Abdullah, A.

Ali, A. M.

Hamzah, Ahmad Sazali

Ismail, N. H.

Jasril,

Lajis, N. H.

Mackeen, Muhammad Mukram

Sukari, Mohd Aspollah

Universiti Putra Malaysia Institutional Repository

UPM Research Report 1998: Volume 2CHEMICAL AND PHARMACOLOGICAL STUDIES OFANTI-MICROBIAL, ANTI-VIRAL AND ANTI-TUMOURCOMPOUNDS FROM SELECTED MALAYSIANPLANTS (MORINDA, HEDYOTIS, GARCINIA ANDJUNIPER SPP.)N.H. Lajis, A.M. Ali, N.H. Ismail, Jasril, A. Abdullah,M.M. Mackeen, M.A. Hj. Sukari and A.S. HarnzahFaculty of Science and Environmental StudiesUniversiti Putra Malaysia, 43400 UPM, Serdang, Selangor,MalaysiaKeywords: anti-microbial activity, anti-tumour activ-ity, Morinda sp., Hedyotis sp., Garcinia sp., Junipersp.IntroductionThere is strong interest lately in the search for new drug fromthe tropical rain forest. This is partly due to the high potentialof discovering new pharmacologically important moleculesfrom the vast and diverse flora and fauna of the tropics. Thediversity of flora and fauna enhance the chances of discoveryresulted from the unlimited number of sample variety avail-able for pharmacological screenings. University Putra Ma-laysia has established several screening programmes to studythe cytotoxic, anti-microbial, anti-viral and anti-oxidativeactivities in biological extracts and pure samples. This proj-ect was aimed at discovering new bio-active compoundsfrom our natural biological resources based on our availableassay systems.Materials and MethodsPlants are collected from several areas of Peninsular Malay-sia and extracted various organic solvents and water. Plantswith relevant medicinal claims are primarily of higher inter-est to our study. The extracts were then subjected to severalbioassay systems and the activity was measured. Plantsshowing high activity from the assays were selected for de-tail investigation to isolate and purify the constituents and fi-nally identified spectroscopically. The activity of each isolatewas measured and the bio-activity-structure relationship wasestablished. Structures showing high activity were synthe-sised or production using alternative methods was pursued,including cell culture approach.Results and DiscussionTwelve anthraquinone compounds from the roots Morindaelliptica. They have been characterised based on their spec-troscopic data and identified as derivatives of 9,10-anthraquinones. One of the compounds isolated was new.The results of this chemical work have been reported (Ismailet al. 1997). Three of the compounds showed strong cyto-toxic activity toward T-lymphoblastic leukemia and Mela-noma cell-lines, in addition to being anti-microbial and anti-HIV virus. Several of these isolates also showed anti-oxidative activity. The synthesis of selected 2-formyl-l-hydroxy-9,IO-anthraquinone, the new compound isolatedfrom this species was completed with good yield and synthe-sis of further derivatives is currently pursued. A large-scalesynthesis is now being planned. Synthesis of other structur-ally modified anthraquinones with potential bio-activities isalso being planned. The structure-activity relationship withregards to anti-microbial, cytotoxicity and anti-oxidative ac-tivities will be pursued. The work on the compounds pro-242duced by the cell culture callus has led to the isolation of IIpure compounds. Several of the isolates are those that occurin the plant, but some of them are not. Further isolation fromthe polar components is continued. The isolation of bio-active compounds from Juniperus chinensis have been con-ducted to result in the identification of a cytotoxic com-pound, deoxypodophyllotoxin which caused up to 100% cellreduction on HeLa cells. It was also active against chronicmyelogenous leukemia, renal carcinoma, melanoma as wellas T-Lymphoblastic leukemia cell-lines. The compound alsoshowed anti-microbial activity. The results of this work havebeen published (Mackeen et al. 1997) The work on isolationof bioactive compounds from the fruits of Garcinia arto-viridis was accomplished. The active compounds identifiedas the dibutyl methyl ester of hydroxycitric acid and the re-spective beta-lactone were found to act strongly against Cla-dosporium herbarum a common agricultural fungus. Extrac-tion of the chemical components from the roots and stembark of G. artoviridis has been completed and bio-activitytest showed that several fractions are very active againstbacteria and strong anti-oxidative. Further isolation andstructure determination is initiated. Isolation and purificationof a Hedyotis herbacea var. was conducted and two flavo-noid-glycosides characterised as quercetin-glucoside andquercetin-rutinoside were isolated along with three two irri-doid compounds and two triterpenoids. The study on the con-stituents of Hedyotis species has been continued. New an-thraquinones were isolated from H. dichotoma (Harnza et al.1997). The isolation of components from the virus/fungus-infected plant was continued and seven compounds wereisolated, sent for NMR and characterised. Four of the com-pounds are quinonoids with two of them being new. The new1,4-anthraquinones were found to be strongly cytotoxic. Inaddition a flavonoid-glycoside, kaempferol rutinoside andtwo triterpenoids were also isolated.ConclusionSeveral anthraquinones were isolated and identified fromMorinda elliptica. Biological activities shown by these com-pounds include cytotoxicity, anti-microbial and anti-viral ac-tivities. The new compound isolated from this study wassynthesised. An approach to alternative production anthra-quinones was also pursued using cell culture technique re-sulted in the useful information on the product profile fromthe process. The cytotoxic component of Juniperus chinen-sis was established as deoxypodophylltoxin. The yield arehowever very low. Investigation on Garcinia atroviridis re-sulted in the isolation of anti-Cladosporium compound iden-tified as hydroxycitric acid butyl ester and its lactone deriva-tive. Several new anthraquinones were also isolated fromHedyotis species, some of which are strongly cytotoxic.ReferencesHamzah, A.S., Ahmad, R., Jasmani, H., Takayama, H., Kitajima, M.,Aimi, N. and Lajis, N.H. 1997. "New Anthraquinones from theRoots of Hedyotis dichotoma (Rubiaceae).", J. Natural Products,76(1): 36.Ismail, N.H., Ali, A.M., Aimi, N., Kitajima, M., Takayama, H. andLajis, N.H. 1997. "Anthraquinones from Morinda Elliptica."Phytochemistry. 45(8): 1723-1725.Mackeen, M.M., Ali, A.M., EI-Sharkawi, S.H., Manap, M.Y., SaHeh,K.M., Lajis, N.H. and Kawazu, K. 1997. "Antimicrobial andCytotoxic Properties of Some Malaysian Traditional Vegetables(Ulam)".lntemational J. Pharmacognosy. 35(3): 174-178.Supported by IRPA Grant03-02-04-0043

Chemical and pharmacological studies of anti-microbial, anti-viral and anti-tumour compounds from selected Malaysian plants (Morinda, Hedyotis, Garcinia and Juniper spp.)

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Chemical and pharmacological studies of anti-microbial, anti-viral and anti-tumour compounds from selected Malaysian plants (Morinda, Hedyotis, Garcinia and Juniper spp.)

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