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Fulltext Anti-Bacillus and nitric oxide inhibitory activities of Malaysian Garcinia mangostana extracts and their major constituents

Karunakaran, T., Ismail, I.S., Ee, G.C.L.

International Food Research Journal, 2019;26(2):705-711.
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Four types of crude extracts were obtained from the stem bark of Garcinia mangostana from which six xanthone derivatives: α-mangostin, β-mangostin, garcinone D, mangostenol, fuscaxanthone C and dulcisxanthone F were isolated. The structures of these compounds were elucidated and determined using spectroscopic techniques such as MS, 1D and 2D NMR. The in vitro anti-Bacillus assay was performed using the crude extracts as well as α-mangostin and β-mangostin against four Bacillus species; B. subtilis ATCC 6633, B. cereus ATCC 33019, B. megaterium ATCC 14581 and B. pumilus ATCC 14884. The ethyl acetate extract showed strong inhibitory activity against B. subtilis, B. cereus, B. megaterium and B. pumilus in disc diffusion assay with 10.33 ± 0.44 mm, 10.33 ± 0.44 mm, 9.00 ± 0.00 mm and 11.33 ± 0.17 mm inhibition zones, respectively. Nitric oxide inhibition activities indicated that two major compounds (α-mangostin, β-mangostin) exhibited very significant activity in the inhibition of LPS/IFN-γ stimulated RAW 264.7 macrophages with IC50 values of 29.81 ± 0.77 and 11.72 ± 1.16 μM, respectively. The chloroform and ethyl acetate extract of G. mangostana showed very potent activities.
Research and publication gaps on kratom and kratom products: a scoping review of current literature

Vicknasingam B, Karunakaran T, Chawarski MC

Curr Opin Psychiatry, 2024 Jul 01;37(4):282-291.
PMID: 38818826 DOI: 10.1097/YCO.0000000000000950

PURPOSE OF REVIEW: Kratom plant, products derived from the plant, and plant phytochemicals are of great interest among researchers, clinicians, and consumers. However, there is a paucity of rigorously collected scientific data on their risk/safety profile and public health impact. This scoping review discusses original research articles published between 2022 and 2023. It focuses on identifying publication gaps on topics related to epidemiology, public health, and risk/safety profiles comparing evidence collected by researchers from Southeast Asia and the West.
RECENT FINDINGS: Our review of the Scopus database identified a total of 55 publications, including clinical case reports and case series reports, surveys, studies enrolling human participants, and publications based on large-scale national surveys or large-scale national or international health system database records.
SUMMARY: Overall, there is dearth of reliable data on key epidemiological factors, including the prevalence rates, and on objective and reliable indices of the risk/safety profiles. Rigorous and systematic studies including improved epidemiological surveillance, human laboratory, and controlled clinical studies are urgently needed to advance our understanding of public health consequences of consuming kratom and kratom-derived products and to improve our understanding of their risk/safety profile and additional analytical studies to better inform development of needed regulatory oversight.
Phytochemicals from Calophyllum macrocarpum Hook.f. and its cytotoxic activities

Karunakaran T, Firouz NS, Santhanam R, Jong VYM

Nat Prod Res, 2022 Jan;36(2):654-659.
PMID: 32674628 DOI: 10.1080/14786419.2020.1795658

Species from the Genus Calophyllum are rich source for bioactive phenolic compounds such as coumarins and xanthones. Phytochemical study carried out on the plant, Calophyllum macrocarpum has led to the isolation of three known prenylated xanthones, ananixanthone (1), trapezifolixanthone (2) and 8-deoxygartanin (3) with two common triterpenoids, stigmasterol (4), and friedelin (5). The structures of these compounds were identified and determined using spectroscopic techniques such as NMR and MS. The cytotoxic activities of compounds 1 and 2 as well as the extracts were tested against HeLa Chang liver and HEK-293 cell lines. Compound 1 exhibited appreciable cytotoxicity with the IC50 value of 11.08 ± 3.09 µM against HeLa Chang liver cell line and moderate cytotoxicity against HEK-293 cell line while compound 2 showed limited toxicity against these two cell lines.
Crystal structure and Hirshfeld surface analysis of 3-(3-hy-droxy-phen-yl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one hemihydrate

Ismail AZ, Gunasekharan M, Karunakaran T, Mohd Faudzi SM

Acta Crystallogr E Crystallogr Commun, 2023 Mar 01;79(Pt 4):287-291.
PMID: 37057012 DOI: 10.1107/S2056989023001925

High-quality single crystals of the title compound, 2C13H11NO2·H2O, were grown and a structural analysis was performed. The asymmetric unit comprises one mol-ecule of 3-(3-hy-droxy-phen-yl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one (3HPPP), which was recently discovered to be a promising anti-MRSA candidate, and a half-mol-ecule of water. The compound crystallizes in the monoclinic space group P2/c. The crystal structure features inter-molecular pyrrole-N-H⋯O (water), carbon-yl/keto-C-O⋯H-O-phenol and phenol-C-O⋯H (water) hydrogen bonds, which help to consolidate the crystal packing. A Hirshfeld surface analysis for the components in the asymmetric unit showed that H⋯H (40.9%) and H⋯C/C⋯H (32.4%) contacts make the largest contributions to the inter-molecular inter-actions of 3HPPP. Considering the presence of water, in its vicinity H⋯O/O⋯H and H⋯C/C⋯H are the most significant contacts, contributing 48.7 and 29.8%, respectively.
In-vitro hepatotoxic activity of mitragynine and paynantheine isolated from the leaves of Mitragyna speciosa Korth. (Kratom)

Karunakaran T, Ganasan J, Rusmadi NN, Santhanam R, Mordi MN

Nat Prod Res, 2024 Jul 09.
PMID: 38982630 DOI: 10.1080/14786419.2024.2375760

Mitragynine, a primary alkaloid found in kratom leaves has been reported to have a broad range of pharmacological and toxicological properties while its congener, paynatheine has comparatively less information available on these aspects. Mitragynine and its congener, paynantheine, were isolated from the ethanol kratom leaves extract using gravity column chromatography techniques. Our study evaluated the cytotoxicity potential of mitragynine and paynantheine on normal human liver cell line, HL-7702, and human hepatoma cell line, HepG2. Mitragynine exhibited a moderate inhibitory effect on the HepG2 cell line with IC50 value of 42.11 ± 1.31 μM in comparison with vinblastine (IC50: 15.45 ± 0.72 μM) while it showed non-cytotoxic properties towards the HL-7702 cell line with concentrations ranging below 200 μM. In contrast, paynantheine exhibited weak cytotoxic properties towards HepG2 and HL-7702 cell lines. Further comprehensive evaluations of both compounds are needed to establish more details on the cytotoxicity potential of kratom alkaloids.
Acetyl- and O-alkyl- derivatives of β-mangostin from Garcinia mangostana and their anti-inflammatory activities

Karunakaran T, Ee GCL, Ismail IS, Mohd Nor SM, Zamakshshari NH

Nat Prod Res, 2018 Jun;32(12):1390-1394.
PMID: 28715912 DOI: 10.1080/14786419.2017.1350666

Pure β-mangostin (1) was isolated from the stem bark of Garcinia mangostana L. One monoacetate (2) and five O-alkylated β-mangostin derivatives (3-7) were synthesised from β-mangostin. The structures of these compounds were elucidated and determined using spectroscopic techniques such as 1D NMR and MS. The cytotoxicities and anti-inflammatory activities of these five compounds against RAW cell 264.7 were tested. The structural-activity relationship studies indicated that β-mangostin showed a significant activity against the LPS-induced RAW cell 264.7, while the acetyl- as well as the O-alkyl- β-mangostin derivatives did not give good activity. Naturally occurring β-mangostin demonstrated comparatively better anti-inflammatory activity than its synthetic counterparts.
Green synthesis of gold nanoparticles from Scutellaria barbata and its anticancer activity in pancreatic cancer cell (PANC-1)

Wang L, Xu J, Yan Y, Liu H, Karunakaran T, Li F

Artif Cells Nanomed Biotechnol, 2019 Dec;47(1):1617-1627.
PMID: 31014134 DOI: 10.1080/21691401.2019.1594862

Nanotechnology has been materialized as a proficient technology for the development of anticancer nanoparticles all the way through an environment-friendly approach. Conventionally, nanoparticles have been assembled by dissimilar methods, but regrettably rely on the negative impact on the natural environment. Amalgamation of nanoparticles by means of plant extract is alternate conservative methods. Scutellaria barbata species was used majorly as food or as medicines against various diseases, and extensive research was conducted for their therapeutic properties. The present research was mainly focused on the synthesis of gold nanoparticles from the Scutellaria barbata by green route method and evaluation of its anticancer activity against pancreatic cancer cell lines (PANC-1). The gold nanoparticles have been characterized by UV-visible spectroscopy, TEM, SAED, AFM, and FTIR analysis. The synthesized gold nanoparticles (AuNPs) possessed effective anticancer activity against pancreatic cancer cell lines (PANC-1). Hence, further research on this plant may lead to the development of novel anticancer drugs which can be used to combat pancreatic cancer.
Fulltext Exploring the Potential Use of Hylocereus polyrhizus Peels as a Source of Cosmeceutical Sunscreen Agent for Its Antioxidant and Photoprotective Properties

Vijayakumar R, Abd Gani SS, Zaidan UH, Halmi MIE, Karunakaran T, Hamdan MR

Evid Based Complement Alternat Med, 2020;2020:7520736.
PMID: 32454871 DOI: 10.1155/2020/7520736

Currently, consumers' demand for sunscreens derived from natural sources that provide photoprotection from ultraviolet (UV) radiation is pushing the cosmetic industry to develop breakthrough formulations of sun protection products by incorporating plant antioxidants as their active ingredients. In this context, the present study was initiated to evaluate the antioxidant and photoprotective properties of the underutilized Hylocereus polyrhizus peel extract (HPPE) using in vitro spectrophotometric techniques. The phytochemical screenings of HPPE conducted via high-performance liquid chromatography (HPLC) and ultra-high-performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-QTOF/MS) revealed the presence of phenolic acids and flavonoids as the major secondary metabolites in HPPE. The antioxidant potentials evaluated based on 2, 2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical and total antioxidant capacity assays were in the range of 22.16 ± 0.24%-84.67 ± 0.03% with 50% inhibitory concentration (IC50) of 36.39 ± 0.04 μg/mL and 23.76 ± 0.14%-31.87 ± 0.26% (IC50 = 21.93 ± 0.07 μg/mL), respectively. For the photoprotective evaluation, the results showed that HPPE had significantly high absorbance values (3.1-3.6) at 290-320 nm with an exceptional sun protection factor (SPF) value of 35.02 ± 0.39 at 1.00 mg/mL. HPPE also possessed a broad-spectrum shielding power against both UVA and UVB radiations. Hence, in terms of practical implications, our findings would offer an exciting avenue to develop a photoprotective formulation incorporating the ethanolic extract of Hylocereus polyrhizus peels as a synergistic active ingredient for its excellent UV absorption properties and the strong antioxidant activities.
Cytotoxicity and nitric oxide inhibitory activities of Xanthones isolated from Calophyllum hosei Ridl

Daud S, Karunakaran T, Santhanam R, Nagaratnam SR, Jong VYM, Ee GCL

Nat Prod Res, 2020 Sep 09.
PMID: 32901512 DOI: 10.1080/14786419.2020.1819273

Previous studies on Calophyllum species have shown the existence of a wide variety of bioactive xanthones and coumarins. Phytochemical investigations carried out on the plant, Calophyllum hosei led to the isolation of eleven known xanthones, ananixanthone (1), 9-hydroxycalabaxanthone (2), dombakinaxanthone (3), thwaitesixanthone (4), caloxanthone B (5), trapezifolixanthone (6), β-mangostin (7), osajaxanthone (8), caloxanthone A (9), calozeyloxanthone (10) and rubraxanthone (11). The structures of these compounds were identified and elucidated using spectroscopic techniques such as NMR and MS. The cytotoxicity and nitric oxide production inhibitory activities of selected xanthones as well as the extracts were tested against HL-60 cells and RAW 264.7 murine macrophages, respectively. Among all tested compounds, β-mangostin exhibited appreciable cytotoxicity against HL-60 cells with the IC50 value of 7.16 ± 0.70 µg/mL and rubraxanthone exhibited significant nitric oxide inhibitory activity against LPS induced RAW 264.7 murine macrophages with the IC50 value of 6.45 ± 0.15 µg/mL.
A new pyranoxanthone from Garcinia nervosa

Wong KW, Ee GCL, Ismail IS, Karunakaran T, Jong VYM

Nat Prod Res, 2017 Nov;31(21):2513-2519.
PMID: 28412841 DOI: 10.1080/14786419.2017.1315717

Phytochemical studies on the stem bark of Garcinia nervosa has resulted in the discovery of one new pyranoxanthone derivative, garner xanthone (1) and five other compounds, 1,5-dihydroxyxanthone (2), 6-deoxyisojacareubin (3), 12b-hydroxy-des-D-garcigerrin A (4) stigmasterol (5), and β-sitosterol (6). The structures of these compounds were elucidated with the aid of spectroscopic techniques, such as NMR and MS. The crude extracts of the plant were assessed for their antimicrobial activity.
Fulltext Accelerated Solvent Extractions (ASE) of Mitragyna speciosa Korth. (Kratom) Leaves: Evaluation of Its Cytotoxicity and Antinociceptive Activity

Goh YS, Karunakaran T, Murugaiyah V, Santhanam R, Abu Bakar MH, Ramanathan S

Molecules, 2021 Jun 17;26(12).
PMID: 34204457 DOI: 10.3390/molecules26123704

Mitragyna speciosa Korth (kratom) is known for its psychoactive and analgesic properties. Mitragynine is the primary constituent present in kratom leaves. This study highlights the utilisation of the green accelerated solvent extraction technique to produce a better, non-toxic and antinociceptive active botanical extract of kratom. ASE M. speciosa extract had a dry yield (0.53-2.91 g) and showed a constant mitragynine content (6.53-7.19%) when extracted with organic solvents of different polarities. It only requires a shorter extraction time (5 min) and a reduced amount of solvents (less than 100 mL). A substantial amount of total phenolic (407.83 ± 2.50 GAE mg/g and flavonoids (194.00 ± 5.00 QE mg/g) were found in ASE kratom ethanol extract. The MTT test indicated that the ASE kratom ethanolic leaf extract is non-cytotoxic towards HEK-293 and HeLa Chang liver cells. In mice, ASE kratom ethanolic extract (200 mg/kg) demonstrated a better antinociceptive effect compared to methanol and ethyl acetate leaf extracts. The presence of bioactive indole alkaloids and flavonols such as mitragynine, paynantheine, quercetin, and rutin in ASE kratom ethanolic leaf extract was detected using UHPLC-ESI-QTOF-MS/MS analysis supports its antinociceptive properties. ASE ethanolic leaf extract offers a better, safe, and cost-effective choice of test botanical extract for further preclinical studies.
Fulltext Green synthesis of silver nanoparticles from aqueous extract of Scutellaria barbata and coating on the cotton fabric for antimicrobial applications and wound healing activity in fibroblast cells (L929)

Veeraraghavan VP, Periadurai ND, Karunakaran T, Hussain S, Surapaneni KM, Jiao X

Saudi J Biol Sci, 2021 Jul;28(7):3633-3640.
PMID: 34220213 DOI: 10.1016/j.sjbs.2021.05.007

Scutellaria barbata is a perennial herb which was vastly prescribed in Chinese medicine to treat inflammations, infections and it is also used a detoxifying agent. We synthesized silver nanoparticles with Scutellaria barbata extract and characterized the nanoparticles with UV-Vis spectroscopic analysis, TEM, AFM, FTIR and XRD. The biofilm inhibiting property of synthesized silver nanoparticles were examined with XTT reduction assay and the antimicrobial property was examined with well diffusion method. The silver nanoparticles were also coated with cotton fabrics and their efficacy against antimicrobials was analyzed to prove its application. The cytotoxic property of synthesized silver nanoparticles was examined with L929 fibroblast cells using MTT assay. Finally we analyzed the wound healing property of synthesized silver nanoparticles with wound scratch assay. The result of our UV-Vis spectroscopic analysis confirms Scutellaria barbata aqueous extract reduced silver ions and synthesized silver nanoparticles. The characterization studies TEM, AFM, FTIR and XRD confirms the synthesized silver nanoparticles are in ideal shape and size to be utilized as a drug. The XTT reduction assay proves silver nanoparticles effectively inhibits the biofilm formation in both resistant and sensitive strains. Antimicrobial sensitivity tests confirms synthesized silver nanoparticles and cotton coated synthesized silver nanoparticles both are effective against gram positive, gram negative and fungal species. Further the results of MTT assay confirms the synthesized silver nanoparticles are non toxic and finally the wound healing potency of the nanoparticles was confirmed with wound scratch assay. Over all our results authentically confirms the silver nanoparticles synthesized with Scutellaria barbata aqueous extract is potent wound healing drug.
Fulltext Preliminary Insight of Pyrrolylated-Chalcones as New Anti-Methicillin-Resistant Staphylococcus aureus (Anti-MRSA) Agents

Gunasekharan M, Choi TI, Rukayadi Y, Mohammad Latif MA, Karunakaran T, Mohd Faudzi SM, et al.

Molecules, 2021 Sep 01;26(17).
PMID: 34500755 DOI: 10.3390/molecules26175314

Bacterial infections are regarded as one of the leading causes of fatal morbidity and death in patients infected with diseases. The ability of microorganisms, particularly methicillin-resistant Staphylococcus aureus (MRSA), to develop resistance to current drugs has evoked the need for a continuous search for new drugs with better efficacies. Hence, a series of non-PAINS associated pyrrolylated-chalcones (1-15) were synthesized and evaluated for their potency against MRSA. The hydroxyl-containing compounds (8, 9, and 10) showed the most significant anti-MRSA efficiency, with the MIC and MBC values ranging from 0.08 to 0.70 mg/mL and 0.16 to 1.88 mg/mL, respectively. The time-kill curve and SEM analyses exhibited bacterial cell death within four hours after exposure to 9, suggesting its bactericidal properties. Furthermore, the docking simulation between 9 and penicillin-binding protein 2a (PBP2a, PDB ID: 6Q9N) suggests a relatively similar bonding interaction to the standard drug with a binding affinity score of -7.0 kcal/mol. Moreover, the zebrafish model showed no toxic effects in the normal embryonic development, blood vessel formation, and apoptosis when exposed to up to 40 µM of compound 9. The overall results suggest that the pyrrolylated-chalcones may be considered as a potential inhibitor in the design of new anti-MRSA agents.
The Malaysian genus Calophyllum (Calophyllaceae): a review on its phytochemistry and pharmacological activities

Zailan AAD, Karunakaran T, Abu Bakar MH, Mian VJY

Nat Prod Res, 2021 Oct 12.
PMID: 34636709 DOI: 10.1080/14786419.2021.1982936

Genus Calophyllum from the family of Calophyllaceae is an evergreen broad-leaved tree that is endemic to Southeast Asia, especially Malaysia. They have been reported for various ethnomedicinal uses in traditional medicine. Previous studies of Malaysian Calophyllum species revealed them to be a rich source of bioactive phytoconstituents such as xanthones, coumarins, terpenoids, and chromanone acids. To date, the extracts and compounds from Malaysian Calophyllum species have shown a broad spectrum of pharmacological activities. For example, calanolide A, a coumarin isolated from Malaysian C. lanigerum, has now reached clinical development to become an anti-HIV drug. This article presents an overview of the significant phytochemical and pharmacological activities of Malaysian Calophyllum species to aid researchers in further discovery of potential benefits of various species of this genus.
Fulltext Di-n-but-yl[N'-(3-meth-oxy-2-oxidobenzyl-idene)-N-phenyl-carbamohydrazono-thio-ato]tin(IV): crystal structure, Hirshfeld surface analysis and computational study

Yusof ENM, Kwong HC, Karunakaran T, Ravoof TBSA, Tiekink ERT

Acta Crystallogr E Crystallogr Commun, 2021 Mar 01;77(Pt 3):286-293.
PMID: 33953953 DOI: 10.1107/S2056989021001870

The title diorganotin Schiff base derivative, [Sn(C4H9)2(C15H13N3O2S)], features a penta-coordinated tin centre defined by the N,O,S-donor atoms of the di-anionic Schiff base ligand and two methyl-ene-C atoms of the n-butyl substituents. The resultant C2NOS donor set defines a geometry inter-mediate between trigonal-bipyramidal and square-pyramidal. In the crystal, amine-N-H⋯O(meth-oxy) hydrogen bonding is found in a helical, supra-molecular chain propagating along the b-axis direction. The chains are assembled into a layer parallel to (01) with methyl-ene-C-H⋯π(phen-yl) inter-actions prominent; layers stack without directional inter-actions between them. The analysis of the calculated Hirshfeld surface showed the presence of weak methyl-ene-C-H⋯π(phen-yl) inter-actions and short H⋯H contacts in the inter-layer region. Consistent with the nature of the identified contacts, the stabilization of the crystal is dominated by the dispersion energy term.
Celastrol attenuates high-fructose diet-induced inflammation and insulin resistance via inhibition of 11β-hydroxysteroid dehydrogenase type 1 activity in rat adipose tissues

Abu Bakar MH, Mohamad Khalid MSF, Nor Shahril NS, Shariff KA, Karunakaran T

Biofactors, 2022 Jan;48(1):111-134.
PMID: 34676604 DOI: 10.1002/biof.1793

High fructose consumption has been linked to low-grade inflammation and insulin resistance that results in increased intracellular 11ß-hydroxysteroid dehydrogenase type 1 (11β-HSD1) activity. Celastrol, a pentacyclic triterpene, has been demonstrated to exhibit multifaceted targets to attenuate various metabolic diseases associated with inflammation. However, the underlying mechanisms by which celastrol exerts its attributive properties on high fructose diet (HFrD)-induced metabolic syndrome remain elusive. Herein, the present study was aimed to elucidate the mechanistic targets of celastrol co-administrations upon HFrD in rats and evaluate its potential to modulate 11β-HSD1 activity. Celastrol remarkably improved glucose tolerance, lipid profiles, and insulin sensitivity along with suppression of hepatic glucose production. In rat adipose tissues, celastrol attenuated nuclear factor-kappa B (NF-κB)-driven inflammation, reduced c-Jun N-terminal kinases (JNK) phosphorylation, and mitigated oxidative stress via upregulated genes expression involved in mitochondrial biogenesis. Furthermore, insulin signaling pathways were significantly improved through the restoration of Akt phosphorylation levels at Ser473 and Thr308 residues. Celastrol exhibited a potent, selective and specific inhibitor of intracellular 11β-HSD1 towards oxidoreductase activity (IC50 value = 4.3 nM) in comparison to other HSD-related enzymes. Inhibition of 11β-HSD1 expression in rat adipose microsomes reduced the availability of its cofactor NADPH and substrate H6PDH in couple to upregulated mRNA and protein expressions of glucocorticoid receptor. In conclusion, our results underscore the most likely conceivable mechanisms exhibited by celastrol against HFrD-induced metabolic dysregulations mainly through attenuating inflammation and insulin resistance, at least via specific inhibitions on 11β-HSD1 activity in adipose tissues.
Phytochemicals from Calophyllum canum Hook f. ex T. Anderson and their neuroprotective effects

Lizazman MA, Jong VYM, Chua P, Lim WK, Karunakaran T

Nat Prod Res, 2023 Jun;37(12):2043-2048.
PMID: 35997666 DOI: 10.1080/14786419.2022.2116021

Previous phytochemical investigations reported that Calophyllum spp have biosynthesized a wide range of bioactive phenolics such as xanthones and coumarins. The phytochemical study conducted on the stem bark of C. canum has led to the isolation of eight trioxygenated xanthones namely: 5-methoxytrapezifolixanthone (1), 5-methoxyananixanthone (2), caloxanthone C (3), 1,5-dihydroxy-3-methoxy-4-isoprenylxanthone (4), 6-deoxyisojacareubin (5), euxanthone (6), trapezifolixanthone (7), ananixanthone (8), together with three common triterpenoids, β-sitosterol (9), friedelin (10), and stigmasterol (11). Furthermore, xanthones 1 and 2 were isolated for the first time as naturally occurring xanthones from the plant extract. The structures of these compounds were identified and elucidated using advanced spectroscopic techniques such as 1 D & 2 D NMR, MS, and FTIR. The neuroprotective property of selected compounds was tested through in vitro stroke model. Among all tested compounds, 1 µm of compounds 8, 9, and 10 showed significant neuroprotective activity via reduction of apoptosis by ∼ 50%.
Phenolics and triterpenoids from stem bark of Calophyllum lanigerum var. austrocoriaceum (Whitmore) P. F. Stevens and their cytotoxic activities

Mokhtar N, Karunakaran T, Santhanam R, Abu Bakar MH, Jong VYM

Nat Prod Res, 2024;38(5):873-878.
PMID: 37005001 DOI: 10.1080/14786419.2023.2196075

Genus Calophyllum is well-known for its phenolic constituents, especially coumarins, which have shown to have a wide range of significant biological activities. In this study, four known phenolic constituents and two triterpenoids have been isolated from the stem bark of Calophyllum lanigerum. The compounds were two pyranochromanone acids are known as caloteysmannic acid (1), isocalolongic acid (2), a simple dihydroxyxanthone, namely euxanthone (3), one coumarin named calanone (4), and two common triterpenoids, friedelin (5), and stigmasterol (6). Chromanone acids were reported for the first time in this Calophyllum species. Cytotoxic evaluations were carried out on n-hexane extract (87.14 ± 2.04 µg/mL; 81.46 ± 2.42 µg/mL) followed by the chromanone acids (1 [79.96 ± 2.39 µM; 83.41 ± 3.39 µM] & 2 [57.88 ± 2.34; 53.04 ± 3.18 µM]) against two cancerous cell lines, MDA-MB-231 and MG-63 cell lines, respectively. The results showed that all tested samples exhibited moderate cytotoxicity.
Chemical constituents from the stem barks of Calophyllum recurvatum P.F. Stevens and Calophyllum andersonii P.F. Stevens, and their in-vitro hepatotoxic activity

Firouz NS, Karunakaran T, Mokhtar N, Santhanam R, Jong VYM, Abu Bakar MH

Nat Prod Res, 2024 Jan 22.
PMID: 38247357 DOI: 10.1080/14786419.2024.2305222

Bioactive phenolics can be found in abundance in Calophyllum species. Phytochemical studies are carried out on the stem bark of Calophyllum recurvatum and Calophyllum andersonii, which has led to the isolation and elucidation of phytochemicals, thwaitesixanthone (1), teysmanone A (2), soulattrolide (3), calanone (4), isocalanone (5) and friedelin (6), respectively. The cytotoxic activities of compounds (2), (3), (4) and (5) as well as plant extracts were tested against HeLa Chang liver, HepG2 and HL-7702 cell lines. Phenylpyranocoumarins, teysmanone A (2) and soulattrolide (3) portrayed appreciable cytotoxicity activities at 42.57 ± 1.20 and 34.53 ± 3.41 µg/mL, respectively against HepG2 cell line comparable to the positive control, curcumin. Meanwhile, n-hexane extract from C. recurvatum exhibited cytotoxicity with the IC50 value of 36.43 ± 0.64 and 26.25 ± 4.83 µg/mL against HeLa Chang liver and HepG2 cell lines. All the tested compounds and plant extracts displayed non-cytotoxic properties on HL-7702 cell line.
Fulltext The Chemical and Pharmacological Properties of Mitragynine and Its Diastereomers: An Insight Review

Karunakaran T, Ngew KZ, Zailan AAD, Mian Jong VY, Abu Bakar MH

Front Pharmacol, 2022;13:805986.
PMID: 35281925 DOI: 10.3389/fphar.2022.805986

Mitragynine, is a naturally occurring indole alkaloid that can be isolated from the leaves of a psychoactive medicinal plant. Mitragyna speciosa, also known as kratom, is found to possess promising analgesic effects on mediating the opioid receptors such as µ (MOR), δ (DOR), and κ (KOR). This alkaloid has therapeutic potential for pain management as it has limited adverse effect compared to a classical opioid, morphine. Mitragynine is frequently regarded to behave like an opioid but possesses milder withdrawal symptoms. The use of this alkaloid as the source of an analgesic candidate has been proven through comprehensive preclinical and clinical studies. The present data have shown that mitragynine is able to bind to opioid receptors, particularly MOR, to exhibit the analgesic effect. Moreover, the chemical and pharmacological aspects of mitragynine and its diastereomers, speciogynine, speciociliatine, and mitraciliatine, are discussed. It is interesting to know how the difference in stereochemical configuration could lead to the difference in the bioactivity of the respective compounds. Hence, in this review, the updated pharmacological and toxicological properties of mitragynine and its diastereomers are discussed to render a comprehensive understanding of the pharmacological properties of mitragynine and its diastereomers based on their structure-activity relationship study.

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