MyMedR

A new phytochemical survey of Malaysia. V. Preliminary screening and plant chemical studies

Teo LE, Pachiaper G, Chan KC, Hadi HA, Weber JF, Deverre JR, et al.

J Ethnopharmacol, 1990 Feb;28(1):63-101.

A large phytochemical survey of the flora of the Malaysian Peninsula and Sabah is described, covering the systematic search for alkaloids, and partly, for saponins and flavonoids. Details of some chemical studies are reported. This emphasizes the great interest of such a study.

Matched MeSH terms: Alkaloids/analysis; Alkaloids/isolation & purification; Alkaloids/pharmacology

New indole alkaloids from Alstonia macrophylla

Kam TS, Choo YM

J Nat Prod, 2004 Apr;67(4):547-52.

PMID: 15104482

Ten new indole alkaloids, alstomaline (1), 10,11-dimethoxynareline (2), alstohentine (3), alstomicine (4), 16-hydroxyalstonisine (5), 16-hydroxyalstonal (6), 16-hydroxy-N(4)-demethylalstophyllal oxindole (7), alstophyllal (8), 6-oxoalstophylline (9), and 6-oxoalstophyllal (10), in addition to 21 other known ones, were obtained from the leaf extract of the Malayan Alstonia macrophylla. The structures were determined using NMR and MS analysis.

Matched MeSH terms: Indole Alkaloids/isolation & purification*; Indole Alkaloids/pharmacology; Indole Alkaloids/chemistry

Fulltext Spectrophotometric Analysis of Caffeine

Ahmad Bhawani S, Fong SS, Mohamad Ibrahim MN

Int J Anal Chem, 2015;2015:170239.

PMID: 26604926 DOI: 10.1155/2015/170239

The nature of caffeine reveals that it is a bitter white crystalline alkaloid. It is a common ingredient in a variety of drinks (soft and energy drinks) and is also used in combination with various medicines. In order to maintain the optimum level of caffeine, various spectrophotometric methods have been developed. The monitoring of caffeine is very important aspect because of its consumption in higher doses that can lead to various physiological disorders. This paper incorporates various spectrophotometric methods used in the analysis of caffeine in various environmental samples such as pharmaceuticals, soft and energy drinks, tea, and coffee. A range of spectrophotometric methodologies including chemometric techniques and derivatization of spectra have been used to analyse the caffeine.

Matched MeSH terms: Alkaloids

Preliminary notes on the substitution of Gossypii cortex (cotton root bark) for Ergota (ergot).

Vardy EC, Rama S

Journal of the Malaya Branch of the British Medical Association, 1941;5:45-50.

Matched MeSH terms: Ergot Alkaloids

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: Indole Alkaloids/isolation & purification*; Indole Alkaloids/pharmacology; Indole Alkaloids/chemistry

The Chemical Constituents of the Stem Bark and Roots of Goniothalamus Tomentosus (Annonaceae)

Hasliza Yusof, Laily Din, Zuriati Zakaria, Kamarudin Mat Salleh

Sains Malaysiana, 2004;33.

A new species from the Goniothalamus genus, G. tomentosus, was investigated. Two alkaloids, aristololactam BII 1 and ouregidione 2 together with a stigmasterol isolated from the stem bark and roots were identified using spectroscopic techniques.
Spesies baru daripada genus Gonitothalamus, G. tomemtosus telah dikaji. Dua sebatian alkaloid aristololaktam BII 1 dan ouregidion 2 serta stigmasterol yang dipencilkan daripada kulit batang dan akar telah ditentukan dengan menggunakan teknik spektroskopi.

Matched MeSH terms: Alkaloids

Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata

Kam TS, Pang HS, Choo YM, Komiyama K

Chem Biodivers, 2004 Apr;1(4):646-56.

PMID: 17191876

Six new indole alkaloids, viz., (3S)-3-cyanocoronaridine (2), (3S)-3-cyanoisovoacangine (3), conolobine A (5), conolobine B (6), conolidine (7), and (3R/3S)-3-ethoxyvoacangine (8), in addition to 36 known ones, were obtained from the stem-bark extract of the Malayan Tabernaemontana divaricata. The structures were determined by NMR and MS analysis. The CN-substituted alkaloids showed appreciable cytotoxicity towards the KB human oral epidermoid carcinoma cell-line.

Matched MeSH terms: Indole Alkaloids/isolation & purification; Indole Alkaloids/toxicity; Indole Alkaloids/chemistry

From Kratom to mitragynine and its derivatives: physiological and behavioural effects related to use, abuse, and addiction

Hassan Z, Muzaimi M, Navaratnam V, Yusoff NH, Suhaimi FW, Vadivelu R, et al.

Neurosci Biobehav Rev, 2013 Feb;37(2):138-51.

PMID: 23206666 DOI: 10.1016/j.neubiorev.2012.11.012

Kratom (or Ketum) is a psychoactive plant preparation used in Southeast Asia. It is derived from the plant Mitragyna speciosa Korth. Kratom as well as its main alkaloid, mitragynine, currently spreads around the world. Thus, addiction potential and adverse health consequences are becoming an important issue for health authorities. Here we reviewed the available evidence and identified future research needs. It was found that mitragynine and M. speciosa preparations are systematically consumed with rather well defined instrumentalization goals, e.g. to enhance tolerance for hard work or as a substitute in the self-treatment of opiate addiction. There is also evidence from experimental animal models supporting analgesic, muscle relaxant, anti-inflammatory as well as strong anorectic effects. In humans, regular consumption may escalate, lead to tolerance and may yield aversive withdrawal effects. Mitragynine and its derivatives actions in the central nervous system involve μ-opioid receptors, neuronal Ca²⁺ channels and descending monoaminergic projections. Altogether, available data currently suggest both, a therapeutic as well as an abuse potential.

Matched MeSH terms: Alkaloids/pharmacology; Alkaloids/chemistry; Secologanin Tryptamine Alkaloids/adverse effects*; Secologanin Tryptamine Alkaloids/pharmacology; Secologanin Tryptamine Alkaloids/therapeutic use

Biologically active vallesamine, strychnan, and rhazinilam alkaloids from Alstonia: Pneumatophorine, a nor-secovallesamine with unusual incorporation of a 3-ethylpyridine moiety

Lim JL, Sim KS, Yong KT, Loong BJ, Ting KN, Lim SH, et al.

Phytochemistry, 2015 Sep;117:317-24.

PMID: 26125941 DOI: 10.1016/j.phytochem.2015.06.024

Four alkaloids comprising two vallesamine, one strychnan, and one pyranopyridine alkaloid, in addition to 32 other known alkaloids were isolated from two Malayan Alstonia species, Alstonia pneumatophora and Alstonia rostrata. The structures of these alkaloids were determined using NMR and MS analyses, and in one instance, confirmed by X-ray diffraction analysis. The nor-6,7-secovallesamine alkaloid, pneumatophorine, is notable for an unusual incorporation of a 3-ethylpyridine moiety in a monoterpenoid indole. The rhazinilam-type alkaloids (rhazinicine, nor-rhazinicine, rhazinal, and rhazinilam) showed strong cytotoxicity toward human KB, HCT-116, MDA-MB-231, and MRC-5 cells, while pneumatophorine, the uleine alkaloid undulifoline, and the strychnan alkaloids, N4-demethylalstogustine and echitamidine, induced concentration dependent relaxation in phenylephrine-precontracted rat aortic rings.

Matched MeSH terms: Alkaloids/pharmacology*; Alkaloids/chemistry*; Indole Alkaloids/pharmacology; Indole Alkaloids/chemistry*; Secologanin Tryptamine Alkaloids/pharmacology; Secologanin Tryptamine Alkaloids/chemistry

Vindogentianine, a hypoglycemic alkaloid from Catharanthus roseus (L.) G. Don (Apocynaceae)

Tiong SH, Looi CY, Arya A, Wong WF, Hazni H, Mustafa MR, et al.

Fitoterapia, 2015 Apr;102:182-8.

PMID: 25665941 DOI: 10.1016/j.fitote.2015.01.019

Vindogentianine, a new indole alkaloid together with six known alkaloids, vindoline, vindolidine, vindolicine, vindolinine, perivine and serpentine were isolated from leaf extract (DA) of Catharanthus roseus (L.) G. Don. Their structures were elucidated by spectroscopic methods; NMR, MS, UV and IR. Vindogentianine is a dimer containing a vindoline moiety coupled to a gentianine moiety. After 24h incubation, vindogentianine exhibited no cytotoxic effect in C2C12 mouse myoblast and β-TC6 mouse pancreatic cells (IC50>50μg/mL). Real-time cell proliferation monitoring also indicated vindogentianine had little or no effect on C2C12 mouse myoblast cell growth at the highest dose tested (200μg/mL), without inducing cell death. Vindogentianine exhibited potential hypoglycemic activity in β-TC6 and C2C12 cells by inducing higher glucose uptake and significant in vitro PTP-1B inhibition. However, in vitro α-amylase and α-glucosidase inhibition assay showed low inhibition under treatment of vindogentianine. This suggests that hypoglycemic activity of vindogentianine may be due to the enhancement of glucose uptake and PTP-1B inhibition, implying its therapeutic potential against type 2 diabetes.

Matched MeSH terms: Alkaloids/isolation & purification; Alkaloids/chemistry*; Indole Alkaloids/isolation & purification; Indole Alkaloids/chemistry*

Bisnicalaterines B and C, atropisomeric bisindole alkaloids from Hunteria zeylanica, showing vasorelaxant activity

Hirasawa Y, Hara M, Nugroho AE, Sugai M, Zaima K, Kawahara N, et al.

J Org Chem, 2010 Jun 18;75(12):4218-23.

PMID: 20469917 DOI: 10.1021/jo1006762

Two new bisindole alkaloids, bisnicalaterines B and C (1 and 2) consisting of an eburnane and a corynanthe type of skeletons, were isolated from the bark of Hunteria zeylanica. Their absolute structures were determined by combination of NMR, CD, and computational methods, and each of them was shown to be in an atropisomeric relationship. Bisnicalaterines B and C (1 and 2) showed potent vasorelaxant activity on isolated rat aorta.

Matched MeSH terms: Alkaloids/chemistry*; Indole Alkaloids/isolation & purification; Indole Alkaloids/pharmacology; Indole Alkaloids/chemistry*

Alstonia scholaris (L.) R. Br. and Alstonia macrophylla Wall. ex G. Don: A comparative review on traditional uses, phytochemistry and pharmacology

Khyade MS, Kasote DM, Vaikos NP

J Ethnopharmacol, 2014 Apr 11;153(1):1-18.

PMID: 24486598 DOI: 10.1016/j.jep.2014.01.025

Alstonia scholaris (L.) R. Br. and Alstonia macrophylla Wall. ex G. Don are two vital medicinal plant species (family: Apocynaceae). In India, the therapeutic use of Alstonia scholaris has been described in both codified and non-codified drug systems for the treatment of malaria, jaundice, gastrointestinal troubles, cancer and in many other ailments. Other species, Alstonia macrophylla has been used in conventional medicines in Thailand, Malaysia and Philippines as a general tonic, aphrodisiac, anticholeric, antidysentery, antipyretic, emmenagogue, and vulnerary agents. In India, Alstonia macrophylla is used as a substitute for Alstonia scholaris in various herbal pharmaceutical preparations. However, one certainly cannot evaluate the truthfulness of a practice (i.e. in scientific terms). In this article we discuss and summarize comparative data about traditional uses, phytochemistry, pharmacology and toxicity of Alstonia scholaris and Alstonia macrophylla. Moreover, in order to unfold future research opportunities, lacunae in the present knowledge are also highlighted.

Matched MeSH terms: Alkaloids/isolation & purification

Angustilobine and andranginine type indole alkaloids and an uleine-secovallesamine bisindole alkaloid from Alstonia angustiloba

Ku WF, Tan SJ, Low YY, Komiyama K, Kam TS

Phytochemistry, 2011 Dec;72(17):2212-8.

PMID: 21889176 DOI: 10.1016/j.phytochem.2011.08.001

A total of 20 alkaloids were isolated from the leaf and stem-bark extracts of Alstonia angustiloba, of which two are hitherto unknown. One is an alkaloid of the angustilobine type (angustilobine C), while the other is a bisindole alkaloid angustiphylline, derived from the union of uleine and secovallesamine moieties. The structures of these alkaloids were established using NMR and MS analysis. Angustilobine C showed moderate cytotoxicity towards KB cells.

Matched MeSH terms: Alkaloids/isolation & purification; Alkaloids/chemistry; Indole Alkaloids/isolation & purification*; Indole Alkaloids/pharmacology; Indole Alkaloids/therapeutic use*; Indole Alkaloids/chemistry

New phenantrene alkaloids from Cryptocarya crassinervia

Awang K, Hadi AH, Saidi N, Mukhtar MR, Morita H, Litaudon M

Fitoterapia, 2008 Jun;79(4):308-10.

PMID: 18313862 DOI: 10.1016/j.fitote.2007.11.025

The bark of Cryptocarya crassinervia provided two new phenantrene alkaloids, 2-hydroxyatherosperminine (1) and N-demethyl-2-methoxyatherosperminine (2).

Matched MeSH terms: Alkaloids/chemistry*

Alkaloids of Kopsia

Kam TS, Lim KH

Alkaloids Chem Biol, 2008;66:1-111.

PMID: 19025097

Matched MeSH terms: Alkaloids/metabolism*

Biologically active indole and bisindole alkaloids from Tabernaemontana divaricata

Kam TS, Pang HS, Lim TM

Org Biomol Chem, 2003 Apr 21;1(8):1292-7.

PMID: 12929658

The ethanol extract of the leaves of Tabernaemontana divaricata (double flower variety) provided a total of 23 alkaloids, including the new aspidosperma alkaloids, taberhanine, voafinine, N-methylvoafinine, voafinidine, voalenine and the new bisindole alkaloid, conophyllinine in addition to the previously known, biologically active bisindole, conophylline and its congener, conofoline. The structures of the new alkaloids were established by spectroscopic methods. The preparation and characterization of the corresponding quinones of the biologically active bisindoles are also described in relation to a structure-activity study of these compounds with respect to their action in stimulating insulin expression.

Matched MeSH terms: Indole Alkaloids/chemistry*

Motives for using Kratom (Mitragyna speciosa Korth.) among regular users in Malaysia

Singh D, Narayanan S, Müller CP, Swogger MT, Chear NJY, Dzulkapli EB, et al.

J Ethnopharmacol, 2019 Apr 06;233:34-40.

PMID: 30594604 DOI: 10.1016/j.jep.2018.12.038

ETHNOPHARMACOLOGICAL RELEVANCE: The leaves of Mitragyna speciosa (Korth.) or kratom have been traditionally used in Malaysia and Thailand mainly to enhance work productivity, as a folk remedy for treating common ailments, and as a mood enhancer.

AIM OF THE STUDY: This present study sought to investigate kratom use motives among regular kratom users in Malaysia.

MATERIALS AND METHODS: A total of 116 regular kratom users were recruited for this cross-sectional survey. The Drinking Motives Questionnaire (DMQ) was administered to measure kratom use motives.

RESULTS: Our results indicate that heavy (>3 glasses daily, each glass contains 48.24-50.4 mg of mitragynine) kratom use was associated with coping (t87.09 =3.544, p 3 glasses daily) kratom consumption (p 3 glasses daily) kratom consumption among regular kratom users in traditional, rural settings.

Matched MeSH terms: Alkaloids/analysis

Kratom (Mitragyna speciosa): worldwide issues

Ramanathan S, McCurdy CR

Curr Opin Psychiatry, 2020 07;33(4):312-318.

PMID: 32452943 DOI: 10.1097/YCO.0000000000000621

PURPOSE OF REVIEW: To inform readers about the increasingly popular Western dietary supplement, kratom (Mitragyna speciosa) and how the products are available in the Western world compared with traditional Southeast Asian use. Kratom has been traditionally used for increasing stamina of outdoor laborers (farmers), mood enhancement, pain, and opium addiction. Interestingly, kratom has been reported to have a paradoxical effect in that stimulant feelings, and sedative feelings can be obtained depending on the amount utilized. There are several biologically active alkaloids present in kratom.

RECENT FINDINGS: Recent studies have been focused on the interactions of mitragynine, the most abundant alkaloid, and opioid-like effects. This has been driven by the harm that kratom products have produced in the Western world, in stark contrast to the lack of harm in Southeast Asian traditional use over centuries. Many users in the Western world ingest kratom for mood enhancement and/or to ween themselves from prescription or illicit opioids. Highly concentrated products and recreational use and misuse have resulted in individuals pushing doses to levels that have not been imagined or ever studied in animal, let alone humans.

SUMMARY: Kratom, as a preparation and how it is utilized is different around the world.

Matched MeSH terms: Secologanin Tryptamine Alkaloids/pharmacology*

Identification of Alkaloid Compounds Arborinine and Graveoline from Ruta angustifolia (L.) Pers for their Antifungal Potential against Isocitrate lyase (ICL1) gene of Candida albicans

Kamal LZM, Adam MAA, Shahpudin SNM, Shuib AN, Sandai R, Hassan NM, et al.

Mycopathologia, 2021 May;186(2):221-236.

PMID: 33550536 DOI: 10.1007/s11046-020-00523-z

Candida albicans has been reported globally as the most widespread pathogenic species contributing candidiasis from superficial to systemic infections in immunocompromised individuals. Their metabolic adaptation depends on glyoxylate cycle to survive in nutrient-limited host. The long term usage of fungistatic drugs and the lack of cidal drugs frequently result in strains that could resist commonly used antifungals and display multidrug resistance (MDR). In search of potential therapeutic intervention and novel fungicidals, we have explored a plant alkaloids, namely arborinine and graveoline for its antifungal potential. Alkaloids belongs to Rutaceae family have been reported with numerous antimicrobial activities. In this study, we aimed to isolate and identify the antifungal active alkaloids of R. angustifolia and assess antifungal effect targeting C. albicans isocitrate lyase (ICL) gene which regulates isocitrate lyase, key enzyme in glyoxylate cycle contributing to the virulence potential of C. albicans. Alkaloids were extracted by bioassay guided isolation technique which further identified by TLC profile and compared with the standard through HPLC and NMR analysis. The antifungal activities of the extracted alkaloids were quantified by means of MIC (Minimum Inhibitory Concentration). The gene expression of the targeted gene upon treatment was analysed using RT-qPCR and western blot. Additionally, this study looked at the drug-likeness and potential toxicity effect of the active alkaloid compounds in silico analysis. Spectroscopic analysis showed that the isolated active alkaloids were characterized as acridone, furoquinoline, 4-quinolone known as arborinine and graveoline. Results showed that each compound significantly inhibited the growth of C. albicans at the dose of 250 to 500 µg/mL which confirm its antifungal activity. Each alkaloid was found to successfully downregulate the expression of both ICL1 gene CaIcl1 protein. Finally, ADMET analysis suggests a good prediction of chemical properties, namely absorption, distribution, metabolism, excretion and toxicity (ADMET) that will contribute in drug discovery and development later on.

Matched MeSH terms: Alkaloids*

Cannabinoid CB1 receptor binding and acetylcholinesterase inhibitory activity of Sceletium tortuosum L.

Lubbe, A., Khatib, A., Yuliana, N.D., Jinap, S., Verpoorte, R.

International Food Research Journal, 2010;17(2):349-355.

MyJurnal

The whole plant extract of plant Sceletium tortuosum, plant native to South Africa, has been known
traditionally to have mood enhancing and stimulant properties. These properties have been confirmed before by proving serotonin-uptake inhibition activity. A further confirmation by using CB1 receptor binding assay has been performed in this study. The unfermented alkaloid extract was proved to posses a higher activity to bind CB1 receptor compared to that of the fermented one. GC-MS analysis confirmed that unfermented alkoloid extract contain more alkaloids than the fermented one. The ethanol extract was also more active than the fermented one, suggesting that non-alkaloid compounds in this extract could posses this activity. An additional test to check wether this extract can improve cognitive function and memory was performed by acetylcholinesterase inhibitory assay. Both fermented and unfermented alkaloid extracts could inhibit acetylcholinesterase with IC50 being 0.303 mg/ml and 0.330 mg/ml, respectively. However, the major alkaloid in the extract, mesembrine, did not show inhibition of the enzyme. A TLC based test proved that other alkaloids in the extract were responsible to the activity.

Matched MeSH terms: Alkaloids; Indole Alkaloids

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