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Please Scroll Down for Article This article was downloaded by: [Australian National University Library] On: 12 December 2008 Access details: Access Details: [subscription number 773444559] Publisher Taylor & Francis Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK Natural Product Research Publication details, including instructions for authors and subscription information: http://www.informaworld.com/smpp/title~content=t713398545 Bioactivity and chemistry of the genus Hortonia Rukmal Ratnayake a; B.M. Ratnayake Bandara a; Siril Wijesundara b; John K. Macleod c; Peta Simmonds c; Veranja Karunaratne a a Department of Chemistry, University of Peradeniya, Peradeniya, Sri Lanka b Royal Botanic Gardens, Peradeniya, Sri Lanka c Research School of Chemistry, Australian National University, Canberra, Australia Online Publication Date: 01 November 2008 To cite this Article Ratnayake, Rukmal, Ratnayake Bandara, B.M., Wijesundara, Siril, Macleod, John K., Simmonds, Peta and Karunaratne, Veranja(2008)'Bioactivity and chemistry of the genus Hortonia',Natural Product Research,22:16,1393 — 1402 To link to this Article: DOI: 10.1080/14786410701722433 URL: http://dx.doi.org/10.1080/14786410701722433 PLEASE SCROLL DOWN FOR ARTICLE Full terms and conditions of use: http://www.informaworld.com/terms-and-conditions-of-access.pdf This article may be used for research, teaching and private study purposes. Any substantial or systematic reproduction, re-distribution, re-selling, loan or sub-licensing, systematic supply or distribution in any form to anyone is expressly forbidden. The publisher does not give any warranty express or implied or make any representation that the contents will be complete or accurate or up to date. The accuracy of any instructions, formulae and drug doses should be independently verified with primary sources. The publisher shall not be liable for any loss, actions, claims, proceedings, demand or costs or damages whatsoever or howsoever caused arising directly or indirectly in connection with or arising out of the use of this material. Natural Product Research Vol. 22, No. 16, 10 November 2008, 1393–1402 Bioactivity and chemistry of the genus Hortonia Rukmal Ratnayakea, B.M. Ratnayake Bandaraa, Siril Wijesundarab, John K. Macleodc, Peta Simmondsc and Veranja Karunaratnea* aDepartment of Chemistry, University of Peradeniya, Peradeniya, Sri Lanka; bRoyal Botanic Gardens, Peradeniya, Sri Lanka; cResearch School of Chemistry, Australian National University, Canberra, Australia (Received 19 October 2006; final version received 22 October 2006) The dichloromethane extracts of the leaves, stem bark, bark and the roots of the three species of the primitive endemic genus Hortonia, H. angustifolia, H. floribunda and H. ovalifolia, collected from nine geographical locations ranging from lower elevations (84–420 m) to higher (2000 m) showed comparable HPLC profiles and mosquito larvicidal and antifungal activities; protein analysis of the leaves of the three species of Hortonia showed identical peaks and bands. The two major metabolites (4S)-4-methyl-2-(11-dodecynyl)-2-butenolide (2) and (4S)-4- methyl-2-(11-dodecenyl)-2-butenolide (3), which were previously reported from all three plants, showed potent larvicidal activities. Compound 2 was excessively high in the extracts of the stem bark and the roots of all three species amounting to approximately 38 and 60%, respectively. A minor new butenolide (4), (4S)-4- methyl-2-((2R)-hydroxy-11-dodecenyl)-2-butenolide, with much reduced larvici- dal activity and ishwarane (1), which showed antifungal activity, were also isolated from all three plants. Treatment of compound 2 with H2/Pd–C afforded the completely reduced compound 5, which showed no larvicidal activity, indicating that unsaturation in both 2 and 3 is necessary for their bioactivity. The foregoing evidence showed that there are major similarities between the three species of Hortonia. Keywords: genus Hortonia; dichloromethane extracts; HPLC analysis; mosquito larvicidal activity; antifungal activity; protein analysis; new butenolide; similarity between species 1. Introduction Hortonia is a genus endemic to Sri Lanka belonging to the family Monimiaceae, order Downloaded By: [Australian National University Library] At: 05:12 12 December 2008 Laurales. This family comprises of about 39 genera, five of which occur in Brazil, and 440 species are widely spread in the Southern Hemisphere, mainly in tropical and subtropical regions of the Americas (Leita˜o, Soares, de Barros, Brito, and Monache, (2000)). This family is represented in Sri Lanka, Oceania, Polynesia, Australia, Malaysia, Madagascar and South America (Claros, da Silva, Vasconcellos, de Brito, and Leitao (2000), Dassanayake, (1996)). They are very rare in Africa and absent in India. Siparuna and Mollinedia, comprising of 150 and 94 species respectively, are the two major genera of *Corresponding author. Email: [email protected] ISSN 1478–6419 print/ISSN 1029–2349 online ß 2008 Taylor & Francis DOI: 10.1080/14786410701722433 http://www.informaworld.com 1394 R. Ratnayake et al. Monimiaceae Claros, et al., (2000). The family Monimiaceae comprises of trees or shrubs and rarely climbers. Hortonia is considered to have originated in Gondwanaland about 100–120 million years ago (Jayasekara, 1997). Wight described three species of Hortonia (H. floribunda, H. ovalifolia, and H. acuminata) from the wet zone of Sri Lanka (Wight, (1853)). Thawaites considered all three species to be varieties of H. floribunda, having numerous intermediate forms (Thawaites (1864)). Trimen, on the other hand, considered H. floribunda and H. angustifolia as two different species (Trimen (1885)). An oval-leaved species collected at Adam’s Peak, in central Sri Lanka, was classified as a variety under H. floribunda. The latest revision of the family Monimiaceae by Dassanayake in 1996 lists three distinct species (H. floribunda Wight ex Arn., H. angustifolia (Thw.) Trimen and H. ovalifolia Wight) in Sri Lanka (Dassanayake, 1996). The present study was initiated with a view to studying the bioactive profile and the chemistry of the genus Hortonia in Sri Lanka. 2. Experimental section 2.1. General experimental procedures Optical rotations were measured with a Bellingham þ Stanley ADP 220 polarimeter using CHCl3 as solvent. UV spectra were obtained in CH2Cl2 using a Shimadzu (UV-160) spectrometer. IR spectra were recorded on a Shimadzu (IR-408) spectrometer as a film on 1 13 NaCl. The H and C NMR spectra were recorded in CDCl3 at 300 and 75 MHz, respectively, on a Varian VXR300S spectrometer and were referenced to the solvent (1H 7.26 ppm; 13C 77.0 ppm). HMQC and HMBC experiments were carried out at 500 MHz on a Varian Inova. All two-dimensional NMR experiments were carried out using standard and in-house modified Varian pulse sequences. EIMS spectra were recorded on a Fisons VG Autospec mass spectrometer operating at 70 eV (direct insertion). Perfluorokerosine was used as the internal reference for HRMS measurements. Medium-pressure liquid chromatography (MPLC) and flash chromatography were performed on Merck Si gel 60 (230–400 mesh). Thin layer chromatography (TLC) was performed on Merck Si gel 60 F254 plates using CH2Cl2 as eluent. 2.2. Plant material Specimens of three species, H. angustifolia, H. floribunda, H. ovalifolia were collected from Downloaded By: [Australian National University Library] At: 05:12 12 December 2008 nine different geographical locations of Sri Lanka ranging from lower elevations to the montane zone: H. angustifolia from Pittabeddara (84–137 m), Atwaltota (127 m), Wewelkandura (140 m), Kotapola (140 m), Kanneliya (165 m), and Deniyaya (420 m); H. floribunda from Kelabokka (1120 m), and Hakgala (1995 m); and H. ovalifolia from the foot hills of Adam’s Peak (2007 m) in September 1998. Air-dried and powdered leaves, stem bark, bark and root (50 g each) collected from each location were separately extracted into CH2Cl2 at 27 C for 2 Â 24 h. The filtrates were concentrated in a rotavap below 30C. Hortonia angustifolia yielded a blackish green CH2Cl2 extract of leaves (5.5 g), a brown semi-solid extract of stem bark (0.43 g), light brown oily bark extract (0.51 g), and light yellow oily extract of root (1.2 g). The other two plants also yielded the extracts in comparable yields. Each of the extracts was subjected to the mosquito larvicidal assay using second instar larvae of Aedes aegypti. Natural Product Research 1395 2.3. HPLC analysis of leaf extracts The CH2Cl2 extracts of leaves collected from nine locations were subjected to HPLC analysis (Waters 2690, separation module; Waters 996, photodiode array detector, UV-visible light spectrophotometer with optical resolution of 1.2 nm per diode and wavelength from 190 to 800 nm). Each of the CH2Cl2 extract of leaves (1.0 mg) was dissolved in 5 mL CH3CN and filtered using sep-pak C18 cartridge; 10 mL of each extract was injected to the HPLC (C8 symmetry, reverse phase, 5 mm, 3.9 Â 150 mm column) using the following solvent mixtures of CH3CN/H2O (1 : 1 until 7 min; 3 : 2 until 28 min; 1 : 1 until 40 min). The PDA detector was set at 200–400 nm. 2.4. Mosquito larvicidal assay Concentrations of 500 ppm for plant extracts, 25 ppm for fractions and 10–0.625 ppm for pure compounds were used for the mosquito larvicidal bioassay against the second instar larvae of Aedes aegypti (Bandara, Kumar, Jacobsson and Molleyres, (2000)). Percentage mortality was determined after 24 h and
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