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New Acetophenones and Chromenes from the Leaves of Melicope Barbigera A

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New Acetophenones and Chromenes from the Leaves of Melicope Barbigera A molecules Article New Acetophenones and Chromenes from the Leaves of Melicope barbigera A. Gray Kim-Thao Le 1, Jan J. Bandolik 2 , Matthias U. Kassack 2 , Kenneth R. Wood 3 , Claudia Paetzold 4,5, Marc S. Appelhans 4 and Claus M. Passreiter 1,* 1 Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-University Duesseldorf, 40225 Duesseldorf, Germany; [email protected] 2 Institute for Pharmaceutical and Medicinal Chemistry, Heinrich-Heine-University Duesseldorf, 40225 Duesseldorf, Germany; [email protected] (J.J.B.); [email protected] (M.U.K.) 3 National Tropical Botanical Garden, 3530 Papalina Road, Kalaheo, HI 96741, USA; [email protected] 4 Institute of Systematics, Biodiversity and Evolution of Plants, Georg-August-University Goettingen, 37073 Goettingen, Germany; [email protected] (C.P.); [email protected] (M.S.A.) 5 Division Botany and Molecular Evolution, Senckenberg Gesellschaft für Naturforschung, Senckenberganlage 25, 60325 Frankfurt am Main, Germany * Correspondence: [email protected]; Tel.: +49-211-81-14472 Abstract: The dichloromethane extract from leaves of Melicope barbigera (Rutaceae), endemic to the Hawaiian island of Kaua’i, yielded four new and three previously known acetophenones and 2H-chromenes, all found for the first time in M. barbigera. The structures of the new compounds obtained from the dichloromethane extract after purification by chromatographic methods were unambiguously elucidated by spectroscopic analyses including 1D/2D NMR spectroscopy and HRESIMS. The absolute configuration was determined by modified Mosher’s method. Compounds 2, 4 and the mixture of 6 and 7 exhibited moderate cytotoxic activities against the human ovarian Citation: Le, K.-T.; Bandolik, J.J.; cancer cell line A2780 with IC50 values of 30.0 and 75.7 µM for 2 and 4, respectively, in a nuclear Kassack, M.U.; Wood, K.R.; Paetzold, shrinkage cytotoxicity assay. C.; Appelhans, M.S.; Passreiter, C.M. New Acetophenones and Chromenes Keywords: Melicope barbigera; Rutaceae; acetophenones; chromenes; melibarbinon A and B; melibar- from the Leaves of Melicope barbigera bichromen A and B; cytotoxicity; ovarian cancer cell line A2780 A. Gray. Molecules 2021, 26, 688. https://doi.org/10.3390/ molecules26030688 1. Introduction Received: 30 November 2020 The genus Melicope J.R. Forst. and G. Forst. is a member of the Rutaceae (Rue or Accepted: 25 January 2021 Published: 28 January 2021 Citrus family) and contains circa 239 species distributed in the Malagasy, Indo-Himalayan, South-East Asian, and Pacific regions [1,2]. With 54 currently accepted endemic species Melicope Publisher’s Note: MDPI stays neutral on the Hawaiian Islands, ranks among the three most speciose lineages of the with regard to jurisdictional claims in archipelago [3,4]. Among Hawaiian Melicope, several species are endangered or even published maps and institutional affil- considered to be extinct [3,5,6]. However, some new Hawaiian species have recently iations. been discovered and botanically described [6–8]. Melicope has been subdivided into four sections based on morphology, and molecular phylogenetic studies have demonstrated that only one of them is monophyletic [1,2]. All Hawaiian species belong to section Pe- lea. Rutaceae are known for their extremely diverse secondary metabolites that include many alkaloids derived from anthranilic acid, limonoids, coumarins, and acetophenones. Copyright: © 2021 by the authors. Melicope Licensee MDPI, Basel, Switzerland. species are proven to be producers of many interesting secondary metabolites This article is an open access article including polymethoxylated flavonoids, furanocoumarins, acetophenones and quinolone distributed under the terms and alkaloids [9–14]. Moreover, several Melicope species are used in traditional and modern conditions of the Creative Commons medicine [15–17]. Since some of the compounds isolated from Melicope possessed antibac- Attribution (CC BY) license (https:// terial, antidiabetic, cytotoxic and antiproliferative activities in human cancer cell lines [15], creativecommons.org/licenses/by/ Melicope species are of special interest for the continuation of our cytotoxicity studies from 4.0/). various plants [18,19]. Molecules 2021, 26, 688. https://doi.org/10.3390/molecules26030688 https://www.mdpi.com/journal/molecules Molecules 2021, 26, 688 2 of 15 Molecules 2021, 26, 688 2 of 14 antiproliferative activities in human cancer cell lines [15], Melicope species are of special interest for the continuation of our cytotoxicity studies from various plants [18,19]. WhileWhile thethe phytochemistryphytochemistry ofof some some species species is sufficientlyis sufficiently characterized, characterized, the informationthe forinformation many species, for many especially species, especially those from those Pacific from Pacific Islands Islands and and rare rare species species with with narrow distributions,narrow distributions, is rather is scarce.rather scarce. Because Beca ofuse the of threatthe threat of extinction, of extinction, it seemsit seems especially importantespecially important to chemically to chemically characterize characte the speciesrize the endemic species endemic to the Hawaiian to the Hawaiian archipelago. In additionarchipelago. to morphologicalIn addition to andmorphological genomic characters, and genomic the patterncharacters, of secondarythe pattern metabolites of secondary metabolites could also serve as a third source of information to distinguish could also serve as a third source of information to distinguish between morphologically between morphologically similar species or populations within a species. In the current Melicope similarstudy, we species focus oron populations Melicope barbigera within, which a species. is an Inexample the current of an understudied study, we focus species on barbigerawith a very, which narrow is andistribution example range, of an understudiedlimited to mesic species forests within North-Western a very narrow Kaua’i. distribution range,This species limited was to only mesic chemically forests ininvestigated North-Western in a single Kaua’i. study This from species 1974, which was reported only chemically investigatedthe isolation inof a four single coumarins study from and 1974, two whichhighly reported methylated the isolationflavones, ofwhich four are coumarins andcharacteristic two highly for methylatedthe genus Melicope flavones, [20]. which are characteristic for the genus Melicope [20]. WeWe concentratedconcentrated on thethe screeningscreening ofof thethe dichloromethanedichloromethane extract obtained from ground leavesground of leavesM. barbigera of M. barbigera. After purification,. After purification, using using various vari chromatographicous chromatographic methods, methods, we isolated thewe acetophenonesisolated the acetophenones1 and 2 as well 1 and as 2the as well 2H-benzopyranes as the 2H-benzopyranes (chromenes) (chromenes)3 and 4, all3 and four found for4, theall four first timefound in for nature, the first in addition time in to na theture, known in addition chromenes to the alloevodionol known chromenes (5)[21] and the isomericalloevodionol melifoliones (5) [21] and6 and the 7isomeric[22], only melifoliones isolated 6 as and mixture 7 [22], (2.5:1)only isolated (see Figure as mixture1). The pure (2.5:1) (see Figure 1). The pure compounds 1–5 and the mixture of 6 and 7 were tested for compounds 1–5 and the mixture of 6 and 7 were tested for their cytotoxic activities against their cytotoxic activities against the human ovarian cancer cell line A2780. Compounds 2 the human ovarian cancer cell line A2780. Compounds 2 and 4 exhibited moderate cytotoxic and 4 exhibited moderate cytotoxic activities with IC50 values of 30.0 µM and 75.7 µM, µ µ activitiesrespectively. with IC50 values of 30.0 M and 75.7 M, respectively. FigureFigure 1. StructuresStructures of of compounds compounds 1−71 isolated−7 isolated from fromthe leaves the leaves of Melicope of Melicope barbigera. barbigera. 2.2. ResultsResults and and Discussion Discussion CompoundCompound 1 1waswas isolated isolated as asa yellowish-brown a yellowish-brown oil. Its oil. molecular Its molecular formula formula was was determineddetermined as as C C1515HH20O205O by5 byhigh high resolution resolution electrospray electrospray ionization ionization mass spectrometry mass spectrometry (HRESIMS),(HRESIMS), requiring requiring six six degrees degrees of unsaturation. of unsaturation. The 13 TheC NMR13C spectrum NMR spectrum of 1 (Table of 11)(Table 1) displayeddisplayed the the signals signals of of fifteen fifteen carbons, carbons, eigh eightt of which of which found found to be protonated to be protonated by their by their proton-carbon correlation in the two-dimensional Heteronuclear Single Quantum Correla- tion spectrum (HSQC). Six carbons were detected at shift values characteristic for a phenolic ring system, bearing four substituents in addition to the phenolic hydroxyl group located at C-20 (d 163.1). Its proton signal was found at d 13.98 (s, 20-OH) in the corresponding 1H NMR spectrum (see Table1), indicating the formation of an intramolecular hydrogen bond with a nearby carbonyl group. Due to the downfield shift and the correlations with three of the benzene carbons found in the two-dimensional Heteronuclear Multiple Molecules 2021, 26, 688 3 of 14 Bond Correlation spectrum (HMBC), an acetyl substituent, and a hydroxylated prenyl side chain were found to be ortho to the phenolic hydroxyl group.
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