Integration of UHPLC/Q-OrbitrapMS-based metabolomics and activities evaluation to rapidly explore the anti-inflammatory components from lasianthus.

Lasianthus, belonging to Rubiaceae, has been verified to improve clinical syndrome in immune diseases (e.g., hepatitis, nephritis, and rheumatoid arthritis). Both the anti-inflammatory function and chemical composition of Lasianthus vary considerably between different species but few studies focus. So essential it is to explore lasianthus and further search for anti-inflammatory substances. The target of this artical is to analyze the anti-inflammatory activity and chemical composition of lasianthus of different species. And the subsequent active compounds were explored. Primary, the anti-inflammatory activity among seven species of lasianthus (e.g., L. fordii., L. wallichii., L. hookeri C., L. verticillatus., L. sikkimensis., L. appressihirtus., and L. hookeri var) were evaluated by vitro experiments (RAW 264.7 cells). Next, UHPLC/Q-Orbitrap-MS-based metabolomics and the mass defect filter (MDF) algorithm were performed to explore metabolites. In addition, principal component analysis (PCA) was to screen out differential compounds in seven species. Finally, the correlation analysis between activities and composition to rapidly discover the active compounds (compounds were verified pharmacologically). Among the 7 species of lasianthus, the L. fordii. and L. hookeri C indicated the best anti-inflammatory activity. Untargeted metabolomics and MDF show 112 compounds, classified into six dominant types (e.g., flavonoids, phenolic acids, alkaloids, iridoids, coumarins, and anthraquinones). Furthermore, 33 differential metabolites were confirmed by PCA. Then according to correlation analysis and pharmacological validation, 7 compounds IC50＜100 (e.g., scopoletin, asperulosidic acid, chlorogenic acid, ferulic acid, betaine, syringic acid, and emodin) were verified as anti-inflammatory compounds and conduct quantitative analysis. Metabolomics integrated with activities evaluation might be a rapid and effective strategy to explore the active compounds from natural products.

Lasibidoupins A and B, two new compounds from the stems of Lasianthus bidoupensis V.S. Dang & Naiki.

From the Lasianthus bidoupensis stems, two new compounds, including one new 9,10-anthraquinone, lasibidoupin A (1), and one new 6,7-benzocoumarin, lasibidoupin B (2), together with one known compound, 11-O-methyldamnacanthol (3) were isolated using chromatographic method. Their structures were determined by extensive HRMS, and NMR assignments. Compound 3 was reported for the first time from this species. New compounds (1 & 2) were tested for the cytotoxicity against three human cancer cell lines (MCF-7, HeLa, and NCI-H460) by SRB assay. As results, 1 & 2 exhibited significant cytotoxic activity against all cancer cell lines (IC50 ranged from 0.058 ± 0.003 to 0.177 ± 0.014 µM).

Six new anthraquinone glycosides from Lasianthus acuminatissimus Merr.

Six new anthraquinones named lasianthuoside F (1), G (2), H (3), I (4), J (5), K (6) were isolated from an acetone extract of the root of Lasianthus acuminatissimus. Their structures were elucidated by physical and chemical evidence and spectral analysis.

Lasianosides F-I: A New Iridoid and Three New Bis-Iridoid Glycosides from the Leaves of Lasianthus verticillatus (Lour.) Merr.

A series of iridoid glycosides were isolated from the leaves of Lasianthus verticillatus (Lour.) Merr., belonging to family Rubiaceae. A new iridoid glycoside, lasianoside F (1), and three new bis-iridoid glycosides, lasianosides G-I (2-4), together with four known compounds (5-8) were isolated. The structures were established by spectroscopic methods, including 1D and 2D NMR experiments (1H, 13C, DEPT, COSY, HSQC, HMBC, and NOESY) in combination with HR-ESI-MS and CD spectra.

Neuroblastoma SH-SY5Y cytotoxicity, anti-amyloidogenic activity and cyclooxygenase inhibition of Lasianthus trichophlebus (Rubiaceae).

The anti-amyloidogenic potential and cyclooxygenase anti-inflammatory activity of Lasianthus trichophlebus extracts were evaluated. The MeOH extract (LTM) and chloroform extract (LTC) exhibited significant cytotoxic inhibition against the neuroblastoma SH-SY5Y cell with an IC50 of 17.52 µg/mL and 12.28 µg/mL, respectively. Thioflavin T assay indicated the LTC extract inhibition (70.56% at 50 µg/mL) to be statistically comparable (p < 0.05) to the positive control. Cyclooxygenase inhibition against COX-1 and COX-2 enzymes gave IC50 values for the LTM extract to be 18.20 and 29.60 µg/mL, respectively; while, the LTC extract showed 4.11 and 2.78 µg/mL, respectively. LC-MS of the LTM extract identified 22 putative compounds, which may prove to be pharmacologically relevant. This study has provided potential insights into the utilization of L. trichophlebus to develop safer plant-based agents for anti-inflammatory or neurodegenerative diseases.

Lasianosides A-E: New Iridoid Glucosides from the Leaves of Lasianthus verticillatus (Lour.) Merr. and Their Antioxidant Activity.

The genus Lasianthus (Rubiaceae) consists of approximately 180 species, of which the greatest species diversity is found in tropical Asia. Some of the Lasianthus species have been used in folk medicine to treat tinnitus, arthritis, fever, and bleeding. Lasianthus verticillatus (Lour.) Merr. (Syn. Lasianthus trichophlebus auct. non Hemsl.) is a shrub, branchlets terete about 1.5-3 m in height. This paper studies the chemical composition of the leaves of L. verticillatus for the first time, which resulted in the isolation of five undescribed iridoid glucosides, lasianosides A-E (1-5), together with three known compounds (6-8). The undescribed structures of isolated compounds (1-5) were characterized by physical and spectroscopic data analyses, including one-dimensional (1D) and two-dimensional (2D) NMR, IR, UV, and high-resolution electrospray ionization mass spectra (HR-ESI-MS). Furthermore, the electronic circular dichroism data determined the absolute configurations of the new compounds. The free radical scavenging properties of isolated compounds was assessed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, and their cytotoxicity was assessed toward human lung cancer cell line A549 by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. Among the isolated compounds, 3 and 4 displayed potent radical scavenging activities with IC50 values of 30.2 ± 1.8 and 32.0 ± 1.2 µM, which were comparable to that of Trolox (29.2 ± 0.39 µM), respectively, while 5 possessed moderate activity with an IC50 value of 46.4 ± 2.3 µM. None of the isolated compounds exerted cytotoxicity against human cell line A549. As a result, lasianosides C, D, and E have the potential to be non-toxic safe antioxidant agents.

Evaluating the Feasibility of Five Candidate DNA Barcoding Loci for Philippine Lasianthus Jack (Lasiantheae: Rubiaceae).

INTRODUCTION: The pantropical genus Lasianthus Jack is identified for high phenotypic plasticity making traditional taxonomic identification difficult. Having some members with important medicinal properties, a precise complimentary identification through DNA barcoding is needed for species delineation. MATERIALS AND METHODS: In this study, 12 samples representing six Philippine Lasianthus species were used to determine the most efficient barcoding loci among the cpDNA markers (matK, rbcL, rps16, and trnT-F) and nrDNA (ITS) based on the criteria of universality, discriminatory power, and resolution of species. RESULTS: The results revealed that ITS has the recommended primer universality, greatest interspecific divergences, and average resolution of species. Among the cpDNA markers, matK and rbcL are recommended but with minimal resolution of species. While trnT-F showed moderate interspecific variations and resolution of Lasianthus species, rps16 has the lowest interspecific divergence and resolution of species. CONCLUSION: Consequently, ITS is the potential ideal DNA barcode for Lasianthus species. SUMMARY: ITS, matK, and rps16 markers have the excellent amplification and sequence qualityITS marker has the highest interspecific divergence with the maximum values, followed by matK, rbcL, trnT-F, and rps16, respectivelyAll markers except rps16 yielded average resolution to Lasianthus speciesITS marker is the most ideal locus in terms of excellent universality, high interspecific discriminatory ability, and average species resolution. Abbreviations used: ITS: Internal Transcribe Spacer, matK: maturase K, rbcL: ribulose-1,5-biphospahte-carboxylase, rps16: ribosomal protein 16 small subunit gene.