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Callicarpa macrophylla Vahl. has widely been used in traditional medicine for the treatment such as gastrointestinal hemorrhage, coughing up blood, vomiting blood, nosebleeds, swollen and painful fall, rheumatism, bone pain, etc. The crude extract of the stem, leaves and fruits of Callicarpa macrophylla Vahl have exhibited demonstrated cytotoxicity against three human cancer cell lines (Lu-1, Hep-G2 va MCF-7) was tested by SRB assay with CS (%) values ranging from 30,23 ± 1,5 to 90,22 ± 0,15%. Inside, The methanol extract of the leaves of Callicarpa macrophylla Vahl have showed relatively potent cytotoxicity with CS (%) values ranging from 30,23 ± 1,5 to 47,84 ± 2,1%. The n-hexane fraction (L.CM.H) of the leaves of Callicarpa macrophylla Vahl have exhibited potent against three human cancer cell lines (Lu-1, Hep-G2 va MCF-7) than ethyl acetate fraction (L.CM.E) and methanol fraction (L.CM.M) with CS (%) values ranging from 12,49 ± 1,4 to 20,18 ± 0,8%.

Crapemyrtle bark scale (CMBS; Acanthococcus lagerstroemiae Kuwana) is an invasive insect that was first discovered in the United States in 2004. The polyphagous feeding habit of CMBS has allowed it to infest a wide range of plant species beyond its primary host, Lagerstroemia. Using molecular approaches, we studied the genetic relationships between CMBS specimens and their hosts from different geographic locations. Naturally occurring CMBS infestations were confirmed on American beautyberry (Callicarpa americana L.), a native plant species in the United States, and spirea (Spiraea L.). The new infestation of CMBS found on Spiraea raises the alarm that other economically important crops in the Amygdaloideae subfamily (subfamily under Rosaceae) might be susceptible to CMBS attacks.

The vexing literary relationship between Kurt Sprengel and Friedrich Dietrich appears to have led to some of Dietrich’s work being willfully disregarded and subsequently forgotten/extinguished/suppressed. Examination of Dietrich’s oeuvre leads to the rehabilitation of fifteen of his new combinations, making securer by up to 175 years, some names in current use for largely New World plants. To take into account Dietrich’s work as a whole, four new combinations and three nomina nova are proposed with the help of authorities in the germane plant groups: Caamembeca andina (A.W. Benn.) J.F.B. Pastore & Mabb. (Bolivia), Callicarpa ekmanii I.E. Méndez & Mabb. (Cuba), Clematis wangiana Mabb., (Madagascar), Coleataenia pulchra (F. Dietr.) Mabb. & LeBlond (USA), Packera dubia (Spreng.) Trock & Mabb. (USA), Piper samainianum Mabb. (Peru), Rostellularia vahliana (Schult.) Mabb. (south Asia), for which a lectotype is designated, with other adjustments of names in Besleria (B. formosa now B. amabilis, tropical America), Oxalis (O. eckloniana now O. biloba, South Africa), Passiflora (P. arborea now P. magnoliifolia, Colombia), Ribes (R. ruizii now R. sylvestre, Chile), and possibly Tocoyena (South America), while further work on Lupinus is called for.

Callicarpins A-D (1-4), possessing an unprecedented A-homoent-clerodane scaffold with a bicyclo[5.4.0]undecane ring system, and callicarpins E-G (5-7), with 5/6-fused ent-clerodane diterpenoid skeletons, were isolated from Callicarpaarborea and C. integerrim. Their structures were elucidated by comprehensive spectroscopic data, X-ray crystal diffraction, chemical derivatization, and electronic circular dichroism (ECD) data. Putative biosynthetic pathways for these callicarpins are proposed. Compounds 2, 3b, and 6-8 showed potent inhibitory effects against the NLRP3 inflammasome with IC50 values from 1.4 to 5.3 μM, and 2 significantly blocked NLRP3 inflammasome-induced pyroptosis by inhibiting Casp-1 activation and IL-1β secretion in J774A.1 cells.

Callicarpa kwangtungensis Chun is a traditional Chinese medicine that has various therapeutic effects. Despite its wide use in Chinese medicine, the study is still quite limited, especially its chemical compositions. In this research, an ultra-high-pressure liquid chromatography coupled with Q Exactive hybrid quadrupole-orbitrap high-resolution accurate mass spectrometry tandem mass spectrometry method was utilized to analyze its chemical compositions for the first time. As a result, a total of 124 compounds, including 20 phenylethanoid glycosides, 31 flavonoids, 36 organic acids, 26 terpenoids and 11 phenols, were identified or tentatively characterized in 30 min. Among them, 49 compounds, including 5 phenylethanoid glycosides, 12 flavonoids, 16 organic acids, 12 terpenoids, and 4 phenols, were identified in Callicarpa kwangtungensis Chun for the first time. Besides, the fragmentation pathways were also discussed. This research established a rapid and reliable method to analyze the chemical compositions of complicated herb without the process of isolation, and provide abundant information on the chemical material basis for further bioactivity and quality control studies.

Phytochemical investigation of the leaves and twigs of Callicarpa cathayana led to the isolation of six new clerodane diterpenoids, cathayanalactones A–F (1–6), together with seven analogues (7–13). Their structures were established by extensive NMR analyses together with experimental and calculated ECD spectra analyses. Compounds 1, 2, 3, 7 and 11 showed inhibitory activities on lipopolysaccharide-induced nitric oxide production in RAW264.7 cells.

Danila JS, Alejandro GJD. 2021. Leaf geometric morphometric analyses of Callicarpa and Geunsia (Lamiaceae) in the Malesian region. Biodiversitas 22: 4379-4390. Leaves are one of the most substantial organs of plants for it serves as a basis of species identification. Leaf morphology provides distinguishing features that help in the discrimination of plant species as well as investigation of leaf features among populations. This study aimed to investigate leaf shape variations between the two genera Geunsia Blume group and its closely related taxon, Callicarpa L. (Lamiaceae) using a landmark-based geometric morphometric method. The differences in the leaf shape among former members of Geunsia, namely C. apoensis, C. basilanensis, C. flavida, C. paloensis, C. pentandra, C. ramiflora, and C. surigaensis are also evaluated. Two primary landmarks and 14 semilandmarks were assigned in all samples to represent changes around the leaf margin. The Procrustes fit was generated using MorphoJ software which displays the mean and landmark position for individual configurations. Canonical Variate Analysis (CVA) and Mahalanobis Distance (MD) were able to discriminate all samples of Geunsia species using a scatter plot. Furthermore, Procrustes ANOVA showed a significant difference (P = 0.0082) among the seven species of the Geunsia group. Based on the results obtained, geometric morphometrics of leaf shape is effective in interspecific discrimination within members of Geunsia. However, the result of Discriminant Analysis (DA) showed that Geunsia and Callicarpa groups made leaf shape differences inefficient in discriminating the two genera. Therefore, further morphological studies on landmark-based geometric morphometrics of leaf shape involving a larger number of samples especially in the study of intergeneric classification are suggested.

Callicarpa siongsaiensis Metcalf is a drought resistance shrub with ornamental potential. In this study, Illumina sequencing data were used to assemble the complete chloroplast genome of Callicarpa siongsaiensis. The length of the circular genome is 154,144 bp. It contains a total of 130 genes, including 87 protein-coding, 36 tRNA, and seven rRNA genes. The GC content of the chloroplast genome of C. siongsaiensis is 38.09%. The phylogenetic analysis fully resolved C. siongsaiensis in a clade with C. formosana.

Adaptive radiation is the diversification of a founding population into multiple taxa that are differentially adapted to diverse ecological niches. The three Callicarpa (Lamiaceae) species endemic to the Bonin Islands are considered to represent an example of adaptive radiation on oceanic islands. All three species are distributed in the Chichijima Island Group and grow in different habitats, while only one species, C. subpubescens, is distributed among other island groups. Particularly, in the Hahajima and Mukojima Island Groups, C. subpubescens grows in various habitats and shows relatively high morphological variation. We investigated genotypes of the three Callicarpa species at 14 microsatellite markers to elucidate genetic differentiation within and between species or island groups and between different habitats or morphologies. We found that genetic differentiation within C. subpubescens in the Hahajima and Mukojima Island Groups was equally as high as that between the three species in the Chichijima Island Group, while differentiation within C. subpubescens in the Chichijima Island Group was much lower. Analyses such as a Bayesian clustering analysis showed that genetically distinct groups were associated with the three species in the Chichijima Island Group, whereas they showed strong genetic structure within C. subpubescens in the Hahajima and Mukojima Island Groups among different habitats and morphologies. These results indicated that ecological diversification occurred in the Hahajima and Mukojima Island Groups. Meanwhile, high genetic differentiation among different island groups was also observed, reflecting isolation by distance. It implies that non-ecological factors such as geographic isolation also played important roles in genetic differentiation in Callicarpa species in the Bonin Islands. These findings suggest that the Callicarpa species in the Bonin Islands are differentiated into multiple genetic groups by both ecological and non-ecological factors.

Four new 3, 4-seco-labdane diterpenoids, nudiflopenes J-M, were isolated from the leaves of Callicarpa nudiflora along with six known compounds. The structures of these diterpenoids were determined by comprehensive spectroscopic analysis. All the isolated compounds were evaluated for their inhibitory effects on NO production in LPS-stimulated RPMs and RAW264.7 cells. The results suggest that nudiflopenes J-M and other four known compounds showed significant inhibitory effects against NO production comparable to the positive control dexamethasone.

A biopolymer membrane chitosan-collagen/organomontmorillonite loaded with Callicarpa nudiflora (CS-COL/CN-OMMT) was prepared as a wound dressing. Three composite membranes including chitosan-collagen (CS-COL), chitosan-collagen/montmorillonite (CS-COL/MMT) and chitosan-collagen/organomontmorillonite (CS-COL/OMMT) were studied from physicochemical, swelling ratio, degradation ratio in vitro and moisture permeability properties. The CS-COL/OMMT composite membrane with porous layered structure exhibited a significantly higher swelling ratio, lower degradation ratio and rather excellent moisture permeability properties than other membranes. Callicarpa nudiflora were loaded on CS-COL/OMMT composite membrane to improve antibacterial activity from 20.20 ± 0.50% to 68.60 ± 0.10%.

A phytochemical investigation was carried out on the extract of a medicinal plant Callicarpa nudiflora, resulting in the characterization of five new 3, 4-seco-isopimarane ( 1 − 5 ) and one new 3, 4-seco-pimarane diterpenoid ( 6 ), together with four known compounds. The structures of the new compounds were fully elucidated by extensive analysis of MS, 1D and 2D NMR spectroscopic data, and time-dependent density functional theory (TDDFT) calculation of electronic circular dichroism (ECD) spectra, and DFT calculations for NMR chemical shifts and optical rotations.

Among the thecate hydroids brought back by the Proteus-Guyane 2017 expedition of the Muséum national d’histoire naturelle of Paris, France, from French Guiana, two interesting species are reported upon. The plumulariid Callicarpa gracilis Fewkes, 1881, known so far from the type specimen only, is comprehensively redescribed 140 years after its original description. It adopts two different morphotypes with respect to both its tropho- and gonosome, forming either simple or ramified colonies, with either structurally-complex or rudimentary phylactocarps, respectively. Taxonomic notes on the genera Callicarpa Fewkes, 1881 and Hippurella Allman, 1877 are provided in light of their intricate history of origin and fate, together with the provisional resurrection of Antomma Stechow, 1919, as an allied genus of the former. The aglaopheniid Aglaophenia trifida L. Agassiz, 1862, whose gonosome was only partly documented to date, is redescribed thoroughly based on specimens bearing male and female corbulae. Scanning electron microscopy and molecular data were also used to document both species. A checklist of the thecate hydroids from French Guiana gathered during Proteus-Guyane 2017 and Guyane 2014 expeditions is provided as an appendix, together with brief notes on some species. Not dealing with the present study, but taking advantage of it, a new name, Antennella billardi Galea, nom. nov., is proposed as a replacement name for Plumularia balei Billard, 1911, which is a permanently invalid junior primary homonym of P. balei Bartlett, 1907.

Callicarpa integerrima var. chinensis is one of the traditional medical herbs which has the potential for multiple diseases’ treatment. In this study, the complete chloroplast genome sequence of C. integerrima var. chinensis was sequenced and assembled. A typical quadripartite structure was observed in the chloroplast genome of C. integerrima var. chinensis which was 154179 bp in length, including a pair of inverted repeat (IR) regions (each 51396 bp) separated by a large single-copy region (LSC) of 84927 bp and a small single-copy region (SSC) of 17856 bp, and the overall GC contents of the chloroplast genome was 38.08%. Additionally, we annotated 132 genes, including 86 protein-coding genes, 38 tRNA genes, and 8 rRNA genes. Phylogenetic analysis was adopted which confirmed the position of C. integerrima var. chinensis was close to the congeneric C. formosana and C. siongsaiensis.

Four new diterpenoids, rubellawus A-D (1-4), along with three known compounds, were isolated and identified from the flowers of Callicarpa rubella. Their structures were elucidated by various spectroscopic analysis. All the compounds were screened for their anti-inflammatory activity and 14α-hydroxyisopimaric acid and isopimaric acid showed significant NLRP3 inflammasome inhibitory activity with IC50 values of 7.02 and 3.99 μM.

Danila JS, Alejandro GJD. 2020. Pollen morphology and infrageneric classification of selected Callicarpa species (Lamiaceae) from the Philippines and Borneo. Biodiversitas 21: 5736-5746. We used pollen grains of ten species representing the controversial genera Geunsia Blume and Callicarpa L. from the key centers of Malesia - Philippines, and Borneo including other countries in Asia. Herbarium specimens and collected samples from the field were examined using Scanning Electron Microscopy (SEM) in search of new characters to establish conclusive evidence that might contribute to the study of the relationship between Geunsia and Callicarpa. Based on SEM observations, both the investigated pollen grains of Geunsia and Callicarpa are mostly small to medium, spheroidal or circular, prolate to oblate, isopolar, and tricolpate. Moreover, the exine surface is mostly coarsely reticulated with a thin perforated colpus edge and sunken finely granulated colpus membrane. However, exine ornamentation shows possible separation of Geunsia and Callicarpa due to various morphological results observed. Several types of exine ornamentation were found in species of the section Callicarpa, i.e., C. erioclona, C. arborea, C. macrophylla, and C. candicans which attributes in the projected separation of these species while four species in the section Geunsia are united as a group having coarsely reticulate exine. Surprisingly, C. arborea samples give additional support to the hypothesis that rugulate exine sculpture might be its plesiomorphic character due to evolutionary evidence of other exine types of this species. On the other hand, pollen size and shape class of the sections of Geunsia and Callicarpa were both observed with similar features having an average pollen size equivalent to medium and a prolate shape supporting the concept of previous studies to nest Geunsia within Callicarpa. This reveals that pollen morphology is useful in the study of infrageneric classification within these groups. However, further morphological studies involving larger number of specimens are needed especially in the study of exine to prove its consistency as diagnostic character in the study of phylogenetic relationship.

Cellular inflammation is the underlying cause of several diseases and development of a safe and effective anti-inflammatory drug is need-of-the hour for treatment of diseases like lung inflammation. Callicarpa integerrima Champ. is a well-known herbal medicine with hemostatic and anti-inflammatory functions. However, the exact ingredient exhibiting anti-inflammatory activity in C. integerrima Champ. is largely unknown. Here, we first isolated, purified and characterized a novel clerodane-type diterpenoid Cintelactone A (CA) from C. integerrima Champ. We demonstrated that CA could significantly inhibit lipopolysaccharide (LPS)-induced pro-inflammatory cytokines and mediators production both in mouse peritoneal macrophages and THP1 cells. Consistently, CA also relieved inflammation and reduced LPS-induced lung injury in mice. We systematically elucidated the mechanism of action as well. CA interacted with Arg78 of tumor necrosis factor receptor-associated factor 6 (TRAF6) by hydrogen bonding. It further promoted the K48-linked ubiquitination and proteasomal degradation of TRAF6, and suppressed the activation of NF-κB and MAPKs signaling pathways. Collectively, our study reveals that new clerodane-type diterpenoid CA suppresses LPS-induced inflammation by promoting TRAF6 degradation, suggesting that CA as the potential therapeutic candidate for the treatment of inflammation associated diseases.

The new concept that Na/K-ATPase acts as a receptor prompted us to look for new ligands from Callicarpa kwangtungensis Chun. Using column chromatography, an undescribed phenethyl alcohol glycoside, callicarpanoside A, and an undescribed benzyl alcohol glycoside, callicarpanoside B, along with twelve known polyphenols were isolated from Callicarpa kwangtungensis Chun. All the isolated compounds were evaluated for their Na/K-ATPase (NKA) inhibitory activities. Using our NKA technology platform-based screening assay protocols, callicarpanoside B was identified as an undescribed Na/K-ATPase agonist. In particular, the newly identified benzyl alcohol glycoside was found to bind NKA and activate the receptor NKA/Src complex, resulting in the activation of protein kinase cascades. These cascades included extracellular signal-regulated kinases and protein kinase C epsilon, as well as NKA α1 endocytosis at nanomolar concentrations. Unlike the class of cardiotonic steroids, callicarpanoside B showed less inhibition of NKA activity and caused less cellular toxicity. Moreover, callicarpanoside B was found to bind NKA at a different site other than the cardiotonic steroids binding site. Thus, we have identified an undescribed NKA α1 agonist that may be used to enhance the physiological processes of NKA α1 signaling.

There are around 140 species in the genus Callicarpa, with 23 species occurring in Vietnam. The Vietnamese Callicarpa species have been poorly studied. In this work, the leaf essential oils of C. bodinieri, C. candicans, C. formosana, C. longifolia, C. nudiflora, C. petelotii, C. rubella, and C. sinuata, have been obtained from plants growing in central Vietnam. The chemical compositions of the essential oils were determined using gas chromatography &ndash, mass spectrometry. Mosquito larvicidal activities of the essential oils were carried out against Aedes aegypti. All of the Callicarpa leaf essential oils showed larvicidal activity, but two samples of C. candicans were particularly active with 48-h LC50 values of 2.1 and 3.8 &mu, g/mL. Callicarpa candicans essential oil should be considered as a potential alternative mosquito control agent.

The poorly known monotypic genus Szovitsia Fisch. & C.A.Mey, in the Apiaceae family, is here revised. Szovitsia callicarpa Fisch. & C.A.Mey. is an annual herb with a restricted distribution in the Caucasus region and adjacent areas of northwestern Iran and northeastern Turkey. The genus is unusual within the family because of the transverse plicae covering its fruits. In this study, morphological, micromorphological, and anatomical characters of S. callicarpa are reviewed. In addition, a previous lectotypification of the name S. callicarpa is discussed and amended. Se revisa Szovitsia Fisch. & C.A.Mey, un género monotípico y poco conocido en la familia de las Apiaceae. Szovitsia callicarpa Fisch. & C.A.Mey. es una hierba anual con una distribución restringida a la región del Cáucaso y áreas adyacentes del noroeste de Irán y noreste de Turquía. El género es inusual dentro de la familia debido a los pliegues transversales que cubren sus frutos. En este estudio se revisan los caracteres morfológicos, micromorfológicos y anatómicos de esta especie. También se discute y modifica una lectotipificación previa del nombre S. callicarpa.

Nine previously undescribed seco-labdane diterpenoids, nudiflopenes A−I, were isolated from the leaves of Callicarpa nudiflora. Their structures were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analysis, and the absolute configurations of these compounds were established by the modified Mosher's method and experimental and calculated electronic circular dichroism spectra. Nudiflopenes A−I belong to the class of seco-labdane diterpenoids. All of the isolates showed inhibitory activities on lipopolysaccharide-induced nitric oxide (NO) production in murine microglial BV-2 cells. The possible mechanism of NO inhibition of some bioactive compounds was also investigated using molecular docking, which revealed interactions of bioactive compounds with the inducible nitric oxide synthase (iNOS) protein.

Background : Callicarpa nudiflora (C. nudiflora), which is a medical herb in genus of Callicarpa, widely grows in the southern part of China. Several investigations had shown that this herb exerts anti-tumor effects. Ezrin is an important membrane-cytoskeleton-binding protein. By organizing membrane proteins and orchestrating their signal transduction, Ezrin contributes to modulation of cytoskeleton rearrangement in cell motility. Purpose To investigate the anti-motile properties of Rhoifolin (RFL), a flavonoid from C. nudiflora, and to determine whether its effects are related to the inhibition on Podocalyxin (PODXL)-Ezrin signal transduction. Methods : To determine suitable concentration of RFL and exposure time on breast cancer cells, the effects of RFL on viability of breast cancer cells were evaluated by MTT assay. Then, the anti-migratory properties of RFL were determined by AP 48 chamber system and ORISTM cell migration assay. F-actin in MDA-MB-231 cells was visualized by Alexa Fluor™ 488 conjugated Phalloidin. Immunoprecipitation was involved to access the effects of RFL on the interaction between Ezrin and PODXL. In addition, several EMT markers, including E-cadherin, Vimentin, Snail and Slug, were measured by Western Blotting assay and cell immunofluorescent analysis. Finally, the effects of RFL on cell migration, expression of Ezrin and EMT markers were verified by small interfering RNA (siRNA) mediated gene silencing. Results : We showed here that treatments with 10 and 40 μM of RFL induced significant inhibitions on cell migration and alterations on the location and organization of actin cytoskeleton in breast cancer cells. Next, it was found that RFL suppressed Ezrin phosphorylation and consequent interaction with PODXL, significantly. Also, this compound showed an obvious inhibitory effect on TGF-β1-induced EMT in MDA-MB-231 cells. Furthermore, data from RNA interfering assay confirmed that the inhibitory effects of RFL on Ezrin was enhanced by the deletion of Ezrin. Conclusion : RFL shows anti-motile properties on breast cancer cells, which is due to its potential to downregulate Podocalyxin-Ezrin interaction during Epithelial Mesenchymal Transition.

Two new iridoid glycosides, callicoside C (1) and callicoside D (2), together with three known compounds (3–5), were isolated from the leaves of Callicarpa nudiflora. Their structures were established by 1D and 2D NMR spectroscopy and mass spectrometry. In an in vitro bioassay, compound 1 showed pronounced hepatoprotective activity against d-galactosamine-induced toxicity in WB-F344 rat hepatic epithelial stem-like cells.

Background and aims Domatia are plant structures within which organisms reside. Callicarpa saccata (Lamiaceae) is the sole myrmecophyte, or ‘ant plant’, that develops foliar (leaf-borne) myrmeco-domatia in this genus. In this work we examined domatium development in C. saccata to understand the developmental processes behind pouch-like domatia. Methods Scanning electron microscopy, sectioning and microcomputed tomography were carried out to compare the leaves of C. saccata with those of the closely related but domatia-less myrmecophyte Callicarpa subaequalis, both under cultivation without ants. Key results Callicarpa saccata domatia are formed as a result of excess cell proliferation at the blade/petiole junctions of leaf primordia. Blade/petiole junctions are important meristematic sites in simple leaf organogenesis. We also found that the mesophyll tissue of domatia does not clearly differentiate into palisade and spongy layers. Conclusions Rather than curling of the leaf margins, a perturbation of the normal functioning of the blade/petiole junction results in the formation of domatium tissue. Excess cell proliferation warps the shape of the blade and disturbs the development of the proximal–distal axis. This process leads to the generation of distinct structures that facilitate interaction between C. saccata and ants.

Ethnopharmacological relevance Callicarpa japonica Thunb., as an herbal medicine has been used for the treatment of inflammatory diseases in China and Korea. Materials and methods Ultra performance liquid chromatography–photodiode array–quadrupole time–of–flight mass spectrometer (UPLC–PDA–QTof MS) was used to detect the major phenylethanoid glycosides in the C. japonica extract. BALB/c mice were intraperitoneally sensitized by ovalbumin (OVA) (on days 0 and 7) and challenged by OVA aerosol (on days 11–13) to induce airway inflammatory response. The mice were also administered with C. japonica Thunb. (CJT) (20 and 40 mg/kg Per oral) on days 9–13. CJT pretreatment was conducted in lipopolysaccharide (LPS)-stimulated RAW264.7 or phorbol 12-myristate 13-acetate (PMA)-stimulated A549 cells. Results CJT administration significantly reduced the secretion of Th2 cytokines, TNF-α, IL-6, immunoglobulin E (IgE) and histamine, and the recruitment of eosinophils in an OVA-exposed mice. In histological analyses, the amelioration of inflammatory cell influx and mucus secretion were observed with CJT. The OVA-induced airway hyperresponsiveness (AHR), iNOS expression and NF-κB activation were effectively suppressed by CJT administration. In addition, CJT led to the upregulation of HO-1 expression. In an in vitro study, CJT pretreatment suppressed the LPS-induced TNF-α secretion in RAW264.7 cells and attenuated the PMA-induced IL-6, IL-8 and MCP-1 secretion in A549 cells. These effects were accompanied by downregulated NF-κB phosphorylation and by upregulated HO-1 expression. Conclusion These results suggested that CJT has protective activity against OVA-induced airway inflammation via downregulation of NF-κB activation and upregulation of HO-1, suggesting that CJT has preventive potential for the development of allergic asthma.

Ethnopharmalogical relevance Callicarpa nudiflora Hook. & Arn. is a perennial evergreen shrub or low arbor in the Genus Callicarpa. Its dried aerial parts are used as traditional Chinese herbal medicine, Luo-hua-zi-zhu (Callicarpa nudiflora), which has been widely used in anti-bacteria and anti-ulcer in China (Commission, 2015; Development, 1994; Ming-Sheng, 2008). Aim of the study The present paper reviewed findings in phytochemistry and pharmacology of Callicarpa nudiflora. Methods Chinese and English studies on Callicarpa nudiflora were collected from databases including Web of Science, SciFinder, PubMed, Elsevier, and CNKI (Chinese), and the phytochemical and pharmacological studies of Callicarpa nudiflora were reviewed. Results A total of 300 small molecules, 173 of which are volatile oils, have been isolated from Callicarpa nudiflora. These small molecules could be divided into seven structural types — phenylpropanoids, flavonoids, triterpenes, diterpenes, iridoid glycosides, volatile oils, and other small molecules. Different types of compounds in Callicarpa nudiflora were summarized as follow: a) diterpenoid compounds can inhibit the generation of nitric oxide (NO) for exerting the function of anti-inflammation; b) triterpene compounds can play a role of anti-thrombus via inhibiting platelet aggregation and oleanane type and arbutane type pentacyclic triterpenes have the hepatoprotective activities; c) iridoid glycosides have cytotoxicity to tumor cells, and phenylpropanoids compounds have an antioxidant effect and could improve the function of memory. Our group further studied the antiviral activities of Callicarpa nudiflora finding that it has significant effects on RSV, EV71, COXB5, and HSV-1.

Although the specific epithet of Callicarpa minutiflora Y. Y. Qian has been revised for many times, during the study of the genus Callicarpa, we find that Callicarpa minutiflora Y. Y. Qian is identical to Callicarpa longifolia Lamarck by a series of morphologic characters. In order to avoid more confusion, here Callicarpa minutiflora Y. Y. Qian is reduced as a synonym of Callicarpa longifolia Lamarck.

Four new iridoid glycoside derivatives (1–4), along with ten known iridoid glycosides (5–14), were isolated from Callicarpa nudiflora Hook et Arn. The structure of the new iridoid glycosides was elucidated as 5″-methoxy-ampicoside (1), 6″-O-trans-caffeoylcatalpol (2), 6″-O-trans-feruloylcatalpol (3) and 3″-methoxy-agnucastoside C (4) on the basis of spectroscopic analysis. Compounds 1–11 were reported from this plant for the first time. The cytotoxic activity of the isolated compounds against human cervical carcinoma Hela cells and ovarian carcinoma HeyA8 cells was evaluated using the microculture tetrazolium assay. Compounds 4, 5, 8, 12 and 13 showed cytotoxic activity against the Hela cell line with IC50 values of 25.3, 48.1, 17.3, 38.3 and 28.2 μM, respectively. While only compound 8 showed cytotoxicity against the HeyA8 cell line, with an IC50 of 35.5 μM

Direct spray such as leaf spray and paper spray ionization mass spectrometry (MS) is a powerful type of ambient MS for phytochemical analysis. In this paper, direct spray MS methods to rapidly distinguish and analyze five species of Callicarpa L. have been developed. To distinguish species, leaf spray MS was employed to directly analyze leaves. A small triangular leaf sample was wetted with 15 μL of spray solvent and a high DC voltage was then simply applied to the wet leaf sample, which was positioned in front of the inlet of a mass spectrometer to produce electrospray ionization. The MS signals of phenylpropanoid glycosides, i.e. forsythiaside B, poliumoside, verbascoside in leaves could be sensitively detected. The content characteristics of the phenylpropanoid glycosides in five species including Callicarpae kwangtungensis Folium, Callicarpae macrophyllae Folium, Callicarpa nudiflora Folium, Callicarpae formosanae Folium, Callicarpa longissima Folium could be used to distinguish them, then the mass spectra of the Callicarpa L. samples were analyzed using principal component analysis(PCA) or partial least squares-discriminant analysis(PLS-DA). For the rapid semi-quantitative analysis, of phenylpropanoid glycosides in leaves, paper spray MS was employed to determine phenylpropanoid glycosides in the extracts of Callicarpa L. leaves. Ginsenoside Rg1 was selected as an internal standard (I.S.). The calibration curves were constructed through ratios of target ion abundance to I.S. ion abundance vs. concentration of targets. The linearity range was 8-250 μg/mL (R(2)=0.9947) for forsythiaside B, 9-280 μg/mL (R(2)=0.9939) for verbascoside, and 9-260 μg/mL (R(2)=0.9917) for poliumoside, respectively. The limit of detection (LOD) was 1 μg/mL, 0.5 μg/mL and 1 μg/mL for forsythiaside B, verbascoside, and poliumoside, respectively.

Nine new diterpenoids, Rubellacrns A − I (1–9), including five isopimaranes (1–4, 9), four pimaranes (5–8), together with five known isopimarane analogues (10–14), were isolated from Callicarpa rubella. The structures of these compounds were unambiguously established by HR-ESIMS and NMR spectroscopic data, the absolute configurations of compounds 5 and 9 were determined by ECD. All the isolated compounds were tested for their anti-inflammatory effects and compounds 2 and 11–14 showed NLRP3-inflammasome inhibitory activity with IC50 values ranging from 7.02 to 14.38 μM.

Plants of the genus Callicarpa are known to possess several medicinal effects. The constituents of the Taiwan endemic plant Callicarpa hypoleucophylla have never been studied. Therefore, C. hypoleucophylla was selected for our phytochemical investigation. Two new clerodane-type diterpenoids, named callihypolins A (1) and B (2), along with seven known compounds were isolated from the leaves and twigs of the Lamiaceae plant C. hypoleucophylla and then characterized. The structures of compounds 1 and 2 were elucidated by spectroscopic data analysis, specifically, two-dimension nuclear magnetic resonance (NMR). The anti-inflammatory activity of compounds 1&ndash, 9 based on the suppression of superoxide anion generation and elastase release was evaluated. Among the isolates, compounds 2&ndash, 4 showed anti-inflammatory activity (9.52&minus, 32.48% inhibition at the concentration 10 &mu, m) by suppressing superoxide anion generation and elastase release. Our findings not only expand the description of the structural diversity of the compounds present in plants of the genus Callicarpa but also highlight the possibility of developing anti-inflammatory agents from Callicarpa endemic species.

Callicarpa nudiflora, belonging to the family Verbenaceae, is widely used to treat inflammation caused by bacterial infection.However, the underlying active substances of C. nudiflora against inflammation remains obscure. In this work, an ultra high-performance liquid chromatography (UHPLC) coupled with quadrupole time-of-flight mass spectrometry method was developed to characterize the ingredients in C. nudiflora, and a validated UHPLC coupled with triple quadrupole tandem mass spectrometry method was applied to quantify major components. As a result, a total of 96 chemical compounds were identified in C. nudiflora, and 26 compounds of them were further quantified in 34 batches of C. nudiflora. Based on the identified components from C. nudiflora, a compound-target network for the anti-inflammation effect was constructed by reverse docking target prediction, disease associated genes screening in DisGeNET and the protein-protein interaction from STRING. The compound-target network showed that C. nudiflora might exert anti-inflammation effect on the target of complement 3 and 5 in the pathway of cells and molecules involved in local acute inflammatory response, and 16 effective candidate compounds were found such as catalpol, acteoside, rutin, etc. This study provided an opportunity to deepen the understanding of the chemical composition and the potential anti-inflammatory mechanism of C. nudiflora.

Species belonging to the genus Callicarpa are used traditionally in Chinese medicine for the treatment of inflammation, rheumatism, and pain. Investigation of the leaves and twigs of Callicarpa bodinieri resulted in the isolation of nine new abietane diterpenoids, bodinieric acids A–I (1–9), along with six known compounds (10–15). The structures of 1–9 were elucidated on the basis of the interpretation of their HRESIMS and NMR data and by ECD calculations. To explore the potential therapeutic target of this plant for immune-mediated disease, the inhibitory activities of the isolates obtained were determined against 13 kinase enzymes. Eight compounds exhibited moderate inhibitory effects on spleen tyrosine kinase (SYK), and the IC50 values of compounds 2 and 6 were 7.2 and 10.7 μM, respectively. In addition, a preliminary structure–activity relationship of this scaffold was analyzed with both molecular docking and a 3D-QSAR pharmacophore model.

Fossil leaves from the Siwalik sedimentary rocks of Darjeeling sub-Himalaya, evidence a variety of plant–insect interactions that operated during the evolution of monsoon-influenced forests from middle Miocene times. We assessed the diversity and frequency of insect herbivory on 137 specimens representing the Darjeeling lower Siwalik flora (DLSF). We also examined the percent of leaf area removed by herbivory as an independent measure of the effect of insect herbivore removal of host plant photosynthetic tissue. Five functional feeding groups (FFGs) are identified in this study namely leaf mining, hole feeding, skeletonizing, galling and margin feeding. These traces indicate that insects interacted with the plants for various purposes, including feeding, egg laying and sheltering. Furthermore, these morphotraces tend to suggest similarities in insect interactions with leaves of extant plant species such as Persea, Woodfordia, Shorea, Artocarpus, Callicarpa, Albizia, Lagerstroemia etc. On the basis of comparison with extant taxa, possible leaf feeders could have belonged to the insect orders Orthoptera, Coleoptera, Lepidoptera and Diptera. Although the morphology of the phytophagous insects associated with the fossil leaves is unknown, present findings reveal that many modern plant–insect relationships were established by the Miocene time and continue to the present, shaping both the present day flora and fauna. In the present study we compare insect herbivory at DLSF to that of our previously investigated Arunachal lower Siwalik flora and two younger floras from that area. We note a similar range of FFGs and damage types observed among these four fossil floras and conclude that compared to biotic factors climate had little influence in determining the evolution of plant-insect interactions in the eastern Himalayan region.

In this paper, we investigated the antibacterial mechanism and potential therapeutic targets of three antibacterial medicinal plants. Upon treatment with the plant extracts, bacterial proteins were extracted and resolved using denaturing gel electrophoresis. Differentially-expressed bacterial proteins were excised from the gels and subjected to sequence analysis by MALDI TOF-TOF mass spectrometry. From our study, seven differentially expressed bacterial proteins (triacylglycerol lipase, N-acetylmuramoyl-L-alanine amidase, flagellin, outer membrane protein A, stringent starvation protein A, 30S ribosomal protein s1 and 60 kDa chaperonin) were identified. Additionally, scanning electron microscope study indicated morphological damages induced on bacterial cell surfaces. To the best of our knowledge, this represents the first time these bacterial proteins are being reported, following treatments with the antibacterial plant extracts. Further studies in this direction could lead to the detailed understanding of their inhibition mechanism and discovery of target-specific antibacterial agents.

Pollen morphology of 36 species and 9 varieties of Callicarpa L. (Lamiaceae) from China was investigated through scanning electron microscopy. Pollen grains of the genus are monads, radiosymmetric and tricolpate, mainly medium in size, spheroidal (rarely subprolate, prolate or suboblate) in equatorial view and (sub) circular or rounded triangular in polar view. The edge of colpus is thin, perforate or thickened but imperforate and the colpus membrane of the investigated taxa is usually uneven (sunken or raised), with finely/coarsely granular or irregular striation. Four different ornamentation types are delimited on the basis of exine sculpturing: (1) coarsely reticulate; (2) microreticulate; (3) rugosely reticulate and (4) rugulate reticulate. The results do not support the traditional infrageneric classification of Callicarpa which is based on stamen characters. However, pollen characters provide evidence to support Callicarpa as the sister to the Australian subfamily Prostantheroideae, a relationship previously suggested by molecular phylogenetic analyses.

Cosmetic industries focus on developing materials and resources that regulate skin pigmentation. Melanin, the major pigment in human skin, protects the skin against damage from ultraviolet light. An ethanolic extract of the leaves of Callicarpa longissima inhibits melanin production in B16F10 mouse melanoma cells by suppressing microphthalmia-associated transcription factor (MITF) gene expression. Following purification and analysis using liquid chromatography-mass spectrometry (LC-MS), NMR, and biochemical assays, carnosol was determined to be responsible for the major inhibitory effect of the C. longissima extract on melanin production. Carnosol is an oxidative product of carnosic acid, whose presence in the extract was also confirmed by an authentic reference. The carnosol and carnosic acid content in the extract was approximately 16% (w/w). These results suggest that C. longissima is a novel, useful, and attractive source of skin-whitening agents.

A phytochemical investigation of the leaves of Callicarpa macrophylla led to the isolation of five new diterpenoids (1-5), macrophypenes A-E, and nine known analogues (6-14). The structures of 1-5 were established on the basis of extensive analysis of NMR spectroscopic data, X-ray diffraction data, and experimental and calculated electronic circular dichroism spectra. Compound 1 is a spiroditerpenoid with a novel skeleton, and compound 5 is a rare ent-abietane diterpenoid possessing a peroxide bridge. Compounds 1, 5-7, and 11-14 stimulate nerve growth factor mediated neurite outgrowth from PC12 cells.

Three new abietane-type diterpenoids, named callicapoic acid M3 (1), callicapoic acid M4 (2) and callicapoic acid M5 (3), were isolated from the Callicarpa macrophylla Vahl. Their structures were established by spectroscopic techniques (IR, UV, MS, 1D and 2D NMR). All the isolated three compounds were evaluated for inhibitory activity on NO production in LPS-activated RAW 264.7 macrophage cells by using MTT assays. Compounds 1, 2 and 3 showed potent inhibitory activity, with inhibition rates of 34.47–40.13%.

Background: The ethanolic extract of Callicarpa lanata (EECL), belonging to the family Verbenaceae, were studied for hepatoprotective activity in Wister rats with liver damage induced by ethanol.Methods: Ethanol treated rats showed significant increase in the levels of serum enzyme activities, total bilirubin and reduction in total proteins reflecting the liver injury caused by ethanol. EECL, at a dose of 400 and 200mg/kg body weight exhibited hepatoprotective effect by lowering the Serum Glutamate Pyruvate Transaminase (SGPT), Serum Glutamate Oxaloacetate Transaminase (SGOT), Serum Alkaline Phosphate (SALP), Gama Glutamyl Transpeptidase (GGTP), total Bilirubin to a significant extent and also significantly increased the levels of total protein in a dose dependent manner.Results: The results were highly significant at dose level of 400mg/kg body weight (p

A new 3,4-seco-labdane diterpenoid, 3,4-seco-12R,13S-dihydroxy-4(18),8(17),14(15)-labdatrien-3-oic acid (1), was isolated from the leaves of Callicarpa nudiflora. The structure of 1 was elucidated by 1D NMR, 2D NMR and HRESIMS data, and confirmed by single-crystal X-ray diffraction analysis. 3,4-seco-12R,13S-Dihydroxy-4(18),8(17),14(15)-labdatrien-3-oic acid (1) exerted inhibitory activity against the production of nitric oxide in RAW264.7 stimulated by lipopolysaccharide.

Two new triterpenoids, 2α,3α,19α,23-tetrahydroxyurs-12,20(30)-dien-28-oic acid (1) and 2α,3α,19α-trihydroxyurs-12-en-28-oic acid-28-O-β-D-xylopyranosyl (1→2)-β-D-glucopyranoside (2), and a new acylated flavone glycoside, luteolin 3'-O-(6″-E-caffeoyl)-β-D-glucopyranoside (3), together with three known compounds (4-6), were isolated from the leaves of Callicarpa nudiflora Hook. Their structures were elucidated on the basis of spectroscopic data and chemical methods. Anti-platelet aggregation activities of these compounds were evaluated in vitro. Compounds 1 and 2 showed inhibitory effects on ADP-induced platelet aggregation with EC50 values of 9.48 μM and 25.31 μM, respectively.

A taxonomic revision of the genus Callicarpa L. (Lamiaceae) in the Philippines is presented here. Twenty seven taxa are recognised, and thirteen names newly reduced to synonymy. A key to all species is included, as well as distribution maps and a preliminary conservation status for each species. This account forms part of a treatment of Callicarpa for the Flora Malesiana project.

Lamiaceae, the sixth largest angiosperm family, contains more than 7000 species distributed all over the world. However, although considerable progress has been made in the last two decades, its phylogenetic backbone has never been well resolved. In the present study, a large-scale phylogenetic reconstruction of Lamiaceae using chloroplast sequences was carried out with the most comprehensive sampling of the family to date (288 species in 191 genera, representing approximately 78% of the genera of Lamiaceae). Twelve strongly supported primary clades were inferred, which form the phylogenetic backbone of Lamiaceae. Six of the primary clades correspond to the current recognized subfamilies Ajugoideae, Lamioideae, Nepetoideae, Prostantheroideae, Scutellarioideae, and Symphorematoideae, and one corresponds to a portion of Viticoideae. The other five clades comprise: 1) Acrymia and Cymaria; 2) Hymenopyramis, Petraeovitex, Peronema, and Garrettia; 3) Premna, Gmelina, and Cornutia; 4) Callicarpa; and 5) Tectona. Based on these results, three new subfamilies—Cymarioideae, Peronematoideae, and Premnoideae—are described, and the compositions of other subfamilies are updated based on new findings from the last decade. Furthermore, our analyses revealed five strongly supported, more inclusive clades that contain subfamilies, and we give them phylogenetically defined, unranked names: Cymalamiina, Scutelamiina, Perolamiina, Viticisymphorina, and Calliprostantherina.

A phytochemical investigation to obtain new NO inhibitors resulted in the isolation of a new diterpenoid with a rare 9,10-seco-abietane skeleton (1) and twelve known terpenoids (2–13) from Callicarpa kwangtungensis. Their structures were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analyses, and the absolute configuration of compound 1 was established by comparison of the calculated and experimental electronic circular dichroism (ECD) spectra. The inhibitory activities on lipopolysaccharide-induced NO production in murine microglial BV-2 cells of these terpenoids were evaluated, and all of the compounds showed inhibitory effects. The following molecular docking studies showed interactions of the bioactive compounds with the iNOS protein.

A phytochemical investigation of the leaves of Callicarpa kwangtungensis led to the isolation of three new diterpenoids (1–3), callipenes A–C, and eleven known analogues (4–14). Their structures were established on the basis of extensive analysis of NMR spectroscopic data, X-ray diffraction data, and experimental and calculated electronic circular dichroism spectra. Compounds 1 and 2 are rare abietane diterpenoids possessing a peroxide bridge. All of the isolates were found to inhibit LPS-induced NO production in BV-2 cells.

A new species, Callicarpa bachmaensis Soejima & Tagane, sp. nov., is described and illustrated from Bach Ma National Park in Thua Thien Hue Province, Central Vietnam. This species has a characteristic liana habit, white corolla, and narrowly elliptic to narrowly lanceolate, entire, occasionally subequal leaves, by which it is clearly distinguished from the other previously known species of this genus.

Callicarpa nudiflora Hook. Et Arn. is one of the most important medicinal plants, but no information is available on optimal extraction of its total flavonoids. Effects of four single-factor treatments on total flavonoids during extraction of C. nudiflora and optimization of extraction condition, namely time, ethanol concentration, liquid-solid ratio, and temperature on the extracting rate of total flavonoids of C. nudiflora were studied in this paper. The optimization processes were conducted using response surface methodology. The results showed that the optimal conditions by central composite experimental design for extracting rate of total flavonoids was at a temperature of 90°C, liquid-solid ratio 41:1, ethanol concentration 73%, and time 3.6 h. Under these conditions, the maximal observed extracting rate (5.378%) of total flavonoids of leaves was obtained. Analysis of variance for quadratic polynomial regression model indicated that the model was extremely significant (P