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  1. Fulltext Antioxidant activity and phenolic content of Paederia foetida and Syzygium aqueum
    Osman H, Rahim AA, Isa NM, Bakhir NM
    Molecules, 2009;14(3):970-8.
    PMID: 19305354 DOI: 10.3390/molecules14030970
    The antioxidant activity of fresh and dried plant extracts of Paederia foetida and Syzygium aqueum were studied using beta-carotene bleaching and the 2,2'-azinobis(3-ethyl-benzothiazoline-6-sulfonic acid) (ABTS) radical cation assay. The percentage of antioxidant activity for all extract samples using both assays was between 58 and 80%. The fresh samples of both plants had higher antioxidant activity than the dried samples. The results of the beta-carotene bleaching assay were correlated (R(2) = 0.9849) with those of the ABTS assay.
    Matched MeSH terms: Rubiaceae/chemistry*
  2. Natural indole butyrylcholinesterase inhibitors from Nauclea officinalis
    Liew SY, Khaw KY, Murugaiyah V, Looi CY, Wong YL, Mustafa MR, et al.
    Phytomedicine, 2015 Jan 15;22(1):45-8.
    PMID: 25636869 DOI: 10.1016/j.phymed.2014.11.003
    Nine monoterpenoid indole alkaloids; naucletine (1), angustidine (2), nauclefine (3), angustine (4), naucline (5), angustoline (6), harmane (7), 3,14-dihydroangustoline (8), strictosamide (9) and one quinoline alkaloid glycoside; pumiloside (10) from Nauclea officinalis were tested for cholinesterase inhibitory activity. All the alkaloids except for pumiloside (10) showed strong to weak BChE inhibitory effect with IC50 values ranging between 1.02-168.55 μM. Angustidine (2), nauclefine (3), angustine (4), angustoline (6) and harmane (7) showed higher BChE inhibiting potency compared to galanthamine. Angustidine (2) was the most potent inhibitor towards both AChE and BChE. Molecular docking (MD) studies showed that angustidine (2) docked deep into the bottom gorge of hBChE and formed hydrogen bonding with Ser 198 and His 438. Kinetic study of angustidine (2) on BChE suggested a mixed inhibition mode with an inhibition constant (Ki) of 6.12 μM.
    Matched MeSH terms: Rubiaceae/chemistry*
  3. Fulltext Neonaucline, a new indole alkaloid from the leaves of Ochreinauclea maingayii (Hook. f.) Ridsd. (Rubiaceae)
    Muktar MR, Osman N, Awang K, Hazni H, Qureshi AK, Hadi AH, et al.
    Molecules, 2011 Dec 28;17(1):267-74.
    PMID: 22205092 DOI: 10.3390/molecules17010267
    A new indole alkaloid; neonaucline (1), along with six known compounds-Cadamine (2), naucledine (3), harmane, benzamide, cinnamide and blumenol A-were isolated from the leaves of Ochreinauclea maingayii (Rubiaceae). In addition to that of compound 1, (13)C-NMR data of cadamine (2) and naucledine (3) were also reported. Structural elucidations of these alkaloids were performed using spectroscopic methods especially 1D- and 2D-NMR, IR, UV and LCMS-IT-TOF. The excellent vasorelaxant activity on isolated rat aorta was observed for the alkaloids 1-3 after injection of each sample at 1 × 10(-5) M.
    Matched MeSH terms: Rubiaceae/chemistry*
  4. Sulfur-containing bis-iridoid glucosides and iridoid glucosides from Saprosmas cortechinii
    Ling SK, Komorita A, Tanaka T, Fujioka T, Mihashi K, Kouno I
    J Nat Prod, 2002 May;65(5):656-60.
    PMID: 12027736
    Six new sulfur-containing bis-iridoid glucosides, saprosmosides A-F (1-6), were isolated from the leaves of Saprosma scortechinii. From the stems of this same plant, two new iridoid glucosides, 3,4-dihydro-3-methoxypaederoside (8) and 10-O-benzoyldeacetylasperulosidic acid (12), were isolated. Their structures were elucidated by means of chemical, NMR, and mass spectroscopic methods. Additionally, 11 known iridoid glucosides were isolated and characterized as deacetylasperuloside, asperuloside, paederoside (7), deacetylasperulosidic acid (9), scandoside, asperulosidic acid, 10-acetylscandoside, paederosidic acid (10), 6-epi-paederosidic acid (11), methylpaederosidate, and monotropein. The structures of the new bis-iridoid glucosides were formed by intermolecular esterification between the glucose and carboxyl groups of three monomeric iridoid glucosides (7, 9, and 10).
    Matched MeSH terms: Rubiaceae/chemistry*
  5. Neolamarckines A and B, new indole alkaloids from Neolamarckia cadamba
    Qureshi AK, Mukhtar MR, Hirasawa Y, Hosoya T, Nugroho AE, Morita H, et al.
    Chem Pharm Bull (Tokyo), 2011;59(2):291-3.
    PMID: 21297315
    Two new indole alkaloids, neolamarckines A and B (1, 2) were isolated from the leaves of Neolamarckia cadamba (Rubiaceae). Structural elucidation of 1 and 2 was performed by combination of 2D-NMR and circular dichroism (CD) spectra, and chemical correlations. Neolamarckine A (1) showed inhibition of inducible nitric oxide synthase (iNOS) dose dependently.
    Matched MeSH terms: Rubiaceae/chemistry*
  6. Fulltext Genus Ophiorrhiza: A Review of Its Distribution, Traditional Uses, Phytochemistry, Biological Activities and Propagation
    Taher M, Shaari SS, Susanti D, Arbain D, Zakaria ZA
    Molecules, 2020 Jun 04;25(11).
    PMID: 32512727 DOI: 10.3390/molecules25112611
    Almost 50 species of Ophiorrhiza plants were reviewed in this work and the main objective is to critically analyse their distribution, phytochemical content, biological activity, and propagation. Moreover, the information would be useful in promoting the relevant uses of the plant, especially in the medicinal fields based on in vitro and in vivo studies. To this end, scientific sources, including theses, PubMed, Google Scholar, International Islamic University Malaysia IIUM EBSCO, PubChem, and Elsevier, were accessed for publications regarding the Ophiorrhiza genus in this review. Scientific literature regarding the Ophiorrhiza plants revealed their wide distribution across Asia and the neighbouring countries, whereby they were utilised as traditional medicine to treat various diseases. In particular, various active compounds, such as alkaloids, flavonoids, and terpenoids, were reported in the plant. Furthermore, the Ophiorrhiza species showed highly diverse biological activities, such as anti-cancer, antiviral, antimicrobial, and more. The genus propagation reported could produce a high quality and quantity of potent anticancer compound, namely camptothecin (CPT). Hence, it is believed that the relevant uses of natural compounds present in the plants can replace the existing crop of synthetic anticancer drugs associated with a multitude of unbearable side effects. Additionally, more future studies on the Ophiorrhiza species should be undertaken to establish the links between its traditional uses, active compounds, and pharmacological activities reported.
    Matched MeSH terms: Rubiaceae/chemistry*
  7. Antioxidant activity and total phenolic content of methanol extracts of Ixora coccinea
    Torey A, Sasidharan S, Latha LY, Sudhakaran S, Ramanathan S
    Pharm Biol, 2010 Oct;48(10):1119-23.
    PMID: 20738154 DOI: 10.3109/13880200903490505
    To investigate the in vitro antioxidant activity of methanol extracts of Ixora coccinea L. (Rubiaceae) flower, leaf and stem.
    Matched MeSH terms: Rubiaceae/chemistry*
  8. Chemical composition and anticholinesterase inhibitory activity of Pavetta graciliflora Wall. ex Ridl. essential oil
    Salleh WMNHW, Khamis S
    Z Naturforsch C J Biosci, 2020 Nov 26;75(11-12):467-471.
    PMID: 32469335 DOI: 10.1515/znc-2020-0075
    Chemical composition and anticholinesterase activity of the essential oil of Pavetta graciliflora Wall. ex Ridl. (Rubiaceae) was examined for the first time. The essential oil was obtained by hydrodistillation and was fully characterized by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). A total of 20 components were identified in the essential oil, which made up 92.85% of the total oil. The essential oil is composed mainly of β-caryophyllene (42.52%), caryophyllene oxide (25.33%), β-pinene (8.67%), and α-pinene (6.52%). The essential oil showed weak inhibitory activity against acetylcholinesterase (AChE) (I%: 62.5%) and butyrylcholinesterase (BChE) (I%: 65.4%) assays. Our findings were shown to be very useful for the characterization, pharmaceutical, and therapeutic applications of the essential oil from P. graciliflora.
    Matched MeSH terms: Rubiaceae/chemistry*
  9. Fulltext Naucline, a new indole alkaloid from the bark of Nauclea officinalis
    Liew SY, Mukhtar MR, Hadi AH, Awang K, Mustafa MR, Zaima K, et al.
    Molecules, 2012 Apr 02;17(4):4028-36.
    PMID: 22469596 DOI: 10.3390/molecules17044028
    A new indole alkaloid, naucline (1) together with four known alkaloids, angustine (2), angustidine (3), nauclefine (4) and naucletine (5), were isolated from the bark of Nauclea officinalis. The structures of all isolated compounds were elucidated with various spectroscopic methods such as 1D- and 2D- NMR, IR, UV and LCMS-IT-TOF. In addition to that of alkaloid 1, the complete 13C-NMR data of naucletine (5) were also reported. Naucline (1) showed a moderate vasorelaxant activity (90% relaxation at 1 × 10(-5) M) whereas, angustine (2), nauclefine (4), and naucletine (5) showed potent vasorelaxant activity (more than 90% relaxation at 1 × 10(-5) M) on an isolated rat aorta.
    Matched MeSH terms: Rubiaceae/chemistry*
  10. Fulltext Rapid Quantification and Validation of Biomarker Scopoletin in Paederia foetida by qNMR and UV-Vis for Herbal Preparation
    Tan DC, Quek A, Kassim NK, Ismail IS, Lee JJ
    Molecules, 2020 Nov 06;25(21).
    PMID: 33171900 DOI: 10.3390/molecules25215162
    Scopoletin has previously been reported as a biomarker for the standardization of Paederia foetida twigs. This study is the first report on the determination and quantification of scopoletin using quantitative nuclear magnetic resonance (qNMR) in the different extracts of Paederia foetida twigs. The validated qNMR method showed a good linearity (r2 = 0.9999), limit of detection (LOD) (0.009 mg/mL), and quantification (LOQ) (0.029 mg/mL), together with high stability (relative standard deviation (RSD) = 0.022%), high precision (RSD < 1%), and good recovery (94.08-108.45%). The quantification results of scopoletin concentration in chloroform extract using qNMR and microplate ultraviolet-visible (UV-vis) spectrophotometer was almost comparable. Therefore, the qNMR method is deemed accurate and reliable for quality control of Paederia foetida and other medicinal plants without extensive sample preparation.
    Matched MeSH terms: Rubiaceae/chemistry*
  11. Chemistry and pharmacology of analgesic indole alkaloids from the rubiaceous plant, Mitragyna speciosa
    Takayama H
    Chem Pharm Bull (Tokyo), 2004 Aug;52(8):916-28.
    PMID: 15304982
    The leaves of a tropical plant, Mitragyna speciosa KORTH (Rubiaceae), have been traditionally used as a substitute for opium. Phytochemical studies of the constituents of the plant growing in Thailand and Malaysia have led to the isolation of several 9-methoxy-Corynanthe-type monoterpenoid indole alkaloids, including new natural products. The structures of the new compounds were elucidated by spectroscopic and/or synthetic methods. The potent opioid agonistic activities of mitragynine, the major constituent of this plant, and its analogues were found in in vitro and in vivo experiments and the mechanisms underlying the analgesic activity were clarified. The essential structural features of mitragynines, which differ from those of morphine and are responsible for the analgesic activity, were elucidated by pharmacological evaluation of the natural and synthetic derivatives. Among the mitragynine derivatives, 7-hydroxymitragynine, a minor constituent of M. speciosa, was found to exhibit potent antinociceptive activity in mice.
    Matched MeSH terms: Rubiaceae/chemistry*
  12. Fulltext Identification of Antidiabetic Metabolites from Paederia foetida L. Twigs by Gas Chromatography-Mass Spectrometry-Based Metabolomics and Molecular Docking Study
    Tan DC, Kassim NK, Ismail IS, Hamid M, Ahamad Bustamam MS
    Biomed Res Int, 2019;2019:7603125.
    PMID: 31275982 DOI: 10.1155/2019/7603125
    Paederia foetida L. (Rubiaceae) is a climber which is widely distributed in Asian countries including Malaysia. The plant is traditionally used to treat various diseases including diabetes. This study is to evaluate the enzymatic inhibition activity of Paederia foetida twigs extracts and to identify the metabolites responsible for the bioactivity by gas chromatography-mass spectrometry (GC-MS) metabolomics profiling. Three different twig extracts, namely, hexane (PFH), chloroform (PFC), and methanol (PFM), were submerged for their α-amylase and α-glucosidase inhibition potential in 5 replicates for each. Results obtained from the loading column scatter plot of orthogonal partial least square (OPLS) model revealed the presence of 12 bioactive compounds, namely, dl-α-tocopherol, n-hexadecanoic acid, 2-hexyl-1-decanol, stigmastanol, 2-nonadecanone, cholest-8(14)-en-3-ol, 4,4-dimethyl-, (3β,5α)-, stigmast-4-en-3-one, stigmasterol, 1-ethyl-1-tetradecyloxy-1-silacyclohexane, ɣ-sitosterol, stigmast-7-en-3-ol, (3β,5α,24S)-, and α-monostearin. In silico molecular docking was carried out using the crystal structure α-amylase (PDB ID: 4W93) and α-glucosidase (PDB ID: 3WY1). α-Amylase-n-hexadecanoic acid exhibited the lowest binding energy of -2.28 kcal/mol with two hydrogen bonds residue, namely, LYS178 and TYR174, along with hydrophobic interactions involving PRO140, TRP134, SER132, ASP135, and LYS172. The binding interactions of α-glucosidase-n-hexadecanoic acid complex ligand also showed the lowest binding energy among 5 major compounds with the energy value of -4.04 kcal/mol. The complex consists of one hydrogen bond interacting residue, ARG437, and hydrophobic interactions with ALA444, ASP141, GLN438, GLU432, GLY374, LEU373, LEU433, LYS352, PRO347, THR445, HIS348, and PRO351. The study provides informative data on the potential antidiabetic inhibitors identified in Paederia foetida twigs, indicating the plant has the therapeutic effect properties to manage diabetes.
    Matched MeSH terms: Rubiaceae/chemistry*
  13. Fulltext Evaluation of the cardiotoxicity of mitragynine and its analogues using human induced pluripotent stem cell-derived cardiomyocytes
    Lu J, Wei H, Wu J, Jamil MF, Tan ML, Adenan MI, et al.
    PLoS One, 2014;9(12):e115648.
    PMID: 25535742 DOI: 10.1371/journal.pone.0115648
    INTRODUCTION: Mitragynine is a major bioactive compound of Kratom, which is derived from the leave extracts of Mitragyna speciosa Korth or Mitragyna speciosa (M. speciosa), a medicinal plant from South East Asia used legally in many countries as stimulant with opioid-like effects for the treatment of chronic pain and opioid-withdrawal symptoms. Fatal incidents with Mitragynine have been associated with cardiac arrest. In this study, we determined the cardiotoxicity of Mitragynine and other chemical constituents isolated using human induced pluripotent stem cell-derived cardiomyocytes (hiPSC-CMs).

    METHODS AND RESULTS: The rapid delayed rectifier potassium current (IKr), L-type Ca2+ current (ICa,L) and action potential duration (APD) were measured by whole cell patch-clamp. The expression of KCNH2 and cytotoxicity was determined by real-time PCR and Caspase activity measurements. After significant IKr suppression by Mitragynine (10 µM) was confirmed in hERG-HEK cells, we systematically examined the effects of Mitragynine and other chemical constituents in hiPSC-CMs. Mitragynine, Paynantheine, Speciogynine and Speciociliatine, dosage-dependently (0.1∼100 µM) suppressed IKr in hiPSC-CMs by 67%∼84% with IC50 ranged from 0.91 to 2.47 µM. Moreover, Mitragynine (10 µM) significantly prolonged APD at 50 and 90% repolarization (APD50 and APD90) (439.0±11.6 vs. 585.2±45.5 ms and 536.0±22.6 vs. 705.9±46.1 ms, respectively) and induced arrhythmia, without altering the L-type Ca2+ current. Neither the expression, and intracellular distribution of KCNH2/Kv11.1, nor the Caspase 3 activity were significantly affected by Mitragynine.

    CONCLUSIONS: Our study indicates that Mitragynine and its analogues may potentiate Torsade de Pointes through inhibition of IKr in human cardiomyocytes.

    Matched MeSH terms: Rubiaceae/chemistry*
  14. Fulltext Hyaluronidase Inhibitory Activity of Pentacylic Triterpenoids from Prismatomeris tetrandra (Roxb.) K. Schum: Isolation, Synthesis and QSAR Study
    Abdullah NH, Thomas NF, Sivasothy Y, Lee VS, Liew SY, Noorbatcha IA, et al.
    Int J Mol Sci, 2016 Feb 14;17(2):143.
    PMID: 26907251 DOI: 10.3390/ijms17020143
    The mammalian hyaluronidase degrades hyaluronic acid by the cleavage of the β-1,4-glycosidic bond furnishing a tetrasaccharide molecule as the main product which is a highly angiogenic and potent inducer of inflammatory cytokines. Ursolic acid 1, isolated from Prismatomeris tetrandra, was identified as having the potential to develop inhibitors of hyaluronidase. A series of ursolic acid analogues were either synthesized via structure modification of ursolic acid 1 or commercially obtained. The evaluation of the inhibitory activity of these compounds on the hyaluronidase enzyme was conducted. Several structural, topological and quantum chemical descriptors for these compounds were calculated using semi empirical quantum chemical methods. A quantitative structure activity relationship study (QSAR) was performed to correlate these descriptors with the hyaluronidase inhibitory activity. The statistical characteristics provided by the best multi linear model (BML) (R² = 0.9717, R²cv = 0.9506) indicated satisfactory stability and predictive ability of the developed model. The in silico molecular docking study which was used to determine the binding interactions revealed that the ursolic acid analog 22 had a strong affinity towards human hyaluronidase.
    Matched MeSH terms: Rubiaceae/chemistry*
  15. Fulltext Comparative study of the antidiabetic potential of Paederia foetida twig extracts and compounds from two different locations in Malaysia
    Tan DC, Idris KI, Kassim NK, Lim PC, Safinar Ismail I, Hamid M, et al.
    Pharm Biol, 2019 Dec;57(1):345-354.
    PMID: 31185767 DOI: 10.1080/13880209.2019.1610462
    Context:Paederia foetida L. (Rubiaceae) is an edible plant distributed in Asian countries including Malaysia. Fresh leaves have been traditionally used as a remedy for indigestion and diarrhea. Several phytochemical studies of the leaves have been documented, but there are few reports on twigs. Objective: This study investigates the enzyme inhibition of P. foetida twig extracts and compound isolated from them. In addition, in silico molecular docking of scopoletin was investigated. Materials and methods: Plants were obtained from two locations in Malaysia, Johor (PFJ) and Pahang (PFP). Hexane, chloroform and methanol extracts along with isolated compound (scopoletin) were evaluated for their enzyme inhibition activities (10,000-0.000016 µg/mL). The separation and identification of bio-active compounds were carried out using column chromatography and spectroscopic techniques, respectively. In silico molecular docking of scopoletin with receptors (α-amylase and α-glucosidase) was carried out using AutoDock 4.2. Results: The IC50 values of α-amylase and α-glucosidase inhibition activity of PFJ chloroform extract were 9.60 and 245.6 µg/mL, respectively. PFP chloroform extract exhibited α-amylase and α-glucosidase inhibition activity (IC50 = 14.83 and 257.2 µg/mL, respectively). The α-amylase and α-glucosidase inhibitory activity of scopoletin from both locations had IC50 values of 0.052 and 0.057 µM, respectively. Discussion and conclusions: Separation of PFJ chloroform extract afforded scopoletin (1), stigmasterol (2) and γ-sitosterol (3) and the PFP chloroform extract yielded (1), (2), (3) and ergost-5-en-3-ol (4). Scopoletin was isolated from this species for the first time. In silico calculations gave a binding energy between scopoletin and α-amylase of -6.03 kcal/mol.
    Matched MeSH terms: Rubiaceae/chemistry*
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