Antimicrobial Prenylated Acetophenones from Berries of Harrisonia abyssinica

Abstract

The ripe berries of Harrisonia abyssinica yielded two new prenylated acetophenones, namely 5-(ethan-1′′′-one)-4,6-dihydroxy-7-(3′′,3′′-dimethylallyl)-2S-(1′S-hydroxy-1′,5′-dimethylhex-4′-enyl)-2,3-dihydrobenzofuran (1) and 5-(2′′′-hydroxyethan-1′′′-one)-4,6-dihydroxy-7-(3′′,3′′-dimethylallyl)-2S-(1′S-hydroxy-1′,5′-dimethylhex-4′-enyl)-2,3-dihydrobenzofuran (2), herein named harronin I and harronin II, respectively. The compounds were isolated following activity guided fractionation and the structures were determined using 1D, 2D NMR spectroscopic, CD and MS spectrometric techniques. The methanol-dichloromethane mixture (1 : 1 v/v) crude extract exhibited strong antimicrobial activity against Candida albicans, Bacillus cereus, Escherichia coli, Salmonella typhimurium, Staphylococcus aureus, and Lactobacillus casei. Harronin I (1) showed a MIC of 5 µg/mL against C. albicans, 6 µg/mL against B. cereus, and more than 20 µg/mL against other tested microorganisms. Harronin II (2) showed much weaker MIC values (> 100 µg/mL) against all the tested microorganisms.

Key words

Harrisonia abyssinica - Simaroubaceae - harronin I - harrorin II - prenylated acetophenones - antimicrobial activity

References

• 1 Irvine F R. Woody plants of Ghana with special reference to their uses. London: Oxford University Press; 1961: 342-366
• 2 Balde A B, Apers S, Claeys M, Pieters L, Vlietinck A J. Cycloabyssinone, a new cycloterpene from Harrisonia abyssinica.  Fitoterapia. 2001;  72 438-440
• 3 Kokwaro J O. Medicinal plants of East Africa. Nairobi: Kenya Literature Bureau; 1993: 325
• 4 Okorie D A. Chromones and limonoids from Harrisonia abyssinica.  Phytochemistry. 1982;  21 2424-2426
• 5 Kubo I, Tanis S P, Lee Y W, Miura I, Nakanishi K, Chapya A. The structure of hanisonin.  Heterocycles. 1976;  5 485-498
• 6 Liu H W, Kubo I, Nakanishi K. A southern army-worm antifeedant, 12β-acetoxyharrisonin from an African shrub Harrisonia abyssinica.  Heterocycles. 1982;  17 67-71
• 7 Fabry W, Okemo P O, Ansorg R. Antibacterial activity of East African medicinal plants.  J Ethnopharmacol. 1998;  60 79-84
• 8 El Tahir A, Satti G M H, Khalid S A. Antiplasmodial activity of selected Sudanese medicinal plants with emphasis on Maytenus senegaleasis LAM Excel.  J Ethnopharmacol. 1999;  64 227-233
• 9 Rugutt J K, Rugutt K J, Berner D K. Deoxyobacunone, a new limonoid which stimulates germination from the root bark of Harrisonia abyssinica.  J Nat Prod. 2001;  64 1434-1438
• 10 Hassanali A, Bentley M D, Slawint A M Z, Williamst D J, Shephardt R N, Chapya A W. Pedonin, a spiro tetranortriterpenoid insect antifeedant from Harrisonia abyssinica.  Phytochemistry. 1987;  26 573-575
• 11 Balde A M, Vanhaelen M, Daloze D. 5-Dehydrooriciopsin, a ring-D cleaved tetranortriterpenoid from Harrisonia abyssinica.  Phytochemistry. 1988;  27 942-943
• 12 Rugutt J K. Control of African Striga species by natural products from native plants [dissertation]. Eunice: Louisiana State University; 1996
• 13 Rajab M S, Fronczek F R, Mulholland D A, Rugutt J K. 11β,12β-Diacetoxyharrisonin, a tetranortriterpenoid from Harrisonia abyssinica.  Phytochemistry. 1999;  52 127-133
• 14 Blunt S B, Chen T B, Wiemer D F. Prenylated benzoic acids from Rapanea myricoides.  J Nat Prod. 1998;  61 1400-1403
• 15 Roussis V, Ampofo S A, Wiemer D F. A prenylated benzoic acid derivative from the leaves of Piper taboganum.  Phytochemistry. 1990;  29 1787-1788
• 16 Ampofo S A, Roussis V, Wiemer D F. New prenylated phenolics from Piper auritum.  Phytochemistry. 1987;  26 2367-2370
• 17 Seeram N P, Jacobs H, McLean S, Reynolds W F. Prenylated hydroxybenzoic acid derivatives from Piper murrayanum.  Phytochemistry. 1996;  43 863-865
• 18 Orjala J, Erdelmeier C A J, Wright A D, Rali T, Sticher O. Two chromenes and a prenylated benzoic acid derivative from Piper aduncum.  Phytochemistry. 1993;  34 813-818
• 19 Phillips W R, Baj N J, Gunatilaka A A L, Kingston D G I. C-geranyl compounds from Mimulus clevelandii.  J Nat Prod. 1996;  59 495-497
• 20 Baz J B, Cañedo L M, Tapiolas D. A new tetraprenylhydroquinone derivative with an acetic acid unit from the marine sponge Ircinia muscarum.  J Nat Prod. 1996;  59 960-961
• 21 Perel'son M E, Scheichenko V I, Sklyar E Y, Andrianova V B. Configuration of kellerin and samarkandin.  Pharm Chem J. 1977;  11 1050-1052
• 22 Rosselli S, Bruno M, Maggio A, Raccuglia R A, Safder M, Lai C Y, Bastow K F, Lee K H. Cytotoxic geranylflavonoids from Bonannia graeca.  Phytochemistry. 2011;  72 942-945
• 23 Batista jr. J M, Batista A N L, Rinaldo D, Villegas W, Cass Q B, Bolzani V S, Kato M J, Lopez S N, Furlan M, Nafie L A. Absolute configuration reassignment of two chromanes from Peperomia obtusifolia (Piperaceae) using VCD and DFT calculations.  Tetrahedron Asymmetry. 2010;  21 2402-2407
• 24 Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Scalmani G, Barone V, Mennucci B, Petersson G A, Nakatsuji H, Caricato M, Li X, Hratchian H P, Izmaylov A F, Bloino J, Zheng G, Sonnenberg J L, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery jr. J A, Peralta J E, Ogliaro F, Bearpark M, Heyd J J, Brothers E, Kudin K N, Staroverov V N, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant J C, Iyengar S S, Tomasi J, Cossi M, Rega N, Millam J M, Klene M, Knox J E, Cross J B, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann R E, Yazyev O, Austin A J, Cammi R, Pomelli C, Ochterski J W, Martin R L, Morokuma K, Zakrzewski V G, Voth G A, Salvador P, Dannenberg J J, Dapprich S, Daniels A D, Farkas O, Foresman J B, Ortiz J V, Cioslowski T, Fox D J. Gaussian 09, Revision B.01. Wallingford: Gaussian, Inc.; 2010
• 25 Anke H, Bergendorff O, Sterner O. Assays of the biological activities of guaiane sesquiterpenoids isolated from the fruit bodies of edible Lactarius species.  Food Chem Toxicol. 1989;  27 393-397