of MTSs in herb medicines. [ABSTRACT FROM AUTHOR]

The saponins in Caulophyllum robustum have not yet been fully characterized. Furthermore these saponins are often present in trace amounts and are structurally complex. Here, a simple direct infusion electrospray ion trap multiple-stage tandem mass spectrometry (DI-ESI-IT-MS n ) method was described for the characterization of trace C. robustum saponins. Eight reference saponins from the C. robustum hairy root were investigated by DI-ESI-IT-MS n in positive ion mode. Some fragmentation approaches were proposed through analysis of the [M+Na] + ions: (1) preferential cleavage of the C-28 ester glycosidic bond to provide complementary [Y 0 α +Na] + and [B α +Na] + ions for bidesmosidic saponins; (2) diagnostically neutral loss of CO 2 from free carboxyl groups at C-28 for monodesmosidic saponins; and (3) the ion intensity ratio between [C 2 β +Na] + and [B 2 β +Na] + , which is sensitive to the structural differences between the two isomeric β -sugar chains (Glc→ 2 Ara and Glc→ 3 Ara). The DI-ESI-IT-MS n method was successfully used for the analysis of trace C. robustum saponins with [M+Na] + ions at m / z 1745.6, 1729.5, 1583.7, 1567.7, 1421.7 and 1405.7. This article highlights the discovery and identification of complex α - and β -oligosaccharide moieties in Caulophyllum saponins by glycosidic product ions along with cross ring cleavage product ions. Five oligosaccharide moieties were unambiguously or tentatively identified as Rha→ 4 Glc→ 6 Glc→ 4 Rha→ 4 Glc→ 6 Glc, Glc→ 4 Glc→ 6 Glc→ 4 Rha→ 4 Glc→ 6 Glc, Rha→Glc→Glc (Glc)→ 2,3 Ara, Glc→Glc (Glc) → 2,3 Ara and Glc (Glc)→ 2,3 Ara. Accuracy of the analytical procedure was demonstrated by structural identification of two saponins isolated using 1D and 2D-NMR spectroscopy. The DI-ESI-IT-MS n method facilitates rapid discovery and analysis of trace Caulophyllum saponins and is a powerful and practical tool for structural characterization of complex oligosaccharide moieties in triterpene saponins. [ABSTRACT FROM AUTHOR]

Triterpene saponins are important bioactive constituents widely distributed in many plants. Saponins present in Caulophyllum (Berberidaceae) have not been fully characterized. In this study, we studied triterpene saponins from Caulophyllum robustum using liquid chromatography combined with electrospray ionization quadrupole time-of-flight mass spectrometry (LC-qTOF-MS). Rapid identification of Caulophyllum saponins was facilitated using low and high MS cone voltages to induce controlled fragmentation in positive mode. The full scan spectra at low cone voltage of 40 V provided considerable structural information relating to aglycone skeletons, sugar types, and linked sequences for Caulophyllum saponins. Seven Caulophyllum aglycones were differentiated and identified by their diagnostic fragment ions combined with accurate mass measurements and characteristic fragmentation pathways. Peak intensity ratio of [aglycone+H−2H 2 O] + to [aglycone+H−H 2 O] + in full scan spectra acquired with low cone voltage is correlated with structural features of hederagenin and echinocystic acid and is useful for the discrimination of these positional isomers. However, at a high voltage of 200 V, the saponin [M+H] + ion and its fragmentation ions were not present; and the single saponin [M+Na] + generated [B α +Na] + and [Y 0α +Na] + by in-source fragmentation, which provided structural information on the α- and β-sugar chains in the saponins. This approach enabled simultaneous acquisition of structural information on both aglycones and sugar chains from full scan spectra in one injection. Based on the developed strategy, 51 triterpene saponins of seven different classes were fully characterized or tentatively identified, of which 32 constituents were the first to be reported in genus Caulophyllum and 18 compounds were characterized as potentially new compounds. [ABSTRACT FROM AUTHOR]

Phytophagous specialists among insects occasionally accept plants they do not or only rarely utilize under natural conditions. This non-host acceptance could represent an initial stage in host-range evolution. Here, we examined adult acceptance of and larval survivorship on a non-host plant - wild thistle, Cirsium kamtschaticum Ledeb. (Asteraceae) - for two geographically separate populations of the phytophagous ladybird beetle Henosepilachna yasutomii Katakura (Coleoptera: Coccinellidae), which normally utilizes blue cohosh, Caulophyllum robustum Maxim. (Berberidaceae), in the wild. The two beetle populations showed lower acceptance of and survivorship on the non-host plant (thistle) than on the normal host plant (blue cohosh). Furthermore, they differed significantly in their responses to thistle but not to blue cohosh. Even for the beetle population that more readily accepted thistle as adults, acceptance was moderate and the eclosion rate was low, indicating reduced performance on the non-host plant. Although studies have infrequently focused on non-host acceptance, this is likely common in phytophagous specialists and thus is a potentially important evolutionary factor, as it may determine the future direction of food-range evolution. [ABSTRACT FROM AUTHOR]

Abstract: Four new fluorenone alkaloids, caulophylline A-D (1–4), and one new dihydroazafluoranthene alkaloid, caulophylline E (5) were isolated from the roots of Caulophyllum robustum Maxim. Their structures were elucidated by spectroscopic analysis. Among the isolated alkaloids, Caulophylline E showed good scavenging effects against DPPH radical with IC50 of 39μM. [Copyright &y& Elsevier]

Ecological speciation is a process by which reproductive isolation evolves as the result of divergent natural selection between populations inhabiting distinct environments or exploiting alternative resources. Ecological hybrid inviability provides direct evidence for ecological speciation. To detect ecological hybrid inviability, we examined survival rates to the second instar of F1 hybrids and backcross hybrids in a pair of sympatric phytophagous ladybird beetles, Henosepilachna niponica Lewis and Henosepilachna yasutomii Katakura (Coleoptera: Coccinellidae: Epilachninae), reared on their respective host plants, thistle [ Cirsium alpicola Nakai (Asteraceae)] and blue cohosh [ Caulophyllum robustum Maxim. (Berberidaceae)], and on a common food plant, Japanese nightshade [ Solanum japonense Nakai (Solanaceae)]. Hybrid larvae reared on leaves of the Japanese nightshade always had high rates of survival, irrespective of the crossing type of their parents, suggesting a lack of intrinsic hybrid inviability between the two species. In contrast, survival rates on thistle and blue cohosh varied greatly. On blue cohosh, the survival rate of F1 hybrids was nearly as high as that of H. yasutomii, but on thistle, survival was significantly lower than of H. niponica. Survival rates of backcross hybrids on the two host plants were intermediate between those of the parents, showing a reversed rank order of different types of backcross hybrids on the two food plant species. These results suggest that ecological hybrid inviability exists between H. niponica and H. yasutomii, although the two species do not show intrinsic hybrid inviability. Thus, our study supports the hypothesis that H. niponica and H. yasutomii underwent ecological speciation by divergent selection. [ABSTRACT FROM AUTHOR]

A novel alkaloid caulophyine A (1) was isolated from the roots of Caulophyllum robustum Maxim., along with six known alkaloids 2-7. The structure of 1 was elucidated by extensive NMR and high resolution-time-of-flight (HR-TOF)-MS analyses, it is a rare nitrogen containing polycyclic aromatic hydrocarbon. The in vitro bioassays revealed that 2 presented remarkable cytotoxicity against A549 with an IC 50 value of 3.83 µM in comparison with the positive control etoposide (IC 50  = 11.63 µM). Compounds 1 and 2 also displayed weak Acetylcholinesterase (AChE) inhibitory activity with IC 50 values of 123.03 and 80.74 µM respectively.

Individual variation in two species of host plants (thistle, Cirsium kamtschaticum, and blue cohosh, Caulophyllum robustum) of the herbivorous ladybird beetle Epilachna pustulosa was examined under laboratory conditions for their acceptability to adult beetles as a food resource, for adult preference and for larval performance. When clones of these plants were subjected to non-choice tests using posthibernating female beetles, there was found to be significant intraspecific variation among clones in terms of their acceptability, but interspecific variation was not detected. Significant intraspecific as well as interspecific variation were frequently detected in the two host plants when clones of these plants were subjected to choice tests using posthibernating female beetles; the magnitude of interspecific plant variation for beetle preference is not necessarily larger than that of intraspecific plant variation. Individual variation across plant species with respect to beetle larval performance was also significant. A positive correlation between adult preference and larval performance is suggested across the two taxonomically remote host plant species, thistle and blue cohosh, although this needs further investigation. [ABSTRACT FROM AUTHOR]

Larval survival of four local populations of Epilachna yasutomii in the southern part of Nagano Prefecture was evaluated on leaves of blue cohosh, Caulophyllum robustum, growing at two different sites, Takatoh and Nakatachi. Based on larval survival on leaves of Takatoh C. robustum, Takatoh E. Yasutomii was clearly distinguishable from the three populations in the Minami-Shinano area (Akasawa, Nakatachi and Tenryu). Takatoh E. yasutomii developed successfully to emergence on C. robustum from both sites, while Minami-Shinano populations showed a very low survival rate when given Takatoh C. robustum. Under controlled plant growth conditions, larval survival of Akasawa E. yasutomii was significantly reduced when given C. robustum leaves, from either site, exposed to direct solar radiation, which suggested that larval survival was influenced by environmental conditions at the growing sites rather than genetic differences between the plant populations. In contrast, Takatoh E. yasutomii developed well on C. robustum leaves from either site exposed to direct solar radiation. Takatoh E. yasutomii appears to have some defensive mechanism that allows it to overcome a substance deterring larval development, which increases in leaves exposed to direct solar radiation. [ABSTRACT FROM AUTHOR]

Caulophyllum robustum Maxim is widely distributed in China and used as a traditional herbal medicine to induce childbirth, ease the pain of labor, rectify delayed or irregular menstruation, alleviate heavy bleeding and pain during menstruation, and treat external injuries and irregular menses. According to our detailed chemical investigation, three new triterpene derivatives (1–3), together with seven known compounds, were isolated from the root and rhizome of C. robustum Maxim. Their structures were elucidated by 1D- and 2D-NMR spectroscopic analysis and physio-chemical methods. They were identified as (1) 23-hydroxy-3,19-dioxo-olean-12-en-28-oic-acid; (2) 23-hydroxy-3,11-dioxo-olean-12-en-28-oic acid; and (3) 16α,23-dihydroxy-3-oxo-olean-12-en-28-oic acid. Compounds (1–10) inhibited the LPS-activated NO production in RAW264.7 cells. Furthermore, the anti-inflammatory characteristics of these compounds were confirmed on the basis of decreases in iNOS and NF-κB protein expression in RAW264.7 cells. [ABSTRACT FROM AUTHOR]