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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: Plant Extracts/chemistry

Muscarinic receptor binding activity of polyoxygenated flavones from Melicope subunifoliolata

Chung LY, Yap KF, Goh SH, Mustafa MR, Imiyabir Z

Phytochemistry, 2008 May;69(7):1548-54.

PMID: 18334259 DOI: 10.1016/j.phytochem.2008.01.024

The bark extract of Melicope subunifoliolata (Stapf) T.G. Hartley showed competitive muscarinic receptor binding activity. Six polymethoxyflavones [melibentin (1); melisimplexin (3); 3,3',4',5,7-pentamethoxyflavone (4); meliternatin (5); 3,5,8-trimethoxy-3',4',6,7-bismethylenedioxyflavone (6); and isokanugin (7)] and one furanocoumarin [5-methoxy-8-geranyloxypsoralen (2)] were isolated from the bark extract. Compounds 2 and 6 were isolated for the first time from M. subunifoliolata. The methoxyflavones (compounds 1, 3, 4, 5, 6, and 7) show moderate inhibition in a muscarinic receptor binding assay, while the furanocoumarin (compound 2) is inactive. The potency of the methoxyflavones to inhibit [(3)H]NMS-muscarinic receptor binding is influenced by the position and number of methoxy substitution. The results suggest these compounds are probably muscarinic modulators, agonists or partial agonists/antagonists.

Matched MeSH terms: Plant Extracts/chemistry

Seco-tabersonine alkaloids from Tabernaemontana corymbosa

Lim KH, Thomas NF, Abdullah Z, Kam TS

Phytochemistry, 2009 Feb;70(3):424-9.

PMID: 19217125 DOI: 10.1016/j.phytochem.2009.01.001

Two seco-tabersonine alkaloids, jerantiphyllines A and B, in addition to a tabersonine hydroxyindolenine, jerantinine H, and a recently reported vincamine alkaloid 7, were isolated from the leaf extract of the Malayan Tabernaemontana corymbosa and the structures were established using NMR and MS analysis. Biomimetic conversion of jerantinines A and E to their respective vincamine and 16-epivincamine derivatives were also carried out.

Matched MeSH terms: Plant Extracts/chemistry*

Lumusidines A-D and villalstonidine F, macroline-macroline and macroline-pleiocarpamine bisindole alkaloids from Alstonia macrophylla

Lim SH, Low YY, Subramaniam G, Abdullah Z, Thomas NF, Kam TS

Phytochemistry, 2013 Mar;87:148-56.

PMID: 23200029 DOI: 10.1016/j.phytochem.2012.11.005

Lumusidines A-D, bisindole alkaloids of the macroline-macroline type, and one of the macroline-pleiocarpamine type, villalstonidine F, were isolated from the stem-bark extract of Alstonia macrophylla (Apocynaceae). The structures and absolute configurations of these alkaloids were established using NMR, MS, and X-ray diffraction analyses.

Matched MeSH terms: Plant Extracts/chemistry*

Medicinal property, phytochemistry and pharmacology of several Jatropha species (Euphorbiaceae): a review

Sabandar CW, Ahmat N, Jaafar FM, Sahidin I

Phytochemistry, 2013 Jan;85:7-29.

PMID: 23153517 DOI: 10.1016/j.phytochem.2012.10.009

The genus Jatropha (Euphorbiaceae) comprises of about 170 species of woody trees, shrubs, subshrubs or herbs in the seasonally dry tropics of the Old and the New World. They are used in medicinal folklore to cure various diseases of 80% of the human population in Africa, Asia and Latin America. Species from this genus have been popular to cure stomachache, toothache, swelling, inflammation, leprosy, dysentery, dyscrasia, vertigo, anemia, diabetis, as well as to treat HIV and tumor, opthalmia, ringworm, ulcers, malaria, skin diseases, bronchitis, asthma and as an aphrodisiac. They are also employed as ornamental plants and energy crops. Cyclic peptides alkaloids, diterpenes and miscellaneous compounds have been reported from this genus. Extracts and pure compounds of plants from this genus are reported for cytotoxicity, tumor-promoting, antimicrobial, antiprotozoal, anticoagulant, immunomodulating, anti-inflammatory, antioxidant, protoscolicidal, insecticidal, molluscicidal, inhibition AChE and toxicity activities.

Matched MeSH terms: Plant Extracts/chemistry*

Venalstonine and dioxokopsan derivatives from Kopsia fruticosa

Kam TS, Choo YM

Phytochemistry, 2004 Jul;65(14):2119-22.

PMID: 15279982

Two new venalstonine derivatives, viz., venacarpines A and B, and one new dioxokopsan derivative, kopsorinine, in addition to the kopsifolines A-F, and 11 other known alkaloids, were isolated from a Malayan Kopsia species. The structures of the new alkaloids were determined using NMR and MS analysis.

Matched MeSH terms: Plant Extracts/chemistry

Alkaloids from Alstonia angustifolia

Kam TS, Choo YM

Phytochemistry, 2004 Mar;65(5):603-8.

PMID: 15003424

Six new alkaloids, viz., alstolactone, affinisine oxindole, lagumicine, N(4)-demethylalstonerine, N(4)-demethylalstonerinal, and 10-methoxycathafoline N(4)-oxide, in addition to 36 other known alkaloids, were obtained from the leaf extract of Alstonia angustifolia var. latifolia. The structures of the new alkaloids were determined using NMR and MS analysis.

Matched MeSH terms: Plant Extracts/chemistry

Medicinal uses, chemistry and pharmacology of Dillenia species (Dilleniaceae)

Sabandar CW, Jalil J, Ahmat N, Aladdin NA

Phytochemistry, 2017 Feb;134:6-25.

PMID: 27889244 DOI: 10.1016/j.phytochem.2016.11.010

The genus Dillenia is comprised of about 100 species of evergreen and deciduous trees or shrubs of disjunct distribution in the seasonal tropics of Madagascar through South and South East Asia, Malaysia, North Australia, and Fiji. Species from this genus have been widely used in medicinal folklore to treat cancers, wounds, jaundice, fever, cough, diabetes mellitus, and diarrhea as well as hair tonics. The plants of the genus also produce edible fruits and are cultivated as ornamental plants. Flavonoids, triterpenoids, and miscellaneous compounds have been identified in the genus. Their extracts and pure compounds have been reported for their antimicrobial, anti-inflammatory, cytotoxic, antidiabetes, antioxidant, antidiarrheal, and antiprotozoal activities. Mucilage from their fruits is used in drug formulations.

Matched MeSH terms: Plant Extracts/chemistry

Laevifins A-G, clerodane diterpenoids from the Bark of Croton oblongus Burm.f

Aziz AN, Ismail NH, Halim SNA, Looi CY, Anouar EH, Langat MK, et al.

Phytochemistry, 2018 Dec;156:193-200.

PMID: 30316148 DOI: 10.1016/j.phytochem.2018.10.002

A phytochemical investigation of the stem barks of the Malaysian Croton oblongus Burm.f. (Syn. Croton laevifolius Blume) (Euphorbiaceae) yielded seven previously undescribed ent-neo-clerodane diterpenoids, laevifins A - G and the known crovatin (3). Structures were established by a combination of spectroscopic methods including HRESIMS, NMR spectroscopy and X-ray crystallography. The absolute configuration of crovatin and laevifins A-G was established by comparison of experimental ECD and theoretical TDDFT ECD calculated spectra. This is the first report on the occurrence of the sesquiterpenoid cryptomeridiol in a Croton species. In vitro cytotoxicity assays on laevifins A, B and G showed moderate activities against the MCF-7 cancer cell line (IC50 102, 115 and 106 μM, respectively) while β-amyrin and acetyl aleuritolic acid showed good anti-inflammatory activity on the LPS-induced NF-κB translocation inhibition in RAW 264.7 cells assay with IC50 values of 23.5 and 35.4 μg/mL, respectively.

Matched MeSH terms: Plant Extracts/chemistry

Rapid identification of cyclic tetrapyrrolic photosensitisers for photodynamic therapy using on-line hyphenated LC-PDA-MS coupled with photo-cytotoxicity assay

Tan PJ, Appleton DR, Mustafa MR, Lee HB

Phytochem Anal, 2012 Jan-Feb;23(1):52-9.

PMID: 21692117 DOI: 10.1002/pca.1324

Photodynamic therapy is a treatment modality that involves site-directed generation of cytotoxic reactive oxygen species by light-activated photosensitisers.

Matched MeSH terms: Plant Extracts/chemistry

Characterisation of galloylated cyanogenic glucosides and hydrolysable tannins from leaves of Phyllagathis rotundifolia by LC-ESI-MS/MS

Hooi Poay T, Sui Kiong L, Cheng Hock C

Phytochem Anal, 2011 Nov-Dec;22(6):516-25.

PMID: 21495106 DOI: 10.1002/pca.1312

Phyllagathis rotundifolia (Jack) Bl. (Melastomataceae) is a creeping herb found in Peninsular Malaysia and Sumatra. Traditionally, a decoction of the leaves is used in the treatment of malaria, fever and stomach ache.

Matched MeSH terms: Plant Extracts/chemistry

Application of Box-Behnken design for ultrasound-assisted extraction and recycling preparative HPLC for isolation of anthraquinones from Cassia singueana

Jibril S, Basar N, Sirat HM, Wahab RA, Mahat NA, Nahar L, et al.

Phytochem Anal, 2019 Jan;30(1):101-109.

PMID: 30288828 DOI: 10.1002/pca.2795

INTRODUCTION: Cassia singueana Del. (Fabaceae) is a rare medicinal plant used in the traditional medicine preparations to treat various ailments. The root of C. singueana is a rich source of anthraquinones that possess anticancer, antibacterial and antifungal properties.

OBJECTIVE: The objective of this study was to develop an ultrasound-assisted extraction (UAE) method for achieving a high extraction yield of anthraquinones using the response surface methodology (RSM), Box-Behnken design (BBD), and a recycling preparative high-performance liquid chromatography (HPLC) protocol for isolation of anthraquinones from C. singueana.

METHODOLOGY: Optimisation of UAE was performed using the Box-Behnken experimental design. Recycling preparative HPLC was employed to isolate anthraquinones from the root extract of C. singueana.

RESULTS: The BBD was well-described by a quadratic polynomial model (R2 = 0.9751). The predicted optimal UAE conditions for a high extraction yield were obtained at: extraction time 25.00 min, temperature 50°C and solvent-sample ratio of 10 mL/g. Under the predicted conditions, the experimental value (1.65 ± 0.07%) closely agreed to the predicted yield (1.64%). The obtained crude extract of C. singueana root was subsequently purified to afford eight anthraquinones.

CONCLUSION: The extraction protocol described here is suitable for large-scale extraction of anthraquinones from plant extracts.

Matched MeSH terms: Plant Extracts/chemistry

Correlation of chemical profiles obtained from 1 H-NMR and LC-MS metabolomics with α-glucosidase inhibition activity for varietal selections of Ficus deltoidea

Kasim N, Afzan A, Mediani A, Low KH, Ali AM, Mat N, et al.

Phytochem Anal, 2022 Dec;33(8):1235-1245.

PMID: 36192845 DOI: 10.1002/pca.3175

INTRODUCTION: Ficus deltoidea Jack (Moraceae) is a plant used in Malaysia to treat various ailments, including diabetes. The presence of several varieties raises essential questions regarding which is the potential bioactive variety and what are the bioactive metabolites.

OBJECTIVES: Here, we explored the phytochemical diversity of the seven varieties from Peninsular Malaysia using Nuclear Magnetic Resonance (NMR) and Liquid Chromatography-Mass Spectrometry (LC-MS) analyses and correlated it with the α-glucosidase inhibitory activity.

METHODOLOGY: The Nuclear Overhauser Effect Spectroscopy (NOESY) One-Dimensional (1D)-NMR and LC-MS data were processed, annotated, and correlated with in vitro α-glucosidase inhibitory using multivariate data analysis.

RESULTS: The α-glucosidase results demonstrated that different varieties have varying inhibitory effects, with the highest inhibition rate being F. deltoidea var. trengganuensis and var. kunstleri. Furthermore, diverse habitats and plant ages could also influence the inhibitory rate. The heat map from NMR and LC-MS profiles showed unique patterns according to varying levels of α-glucosidase inhibition rate. The Partial Least Squares (PLS) model constructed from both NMR and LC-MS further confirmed the correlation between the α-glucosidase inhibition rate of F. deltoidea varieties and its metabolite profiles. The Variable Influence on Projection (VIP) and correlation coefficient (p(corr)) values values were used to determine the highly relevant metabolites for explaining the anticipated inhibitory action.

CONCLUSION: NMR and LC-MS annotations allow the identification of flavan-3-ols and proanthocyanidins as the key bioactive factors. Our current results demonstrated the value of multivariate data analysis to predict the quality of herbal materials from both biological and chemical aspects.

Matched MeSH terms: Plant Extracts/chemistry

Radioprotective activity of Polyalthia longifolia standardized extract against X-ray radiation injury in mice

Jothy SL, Saito T, Kanwar JR, Chen Y, Aziz A, Yin-Hui L, et al.

Phys Med, 2016 Jan;32(1):150-61.

PMID: 26526749 DOI: 10.1016/j.ejmp.2015.10.090

The radioprotective effect of Polyalthia longifolia was studied in mice. P. longifolia treatment showed improvement in mice survival compared to 100% mortality in the irradiated mice. Significant increases in hemoglobin concentration, and red blood cell, white blood cell and platelet counts were observed in the animals pretreated with leaf extract. Pre-irradiation administration of P. longifolia leaf extract also increased the CFU counts of the spleen colony and increased the relative spleen size. A dose-dependent decrease in lipid peroxidation levels was observed in the animals pretreated with P. longifolia. However, although the animals pretreated with P. longifolia exhibited a significant increase in superoxide dismutase and catalase activity, the values remained below normal in both liver and the intestine. Pre-irradiation administration of P. longifolia also resulted in the regeneration of the mucosal crypts and villi of the intestine. Moreover, pretreatment with P. longifolia leaf extract also showed restoration of the normal liver cell structure and a significant reduction in the elevated levels of ALT, AST and bilirubin. These results suggested the radioprotective ability of P. longifolia leaf extract, which is significant for future investigation for human applications in developing efficient, economically viable, non-toxic natural and clinically acceptable novel radioprotectors.

Matched MeSH terms: Plant Extracts/chemistry*

A new naturally derived photosensitizer and its phototoxicity on head and neck cancer cells

Lim SH, Lee HB, Ho AS

Photochem Photobiol, 2011 Sep-Oct;87(5):1152-8.

PMID: 21534974 DOI: 10.1111/j.1751-1097.2011.00939.x

In our screening for photosensitizers from natural resources, 15(1)-hydroxypurpurin-7-lactone ethyl methyl diester (compound 1) was isolated for the first time from an Araceae plant. To evaluate the efficacy of compound 1 as a photosensitizer for head and neck cancers, compound 1 was studied in reference to a known photosensitizer pheophorbide-a (Pha), in terms of photophysical properties, singlet oxygen generation and in in vitro experiments (intracellular uptake and phototoxicity assays) in two oral (HSC2 and HSC3) and two nasopharyngeal (HK1 and C666-1) cancer cell lines. In this study, compound 1 exhibited higher intracellular uptake over 24 h compared with Pha in both HSC3 and HK1 cells. When activated by ≥4.8 J cm(-2) of light, compound 1 was slightly more potent as a photosensitizer than Pha by consistently having marginally lower IC(50) values across different cell lines. In flow cytometry experiments to study the mechanism of photoactivated cell death in HSC3, compound 1 was observed to induce more pronounced apoptosis compared with Pha, which may have been driven by the transient G(2)/M cell cycle block which was also observed. These promising results on compound 1 warrant its further investigation as a clinically useful photodynamic therapy agent for head and neck cancer.

Matched MeSH terms: Plant Extracts/chemistry

Dillenia species: A review of the traditional uses, active constituents and pharmacological properties from pre-clinical studies

Saiful Yazan L, Armania N

Pharm Biol, 2014 Jul;52(7):890-7.

PMID: 24766363 DOI: 10.3109/13880209.2013.872672

Dillenia (Dilleniaceae) is a genus of about 100 species of flowering plants in tropical and subtropical trees of Southern Asia, Australasia, and the Indian Ocean Islands. Until now, only eight Dillenia species have been reported to be used traditionally in different countries for various medical purposes. Out of eight species, D. pentagyna (Roxb), D. indica (Linn.) and D. suffruticosa (Griffith Ex. Hook. F. & Thomsom Martelli) have been reported to be used to treat cancerous growth.

Matched MeSH terms: Plant Extracts/chemistry

Antiulcer activity of the chloroform extract of Bauhinia purpurea leaf

Hisam EE, Zakaria ZA, Mohtaruddin N, Rofiee MS, Hamid HA, Othman F

Pharm Biol, 2012 Dec;50(12):1498-507.

PMID: 22954284 DOI: 10.3109/13880209.2012.685945

CONTEXT: Bauhinia purpurea L. (Fabaceae) is a native plant species of many Asian countries, including Malaysia and India. In India, the root, stem, bark, and leaf of B. purpurea are used to treat various ailments, including ulcers and stomach cancer.
OBJECTIVE: In an attempt to establish its pharmacological potential, we studied the antiulcer activity of lipid-soluble extract of B. purpurea obtained via extraction of air-dried leaves using chloroform.
MATERIALS AND METHODS: The rats were administered the chloroform extract (dose range of 100-1000 mg/kg) orally after 24 h fasting. They were subjected to the absolute ethanol- and indomethacin-induced gastric ulcer, and pyloric ligation assays after 30 min. The acute toxicity study was conducted using a single oral dose of 5000 mg/kg extract and the rats were observed for the period of 14 days. omeprazole (30 mg/kg) was used as the standard control.
RESULTS: At 5000 mg/kg, the extract produced no sign of toxicity in rats. The extract exhibited significant (p < 0.05) dose-dependent antiulcer activity for the ethanol-induced model. The extract also significantly (p < 0.05) increased the gastric wall mucus production and pH of gastric content, while significantly (p < 0.05) reducing the total volume and total acidity of the gastric content in the pylorus ligation assay.
DISCUSSION AND CONCLUSION: The extract possesses antiulcer, antisecretory and cytoprotective activities, which could be attributed to its flavonoid and tannin content. These findings provide new information regarding the potential of lipid-soluble compounds of B. purpurea for the prevention and treatment of gastric ulcers.

Matched MeSH terms: Plant Extracts/chemistry

Antifungal activity of Andrographis paniculata extracts and active principles against skin pathogenic fungal strains in vitro

Sule A, Ahmed QU, Latip J, Samah OA, Omar MN, Umar A, et al.

Pharm Biol, 2012 Jul;50(7):850-6.

PMID: 22587518 DOI: 10.3109/13880209.2011.641021

Andrographis paniculata Nees. (Acanthaceae) is an annual herbaceous plant widely cultivated in southern Asia, China, and Europe. It is used in the treatment of skin infections in India, China, and Malaysia by folk medicine practitioners.

Matched MeSH terms: Plant Extracts/chemistry

The physicochemical properties of geraniin, a potential antihyperglycemic agent

Elendran S, Wang LW, Prankerd R, Palanisamy UD

Pharm Biol, 2015;53(12):1719-26.

PMID: 25853977 DOI: 10.3109/13880209.2014.1003356

Natural products play a vital role in the discovery of leads for novel pharmacologically active drugs. Geraniin (GE) was identified as the major compound in the rind of Nephelium lappaceum L. (Sapindaceae), while ellagic and gallic acids have been shown to be its main metabolites. GE and its metabolites possess a range of bioactive properties including being an anti-infective, anticarcinogenic, antihyperglycemic, and antihypertensive.

Matched MeSH terms: Plant Extracts/chemistry*

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: Plant Extracts/chemistry

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