Search

Four new triterpenoids which were identifed as 2α,3β,6β,19α-tetrahydroxy- oleanolic acid 28-O-β-D-glucopyranoside (1), 2-O-β-D-glucopyranosyloxy-3α,19α-di-hydroxyoleanolic acid (2), 2-O-β-D-glucopyranosyloxy-3α,19α-dihydroxyursolic acid (3), 2α,3α,6β,19α-tetrahydroxyursolic acid 28-O-β-D-glucopyranoside (4), were isolated from the aerial parts of Callicarpa kwangtungensis together with three known triterpenoids identified as 2α,3β,21β-trihydroxyursolic acid 28-O-β-D-glucopyranoside (5), 2α,3α,19α,23-tetrahydroxyoleanolic acid 28-O-β-D-glucopyranoside (6), 2α,3α,19α,23-tetrahydroxyursolic acid 28-O-β-D-glucopyranoside (7). Their structures were elucidated by the combination of mass spectrometry (MS), one and two-dimensional NMR experiments.

We previously reported that ten phenylethanoid glycosides including acteoside isolated from the leaves and twigs of Callicarpa dichotoma significantly attenuated glutamate-induced neurotoxicity. In the present study, we examined anti-amnesic activity of acteoside using scopolamine-induced (1 mg/kg body weight, s.c.) amnesic mice with both passive avoidance and Morris water maze tests. Acute oral treatment (single administration prior to scopolamine treatment) of mice with acteoside (1.0, 2.5 mg/kg body weight) significantly mitigated scopolamine-induced memory deficits in the passive avoidance test. It is interesting to note that prolonged oral daily treatment of mice with much lower amount (0.1 mg/kg body weight) of acteoside for 10 d reversed the scopolamine-induced memory deficits. In the Morris water maze, prolonged oral treatment with acteoside (prolonged daily administration of 1.0 mg/kg body weight for 10 d) significantly ameliorated scopolamine-induced memory deficits showing the formation of long-term and/or short-term spatial memory. We suggest, therefore, that acteoside has anti-amnesic activity that may ultimately hold significant therapeutic value in alleviating certain memory impairment observed in Alzheimer's disease.

The three new lignanoids 1–3 and the five new phyllocladane diterpenoids 7–11 were isolated from the leaves of Callicarpa furfuraceae, together with two known lignanoids, lariciresinol (4) and (+)-sesamin (5), and five known diterpenoids, 17-norphyllocladane-3,16-dion (6), calliterpenone (12), calliterpenone 17-acetate (13), (3β,16α)-phyllocladane-3,16,17-triol (14), and (3β,16α)-phyllocladane-3,16,17-triol 17-acetate (15). Their structures were established by spectral-data interpretation.

The chemical consitituents from cytotoxic fraction of the Callicarpa nudiflora extract were isolated and purified by a combination of HP-20 macroporous resin, silica gel and Sephadex LH-20 column chromatographies. The structures were elucidated on the basis of the spectroscopic data and comparison of their spectroscopic data with reported data. The cytotoxicity was evaluated by the MTT assay. The 50% and 70% EtOH elutions of EtOH-extract showed significant cytotoxic activities, leading to the isolation of twelve compounds, which were identified as luteoloside(1), lutedin-4'-O-β-D-glucoside(2), 6-hydroxyluteolin-7-O-β-glucoside(3), lutedin-7-O-neohesperidoside(4), rhoifolin (5), luteolin-7, 4'-di-O-glucoside (6), forsythoside B (7), acteoside (8), alyssonoside (9), catalpol(10), nudifloside(11), and leonuride(12). Compounds 3-6, 10 and 12 were isolated from this genus for the first time, and compound 9 was isolated from this plant for the first time. The cytotoxicity assay demonstrated that flavonoids 1-6, in various concentrations, showed monolithic proliferation inhibitory activities against Hela, A549 and MCF-7 cell lines. Compounds 3, 5 and iridoid glycoside 11 possessed higher cytotoxicacivities. In short, flavonoids are the main components of cytotoxic extract from C. nudiflora, while phenylethanoid glycosides are the predominant ingredient but inactive to cancer cell lines. In addition, the minor iridoid glycoside expressed weak cytotoxic activity.

Eighteen species of endophytic fungi were isolated from bark, stem and leaf segments of five medicinal plant species growing within the Kudremukh range in the Western Ghats of India. The dominant endophytic fungal species isolated from these plant species were Curvularia clavata, C. lunata, C. pallescens and Fusarium oxysporum. The highest species richness as well as frequency of colonization of endophytic fungi was found in the leaf segments, rather than the stem and bark segments, of the host plant species. The greatest number of endophytic fungal species were found within Callicarpa tomentosa (11 species), whereas Lobelia nicotinifolia harbored the lowest number of fungal endophytes (5 species). This study provides evidence that fungal endophytes are host and tissue specific.

Callicarpa x shirasawana is a natural hybrid between C. japonica and C. mollis, and has a morphology that is intermediate between those of the parent species. Characterization of natural Callicarpa populations in the Atsumi Peninsula of central Japan, which all three of the above species inhabit sympatrically, revealed hybrids with various morphologies. Molecular analysis revealed a high occurrence of introgression of the C. japonica genome into that of C. mollis. Moreover, all individuals examined with morphology similar to that of C. mollis had genetic traces of hybridization with C. japonica. Molecular analysis of individual C. mollis and C. japonica from five other areas of Japan showed that introgression of C. japonica into C. mollis occurs widely. Molecular data also strongly suggested that the previously recognized C. x shirasawana individuals with intermediate morphology are not F1 hybrids between C. japonica and C. mollis, but instead are progeny of C. x shirasawana backcrossed with C. japonica. Moreover, it was revealed that individuals with F1-type genotypes are indistinguishable morphologically from pure C. mollis. The results of the present study point to the need for re-evaluation of natural populations of C. mollis and C. x shirasawana.

Two new subfamilies, Callicarpoideae Bo Li & R.G.Olmstead and Tectonoideae Bo Li & R.G.Olmstead, are established within the mint family. Their morphology, distribution, generic and species diversity, homotypic tribes, and phylogenetic position are noted.

'Callicarpa peichieniana W. Y. Chun & S. L. Chen ex W. Z. Fang' is a replacement name for Premna peii W. Y. Chun ex H. T. Chang. However, this replacement name was not validly published in 1982 by W. Z. Fang because the reference citation of the replaced synonym P. peii that was published in 1960 was contrary to Article 33.4 of ICBN. The first publication of Premna peii in 1960 was invalid due to lack of type indication, in conflict with Article 37.1, and it was subsequently validated in 1963. In this study, we correct the place of valid publication of P. peii, thereby validating C. peichieniana W. Y. Chun & S. L. Chen ex H. Ma & W. B. Yu.

Two new triterpenoids, 2α,3β,16α,19α,23-pentahydroxyolean-12-en-28-oic acid (1) and 2α,3α,11α,21α,23-pentahydroxyurs-12-en-28-oic acid (2), were isolated from the aerial parts of Callicarpa kwangtungensis. Their structures were elucidated by 1D and 2D analyses, as well as MS and IR spectra.

To establish HPLC fingerprint method for the quality evaluation and discrimination of Callicarpa nudiflora.The chromatographic fingerprint of the 12 samples was determined by injecting 20 microL of the sample solution each time on a reversed phase Agilent TC-C18 column with the gradient elution solvent system composed of 0.30% HAc solution and acetonitrile. The flow rate was 1.0 mL/min, the column temperature was maintained at 30 degrees C and the detection wavelength was set at 254 nm.The HPLC fingerprint of Callicarpa nudiflora was set up,which included 20 common peaks, and the similarities of 12 samples were basically more than 0.90. Also,3 components were identified.The method is accurate, repeatable, reliable and can fully reflect the chemical composition information, which can be used for the discrimination and the quality control of Callicarpa nudiflora.

Four new triterpenoid saponins, 2α,3α,19α,24-tetrahydroxyolean-12-en-28-oic-acid 28-O-β-D-glucopyranosyl ester (1), 2α,3α,19α,23-tetrahydroxyolean-12-en-28-oic-acid 28-O-β-D-xylopyranosyl-(1→2)-β-D-glu-copyranosyl ester (2), 2α,3α,19α-trihydroxyolean-12-en-28-oic-acid 28-O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl ester (3), 2α,3α,23,29-tetrahydroxyurs-12,19-dien-28-oic-acid 28-O-β-D-glucopyranosyl ester (4), together with three known compounds (5-7), were isolated from the leaves of Callicarpa nudiflora HOOK. Their structures were established by means of spectroscopic methods and chemical evidence. Hepatoprotective activities of the isolated compounds against D-galactosamine-induced toxicity have been tested. Among them, compounds 1-3 showed pronounced hepatoprotective activities against D-galactosamine-induced toxicity in WB-F344 rat hepatic epithelial stem-like cells.

From the fermentation mycelium of the endophytic fungus Edenia gomezpompae were obtained several phytotoxic compounds including two new members of the naphthoquinone spiroketal family, namely, palmarumycin EG1 (1) and preussomerin EG4 (4). In addition, preussomerins EG1–EG3 (7–9) and palmarumycins CP19 (2), CP17 (3), and CP2 (6), as well as ergosta-4,6,8(14),22-tetraen-3-one (5), were obtained. Compounds 2, 3, and 5 are new to this species. The structures of palmarumycins CP19 (2) and CP17 (3) were unambiguously determined by X-ray analysis. The isolates and mycelium organic extracts from four morphological variants of E. gomezpompae caused significant inhibition of seed germination, root elongation, and seedling respiration of Amaranthus hypochondriacus, Solanum lycopersicum, and Echinochloa crus-galli. The treatments also affected respiration on intact mitochondria isolated from spinach.

The RP-HPLC method was used to determinate the contents of forsythiaside B and poliumoside in different origin and parts from Callicarpa kwangtungensis. The linear ranges of forsythiaside B and poliumoside were 0. 106-3. 18 and 0. 105 2-3. 156 microg, respectively. The average recoveries of forythiaside B and poliumoside were 99. 01% ( RSD 1. 2%) and 100. 13% (RSD 0. 90% ), respectively. The contents of forsythiaside B and poliumoside were changed in different origin and parts from C. kwangtungensis. The sample from the area of Luxi, Pingxiang City, Jiangxi Province has the highest contents of forsythiaside B and poliumoside. The contents of forsythiaside B and poliumoside in different parts from C. kwangtungensis in Luxi are: leafstemfruit. This result will provide a scientific basis for quality control and reasonable utilzation of C. kwangtungensis.

Ten microsatellite loci were isolated and characterized for Callicarpa subpubescens (Verbenaceae), an endemic tree species of the Bonin Islands. The observed number of alleles at each locus ranged from two to eight with an average of 4.9, and the expected heterozygosity ranged from 0.238 to 0.690 with an average of 0.483. All 10 loci were screened in cross-amplification tests for two other endemic Callicarpa species that also inhabit the Bonin Islands. All loci were successfully amplified in these species.

Ten phenylethanoid glycosides, forsythoside B, acteoside, 2'-acetylacteoside, poliumoside, brandioside, echinacoside, isoacteoside, cistanoside H and E-tubuloside E as well as a new compound, Z-tubuloside E, were isolated from the n-BuOH fraction of Callicarpa dichotoma Raeuschel (Verbenaceae) by bioactivity-guided fractionation using glutamate-injured primary cultures of rat cortical cells as a screening system. These phenylethanoid glycosides significantly attenuated glutamate-induced neurotoxicity at concentrations ranging from 0.1 to 10 microM.

To study the chemical constituents of Callicarpa peii.The chemical constituents were isolated and purified by chromatographic methods and elucidated by spectral analysis, including UV, IR, MS, 1H-NMR and 13C-NMR.Ten compounds were obtained and identified as oleanolic acid (1), 2beta, 3beta,19alpha-trihydroxy-12-en-28-ursolic acid (2), luteolin -7,4'-dimethylether (3), luteolin -3', 4', 7, -trimethylether (4), luteolin -4'-methylether (5), hydnocarpin (6), luteolin (7), lyoniresinol 3alpha-O-beta-D-glucopyranoside (8), kelampayoside A (9), kaempferol -3-O-glucuronide (10).All these compounds are isolated from Callicarpa peii for the first time and compounds 3, 4, 6, 8 and 10 are isolated from this genus for the first time.

Background:Callicarpae Caulis et Folium (CCF) is a traditional Chinese medicine usually used for hemostasis in clinics. In this study, a novel LC–MS/MS method was developed and validated for the simultaneous quantification of three phenylethanoid glycosides in rat plasma (verbascoside, forsythoside B and poliumoside), which are the major bioactive compounds of CCF; MS was operated in negative mode. Results: This method was linear between 5.2 and 1010 ng/ml for poliumoside, 7.0 and 420 ng/ml for forsythoside B and 2.60 and 260.0 ng/ml for verbascoside. The MS/MS ion transitions monitored were m/z 769.4→160.5, m/z 755.3→593.3, m/z 623.1→160.5 and m/z 179.0→133.6 for poliumoside, forsythoside B, verbascoside and caffeic acid (IS), respectively. Linearity, accuracy, precision and extraction recovery of three analytes were all satisfactory. Conclusion: The method developed was sensitive, specific and rapid. It has been successfully applied in a PK study of three phenylethanoid glycosides after a single oral administration of CCF extract to rats.

As a part of our ongoing search for bioactive compounds from the leaves of Callicarpa nudiflora that inhibit nitric oxide (NO) production, the 90% EtOH fraction eluted by macroporous resin adsorption was found to show significant inhibitory activity against the production of NO in RAW 264.7 stimulated by lipopolysaccharide (LPS). Bioactivity-guided isolation of the fraction yielded three new bioactive diterpenoids, named ent-3, 4-seco-14-carbonyl-15, 16-epoxy-4(18), 8(17), 13(14)-labdatrien-3-oic acid (1), syn-3, 4-seco-12R-hydroxy-15, 16-epoxy-4(18), 8(17), 13(16), 14(15)-labdatetraen-3-oic acid (2) and syn-3, 4-seco-12S-hydroxy-15, 16-epoxy-4(18), 8(17), 13(16), 14(15)-labdatetraen-3-oic acid (3). Their structures and configurations were elucidated by comprehensive spectroscopic analysis. All the three compounds exhibited potent inhibitory activity on NO production in LPS-activated RAW 264.7 macrophage cells.

Experiments were conducted to evaluate the efficacy of calliterpenone, a natural plant growth promoter from a shrub Callicarpa macrophylla Vahl., in enhancing the growth and yield promoting effects of plant growth promoting rhizobacteria (PGPRs), in menthol mint (Mentha arvensis L).This study is based on our previous results indicating the microbial growth promotion by calliterpenone and assumption that application of calliterpenone along with PGPRs will improve the population of PGPRs resulting in higher impacts on plant growth and yield. Of the 15 PGPRs (identified as potent ones in our laboratory), 25 μl of 0.01 mM calliterpenone (8.0 μg/100 ml) was found to be useful in improving the population of nine PGPRs in culture media. The five selected strains of PGPRs exhibiting synergy with calliterpenone in enhancing growth of maize compared to PGPR or calliterpenone alone were selected and tested on two cultivars (cvs. Kosi and Kushal) of M. arvensis. Of the five strains, Bacillus subtilis P-20 (16S rDNA sequence homologous to Accession No NR027552) and B. subtilis Daz-26 (16SrDNA sequence homologuos to Accession No GU998816) were found to be highly effective in improving the herb and essential oil yield in the cultivars Kushal and Kosi respectively when co-treated with calliterpenone. The results open up the possibilities of using a natural growth promoter along with PGPRs as a bio-agri input for sustainable and organic agriculture.

Three Callicarpa species, namely Callicarpa nudiflora Hook. et Arn., Callicarpa macrophylla Vahl. and Callicarpa kwangtungensis Chun. are astringency and hemostasis herbs in the traditional Chinese medical systems. Despite their wide use in Chinese medicine, no report on system comparison on their chemical constituents is available so far. High-performance liquid chromatography coupled with diode array detector and electrospray ionization trap mass spectrometry (HPLC–DAD–ESI-Trap MS) technique was used for qualitative and quantitative analyses of the three Callicarpa herbs. Phenylpropanoid glycosides, flavonoids and organic acids were identified by comparing with reference standards or according to their MS/MS fragmentation behaviors. A total of 33 compounds were identified identified or tentatively identified, and 23 of them were reported from these herbs for the first time. Phenylpropanoid glycosides were featured in the three species with their types and contents presenting significant differences. Furthermore, quantitative analysis was conducted by determining four marker phenylpropanoid glycosides (forsythoside B (14), acteoside (15), poliumoside (19), isoacteoside (21)) and two flavonoids (luteolin (30), apigenin (32)). Three flavonoid glucuronides (luteolin-diglucuronide-glucuronide (5), luteolin-diglucuronide (12), apigenin-7-O-β-glucuronide (24)) were semi-quantified according to their corresponding aglycones. The total contents of the nine major compounds in the three species varied significantly from 8.92 to 40.89 mg/g.

Ethnopharmacological relevance Callicarpa L. (Verbenaceae) has been used for centuries in Traditional Chinese Medicine (TCM) for the prevention and treatment of a wide number of health disorders such as inflammation, rheumatism, hematuria, fracture, hematemesis, menoxenia, gastrointestinal bleeding, scrofula, etc. Aims of the review To assess the scientific evidence for therapeutic Callicarpa in TCM and to identify future research needs. Methods The available information on the ethnopharmacological uses in Chinese medicine, phytochemistry, pharmacology and clinical practice of Callicarpa species was collected via a library and electronic search (PubMed, ScienceDirect, Google Scholar and CNKI). Results A variety of ethnomedical use of Callicarpa has been recorded in many ancient Chinese books. Phytochemical investigation of this genus has resulted in identification of more than 200 chemical constituents, among which diterpenes, triterpenoids and flavonoids are the predominant groups. The isolates and crude extract have exhibited a wide spectrum of in vitro and in vivo pharmacological effects involving anti-inflammatory, hemostatic, neuroprotective, anti-amnesic, antitubercular, antioxidant, antimicrobial and analgesic activities. Preparations containing Callicarpa species exerted good efficacy on clinical applications of gynecological inflammation, internal and external hemorrhage as well as acne vulgaris and chronic pharyngitis, etc. From the toxicity perspective, only three Callicarpa species have been assessed. Conclusions Pharmacological results have validated the use of Callicarpa species in the traditional medicine. As literature demonstrated, terpenoids and flavonoids are perhaps responsible for most of the activities shown by the plants of this genus. However, the detailed active compounds and the underlying mechanisms remain a work in progress. In addition, more attention should be paid to C. nudiflora as well as the domain of rheumatism.

To analyze the chemical constituents of the essential oil from Callicarpa kwangtungensis and investigate their antimicrobial activity in vitro.The essential oil of Callicarpa kwangtungensis were extracted by steam distillaton. The chemical constituents were separated and analyzed by GC-MS. Their relative percentages were calculated with peak area normalization method.38 compounds were identified, accounting for 76.01% of the peak area of the total ion-current chromatogram. The essential oil had different antimicrobial activities.The main constituent of the essential oil is terpenoids (59.25%), and showing different activities against Staphylococcus aureus, Escherichia coli and Candida albicans.

Different biological methods are gaining recognition for the production of silver nanoparticles (Ag-NPs) due to their multiple applications. The use of plants in the green synthesis of nanoparticles emerges as a cost effective and eco-friendly approach. In this study the green biosynthesis of silver nanoparticles using Callicarpa maingayi stem bark extract has been reported. Characterizations of nanoparticles were done using different methods, which include; ultraviolet-visible spectroscopy (UV-Vis), powder X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive X-ray fluorescence (EDXF) spectrometry, zeta potential measurements and Fourier transform infrared (FT-IR) spectroscopy. UV-visible spectrum of the aqueous medium containing silver nanoparticles showed absorption peak at around 456 nm. The TEM study showed that mean diameter and standard deviation for the formation of silver nanoparticles were 12.40 ± 3.27 nm. The XRD study showed that the particles are crystalline in nature, with a face centered cubic (fcc) structure. The most needed outcome of this work will be the development of value added products from Callicarpa maingayi for biomedical and nanotechnology based industries.

A new triterpenoid saponin and fourteen known triterpenoids were isolated from the methanol extract of the stems and leaves of Callicarpa integerrima Champ, which is used in Chinese folk medicine for stopping bleeding, expelling the wind, dissipating stagnation, and treating scrofula, by using various chromatographies, such as silica gel, Sephadex LH-20 and RP-C18 column chromatography. Their structures were identified as a new compound 2alpha, 3beta, 19alpha, 23-tetrahydroxy-olean-12-en-28-oic acid-28-O-beta-D-glucopyranosyl-(1 --4)-beta-D-glucopyranoside (1), together with fourteen known compounds: oleanolic acid (2), 3-acetyl oleanolic acid (3), 3beta-O-acetyl ursolic acid (4), 2alpha-hydroxy-ursolic acid (5), 2alpha, 3beta, 19alpha, 23-tetrahydroxy-urs-12-en-28-oic acid (6), alpha-amyrin-3-O-beta-D-glucopyranoside (7), pomolic acid (8), betulinic acid (9), ursolic acid (10), 2alpha, 3beta, 19alpha, 23-tetrahydroxy-olean-12-en-28-oic acid (arjungenin) (11), 2alpha-hydroxy-oleanolic acid (12), hederagenin (13), 2alpha, 19alpha-dihydroxy-ursolic acid (14) and pruvuloside A (15), by the spectroscopic techniques of NMR, HMBC, IR and MS, separately. All these compounds were obtained from this plant for the first time, and compounds 3, 4 and 15 were isolated from genus Callicarpa L. for the first time.

To study the hemostatic effect of chemical constituents from Callicarpa nudiflora.The chemical constituents were isolated and purified via silica gel and Sephadex LH-20 column chromatography. Their structures were determined on the basis of spectral analysis. prothrombin time (PT), activated partial thromboplastin time (APTT), thrombin time (TT) and fibrinogen (FIB) of the constituents rabbit blood samples were tested with rabbit blood in vitro.Eleven compounds were isolated and identified as two diterpenens: 7alpha-hydroxy sandaracopimaric acid (1), 16, 17-dihydroxy-3-oxophyllocladane (2). Two phenoic glycosides: acteoside (3), samioside(4). Three triterpenes: 2alpha, 3alpha, 24-trihydroxy-ursa-12-en-28-oic acid (5), 2alpha, 3alpha, 19alpha-trihydroxyursa-12-en-28-oic acid-28-0-beta-D-glucopyranosyl ester (6), and 2alpha, 3alpha, 19alpha, 23-tetrahydroxy-ursa-12-en-28-oic acid-28-0-beta-D-glucopyranosyl ester (7). Four flavones: rhamnazin (8), 5-Hydroxy-3, 7, 4'-trimethoxy-flavone (9) , 5-Hydroxy-3, 7, 3', 4'-tetramethoxyflavone (10), and luteoloside (11). All Compounds cannot significantly shorten the PT (P0.01), compounds 3, 4, 7, 10 can remarkedly increase APTT (P0.01), compound 5 can prolong the T( P0.01) obviously, and compound 8 can significantly increase the contents of FIB (P0.01).Compounds 2, 4 and 10 were isolated from this genus for the first time, and compounds 1, 3, 5, 6, 7 and 9 had been isolated from this plant for the first time. The hemostatic effect of C. nudiflora may be related to the activation of the intrinsic blood coagulation system.

To study on the chemical constituents of Callicarpa kochiana.The chemical constituents were isolated by chromatographic methods and structurally elucidated by spectral analysis.Twelve compounds were obtained and identified as alpha-amyrin(I), 2beta, 3beta, 19alpha-trihydroxy-12-en-28-ursolic acid (II), oleanolic aicd (III), alpha-amyrin-3-0-beta-D-glucopyranoside (IV), ursolic acid (V), betulinic acid (VI), 2alpha, 3beta,23-trihydroxy-12-en-28-oic-0-beta-D-glucopyranoside (VII), 0-hydroxybenzoic acid (VI), pomolic acid (IX), myrianthic acid (X), beta-sitosterol (XI), dauricine (XII).All of these compounds are isolated from Callicarpa kochiana for the first time and compounds II, IV, VII, VIII, IX and X are reported for the first time from Callicarpa genus.

To analyze the compositions of the essential oil from the leaves of Callicarpa integerrima.GC-MS method was used.42 chemical constituents, accounting for 97.62% of total content were identified.The main components were beta-caryophyllene (33.74%), Elixene (12.86%), tau-Cadinene (9.57%) and (-) -Spathulenol (8.99%). Besides, some sesquiterpenes and their oxides, such as Copaene (4.21%), Globulol (3.81%), alpha-Caryophyllene (2.48%), 2-Naphthalenemethanol, decahydro-alpha, alpha, 4a-trimethyl-8-methylene-[2R-(2alpha, 4aalpha, 8alphabeta)]-(2.37%) and 1,6-Cyclodecadiene (2.24%) had also relatively high contents.

Variations in volatile composition of the leaf and fruit oils from Callicarpa macrophylla were compared, using GC-FID, Kovat's Index calculation, and GC/MS. The oils were rich in selinene derivatives. The fruit oil was comprised of 41.6% β-selinene and 6% α-selinene. The leaves from both the harvests contained 29% and 20% β-selinene and 1.7% α-selinene. In addition, dendrolasin, a potential perfumery natural furanoid sesquiterpenoid, was a characteristic of both leaf and fruit essential oils.

Six new compounds, including five new seco-abietane diterpenoids, 12-deoxy-seco-hinokiol methyl ester (1), 12-deoxy-11,12-dihydro-seco-hinokiol methyl ester (2), callicarpic acid A (3), 9alpha-hydroxycallicarpic acid A (4), and callicarpic acid B (5), and a new phenylethanoid derivative, 4-hydroxyphenethyl tetradecanoate (6), have been isolated from the leaves and twigs of Callicarpa pilosissima, together with 14 known compounds (7-20). The structures of these new compounds were determined through analyses of physical data. 12-Deoxy-11,12-dihydro-seco-hinokiol methyl ester (2), callicarpic acid B (5), and alpha-tocopherol trimer B (15) exhibit antitubercular activities (MICs

The crude extract of the roots from the Australian medicinal plant Dianella callicarpa (Liliaceae) displayed significant antimicrobial and antiviral activities. This prompted a chemical investigation, resulting in the isolation of the new naphthalene glycoside, dianellose (10), together with dianellin (1), dianellidin (2), dianellinone (3), stellalderol (9) and 5-hydroxydianellin (11). The structures for compounds 1, 9 and 10 were secured by detailed spectroscopic analyses, while compounds 2, 3 and 11 were identified on the basis of comparisons to literature data. Whilst the chemistry of the genus Dianella has previously been investigated, we report the first isolation of stellalderol (9) from this genus, together with the chemical and biological evaluation of the callicarpa species. Biological evaluation of the isolated compounds established that 2 showed antiviral and mild antimicrobial properties and that compounds 1, 9 and 10 displayed moderate antitumour activities.

A new abietane-type diterpenoid and a new oleanane-type triterpenoid glucosyl ester were isolated from the leaves of Callicarpa japonica Thunb. var. luxurians Rehd. (Verbenaceae) along with 11 known compounds, comprising seven triterpenoids, two sterols, a flavonoid, and an aliphatic glycoside. Their chemical structures were determined on the basis of spectroscopic data.

To establish an RP-HPLC method for determination of betulinic acid in Callicarpa macrophylla, a commonly used herbal in Yunnan.A Kromasil-C18 column (4.6 mm x 200 mm, 5 microm) and a mobile phase consisted of acetonitrile-0.1% phosphoric acid (63: 37) were used. The flow rate was 1.0 mL x min(-1) and the UV detector wavelength was 205 nm.Betulinic acid was well separated from other compounds in C. macrophylla. The content of betulinic acid in C. macrophylla from different origins showed apparent differences, the content of betulinic acid in C. macrophylla from Yunnan was the highest. The calibration curve was linear in the range of 0.016 6-0.332 mg x mL(-1) of betulinic acid with correlation coefficient 0.999 8. The average recovery of betulinic acid was 98.5%.The method is simple, accurate and reproducible, and is suitable for the quality control of C. macrophylla.

The morphology and function of the flowers of three species of the genusCallicarpa, C. glabra, C. nisnimurae andC. subpubescens, endemic to the Bonin Islands, revealed that all three species were dioecious. Male plants had short-styled flowers with sterile ovaries, while female plants had long-styled flowers with non-germinating inaperturate pollen grains. Such dioecism has never been reported from the family Verbenaceae. This curious sexual system with non-germinating pollen grains may have been maintained as a reward to insect pollinators.

Tomex tomentosa Linnaeus, Species Plantarum 1: 118. 1753. "Habitat in India." RCN: 972. Basionym of: Callicarpa tomentosa (L.) L. (1774); Callicarpa lanata L. (1771), nom. illeg. Lectotype (Trimen in J. Linn. Soc., Bot. 24: 136. 1887): Herb. Hermann 1: 64, No. 59 (BM-000594496). Generitype of Tomex Linnaeus. Current name: Callicarpa tomentosa (L.) L. (Verbenaceae)., Published as part of Jarvis, Charlie, 2007, Chapter 7: Linnaean Plant Names and their Types (part T), pp. 878-905 in Order out of Chaos. Linnaean Plant Types and their Types, London :Linnaean Society of London in association with the Natural History Museum on page 889, DOI: 10.5281/zenodo.291971

Callicarpa americana Linnaeus, Species Plantarum 1: 111. 1753. "Habitat in Virginia, Carolina." RCN: 906. Lectotype (Moldenke in Repert. Spec. Nov. Regni Veg. 39: 306. 1936): Clayton 764, Herb. Linn. No. 136.1 (LINN; iso- BM). Generitype of Callicarpa Linnaeus. Current name: Callicarpa americana L. (Verbenaceae)., Published as part of Jarvis, Charlie, 2007, Chapter 7: Linnaean Plant Names and their Types (part C), pp. 370-473 in Order out of Chaos. Linnaean Plant Types and their Types, London :Linnaean Society of London in association with the Natural History Museum on page 375, DOI: 10.5281/zenodo.291971

Bioassay-guided fractionation of the combined fruits, leaves, and twigs (fruiting branches) of Callicarpa americana, collected from a plot in a forested area in southern Florida, led to the isolation of six new clerodane diterpenes (1-6) and eight known compounds. The structures of 1-6 [12(S),16xi-dihydroxycleroda-3,13-dien-15,16-olide (1), 12(S)-hydroxy-16xi-methoxycleroda-3,13-dien-15,16-olide (2), 12(S)-hydroxycleroda-3,13-dien-15,16-olide (3), 16xi-hydroxycleroda-3,11(E),13-trien-15,16-olide (4), 3beta,12(S)-dihydroxycleroda-4(18),13-dien-15,16-olide (5), and 12(S)-hydroxycleroda-3,13-dien-16,15-olide (6)] were elucidated by interpretation of spectroscopic data and chemical methods. The absolute configuration at C-12 in 1 and 3 was ascertained using the Mosher ester technique. The cytotoxicity of all isolates was tested against a panel of human cancer cell lines, and compounds 1, 4, and 6, and the known compounds genkwanin, 16xi-hydroxycleroda-3,13-dien-15,16-olide, and 2-formyl-16xi-hydroxy-3-A-norcleroda-2,13-dien-15,16-olide were active (ED505 microg/mL). However, 1 was found to be inactive against human cancer cells implanted in mice using a hollow-fiber tumor model.

The genus Callicarpa Linnaeus (1753: 111) with about 140 species is mainly distributed in temperate, subtropical and tropical Asia, America, Australia and the Pacific Islands (Harley et al. 2004; Bramley 2013; Zhang 2014; Ma & Su 2015), with 48 species and 13 varieties occurring in China (Chen & Gilbert 1994). Callicarpa was long thought to be included in Verbenaceae. However, based on morphological and molecular phylogenetic studies on the Verbenaceae and Lamiaceae, Callicarpa was transferred to Lamiaceae, along with Viticoideae and several other genera (Bramley 2009, 2013; Ma et al. 2015). During a taxonimic study of this genus in China, the name C. integerrima Champion ex Bentham (1853: 135) tourned out not yet typified. C. integerrima is currently accepted as endemic species of China (Chen & Gilbert 1994) and was described based on plants collected in Hongkong (Bentham 1853), but no specimens were cited in the protologue. We traced in K two duplicate specimens (K barcodes K000674744 and K000674745) collected by J.G. Champion in Hongkong that fit the protologue and can be regarded as syntypes (Art. 9.5 of the ICN, McNeill et al. 2012). The specimen K barcode K000674744 is better preserved and complete (flowers and fruits), and is selected here as the lectotype.

Callicarpenal (13, 14, 15, 16-tetranor-3-cleroden-12-al) and intermedeol [(4S,5S,7R,10S)-eudesm-11-en-4-ol], isolated from American beautyberry, Callicarpa americana (Lamiaceae), were evaluated in laboratory bioassays for repellent activity against host-seeking nymphs of the blacklegged tick, Ixodes scapularis, and lone star tick, Amblyomma americanum. A strip of organdy cloth treated with test solution was doubly wrapped (treatment on outer layer) around the middle phalanx of a forefinger and ticks released on the fingertip. Callicarpenal and intermedeol, at 155 nmole/cm(2) cloth repelled 98 and 96% of I. scapularis nymphs, respectively. Dose response tests with I. scapularis nymphs showed no difference in repellency among callicarpenal, intermedeol and Deet (N,N-diethyl-3-methylbenzamide), however, SS220 ((1S,2'S)-2-methylpiperidinyl-3-cyclohexene-1-carboxamide) was significantly more repellent than the other compounds. Callicarpenal, at 155 nmole/cm(2 )cloth, repelled 100 and 53.3% of I. scapularis nymphs at 3 and 4 h, respectively, after the cloth was treated, whereas intermedeol repelled 72.5% of I. scapularis nymphs 3 h after treatment. In comparison with the results obtained with I. scapularis, callicarpenal, intermedeol, Deet and SS220 were less effective against A. americanum. Only intermedeol and SS220 repelled significantly more A. americanum than ethanol controls at 155 nmole compound/cm(2) cloth. At 1,240 nmole/cm(2 )cloth, callicarpenal and intermedeol repelled 20 and 40% of A. americanum nymphs.

This study investigated metabolites with activities against plant parasite nematodes from the fresh-water fungus Caryospora callicarpa YMF1.01026. We obtained three novel tetradecalactone metabolites, caryospomycins A–C, with such activities. The chemical structures of these were determined through NMR spectroscopic analysis and were found to belong to the 14-membered macrolides with a fused 1,2-dimethoxy-4-hydroxybenzene ring, a rare structure among the resorcylides. In the in vitro tests, all three compounds exhibited moderate killing activity against the nematode Bursaphelenchus xylophilus. To our knowledge, this is the first report of secondary metabolites in the aquatic fungal genus Caryospora.

• Background and Aims Morphological descriptions of the extrafloral nectaries (EFNs) of certain plant species are common in the literature, but they rarely relate morphology with histology, gland distribution and secretory attributes. In this study a morphological/secretory characterization of EFNs occurring on several plant species in a tropical coastal community is made and the implications of gland attributes discussed from a functional perspective. • Methods The morphology and nectar secretion of the EFNs of 20 plant species are characterized through scanning electron microscopy, histochemical detection of reducing sugars (Fehling's reagent) and nectar volume/concentration estimates. • Key Results Sixty-five per cent of plant species in coastal communities had EFNs on vegetative structures and 35 % of species had glands on reproductive and vegetative organs. The Fabaceae is the plant family with the most species with EFNs and most diversity of gland morphologies. Four types of vascularized nectaries and four of glandular trichomes are described; sugar-secreting trichomes are characterized using Fehling's technique, and the first descriptions of unicellular and peltate trichomes functioning as EFNs are provided. Glands of ten plant species and six genera are described for the first time. Four plant species possess more than one morphological type of EFN. Eleven species have EFNs in more than one location or organ. More complex glands secrete more nectar, but are functionally homologous to the aggregations of numerous secretory trichomes on specific and valuable plant organs. • Conclusion Important diversity of EFN morphology was foundin the coastal plant community studied. Both vascularized and non-vascularized EFNs are observed in plants and, for the latter, previously non-existent morpho-secretory characterizations are provided with a methodological approach to study them. It is recommended that studies relating EFN attributes (i.e. morphology, distribution) with their differential visitation by insects (i.e. ants) and the cost of maintenance to the plants are carried out to understand the evolution of these glands.

Essential oil extracts from Callicarpa americana and Callicarpa japonica were investigated. Bioassay-guided fractionation of C. americana extracts using the yellow fever mosquito, Aedes aegypti, led to the isolation of alpha-humulene, humulene epoxide II, and intermedeol and a newly isolated terpenoid (callicarpenal). Similar work involving C. japonica resulted in the isolation of an additional compound, spathulenol, as well as the four compounds isolated from C. americana. Structure elucidation was performed on all isolated compounds using a combination of gas chromatography-mass spectrometry-electron ionization, high-resolution liquid chromatography-MS-electrospray ionization, and one- and two-dimensional NMR experiments. Heretofore, 13,14,15,16-tetranorclerodane, callicarpenal, has never been identified from natural sources. Complete (1)H and (13)C NMR assignment data are provided for this compound. In bite deterrent studies, spathulenol, intermedeol, and callicarpenal showed significant repellent activity against A. aegypti and Anopheles stephensi.

This paper analyzed the population structure of Alsophila spinulosa in seven plots by the method of spatial sere substituting for time sere, and measured its spatial distribution pattern and dynamics by applying five aggregate indices, C, K, m*, m*/m and Idelta. The spatial distribution pattern with different quadrat scale was examined, according to the map of individual location. The results indicated that the population structure of Alsophila spinulosa in the seven plots presented growing, stable, adult or senescent type, and the spatial distribution pattern was changed from clump to random with the development of Alsophila spinulosa population. The values of dispersion index Idelta of the population decreased with increasing quadrat scale.

The allelochemical potential of Callicarpa acuminata (Verbenaceae) was investigated by using a biodirected fractionation study as part of a long-term project to search for bioactive compounds among the rich biodiversity of plant communities in the Ecological Reserve El Eden, Quintana Roo, Mexico. Aqueous leachate, chloroform-methanol extract, and chromatographic fractions of the leaves of C. acuminata inhibited the root growth of test plants (23-70%). Some of these treatments caused a moderate inhibition of the radial growth of two phytopathogenic fungi, Helminthosporium longirostratum and Alternaria solani (18-31%). The chloroform-methanol (1:1) extract prepared from the leaves rendered five compounds: isopimaric acid (1), a mixture of two diterpenols [sandaracopimaradien-19-ol (3) and akhdarenol (4)], alpha-amyrin (5), and the flavone salvigenin (6)]. The phytotoxicity exhibited by several fractions and the full extract almost disappeared when pure compounds were evaluated on the test plants, suggesting a synergistic or additive effect. Compounds (4), (5), and the semisynthetic derivative isopimaric acid methyl ether (2) had antifeedant effects on Leptinotarsa decemlineata. Compound 5 was most toxic to this insect, followed by (2), (4), and (6) with moderate to low toxicity. No correlation was found between antifeedant and toxic effects on this insect, suggesting that different modes of action were involved. All the test compounds were cytotoxic to insect Sf9 cells while (6), (4), and (1) also affected mammalian Chinese Hamster Ovary (CHO) cells. Compound 5 showed the strongest selectivity against insect cells. This study contributes to the knowledge of the defensive chemistry and added value of C. acuminata.

Volatile substances of Callicarpa japonica Thunb. were examined for their antibacterial activities against six foodborne microorganisms using the optical densitometer Bioscreen C. Extracts of C. japonica were obtained by simultaneous steam distillation and solvent extraction (SDE), and those extracted for 1.5 and 2.0 h at pH 6.0 strongly inhibited the growth of Bacillus cereus and Salmonella typhimurium; the content of the volatile substances of leaves at these pH levels were 543.1 and 706.7 mg/kg, respectively. All foodborne microorganisms tested were strongly inhibited by the addition of >8% (v/v) of the SDE extracts to broth medium. The major volatile components of the SDE extracts obtained at 1.5 h and pH 6.0 were gamma-caryophyllene, 1-octen-3-ol, 2-hexenal, germacrene B, and aromadendrene II, with corresponding peak areas of 44.14, 15.6, 9.86, 5.24, and 4.01%, respectively, and major antibacterial components were 1-octen-3-ol and 2-hexenal. Among the 32 materials identified as volatile flavor components, 2-hexenal, 2,4-hexadienal, 1-octen-3-ol, 2,4-heptadienal, and epiglobulol strongly inhibited microorganism growth. In particular, 2-hexenal (107.52 mg/L) and 1-octen-3-ol (678.64 mg/L) inhibited the growth of most microorganisms tested by >90%.