Heptaellipside A, a rare new 2,28-bidesmosidic lupane-type saponin from the leaves of Heptapleurum ellipticum.

For the first time, phytochemical constituents of the leaves of Heptapleurum ellipticum were investigated. One rare new 2,28-bidesmosidic lupane-type saponin, named heptaellipside A (1), along with four other lupane-type analogs (2-5) were purified by combining differently chromatographic methods. All of the separated compounds (1-5) were communicated for the first time from H. ellipticum. The structures of them were definitely illustrated following extensive and comprehensive UV/VIS, FTIR, HRMS/ESI, and NMR techniques. Further, all isolated compounds were evaluated for their α-glucosidase and α-amylase inhibition. As the results, compound 3 respectively exhibited stronger in both inhibitory activities against α-glucosidase and α-amylase (IC50 values of 15.53 and 26.93 µM), than the acarbose standard (IC50 values of 214.50 and 143.48 µM).

Identification of lignans as selective cyclooxygenase-2 inhibitors from the extract of Acanthopanacis cortex.

Acanthopanacis cortex (the dried root bark of Acanthopanax gracilistylus W. W. Smith) has been used for the treatment of rheumatic diseases in China for over 2000 years. Four previously undescribed lignans (1-4) and 12 known lignans (5-16) were isolated from Acanthopanacis cortex. In this study, the inhibitory activities of compounds 1-16 against neutrophil elastase (NE), cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) are reported. The results show that compounds 1-16 exhibit weak inhibitory activities against NE and COX-1. However, compounds 2, 6∼8 and 13∼16 demonstrate better COX-2 inhibitory effects with IC50 values from 0.75 to 8.17 µΜ. These findings provide useful information for the search for natural selective COX-2 inhibitors.

Triterpenoids from the leaves of Eleutherococcus sessiliflorus, and their antiproliferative activities in TNF-α induced HFLS-RA cells.

Five undescribed elesesterpenes L-U, along with nine known 3,4-seco-lupane-type triterpenoids were isolated from the leaves of Eleutherococcus sessiliflorus (Rupr. & Maxim.) S. Y. Hu. Elesesterpene L-S, and U were lupane-type triterpenoids, whereas elesesterpene T was an oleanane-type triterpenoid, probably artifact, as suggested by LC-MS analysis. Out of the nine known compounds, five were initially identified in E. sessiliflorus. Moreover, their structures were definitively determined using spectroscopic analyses, and the absolute configurations of elesesterpenes L-M and sachunogenin 3-O-glucoside were clarified using X-ray crystallographic techniques. The absolute configuration of elesesterpene T was determined by measuring and calculating its ECD. In addition, all compounds were tested to examine their ability to inhibit the proliferation of HFLS-RA cells induced by TNF-α in vitro. Elesesterpene M, chiisanogenin, chiisanoside, and 3-methylisochiisanoside significantly inhibited HFLS-RA proliferation.

Three new triterpenoids from the fruit of Eleutherococcus senticosus (Rupr.) Harms.

A phytochemical investigation on the 70% EtOH extract of the fruit of Acanthpanax senticosus resulted in the isolation of three new triterpenoids, Falcatane C (1), Acasentrioid F (2), Acasentrioid G (3) together with twenty-seven known ones (4-30). Structural elucidation of all the compounds was performed by spectral methods such as 1D or 2D (1H-1H COSY, HSQC, and HMBC), NMR spectroscopy, and high-resolution mass spectrometry. Moreover, all compounds were evaluated for their effects on H2O2-induced neurotoxicity in human neuroblastoma SH-SY5Ycells. Compounds 13 and 15 showed significant neuroprotective impact at a specific concentration, and compounds 1, 3, 5, 9, 11, 13-15, 17, 20-21, 23-25, 27, 29-30 showed moderate neuroprotective effect. The current study suggests that triterpenes in Eleutherococcus senticosus (Rupr.) Harms may play an essential role in the neuroprotective properties.

Newly found leaf arrangement to reduce self-shading within a crown in Japanese monoaxial tree species.

A newly found leaf arrangement to reduce self-shading was observed in a Japanese warm-temperate forest. For monoaxial trees that deploy leaves directly on a single stem, leaf arrangements involving progressive elongation of the petiole and progressive increase in deflection angle (the angle between stem and petiole) from the uppermost to the lowermost leaves act to reduce self-shading. However, the progressive reduction in petiole length and deflection angle from the uppermost to the lowermost leaves should also result in the reduction of self-shading. Nevertheless, the latter leaf arrangement has not been reported previously for any tree species. Four Araliaceae species, namely, Gamblea innovans, Chengiopanax sciadophylloides, Dendropanax trifidus and Fatsia japonica, which are typical monoaxial tree species in Japan, were studied. We examined the crown structure of saplings growing in the light-limited understorey in a Japanese warm-temperate forest. Two evergreen species, Dendropanax trifidus and F. japonica showed progressive petiole elongation and progressive increase in the deflection angle from the uppermost to the lowermost leaves. In contrast, saplings of deciduous species, G. innovans and C. sciadophylloides had a leaf arrangement involving progressive reduction in petiole length and deflection angle from the uppermost to the lowermost leaves. The leaf arrangement has diversified among members of the same family, but all four studied species develop a crown with little self-shading that is adapted for growth in the light-limited understorey. Although trees are likely to be under the same selective pressure to reduce self-shading, this study revealed that there is flexibility in its morphological realisation, which has been poorly appreciated previously.

Panaxsiamensis J. Wen, a new species of the ginseng genus (Panax, Araliaceae) from northern Thailand.

We herein describe a new species, Panaxsiamensis J. Wen, from the tropical monsoon forests in northern Thailand. Panaxsiamensis is characterized by a combination of characters including horizontally elongated rhizomes with thick internodes, 3-5 whorled leaves each with 7-9 sessile and lanceolate leaflets, lanceolate bracteoles not persisting at the fruiting stage, 2-locular ovaries, and red fruits with a black top. The new species is most closely related to Panaxzingiberensis C.Y. Wu & Feng from southeastern Yunnan province of China, sharing the character of sessile leaflets, but differing in that P.siamensis has well developed, elongated rhizomes (vs. compact, ginger-like rhizomes and rootstock in P.zingiberensis), and 7-9 leaflets (vs. (3-) 5-7 leaflets in P.zingiberensis). We also compare Panaxsiamensis to other related Asian Panax species, including P.assamicus Banerjee, P.bipinnatifidus Seem., P.pseudoginseng Wallich, and P.vietnamensis Ha & Grushv. The new taxon is preliminarily assessed as Vulnerable (VU D2), according to the IUCN Red List criteria. A taxonomic key is provided to facilitate the identification of P.siamensis and its close allies.

Monoterpenoids from the root bark of Acanthopanax gracilistylus and their inhibitory effects on neutrophil elastase, 5-lipoxygenase, andcyclooxygenase-2 in vitro.

Twenty-four monoterpenoids, including three previously undescribed compounds (1-3), were isolated from the root bark of Acanthopanax gracilistylus W. W. Smith (Acanthopanacis Cortex). Their structures were unambiguously established based on spectroscopic analysis (HR-ESIMS, IR, 1D, and 2D NMR), and the absolute configurations of 1-3 were elucidated by comparing their experimental and calculated electronic circular dichroism spectra. In addition, the structure of 8 was confirmed by single-crystal X-ray diffraction. The inhibitory activities of 1-24 against neutrophil elastase, 5-lipoxygenase, and cyclooxygenase-2 (COX-2) were studied in vitro for the first time, and the results showed that compound 24 possessed a significant inhibitory effect on COX-2 with an IC50 value of 1.53 ± 0.10 µΜ. This research first reported the presence of monoterpenoids in Acanthopanacis Cortex, including one monoterpenoid 2 with an unusual 4/5 bicyclic lactone system, and compounds 4 and 5 have never been reported in nature.

Polysciasoside B and C: new dammarane-type triterpene glycosides from the leaves of Australian rainforest plant Polyscias australiana (F.Muell.) Philipson (Araliaceae).

Phytochemical investigation of the leaves of Polyscias australiana (F.Muell.) Philipson (family Araliaceae) led to the isolation and identification of two new analogues belonging to the rare dammarane-type triterpene glycosides, polysciasosides B (1) and C (2). Also isolated in high yields from this plant was the known saponin, ß-hedrin (3). The two new polysciasoside analogues exhibited no anti-inflammatory activity (inhibitory effects on NO inhibition and cell viability in RAW 264.7 macrophages) or cytotoxic activity against AGS gastric adenocarcinoma or the MCF7 breast adenocarcinoma cell lines. In contrast, the known compound ß-hedrin exhibited potent anti-inflammatory and cytotoxicity in these biological assays.

Phylogenomics of Aralia sect. Aralia (Araliaceae): Signals of hybridization and insights into its species delimitations and intercontinental biogeography.

Genome-scale data have significantly increased the number of informative characters for phylogenetic analyses and recent studies have also revealed widespread phylogenomic discordance in many plant lineages. Aralia sect. Aralia is a small plant lineage (14 spp.) of the ginseng family Araliaceae with a disjunct distribution between eastern Asia (11 spp.) and North America (3 spp.). We herein employ sequences of hundreds of nuclear loci and the complete plastomes using targeted sequence capture and genome skimming to reconstruct the phylogenetic and biogeographic history of this section. We detected substantial conflicts among nuclear genes, yet different analytical strategies generated largely congruent topologies from the nuclear data. Significant cytonuclear discordance was detected, especially concerning the positions of the three North American species. The phylogenomic results support two intercontinental disjunctions: (1) Aralia californica of western North America is sister to the eastern Asian clade consisting of A. cordata and A. continentalis in the nuclear tree, and (2) the eastern North American A. racemosa forms a clade with A. bicrenata from southwestern North America, and the North American A. racemosa - A. bicrenata clade is then sister to the eastern Asian clade consisting of A. glabra (Japan), A. fargesii (C China), and A. apioides and A. atropurpurea (the Hengduan Mountains). Aralia cordata is supported to be disjunctly distributed in Japan, Taiwan, the Ulleung island of Korea, and in Central, Southwest and South China, and Aralia continentalis is redefined with a narrower distribution in Northeast China, eastern Russia and peninsular Korea.

In vitro and in silico cytotoxic activities of triterpenoids from the leaves of Aralia dasyphylla Miq. and the assessment of their ADMET properties.

From the methanol extract of the leaves of Aralia dasyphylla Miq. (Araliaceae), ten triterpenoids including five ursane-type triterpenoids, ursolic acid (1), 3-O-α-l-arabinopyranosyl ursolic acid (2), ursolic acid 28-O-ß-D-glucopyranosyl ester (3), 3-O-[ß-D-glucopyranosyl (l→3)]-α-L-arabinopyranosyl ursolic acid (4), and matesaponin 1 (5), and five oleanane-type triterpenoids, elatoside E (6), elatoside F (7), 3-O-[ß-D-glucopyranosyl (l→3)]-α-L-arabinopyranosyl oleanolic acid (8), 3-O-α-L-arabinopyranosyl oleanolic acid (9) and oleanolic acid 28-O-ß-D-glucopyranosyl ester (10) were isolated. Their structures were elucidated based on 1D-, 2D-NMR and ESI-MS spectra as well as by comparison with those reported in the literature. All isolated compounds were evaluated in vitro for their cytotoxic activities against three human cancer cell lines (HepG2, LU-1 and RD) and in silico by molecular docking studies on human glucose transporter 1 (hGLUT1) protein. The triterpenoids 2, 4, 6, 8 and 9 exhibited good growth inhibition of HepG2 and LU-1 cancer cell lines with IC50 values in the range 1.76 - 7.21 (µM). The oleanane type triterpenoid 8 was the highest cytotoxic compound to inhibit all the tested cancer cell lines with IC50 values of 2.73 ± 0.12, 1.76 ± 0.11, 2.63 ± 0.10 µM, respectively. The in silico molecular docking study results showed that compounds 4 and 6 had the highest binding affinity. Compounds 1-10 were evaluated for their in silico ADMET of absorption, distribution, metabolism, excretion and oral toxicity parameters. Compounds 6, 8, 9 and 10 from A. dasyphylla are potential hGLUT1 inhibitors and worth of further investigation for the prevention or treatment of diabetes and cancer.Communicated by Ramaswamy H. Sarma.

Responses of invasive and native plants to different forms and availability of phosphorus.

PREMISE: Many studies have assessed the various responses of alien plants to changes in overall nutrient or different nitrogen (N) availabilities. However, in natural soils, nutrients are present as different elements (e.g., N and phosphorus [P]) and forms (e.g., inorganic and organic). Few studies have explored whether invasive and native species differ in their responses to varying P availability and forms. METHODS: We grew five taxonomically related pairs of common herbaceous, invasive and native species alone or in competition under six different conditions of P availability or forms and assessed their growth performance. RESULTS: Invasive species overall did not produce more biomass than native species did in the various P conditions. However, the biomass response to organic forms of P was, relative to the response to inorganic forms of P, stronger for the invasive species than that for the native species and agreed with invasive species mainly allocating biomass to the root system under organic P conditions. CONCLUSIONS: While invasive species were not more promiscuous than the native species, they took great advantage of the organic P forms. Therefore, the invasion risk of alien species may increase in habitats with more organic P sources.

Evaluation of tropical-temperate transitions: An example of climatic characterization in the Asian Palmate group of Araliaceae.

PREMISE: There has been a great increase in using climatic data in phylogenetic studies over the past decades. However, compiling the high-quality spatial data needed to perform accurate climatic reconstructions is time-consuming and can result in poor geographical coverage. Therefore, researchers often resort to qualitative approximations. Our aim was to evaluate the climatic characterization of the genera of the Asian Palmate Group (AsPG) of Araliaceae as an exemplar lineage of plants showing tropical-temperate transitions. METHODS: We compiled a curated worldwide spatial database of the AsPG genera and created five raster layers representing bioclimatic regionalizations of the world. Then, we crossed the database with the layers to climatically characterize the AsPG genera. RESULTS: We found large disagreement in the climatic characterization of genera among regionalizations and little support for the climatic nature of the tropical-temperate distribution of the AsPG. Both results are attributed to the complexity of delimiting tropical, subtropical, and temperate climates in the world and to the distribution of the study group in regions with transitional climatic conditions. CONCLUSIONS: The complexity in the climatic classification of this example of the tropical-temperate transitions calls for a general climatic revision of other tropical-temperate lineages. In fact, we argue that, to properly evaluate tropical-temperate transitions across the tree of life, we cannot ignore the complexity of distribution ranges.

The complete chloroplast genome of Hydrocotyle pseudoconferta Masamune 1932 (Araliaceae).

Hydrocotyle pseudoconferta was an important medicinal plant. The complete plastid genome of this species was reported for the first time. The full length of the complete chloroplast genome is 153,302 bp, with a typical quadripartite organization: a large single-copy (LSC) region of 84,417 bp, a small single-copy (SSC) region of 18,767 bp, and a pair inverted repeat regions (IRa and IRb) with 25,059 bp for each. The complete chloroplast genome of H. pseudoconferta encoded 133 genes, comprising 86 protein-coding genes, 37 tRNA genes, 8 rRNA genes, and 2 pseudogenes. The phylogenetic analysis suggested the closest relationship between H. pseudoconferta and Hydrocotyle nepalensis.

Undescribed specialised metabolites from the endophytic fungus Emericella sp. XL029 and their antimicrobial activities.

The fungus Emericella sp. XL029 isolated from leaves of Panax notoginseng was investigated for agents with potential antibacterial and antifungal activities using a one strain-many compounds (OSMAC) strategy. Fifteen compounds, including seven undescribed structures, were obtained from this species. Their structures were confirmed by extensive spectroscopic data, single-crystal X-ray crystallography and quantum chemistry calculations. Emerlactam A exhibited better antibacterial activity against multidrug-resistant Enterococcus faecium and antifungal activity against Helminthosporium maydis, with an MIC value of 12.5 µg/mL. Quiannulatic acid displayed significant antibacterial activity against multidrug-resistant Enterococcus faecium and multidrug-resistant Enterococcus faecalis with MIC values of 1.56 µg/mL and 3.13 µg/mL, respectively. 5-alkenylresorcinol exhibited significant antifungal activity against all tested phytopathogenic fungi with MIC values ranging from 6.25 to 12.5 µg/mL.

Acanthoic acid, unique potential pimaradiene diterpene isolated from Acanthopanax koreanum Nakai (Araliaceae): A review on its pharmacology, molecular mechanism, and structural modification.

Acanthoic acid (AA) is a pimaradiene diterpene isolated from the root bark of Acanthopanax koreanum Nakai (Araliaceae) with a wide range of pharmacological activities, including anti-cancer, anti-inflammatory, anti-diabetes, liver protection, gastrointestinal protection, and cardiovascular protection. In addition, AA promotes its pharmacological effects by targeting liver X receptors (LXRs), nuclear factor-kappa B (NF-κB), Toll-Like Receptor 4 (TLR4) and IL-1 receptor-associated kinase (IRAK) signaling pathways, or AMP-activated protein kinase (AMPK) signaling pathway, etc. Also, some studies focus on the structural modification of AA to improve its pharmacological activities. The review summarizes the pharmacological activities, molecular mechanism, and the structural modification of AA, which might supply information for the development of AA in the future.

The mechanism of the cytotoxic effect of Panax notoginseng extracts on prostate cancer cells.

INTRODUCTION: Panax notoginseng (Burkill) F.H. commonly referred to as Sanqi, is a Chinese herb that has long been used to treat various conditions including blood disorders and cardiovascular diseases. While Panax notoginseng has been used as an anti-cancer medicinal herb in recent years, how it achieves this therapeutic effect has not been thoroughly elucidated. The purpose of this study was to reveal more about the mechanism of the cytotoxic effect of Panax notoginseng on prostate cancer (PCa) cells. METHODS: Ethanol extract of Panax notoginseng root was authenticated using high-performance liquid chromatography (HPLC). The cytotoxic activity of this herb against PCa cells was determined using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method, flow cytometry, and enzyme-linked immunosorbent assay (ELISA). RESULTS: The assessment of cellular metabolic activity demonstrated that Panax notoginseng reduces the viability of LNCaP and 22Rv1 cells in a dose-dependent manner. Annexin-V binding flow cytometry assay showed that Panax notoginseng induces apoptosis in PCa cells. Cell cycle analysis by quantification of DNA content using flow cytometry showed that Panax notoginseng arrests the cell cycle at the G2/M phase in both LNCaP and 22Rv1 cells. Moreover, ELISA demonstrated that Panax notoginseng-treated PCa cells secrete significantly less tumor-promoting cytokine interleukin-4 (IL-4) to the supernatant compared with controls. CONCLUSIONS: These results provide evidence for the cytotoxic effects of Panax notoginseng on PCa cell lines. This botanical is a promising candidate for the complementary and integrative medicine treatment of PCa and further studies are indicated to determine the anti-cancer mechanism of Panax notoginseng.

PTP1B and α-glucosidase inhibitory activities of the chemical constituents from Hedera rhombea fruits: Kinetic analysis and molecular docking simulation.

In this study, we present the first investigation of Hedera rhombea Bean fruit, which led to the isolation of six undescribed compounds including two megastigmane glucosides, two rare 1,4-dioxane neolignanes, and two quinic acid derivatives, together with 26 known compounds. Their structures and absolute configurations were elucidated by extensive analysis of NMR spectroscopic data, HRMS, and ECD calculations. This is the first report on the isolation of methyl 3-O-caffeoyl-5-O-p-coumaroylquinate from a natural source. Among the isolated compounds, falcarindiol and caffeoyltryptophan showed significant PTP1B inhibition with IC50 values of 7.32 and 16.99 µM, respectively, compared to those of the positive controls [sodium orthovanadate (IC50 = 17.96 µM) and ursolic acid (IC50 = 4.53 µM)]. These two compounds along with several other compounds displayed significant α-glucosidase inhibitions with IC50 values ranging from 12.88 to 91.89 µM, stronger than that of the positive control (acarbose, IC50 = 298.07 µM). Enzyme kinetic analysis indicated that caffeoyltryptophan and falcarindiol displayed competitive and mixed-type PTP1B inhibition, respectively, whereas the α-glucosidase inhibition type was mixed-type for caffeoyltryptophan and uncompetitive (rarely reported for a-glucosidase inhibitors) for falcarindiol. In addition, molecular docking results showed that these active compounds exhibited good binding affinities toward both PTP1B and α-glucosidase with negative binding energies. The results of the present study demonstrate that these active compounds might be beneficial in the treatment of type 2 diabetes.

Chemical Components in Hedera rhombea Leaves and Their Cytotoxicity.

Two novel triterpene glycosides (1 and 2), 17 known triterpene glycosides (3-19), two known flavonoid glycosides (20 and 21), and two known norsesquiterpene glucosides (22 and 23) were isolated from Hedera rhombea (Araliaceae) leaves. The structures of 1 and 2 were determined by spectroscopic analysis, including two-dimensional NMR spectroscopy, and chromatographic analysis of the hydrolyzed products. The cytotoxicity of the isolated triterpene glycosides (1-19) against HL-60 human promyelocytic leukemia cells was evaluated. Compounds 9, 10, and 11 were cytotoxic to HL-60 cells with IC50 values of 7.2, 21.9, and 32.8 µM, respectively. Other compounds isolated from the leaves were not cytotoxic at sample concentrations of 50 µM.

Two new triterpenoid fatty acid esters from Schefflera barteri Harms (Araliaceae)§.

Two new fatty acid esters of triterpenoids (1-2) together with eleven known compounds (3-13) were obtained after investigation of the CH2Cl2-MeOH (1:1) crude extract from the leaves of Schefflera barteri Harms. All these compounds (1-13) were isolated for the first time from this plant among which compounds 3, 4, 6 and 9-13 were also isolated from the genus Schefflera for the first time. The structures of the isolated compounds were elucidated by analyses of their spectroscopic data (1D and 2D NMR, and MS). The antibacterial and cytotoxic activities of crude extracts, fractions and compounds (1, 2, 5, 6, 8 and 9) were investigated against both Gram-negative and Gram-positive bacteria strains as well as on human cervix carcinoma and colon adenocarcinoma cancer cell lines, respectively. They showed weak to significant activity towards the strains and malignant cells used.

Bioactive constituents from the leaves of Metapanax delavayi with anti-benign prostatic hyperplasia activities.

In the course of our continuing search for biologically active compounds from medicinal sources, we further investigated the aqueous extract of Metapanax delavayi (Franch.) J. Wen & Frodin (Araliaceae) leaves. Five undescribed terpene glycosides, liangwanosides B-F referring to two megastigmane glycosides, one monoterpene glycoside, and two sesquiterpene glycosides, together with seven known compounds were isolated. Their chemical structures were elucidated by detailed spectroscopy (1D/2D NMR), HRESIMS data analysis, hydrolysis, and comparison of experimental and calculated electronic circular dichroism (ECD) data. The biological evaluation of benign prostate hyperplasia (BPH) inhibition revealed that some compounds, including liangwanosides B-D, benzyl-O-α-L-rhamnopyranosyl-(1 â†’ 6)-ß-D-glucopyranoside, methyl 2-O-ß-D-glucopyranosylbenzoate, and 3,4-dihydroxybenzaldehyde, exhibited moderate inhibitory activity against BPH-1 cells with inhibition rates ranging from 13.8% to 23.8% at 100 µM. Among them, liangwanoside B showed the comparable effect to positive control (finasteride) at 100 µM, and its possible mechanism was then explored by molecular docking studies.