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The fruit-piercing moth (FPM) Eudocima phalonia is widely present in the tropics, causing major damages to the citrus industry. In its ancestral distribution range, e.g. Australia, FPM develops on vines from the Menispermaceae family. But in more recently colonized islands, e.g. New Caledonia, FPM populations have shifted to new host plants of the Fabaceae family, Erythrina spp.. To understand this host shift, we studied the chemical ecology of FPM as a mechanism driving host plant acceptance. We collected volatile headspace samples of Erythrina species and Menispermaceae and compared their chemical spectra. We assessed the electrophysiological responses of FPM populations from the two countries to the plant chemical extracts and identified bioactive compounds. The volatile profiles from each species were quite different between and within each plant family. However, five compounds common across the two families triggered electrophysiological responses in both FPM populations. Those common bioactive compounds could have facilitated the host shift to completely different plant family. Furthermore, the diverging history between the two FPM populations may explain differences in electrophysiological sensitivity to other specific compounds. These results are discussed in the context of the production of a generic lure that could be attractive to all FPM populations. [ABSTRACT FROM AUTHOR]

Fibraurea tinctoria Lour. (Menispermaceae) is a medicinal plant used by many local tribes in Indonesia and other countries. This species has pharmacological potential, such as antimalaria, antibacterial, antitumor, antioxidant, anticancer, antidiabetic, anti‐inflammatory, and hepato‐protector. However, the secretory structures and sites of secondary metabolite accumulation still need to be studied. This study aimed to explore the secretory structures and reveal the accumulation sites of the main classes of secondary metabolites in the root, stem, and leaves of F. tinctoria. Histochemical analysis using various specific reagents was performed on freehand sections of the fresh organs to detect alkaloids, phenolics, terpenoids, and lipophilic compounds. Observations of secretory structures were carried out using light microscopy. The result showed that idioblast was the predominant secretory structure in the plant organs and contained all the chemical groups investigated, while laticifer accumulated alkaloids were found only in the stem. Some secondary metabolites were localized in the xylem, intercellular space, and cuticle layer. Crystals were observed in the root, stem, and leaf of this species. These results might be helpful as guide information for extracting the particular plant parts to obtain the desired secondary metabolites. It suggested that leaves are a potential alternative source of medicinal raw material of this species, in addition to the stem. Research Highlights: The first study on secretory structures of Fibraurea tinctoria.Secondary metabolites in F. tinctoria organs accumulate in specialized and unspecialized structures.The idioblast is the primary secretory structure in the organs of F. tinctoria spreading over the root, stem, and leaves. [ABSTRACT FROM AUTHOR]

Benzylisoquinoline alkaloids (BIAs) are a class of secondary metabolites that possess diverse pharmaceutical properties and are exclusively accumulated in specific plant genera. The Pictet–Spengler condensation, catalyzed by norcoclaurine synthase (NCS), represents a key enzymatic reaction in the biosynthetic pathway of BIAs. While NCS genes have been identified in several plant families such as Papaveraceae, Berberidaceae, and Ranunculaceae, no NCS genes have been reported in Menispermaceae, which is another genus known to accumulate BIAs. Here, NCSs were isolated and functionally characterized from the Menispermaceae family plant Stephania tetrandra. In vitro enzyme assay identified two functional StNCSs which could catalyze the formation of (S)‐norcoclaurine. These functionally characterized genes were then integrated into engineered yeast to enable the production of norcoclaurine. Phylogenetic analysis of the NCS enzymes revealed that the StNCSs predominantly clustered into two clades. The functional StNCSs clustered with known NCSs, highlighting the presence of a specific NCS catalytic domain. This study not only provides additional genetic components for the synthetic biology‐based production of BIAs in yeast but also contributes to the understanding of the phylogenetic relationships and structure–function relationship of NCS genes involved in the origin and production of BIAs. [ABSTRACT FROM AUTHOR]

Menispermaceae are an angiosperm family of mostly climbing plants distributed throughout tropical regions. The fruits in this family have a strong sclerified endocarp and can be used for reliable species‐level identifications, even in a fossilized form. New Paleocene‐age menispermaceous endocarps have recently been discovered in South America and Asia, while in Europe, they are mostly found in the Eocene. This paper focuses on the study of fossil endocarps belonging to Menispermaceae, found in the Petit‐Pâtis locality, which is one of the few Paleocene localities in Europe. The locality is dated to the late Paleocene (57–56 Ma) and the fossils represent flora and fauna in the Paris Basin before the onset of the Paleocene–Eocene Thermal Maximum. Lignitized fossils were photographed and their morphology was analyzed using computed tomography, scanning electron microscope, and geometric morphometric analysis. The analysis of 36 fossils belonging to Menispermaceae revealed that three genera (Stephania, Palaeosinomenium, Tinospora) were present in the late Paleocene of Paris Basin. Differences in internal morphology and a more inflated endocarp base led to a description of a new fossil species—Palaeosinomenium oisensis sp. nov. The occurrence of these genera in the Paleocene of France is consistent with the suggestion that megathermal flora was present in the Paris Basin before the Paleocene–Eocene Thermal Maximum. These three genera are currently the oldest occurrences in Europe, highlighting the connection between paleofloras of the Americas, Europe, and Asia in the Paleocene. [ABSTRACT FROM AUTHOR]

Phytochemical studies of the stems and leaves of Stephania dielsiana Y.C.Wu yielded two new aporphine alkaloids (1 and 5), along with six known alkaloids (2–4 and 6–8). Their structures were characterised based on analyses of spectroscopic data, including one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopy and high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS). The cytotoxic activities of the isolated compounds against a small panel of tumour cell lines were assessed by MTS assay. Interestingly, compound 2 exhibited particularly strong cytotoxic activities against HepG2, MCF7 and OVCAR8 cancer cell lines, with IC50 values of 3.20 ± 0.18, 3.10 ± 0.06 and 3.40 ± 0.007 µM, respectively. Furthermore, molecular docking simulations were carried out to explore the interactions and binding mechanisms of the most active compound (compound 2) with proteins. Our results contribute to understanding the secondary metabolites produced by S. dielsiana and provide a scientific rationale for further investigations of cytotoxicity of this valuable medicinal plant. [ABSTRACT FROM AUTHOR]

• Good safety profile and hepatoprotective effect is vital in tuberculosis chemotherapy. • Safety profile, hepatoprotective effect and selectivity index markers for herbal drug. • Plant extracts with LC 50 20 µg/mL and below are cytotoxic comparable with doxorubicin. • Menispermaceae species have global therapeutic effect due to their alkaloid content. Tuberculosis, caused by Mycobacterium tuberculosis , is a worldwide disease affecting millions of people. The rise of resistant strains, coupled with toxicity of current chemotherapy, requires effective alternatives against mycobacterial infections. Some plants from the Menispermaceae family have been used to treat tuberculosis and cough related symptoms. In this study, acetone, methanol:water (4:1), dichloromethane:methanol (1:1) and hot water extracts of different plant parts of Cissampelos owariensis, Cissampelos mucronata and Tinospora fragosa were tested against M. aurum, M. bovis, M. fortuitum, M. smegmatis and M. tuberculosis using a two-fold serial microdilution assay. Cytotoxicity of the active extracts was determined against Vero and HepG2 cells. The hepatoprotective effect of the active extracts was evaluated using rifampicin and acetaminophen as toxic drugs against HepG2 cells. The hot water leaf extracts were most active with promising minimum inhibitory concentration (MIC) values of 20 and 40 µg/mL against M. smegmatis and M. fortuitum respectively. The acetone extracts of C. owariensis, C. mucronata and T. fragosa had the lowest MIC values (0.03 – 1.67 mg/mL). The root extract of C. owariensis was not toxic to Vero cells while the leaf extract was more toxic. The acetone extract of C. mucronata leaves was toxic to Vero cells but the other extracts had low toxicity. The active leaf and root extracts had protective effects on rifampicin-induced toxicity on HepG2 cells. The root extract also had a protective effect on acetaminophen-induced toxicity on HepG2 cells but the leaf extract had no protective effect. The hot water extracts of C. owariensis, C. mucronata and T. fragosa had a more protective effect on the toxin-induced cells than the acetone extracts. These results support further investigation on the bioactive compounds in these plant extracts. [ABSTRACT FROM AUTHOR]

Two new combinations, Anomospermum prancei (Barneby & Krukoff) R. Ortiz and A. verruculosum (Krukoff & Barneby) R. Ortiz, are made in the Neotropical genus Anomospermum Miers (Anomospermeae--Menispermaceae) to conform with the newly revised classification based on morphology and DNA sequence data. [ABSTRACT FROM AUTHOR]

Chemical investigation of the Tinospora sinensis led to the isolation of a new cadinane sesquiterpene (1) and twelve known sesquiterpenes (2 − 13). The structures of these compounds were deduced using a suite of comprehensive spectroscopic techniques including NMR, MS etc. , and the absolute configuration of 1 was established through a combination of TDDFT calculations and chemical methods. Compound 1 demonstrated mild cytotoxicity against MDA-MB-231 cell line, with an inhibition rate of 46.8% and 54.2% at 50 μmol/L and 100 μmol/L, respectively. Compounds 1 , 5 − 13 were reported to exist in the Menispermaceae family for the first time. Furthermore, the chemotaxonomic significance of the isolates is also discussed. • Thirteen sesquiterpenes were isolated from the Tinospora sinensis. • A new cadinane sesquiterpene was isolated from the Tinospora sinensis. • Compounds 1 , 5–13 were isolated from Menispermaceae for the first time. • The chemotaxonomic significance of the isolates is discussed. [ABSTRACT FROM AUTHOR]

Eleven alkaloids including four previously undescribed oxoisoaporphine alkaloids, menisoxoisoaporphines A-D (1 – 4), four known analogues (5 – 8), and three aporphine alkaloids (9 – 11), were isolated and identified from the rhizomes of Menispermum dauricum. Their structures were elucidated by extensive spectroscopic data and single-crystal X-ray diffraction analyses. Among them, compounds 1 and 4 were the first samples of oxoisoaporphine with C-6 isopentylamino moiety, and 2 was a rare C-4 methylation product of oxoisoaporphine alkaloid. The in vitro anti-inflammatory activity of compounds 1 – 11 was performed by evaluating the inhibition of NO level in LPS-induced RAW264.7 macrophages. Among them, compound 4 exhibited the most potent NO inhibition activity with an IC 50 value of 1.95 ± 0.33 μ M. The key structure-activity relationships of those oxoisoaporphine alkaloids for anti-inflammatory effects have been summarized. Four undescribed oxoisoaporphine alkaloids, together with seven known analogues were isolated from the rhizomes of Menispermum dauricum DC., which were evaluated for their their inhibitory activity towards the LPS-induced NO production in RAW 264.7 cells. Menisoxoisoaporphine D exhibited the most potent NO inhibition activity with an IC 50 value of 1.95 ± 0.33 μM. [Display omitted] • Four undescribed alkaloids were isolated from the rhizomes of Menispermum dauricum. • Menisoxoisoaporphine A was the first sample of oxoisoaporphine with C-6 isopentylamino moiety. • Menisoxoisoaporphine B was a rare C-4 methylation product of oxoisoaporphine alkaloid. • Menisoxoisoaporphine D showed the most potent NO inhibition activity (IC 50 1.95 ± 0.33 μM). [ABSTRACT FROM AUTHOR]

Phytochemical study on the methanol extract of the stems of Tinospora crispa (L.) Hook.f. & Thomson led to the isolation of thirteen compounds including three undescribed cis-clerodane-type furanoditerpenoids (1-3) and ten known ones (4-13). Their chemical structures were determined by IR, HR-ESI-MS, 1D-, and 2D-NMR spectra. Compounds 2-4, 6 and 8 inhibited moderately NO production in LPS activated RAW 264.7 cells with the IC 50 values of 83.5, 57.6, 75.3, 78.1, and 74.7 μM, respectively., (© 2024 Wiley-VHCA AG, Zurich, Switzerland.)

Twenty-six clerodane diterpenoids have been isolated from T. sagittata , a plant species of traditional Chinese medicine Radix Tinosporae , also named as " Jin Guo Lan ". Among them, there are eight previously undescribed clerodane diterpenoids (tinotanoids A-H: 1 – 8), and 18 known diterpenoids (9 – 26). The absolute configurations of compounds 1 , 2 , 5 , 8 , 13, 17 and 20 were determined by single-crystal X-ray diffraction. Compound 1 is the first example of rotameric clerodane diterpenoid with a γ -lactone ring which is constructed between C-11 and C-17; meanwhile, compounds 3 and 4 are two pairs of inseparable epimers. Compounds 2 , 12 and 17 demonstrated excellent inhibitory activity on NO production against LPS-stimulated BV-2 cells with IC 50 values of 9.56 ± 0.69, 9.11 ± 0.53 and 11.12 ± 0.70 μM, respectively. These activities were significantly higher than that of the positive control minocycline (IC 50 = 23.57 ± 0.92 μM). Moreover, compounds 2 , 12 and 17 dramatically reduced the LPS-induced upregulation of iNOS and COX-2 expression. Compounds 2 and 12 significantly inhibited the levels of pro-inflammatory cytokines TNF- α , IL-1 β and IL-6 that were increased by LPS stimulation. Twenty-six clerodane diterpenoids including eight undescribed ones were isolated from Tinospora sagittata (Oliv.) Gagnep, and some of them exhibited potent anti-neuroinflammatory activity. [Display omitted] • 8 undescribed clerodane diterpenoids were isolated from Tinospora sagittata. • Compound 1 is the first example of clerodane diterpenoid with a γ -lactone ring constructed between C-11 and C-17. • 3 compounds showed excellent inhibitory activity on NO production. • 2 compounds can reduce the expressions of iNOS, COX-2, TNF-α, IL-1 β and IL-6. [ABSTRACT FROM AUTHOR]

Tinospora crispa (L.) Hook. f. & Thomson stem (TCS) has long been used as folk medicine for the treatment of diabetes mellitus. Previous study revealed that TCS possesses multi-ingredients and multi-targets characteristic potential as insulin sensitizer activity. However, its mechanisms of action and molecular targets are still obscure. In the present study, we investigated the effects of TCS against insulin resistance in muscle cells through integrating in vitro experiment and identifying its active biomarker using metabolomics and in molecular docking validation. We used centrifugal partition chromatography (CPC) to isolate 33 fractions from methanolic extract of TCS, and then used UHPLC-Orbitrap-HRMS to identify the detectable metabolites in each fraction. We assessed the insulin sensitization activity of each fraction using enzyme-linked immunosorbent assay (ELISA), and then used confocal immunocytochemistry microscopy to measure the translocation of glucose transporter 4 (GLUT4) to the cell membrane. The identified active metabolites were further simulated for its molecular docking interaction using Autodock Tools. The polar fractions of TCS significantly increased insulin sensitivity, as measured by the inhibition of phosphorylated insulin receptor substrate-1 (pIRS1) at serine-312 residue (ser312) also the increasing number of translocated GLUT4 and glycogen content. We identified 58 metabolites of TCS, including glycosides, flavonoids, alkaloids, coumarins, and nucleotides groups. The metabolomics and molecular docking simulations showed the presence of minor metabolites consisting of tinoscorside D, higenamine, and tinoscorside A as the active compounds. Our findings suggest that TCS is a promising new treatment for insulin resistance and the identification of the active metabolites in TCS could lead to the development of new drugs therapies for diabetes that target these pathways. [Display omitted] • TCS attenuated insulin resistance in skeletal muscle by lowering IRS ser312 phosphorylation. • TCS increasing translocation of GLUT4 and glycogen content. • Tinoscorside D, tinoscorside A, and higenamine are potential as the primary bioactive compounds of TCS. [ABSTRACT FROM AUTHOR]

The rising geriatric population is expected to increase the demand for drugs treating neurodegenerative diseases. The present work is aimed to discover acetylcholinesterase (AChE) inhibitors from Cissampelos pareira Linn. aerial parts ( Family: Menispermaceae ). Bioassay-guided isolation, AChE inhibition study and estimation of the therapeutic marker in different parts of raw herbs were conducted. The structure of the compound (1) was elucidated as N-methylneolitsine by using NMR (1D and 2D) and ESI-MS/MS spectral data, which is a new natural analogue of neolitsine. It showed good AChE inhibition with an IC 50 value of 12.32 µg/mL. It was densitometrically estimated to be 0.074 - 0.33% in aerial parts of C. pareira, collected from various locations. The alkaloid reported here could be potentially useful for the treatment of various neurodegenerative diseases and the aerial part of C. pareira could be used as a promising ingredient for various preparations treating neurodegenerative diseases.