{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,6]],"date-time":"2026-02-06T13:36:07Z","timestamp":1770384967125,"version":"3.49.0"},"reference-count":43,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2013,7,8]],"date-time":"2013-07-08T00:00:00Z","timestamp":1373241600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A dichloromethane extract of the stem bark of Cryptocarya nigra showed strong  in vitro inhibition of Plasmodium falciparum growth, with an IC50 value of 2.82 \u03bcg\/mL. The phytochemical study of this extract has led to the isolation and characterization of four known alkaloids: (+)-N-methylisococlaurine (1), atherosperminine (2), 2-hydroxyathersperminine (3), and noratherosperminine (4). Structural elucidation of all alkaloids was accomplished  by means of high field 1D- and 2D-NMR, IR, UV and LCMS spectral data. The  isolated extract constituents (+)-N-methylisococlaurine (1), atherosperminine (2) and  2-hydroxy-atherosperminine (3) showed strong antiplasmodial activity, with IC50 values of 5.40, 5.80 and 0.75 \u03bcM, respectively. In addition, (+)-N-methylisocolaurine (1) and atherosperminine (2) showed high antioxidant activity in a DPPH assay with IC50 values of 29.56 ug\/mL and 54.53 ug\/mL respectively. Compounds 1 and 2 also both showed high antioxidant activity in the FRAP assay, with percentages of 78.54 and 70.66 respectively and in the metal chelating assay, with IC50 values of 50.08 ug\/mL and 42.87 ug\/mL, respectively.<\/jats:p>","DOI":"10.3390\/molecules18078009","type":"journal-article","created":{"date-parts":[[2013,7,8]],"date-time":"2013-07-08T11:37:18Z","timestamp":1373283438000},"page":"8009-8017","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":35,"title":["Antiplasmodial Alkaloids from the Bark of  Cryptocarya nigra (Lauraceae)"],"prefix":"10.3390","volume":"18","author":[{"given":"Ayu","family":"Nasrullah","sequence":"first","affiliation":[{"name":"Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Azeana","family":"Zahari","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6329-362X","authenticated-orcid":false,"given":"Jamaludin","family":"Mohamad","sequence":"additional","affiliation":[{"name":"Institute of Biological Sciences, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Khalijah","family":"Awang","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2013,7,8]]},"reference":[{"key":"ref_1","unstructured":"World Health Organization Available online: http:\/\/www.who.int\/malaria\/publications\/world_malaria_report_2012\/wmr2012_full_report.pdf."},{"key":"ref_2","unstructured":"World Health Organization Available online: http:\/\/www.who.int\/malaria\/publications\/world_malaria_report_2012\/wmr2012_factsheet.pdf."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"242","DOI":"10.1186\/1475-2875-10-242","article-title":"Global gene expression profiling of Plasmodium falciparum in response to the anti-malarial drug pyronaridine","volume":"10","author":"Kritsiriwuthinan","year":"2011","journal-title":"Malar. J."},{"key":"ref_4","first-page":"49","article-title":"Antimicrobial activity of some Malaysian plants","volume":"18","author":"Ali","year":"1995","journal-title":"Pertanika J.Trop.Agric.Sci."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"3417","DOI":"10.1016\/j.bmcl.2011.03.104","article-title":"New antiplasmodial indole alkaloids from Hunteria zeylanica","volume":"21","author":"Nugroho","year":"2011","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"567","DOI":"10.1080\/14786410500183944","article-title":"New alkaloids from Phoebe grandis (Nees) Merr","volume":"20","author":"Awang","year":"2006","journal-title":"Nat. Prod. Res."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"867","DOI":"10.1248\/cpb.57.867","article-title":"Delaumonones A and B, new antiplasmodial quassinoids from Laumoniera bruceadelpha","volume":"57","author":"Oshimi","year":"2009","journal-title":"Chem. Pharm. Bull."},{"key":"ref_8","first-page":"115","article-title":"Alkaloids isolated from Dehaasia candolleana (Meisn.) Kosterm","volume":"27","author":"Hadi","year":"2008","journal-title":"Malays. J. Sci."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"7218","DOI":"10.3390\/molecules15107218","article-title":"Anthraquinones with antiplasmodial activity from the roots of Rennellia elliptica Korth. (Rubiaceae)","volume":"15","author":"Osman","year":"2010","journal-title":"Molecules"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"727","DOI":"10.1016\/j.bmc.2008.11.048","article-title":"Ceramicines B-D, new antiplasmodial limonoids from Chisocheton ceramicus","volume":"17","author":"Mohamad","year":"2009","journal-title":"Bioorg. Med. Chem."},{"key":"ref_11","unstructured":"Slik, J.W.F. Trees of Sungai Wain. Available online: http:\/\/www.nationaalherbarium.nl\/sungaiwain."},{"key":"ref_12","unstructured":"Whitmore, T.C., and Ng, F.S.P. (1989). Tree Flora of Malaya: a Manual for Foresters, Longman."},{"key":"ref_13","unstructured":"Corner, E.J.H. (1997). Wayside Trees of Malaya, United Selangor Press. [4th ed.]."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"602","DOI":"10.1016\/j.bse.2008.05.001","article-title":"Intraspecific variability of flavonoid glycosides and styrylpyrones from leaves of Cryptocarya mandioccana Meisner (Lauraceae)","volume":"36","author":"Nehme","year":"2008","journal-title":"Biochem. Syst. Ecol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1404","DOI":"10.1021\/np010258i","article-title":"Alkaloids of the wood of Cryptocarya chinensis","volume":"64","author":"Wu","year":"2001","journal-title":"J. Nat. Prod."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2243","DOI":"10.1071\/CH9892243","article-title":"Alkaloids of Cryptocarya phyllostemon","volume":"42","author":"Cave","year":"1989","journal-title":"Aust. J. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"3825","DOI":"10.1021\/ol061435f","article-title":"Novel seco-Dibenzopyrrocoline Alkaloid from Cryptocarya oubatchensis","volume":"8","author":"Toribio","year":"2006","journal-title":"Org. Lett."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1292","DOI":"10.1248\/cpb.49.1292","article-title":"Alkaloids from the leaves of Cryptocarya chinensis HEMSL","volume":"49","author":"Lin","year":"2001","journal-title":"Chem. Pharm. Bull."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"119","DOI":"10.1016\/S0031-9422(97)01102-3","article-title":"Formation of pavine alkaloids by callus culture of Cryptocarya chinensis","volume":"48","author":"Chang","year":"1998","journal-title":"Phytochemistry"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"157","DOI":"10.1248\/cpb.50.157","article-title":"New pavine N-oxide alkaloids from the stem bark of Cryptocarya chinensis Hemsl","volume":"50","author":"Lin","year":"2002","journal-title":"Chem. Pharm. Bull."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1971","DOI":"10.1021\/np50101a016","article-title":"Quaternary alkaloids from Litsea cubeba and Cryptocarya konishii","volume":"56","author":"Lee","year":"1993","journal-title":"J. Nat. Prod."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"461","DOI":"10.22146\/ijc.21516","article-title":"Aporphine Alkaloids from Bark of Cryptocarya ferra","volume":"9","author":"Saidi","year":"2009","journal-title":"Indo. J. Chem"},{"key":"ref_23","first-page":"48","article-title":"Two Oxoaporphine Alkloids from Bark of Cryptocarya rugulosa","volume":"11","author":"Saidi","year":"2011","journal-title":"Jur. Nat."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"308","DOI":"10.1016\/j.fitote.2007.11.025","article-title":"New phenantrene alkaloids from Cryptocarya crassinervia","volume":"79","author":"Awang","year":"2008","journal-title":"Fitoterapia"},{"key":"ref_25","first-page":"57","article-title":"Coumarins and flavonoids from leaves of Cryptocarya nigra (Lauraceae) and their cytotoxic activity against murine leukemia P-388 cells","volume":"22","author":"Yen","year":"2008","journal-title":"ACGC Chem. Res. Commun."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"699","DOI":"10.1016\/S0031-9422(00)84467-2","article-title":"Alkaloids of Nelumbo nucifera XVI","volume":"12","author":"Kunitomo","year":"1973","journal-title":"Phytochemistry"},{"key":"ref_27","first-page":"1456","article-title":"A novel antimicrobial phenanthrene alkaloid from Bryopyllum pinnatum","volume":"8","author":"Okwu","year":"2011","journal-title":"J. Chem."},{"key":"ref_28","first-page":"99","article-title":"Chapter 3 Phenanthrene Alkaloids","volume":"Volume 39","author":"Arnold","year":"1990","journal-title":"The Alkaloids: Chemistry and Pharmacology"},{"key":"ref_29","unstructured":"Cordell, G.A. (2005). The Alkaloids: Chemistry and Physiology, Academic Press."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"5042","DOI":"10.3390\/molecules14125042","article-title":"Synthesis and antitumor activities of phenanthrene-based alkaloids","volume":"14","author":"Li","year":"2009","journal-title":"Molecules"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1007\/BF00428026","article-title":"Psychopharmacological studies on (\u2212)-nuciferine and its Hofmann degradation product atherosperminine","volume":"59","author":"Bhattacharya","year":"1978","journal-title":"Psychopharmacology (Berlin)"},{"key":"ref_32","first-page":"585","article-title":"Biochemical changes of enzymatic defense system after phenanthrene exposure in olive flounder, Paralichthys olivaceus","volume":"54","author":"Jee","year":"2005","journal-title":"Physiol. Res. (Prague, Czech Repub.)"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"343","DOI":"10.1042\/bj20020793","article-title":"Fate of haem iron in the malaria parasite Plasmodium falciparum","volume":"365","author":"Egan","year":"2002","journal-title":"Biochem. J."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"2094","DOI":"10.1128\/AAC.40.9.2094","article-title":"In vitro activities of novel catecholate siderophores against Plasmodium falciparum","volume":"40","author":"Pradines","year":"1996","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1093\/jac\/dkf104","article-title":"Iron chelators as antimalarial agents: in vitro activity of dicatecholate against Plasmodium falciparum","volume":"50","author":"Pradines","year":"2002","journal-title":"J. Antimicrob. Chemother."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"581","DOI":"10.1016\/j.foodchem.2008.12.055","article-title":"Evaluation of antioxidant and immune activity of Phellinus ribis glucan in mice","volume":"115","author":"Yuan","year":"2009","journal-title":"Food Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"e1000963","DOI":"10.1371\/journal.ppat.1000963","article-title":"Cognitive dysfunction is sustained after rescue therapy in experimental cerebral malaria, and is reduced by additive antioxidant therapy","volume":"6","author":"Reis","year":"2010","journal-title":"PLoS Pathog."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"16346","DOI":"10.3390\/ijms131216346","article-title":"Oxidative stress in malaria","volume":"13","author":"Percario","year":"2012","journal-title":"Int. J. Mol. Sci."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"673","DOI":"10.1126\/science.781840","article-title":"Human malaria parasites in continuous culture","volume":"193","author":"Trager","year":"1976","journal-title":"Science"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"418","DOI":"10.2307\/3280287","article-title":"Synchronization of Plasmodium falciparum erythrocytic stages in culture","volume":"65","author":"Lambros","year":"1979","journal-title":"J Parasitol"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"945","DOI":"10.1021\/jf00018a005","article-title":"Antioxidative properties of xanthan on the autoxidation of soybean oil in cyclodextrin emulsion","volume":"40","author":"Shimada","year":"1992","journal-title":"J. Agric. Food Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"307","DOI":"10.5264\/eiyogakuzashi.44.307","article-title":"Studies on product of browning reaction prepared from glucose amine","volume":"44","author":"Oyaizu","year":"1986","journal-title":"Jpn. J. Nutr."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1006\/abbi.1994.1485","article-title":"Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavenger","volume":"315","author":"Dinis","year":"1994","journal-title":"Arch. Biochem. Biophys."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/18\/7\/8009\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T21:47:47Z","timestamp":1760219267000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/18\/7\/8009"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,7,8]]},"references-count":43,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2013,7]]}},"alternative-id":["molecules18078009"],"URL":"https:\/\/doi.org\/10.3390\/molecules18078009","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,7,8]]}}}