MyMedR

A new coumarin and triterpenes from Malaysian Micromelum minutum

Asmah Susidarti R, Rahmani M, Ismail HB, Sukari MA, Yun Hin TY, Ee Cheng Lian G, et al.

Nat Prod Res, 2006 Feb;20(2):145-51.

PMID: 16319008

A new coumarin, 8,4''-dihydroxy-3'',4''-dihydrocapnolactone-2',3'-diol (1) and two known triterpenes, 5(6)-gluten-3-one (2) and 5(6)-gluten-3alpha-ol (3) were isolated from the leaves of Micromelum minutum (Rutaceae) collected from Sepilok, Sabah, Malaysia and their structures were characterized by spectroscopic methods.

Matched MeSH terms: Coumarins/isolation & purification*

Coumarins from Malaysian Micromelum minutum

Rahmani M, Susidarti RA, Ismail HB, Sukari MA, Hin TY, Lian GE, et al.

Phytochemistry, 2003 Oct;64(4):873-7.

PMID: 14559284

In a continuation of our study of the Rutaceae, detailed chemical investigation on Micromelum minutum (Rutaceae) collected from Sepilok, Sabah, Malaysia gave four new coumarins. The structures of the coumarins have been fully characterised by spectroscopic methods as 3",4"-dihydrocapnolactone 1, 2',3'-epoxyisocapnolactone 2, 8-hydroxyisocapnolactone-2',3'-diol 3 and 8-hydroxy-3",4"-dihydrocapnolactone-2',3'-diol 4.

Matched MeSH terms: Coumarins/isolation & purification*

Antioxidant activity-guided separation of coumarins and lignan from Melicope glabra (Rutaceae)

Kassim NK, Rahmani M, Ismail A, Sukari MA, Ee GC, Nasir NM, et al.

Food Chem, 2013 Aug 15;139(1-4):87-92.

PMID: 23561082 DOI: 10.1016/j.foodchem.2013.01.108

The ethyl acetate and methanol bark extracts of Melicope glabra were evaluated for their antioxidant capacities by 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity and β-carotene bleaching/linoleic acid system. Both extracts exhibited strong inhibition against the DPPH radical (IC50 values of 24.81 and 13.01 μg ml(-1), respectively) and strong antioxidant activity in β-carotene bleaching assay. Both samples were found to have high phenolic content with values of 39 and 44 mg GAE/g as indicated by Follin-Ciocalteau's reagent. Antioxidant TLC assay-guided isolation on the methanol extract led to the isolation of a new pyranocoumarin, glabranin (1), umbelliferone (2), scopoletin (3) and sesamin (4), and their structures were determined by spectroscopy. Compounds (1-3) showed significant activities on DPPH free radical with the IC50 of 240.20, 810.02 and 413.19 μg ml(-1), respectively. However, in β-carotene bleaching assay, sesamin (4) showed higher inhibitory activity (1 mg ml(-1), 95%) than glabranin (1) (1 mg ml(-1), 74%), whilst umbelliferone (2) and scopoletin (3) were slightly pro-oxidant.

Matched MeSH terms: Coumarins/isolation & purification

Fulltext Soulamarin, a new coumarin from stem bark of Calophyllum soulattri

Ee GC, Mah SH, Teh SS, Rahmani M, Go R, Taufiq-Yap YH

Molecules, 2011 Nov 23;16(11):9721-7.

PMID: 22113580 DOI: 10.3390/molecules16119721

The extracts of the stem bark of Calophyllum soulattri gave a new pyranocoumarin, soulamarin (1), together with five other xanthones caloxanthone B (2), caloxanthone C (3), macluraxanthone (4), trapezifolixanthone (5) and brasixanthone B (6) one common triterpene, friedelin (7), and the steroidal triterpene stigmasterol (8). The structures of these compounds were established based on spectral evidence (1D and 2D NMR).

Matched MeSH terms: Coumarins/isolation & purification*

Fulltext A novel cyclodione coumarin from the stem bark of Mesua beccariana

Ee GC, Teh SS, Mah SH, Rahmani M, Taufiq-Yap YH, Awang K

Molecules, 2011 Aug 25;16(9):7249-55.

PMID: 21869752 DOI: 10.3390/molecules16097249

Our ongoing investigations on the stem bark of Mesua beccariana afforded a novel cyclodione coumarin, beccamarin, together with two known xanthones, mesuarianone, mesuasinone, two anthraquinones, 4-methoxy-1,3,5-trihydroxy-anthraquinone and 2,5-dihydroxy-1,3,4-trimethoxyanthraquinone and one coumarin, mammea A/AB. The structures were elucidated by 1D and 2D NMR and MS techniques.

Matched MeSH terms: Coumarins/isolation & purification*

4-Phenylcoumarins from Mesua elegans with acetylcholinesterase inhibitory activity

Awang K, Chan G, Litaudon M, Ismail NH, Martin MT, Gueritte F

Bioorg Med Chem, 2010 Nov 15;18(22):7873-7.

PMID: 20943395 DOI: 10.1016/j.bmc.2010.09.044

A significant acetylcholinesterase (AChE) inhibitory activity was observed for the hexane extract from the bark of Mesua elegans (Clusiaceae). Thus, the hexane extract was subjected to chemical investigation, which led to the isolation of nine 4-phenylcoumarins, in which three are new; mesuagenin A (1), mesuagenin C (3), mesuagenin D (4) and one new natural product; mesuagenin B (2). The structures of the isolated compounds were characterized by spectroscopic data interpretation, especially 1D and 2D NMR. Four compounds showed significant AChE inhibitory activity, with mesuagenin B (2) being the most potent (IC(50)=0.7μM).

Matched MeSH terms: Coumarins/isolation & purification

Phenolic Compounds from Atriplex littoralis and Their Radiation-Mitigating Activity

Gođevac D, Stanković J, Novaković M, Anđelković B, Dajić-Stevanović Z, Petrović M, et al.

J Nat Prod, 2015 Sep 25;78(9):2198-204.

PMID: 26290401 DOI: 10.1021/acs.jnatprod.5b00273

From the aerial parts of Atriplex littoralis, three new flavonoid glycosides named atriplexins I-III (1-3), a known flavonoid glycoside, spinacetin 3-O-β-d-glucopyranoside (4), arbutin (5), and 4-hydroxybenzyl-β-d-glucopyranoside (6) were isolated. Their structures were elucidated on the basis of detailed spectroscopic analysis, including 1D and 2D NMR (COSY, NOESY, TOCSY, HSQC, HMBC) and HRESITOF MS data. The compounds were tested for in vitro protective effects on chromosome aberrations in peripheral human lymphocytes using a cytochalasin-B-blocked micronucleus (MN) assay in a concentration range of 0.8-7.4 μM of final culture solution. Chromosomal damage was induced by 2 Gy of γ-radiation on binucleated human lymphocytes, and the effects of the compounds were tested 2 to 19 h after irradiation. The frequency of micronuclei (MNi) was scored in binucleated cells, and the nuclear proliferation index was calculated. The highest prevention of in vitro biochemical and cytogenetic damage of human lymphocytes induced by γ-radiation was exhibited by 3 (reduction of MN frequency by 31%), followed by 4 and 6.

Matched MeSH terms: Coumarins/isolation & purification*

Mucigerin, a new coumarin from Calophyllum mucigerum (Guttiferae)

Ee GC, Ng KN, Taufiq-Yap YH, Rahmani M, Ali AM, Muse R

Nat Prod Res, 2004 Apr;18(2):123-8.

PMID: 14984084

Our recent studies on the stem bark of Calophyllum mucigerum (Guttiferae) have yielded a new coumarin mucigerin, a prenylated xanthone cudraxanthone C and the common steroidal triterpenes friedelin and stigmasterol. Structural elucidations of these compounds were achieved using 1H NMR, 13C NMR, DEPT, COSY, HETCOR and HMBC experiments while MS gave the molecular masses. Cytotoxic assays using CEM-SS cell line (T-lymphoblastic leukemia) on the crude extracts of the stem bark indicated some activity. The crude extracts were also found to be moderately toxic against the larvae of Aedes aegypti. This article reports the isolation and identification of mucigerin as well as bioassay data.

Matched MeSH terms: Coumarins/isolation & purification

A new coumarin from Calophyllum hosei

Daud SB, Ee GC, Malek EA, Teh SS, See I

Nat Prod Res, 2014;28(19):1534-8.

PMID: 24897077 DOI: 10.1080/14786419.2014.924001

A new coumarin, hoseimarin (1), together with four other xanthones, trapezifolizanthone (2), osajaxanthone (3), β-mangostin (4) and caloxanthone A (5), were isolated from the stem bark of Calophyllum hosei. The structures of these compounds were established by using spectroscopic analysis which included (1)H NMR, (13)C NMR, COSY, DEPT, HMQC and HMBC experiments.

Matched MeSH terms: Coumarins/isolation & purification*

Lepidotol A from Mesua lepidota Inhibits Inflammatory and Immune Mediators in Human Endothelial Cells

Rouger C, Derbré S, Charreau B, Pabois A, Cauchy T, Litaudon M, et al.

J Nat Prod, 2015 Sep 25;78(9):2187-97.

PMID: 26301802 DOI: 10.1021/acs.jnatprod.5b00222

Phytochemical investigation on the fruits of Mesua lepidota (Calophyllaceae) led to the isolation of seven new phenylcoumarin derivatives named lepidotols A-E (1-5) and lepidotins A and B (6, 7). These structures were elucidated by spectroscopic and spectrometric methods including UV, NMR, and HRMS. Lepidotol A (1), the major compound, was evaluated for its inhibitory effect on inflammation and immunity using endothelial cell-based cellular assays. At 10 μM, 1 exhibited an anti-inflammatory activity, with a significant inhibition of vascular cell adhesion molecule 1 and intercellular adhesion molecule 1 expression induced by tumor necrosis factor-α. Lepidotol A also showed a mild immunosuppressive effect, with inhibition of the major histocompatibility complex molecules, namely, human leukocyte antigen (HLA)-DR and HLA-E.

Matched MeSH terms: Coumarins/isolation & purification*

Fulltext Geranylated 4-Phenylcoumarins Exhibit Anticancer Effects against Human Prostate Cancer Cells through Caspase-Independent Mechanism

Suparji NS, Chan G, Sapili H, Arshad NM, In LL, Awang K, et al.

PLoS One, 2016;11(3):e0151472.

PMID: 26974436 DOI: 10.1371/journal.pone.0151472

Geranylated 4-phenylcoumarins, DMDP-1 & -2 isolated from Mesua elegans were investigated for anticancer potential against human prostate cancer cells. Treatment with DMDP-1 & -2 resulted in cell death in a time and dose dependent manner in an MTT assay on all cancer cell lines tested with the exception of lung adenocarcinoma cells. DMDP-1 showed highest cytotoxic efficacy in PC-3 cells while DMDP-2 was most potent in DU 145 cells. Flow cytometry indicated that both coumarins were successful to induce programmed cell death after 24 h treatment. Elucidation on the mode-of-action via protein arrays and western blotting demonstrated death induced without any significant expressions of caspases, Bcl-2 family proteins and cleaved PARP, thus suggesting the involvement of caspase-independent pathways. In identifying autophagy, analysis of GFP-LC3 showed increased punctate in PC-3 cells pre-treated with CQ and treated with DMDP-1. In these cells decreased expression of autophagosome protein, p62 and cathepsin B further confirmed autophagy. In contrary, the DU 145 cells pre-treated with CQ and treated with DMDP-2 has reduced GFP-LC3 punctate although the number of cells with obvious GFP-LC3 puncta was significantly increased in the inhibitor-treated cells. The increase level of p62 suggested leakage of cathepsin B into the cytosol to trigger potential downstream death mediators. This correlated with increased expression of cathepsin B and reduced expression after treatment with its inhibitor, CA074. Also auto-degradation of calpain-2 upon treatment with DMDP-1 &-2 and its inhibitor alone, calpeptin compared with the combination treatment, further confirmed involvement of calpain-2 in PC-3 and DU 145 cells. Treatment with DMDP-1 & -2 also showed up-regulation of total and phosphorylated p53 levels in a time dependent manner. Hence, DMDP-1 & -2 showed ability to activate multiple death pathways involving autophagy, lysosomal and endoplasmic reticulum death proteins which could potentially be manipulated to develop anti-cancer therapy in apoptosis resistant cells.

Matched MeSH terms: Coumarins/isolation & purification

A new coumarin from stem bark of Calophyllum wallichianum

Tee KH, Ee GCL, Ismail IS, Karunakaran T, Teh SS, Jong VYM, et al.

Nat Prod Res, 2018 Nov;32(21):2565-2570.

PMID: 29355031 DOI: 10.1080/14786419.2018.1428588

A phytochemical study carried out on the plant, Calophyllum wallichianum has led to the isolation of a new coumarin, wallimarin T (1) and a known coumarin, calanolide E (2) along with two common triterpenes, friedelin (3) and stigmasterol (4). The structures of these compounds were elucidated with the aid of spectroscopic analyses such as FT-IR, GC-MS, and NMR. MIC assay against the Bacillus bacteria were conducted on the extracts and this gave MIC values ranging from 0.313 to 1.25 mg/mL. Compound 2 was weakly inhibitory towards the Bacilli strains with MIC values ranging from 0.25-0.50 mg/mL. Wallimarin T (1) was not active towards all four bacteria. Overall, the extracts exhibited weak bactericidal properties whereas compound 2 was not bactericidal on the tested bacteria. The hexane and chloroform extracts of the plant were found to be inhibitors to the growth of Bacillus megaterium, Bacillus cereus, Bacillus pumilus and Bacillus subtilis.

Matched MeSH terms: Coumarins/isolation & purification

Plant-derived and semi-synthetic calanolide compounds with in vitro activity against both human immunodeficiency virus type 1 and human cytomegalovirus

Xu ZQ, Kern ER, Westbrook L, Allen LB, Buckheit RW, Tseng CK, et al.

Antivir Chem Chemother, 2000 Jan;11(1):23-9.

PMID: 10693651

Plant-derived and semi-synthetic calanolide compounds with anti-human immunodeficiency virus type 1 (HIV-1) activity were tested for anti-human cytomegalovirus (HCMV) activity in both cytopathic effect inhibition and plaque reduction assays. The results indicated that the anti-HCMV activity of calanolide compounds does not correlate with their activity against HIV-1. The semi-synthetic 12-keto derivatives tended to be more active against HCMV than the corresponding 12-OH congeners, which were more active against HIV-1. It appeared that the 7,8-unsaturated double bond in the chromene ring played a certain role in maintaining activities against both HCMV and HIV-1. Saturation of the double bond increased the EC50 values against both viruses, with concomitant increase in toxicity. The calanolide compounds reported here are the first non-nucleoside analogues capable of inhibiting both HIV-1 and HCMV and, therefore, may be useful chemoprophylactic agents for HCMV in HIV-infected people or vice versa.

Matched MeSH terms: Coumarins/isolation & purification

Fulltext In silico and in vivo characterization of cabralealactone, solasodin and salvadorin in a rat model: potential anti-inflammatory agents

Malik A, Arooj M, Butt TT, Zahid S, Zahid F, Jafar TH, et al.

Drug Des Devel Ther, 2018;12:1431-1443.

PMID: 29872266 DOI: 10.2147/DDDT.S154169

Background: The present study investigates the hepato- and DNA-protective effects of standardized extracts of Cleome brachycarpa (cabralealactone), Solanum incanum (solasodin), and Salvadora oleioides (salvadorin) in rats.

Materials and methods: Hepatotoxicity was induced with intraperitoneal injection of carbon tetrachloride (CCl4) (1 mL/kg b.wt.) once a week for 12 weeks. The hepato- and DNA protective effects of the extracts in different combinations were compared with that of a standard drug Clavazin (200 mg/kg b.wt.). Tissue alanine aminotransferase, alpha-fetoprotein, tumor necrosis factor alpha (TNF-α), isoprostanes-2α, malondialdehyde, and 8-hydroxydeoxyguanosine, the significant hallmarks of oxidative stress, were studied.

Results: Histopathological findings of the liver sections from the rat group which received CCl4+cabralealactone, solasodin, and salvadorin demonstrated improved centrilobular hepatocyte regeneration with moderate areas of congestion and infiltration comparable with Clavazin. For in silico study, the identified compounds were subjected to molecular docking with cyclooxygenase-2 and TNF-α followed by a molecular dynamics study, which indicated their potential as anti-inflammatory agents.

Conclusion: Cabralealactone, solasodin, and salvadorin confer some hepatoprotective and DNA-damage protective effects against CCl4-induced toxicity. They successfully restored the normal architecture of hepatocytes and have the potential to be used as inhibitor to main culprits, that is, cyclooxygenase-2 and TNF-α. They can combat oxidative stress and liver injuries both as mono and combinational therapies. However, combination therapy has more ameliorating effects.

Matched MeSH terms: Coumarins/isolation & purification

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