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Natural Product Communications
A Novel Biflavonoid from Rhus leptodictya
2016 Vol. 11 No. 9 1279 - 1280
Tshifhiwa Matamelab, Ivan R. Greena* and Fanyana M. Mtunzib a
Department of Chemistry and Polymer Science, University of Stellenbosch, P/BagX1, Matieland, Stellenbosch, 7602, South Africa b Department of Chemistry, Vaal University of Technology, P/BagX021, Vanderbijlpark,1900, South Africa
[email protected],
[email protected] Received: April 15th, 2016; Accepted: July 6th, 2016
An investigation of the leaves of Rhus leptodictya led to the isolation of the new biflavonoid: 5,5'',6'',7,8-pentahydroxy-2,2''-bis(p-hydroxyphenyl)-4H,4''H3,7''-bichromene-4,4''-dione the structure of which was established by NMR spectroscopy and mass spectrometry. Keywords: Rhus leptodictya, Biflavonoids5,5'',6'',7,8-Pentahydroxy-2,2''-bis(p-hydroxyphenyl)-4H,4''H(3,7''-bichromene)-4,4''-dione, Anacardiaceae.
Some 20000 plant species have been documented as being used for medicinal purposes by the World Health Organization [1]. Natural products, either as pure compounds or as standardized plant extracts represent an unlimited source for new drug leads due to their plentiful availability and chiral integrity [2]. On the other hand, natural products derived from microorganisms are considered to be the primary source for antibiotics and with the increasing acceptance of herbal medicine as a viable alternative form of health care, especially among the less affluent sections of society [3], the screening of medicinal plants for bioactive compounds has become a promising source of novel antibiotic prototypes [4]. The popularity in the curative potential of traditional medicine is clearly exemplified by the fact that it forms the basis of primary health care in 80% of the developing world [5]. The therapeutic benefit of medicinal plants is often attributed to their antioxidant property [6] since they often play distinctive roles in coetaneous tissue repair where they significantly reduce tissue damage and stimulate wound healing processes [7]. Medicinal plants have now been recognized as a useful source of natural antioxidant compounds and which mainly comprise phenolic compounds. Oxidation is recognized as one of the most important processes producing free radicals in food, in chemical as well as in living systems [8]. The family of flavonoids and similar natural compounds have been shown to be important bioactive constituents of many plant sources [9, 10] . Rhus belongs to a genus consisting of 250 species commonly known as sumac or sumach and are flowering individual plants of the family Anacardiceae [11, 12]. Rhus leptodictya (Rhus leptodictya Diels) is commonly known as mountain karee, rock karee and berg karee. It is a large green shrub native to South Africa. Its leaves appear as three bright green leaflets with toothed margins. Rhus leptodictya can grow up to nine meters tall but is usually encountered as a rather shrubby bush of about three to four meters [13]. Some Anacardiceae are well known poisonous plants viz., rhustoxicodendron (poisonous ivy) while others have been used as herbal medicines [14]. In South Africa, several Rhus species have been used to treat epilepsy and flavonoids have been found to be present in the sumac genus [15,16]. Our work was guided to a significant degree by the work of Eloff [17]. This resulted in the finding that the crude acetone extract of dried Rhus leptodictya leaves displayed a strong antibacterial activity against S. aureus, E. faecalis, P. aeruginosa and E.coli. As a result of this we investigated the extract further and report on the isolation of a new biflavonoid (1) from the dried leaves (Figure 1).
(A) (B) Figure 1: (A) 5,5'',6'',7,8-pentahydroxy-2,2''-bis(p-hydroxyphenyl)-4H,4''H(3,7''bichromene)-4,4''-dione (1) and (B) HMBC correlations.
The novel biflavonoid (1) displayed a positive ion in the HRMS with a peak at m/z 555.0924[M+H]+ which is consistent with the molecular formula of C30H18O11 ( requires 555.0922). Evidence of the presence of 30 carbon atoms is in good agreement with the 13C NMR spectrum. The IR spectrum exhibited absorption bands at 3672, 1704, 1640, 1512 and 1463 cm-1 for H-bonded OH groups, carbonyl and aromatic functionalities, respectively. The 1H NMR spectrum was run in DMSO-d6 and illustrated the presence of 7 OH groups, 3 of which were strongly H-bonded giving signals at δ 13.18 (5-OH), 11.56 (5''-OH) and 11.38 (6''-OH) based on their Hbonding abilities. The remaining 4 OH groups had signals at δ 10.14, 9.71, 9.67 and 8.88. Additionally the NMR spectrum showed the presence of 11 aromatic protons assigned as follows: two superimposed doublets at δ 7.22 (4H, d, J = 8.5 Hz, H-2'/6' and H2'''/6'''), a two proton doublet at δ 6.82 ( J = 8.5 Hz, H-3'/5'), a two proton doublet at δ 6.69 (J = 8.5 Hz, H-3'''/5''') for the two different p-hydroxyphenyl substituents at C-2 and C-2''. Three 1-proton singlets were observed at δ 6.58 for H-8'', δ 5.97 for H-3'' and δ 5.93 for H-6, respectively. The DEPT spectrum displayed 11 signals for C-H groups: 8 for the two p-hydroxyphenyl ring systems at δ 115.3, 115.7, 129.3 and 129.9 and at δ 95.1, 95.6 and 97.3 for C-8'', C-6, and C-3'', respectively based on the HSQC spectral correlation data. The HMBC spectrum illustrates correlation between the H-6 signal at δ 5.93 with the two C-O signals at δ 164.4 and 164.7 for C-7 and C-5, respectively together with a correlation to C-4 at δ 185.5. In addition H-6 shows a correlation to C-4a and C-8a at δ 105.4 and 151.6, respectively. Further correlations were observed between H3'' at δ 5.97 and C-4'' at δ 176.7 together with C-2'', C-4a'' and C-5'' at 170.8, 107.2 and 162.8 respectively. The signal for H-8'' correlated with C-8a'', C-3 and C-7'' at δ 159.8, 136.5 and 147.2 respectively. Regarding the two para-hydroxyphenyl groups at C-2 and C-2'', clear correlations between H-3'/5' at δ 6.82 and H-3'''/5''' at δ 6.69 with C-4' and C-4''' at δ 169.2 and 165.7, respectively were
1280 Natural Product Communications Vol. 11 (9) 2016
observed. Correlations between the H-2'/6' protons at δ 7.32 with the signal for C-2 at δ 165.6 as well as the corresponding signals for H-2'''/6''' signals at δ 7.28 with C-2ꞌꞌ at δ170.8 placed these groups at C-2 and C-2ꞌꞌ in the spectrum run in MeOD-acetone-d6 (Figure 1B). NOESY correlations were observed between H-8ꞌꞌ and H-2ꞌ/6ꞌ as well as between H-3ꞌꞌand H-2ꞌꞌꞌ/6ꞌꞌꞌ supporting the assigned structure. Experimental Rhus leptodictya was collected at Pretoria under the supervision of Prof Eloff and identified by the University of Pretoria Botanical Garden. A voucher specimen is lodged at the archives (RSA tree Number 387). Powdered leaves (200 g) of Rhus leptodictya were shaken on a laboratory shaker for twelve hours with acetone (2 L) and then filtered. This was repeated twice more. The residue (15.5 g) was then treated with ethyl acetate (500 mL) and stirred for 12 hours and filtered. Evaporation of the solvent yielded a residue (7.6 g) which was subjected to gravity liquid column chromatography (GLCC) using Silica Gel (70-240 mesh) and the eluent hexane-ethyl acetate gradient (85:15 to 80:20). Fractions with similar TLC profiles were pooled and concentrated to afford a major fraction (0.220 g). This fraction was rechromatographed using hexane-ethyl acetate (80:20) as eluent to afford the pure biflavonoid 1 (0.120 g; 0.06% yield based on dry mass) as a yellow amorphous powder. 5,5'',6'',7,8-pentahydroxy-2,2''-bis(p-hydroxyphenyl)-4H,4''H3,7''-bichromene-4,4''-dione (1) Yellow amorphous powder. Rf: 0.6 (Hexane-ethyl acetate 4:1).
Matamela et al.
IR (KBr): 3672, 1704, 1640, 1512, 1463 cm-1. 1 H NMR (500 MHz, DMSO-d6): 13.18 (1H, s, 5-OH), 11.56 (1H, s, 5''-OH), 11.38 (1H, s, 6''-OH), 10.14 (1H, s, 8-OH), 9.71 (1H, s, 7OH), 9.67 (1H, s, 4'-OH), 8.88 (1H, s, 4'''-OH), 7.22 (4H, d, J = 8.5 Hz, 2'/6'-H and 2'''/6'''-H), 6.82 (2H, d, J = 8.5 Hz, 3'/5'-H), 6.69 (2H, d, J = 8.5 Hz, 3'''/5'''-H), 6.58 (1H, s, H-8''), 5.97 (1H, s, H-3''), 5.93 (1H, s, H-6). 13 C NMR (125 MHz, DMSO-d6): 95.1 (C-8ꞌꞌ), 95.6 (C-6), 97.3 (C3ꞌꞌ), 105.4 (C-4a), 107.2 (C-4aꞌꞌ), 115.3 (C-3ꞌ/5ꞌ), 115.7 (C-3ꞌꞌ/5ꞌꞌ), 121.6 (C-1ꞌ), 124.8 (C-1ꞌꞌꞌ), 129.3 (C-2ꞌ/6ꞌ), 129.9 (C-2ꞌꞌꞌ/6ꞌꞌꞌ), 136.5 (C-3), 147.2 (C-7ꞌꞌ), 151.6 (C-8a), 158.3 (C-8), 159.1 (C-6ꞌꞌ), 159.8 (C-8aꞌꞌ), 162.8 (C-5ꞌꞌ), 164.4 (C-7), 164.7 (C-5), 165.6 (C-2), 165.7 (C-4ꞌꞌ), 169.2 (C-4ꞌ), 170.8 (C-2ꞌꞌ), 176.7 (C-4ꞌꞌ), 185.5 (C-4). 1 H NMR (500 MHz, MeOD-acetone-d6): 7.32 (2H, d, J = 8.5 Hz, 2'/6'-H), 7.28 (2H, d, J = 8.5 Hz, 2'''/6'''-H), 6.83 (2H, d, J = 8.5 Hz, 3'/5'-H), 6.65 (2H, J = 8.5 Hz, 3'''/5'''-H), 6.40 (1H, s, 8''-H), 6.02 (1H, s, 3''-H), 5.97 (1H, s, 6-H). 13 C NMR (125 MHz MeOD-acetone-d6): 95.2 (C-8ꞌꞌꞌ), 96.7 (C-6), 97.4 (C-3ꞌꞌ), 106.2 (C-4a), 108.5 (C-4aꞌꞌ), 115.9 (C-3ꞌ/5ꞌ), 116.1 (C1ꞌ), 123.1 (C-1ꞌꞌꞌ), 126.6 (C-3), 130.4 (C-2ꞌ/6ꞌ), 130.8 (C-2ꞌꞌꞌ/6ꞌꞌꞌ), 137.3 (C-7ꞌꞌ), 147.9 (C-8a), 150.2 (C-8), 153.1 (C-6ꞌꞌ), 159.1 (C8aꞌꞌ), 160.5 (C-5ꞌꞌ), 164.3 (C-7), 164.4 (C-5), 165.6 (C-2), 166.4 (C4ꞌꞌꞌ), 167.4 (C-4ꞌ), 170.4 (C-2), 173.1 (C),177.4 (C-4ꞌꞌ), 186.8 (C-4). HRMS: m/z [M + H+] calcd for C30H18 O11: 555.0922; found: 555.0924. Acknowledgments – The authors acknowledge the Universities of Stellenbosch and Vaal University of Technology for financial support and Prof JN Eloff for providing the plant material.
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Natural Product Communications 2016 Volume 11, Number 9 Contents Original Paper A Computational Examination of the Uncatalyzed Meinwald Rearrangement of Monoterpene Epoxides William N. Setzer The Iridoid Myodesert-1-ene and Elemol/Eudesmol are found in Distinct Chemotypes of the Australian Aboriginal Medicinal Plant Eremophila dalyana (Scrophulariaceae) Nicholas J. Sadgrove, Timothy L. Collins, Sarah V.A.-M. Legendre, Julian Klepp, Graham L. Jones and Ben W. Greatrex Harpagoside Content in Devil’s Claw Extracts Narasimharao Kondamudi, Matthew W. Turner and Owen M. McDougal A Study on the Lipase-catalysed Acylation of 6,7-Dihydroxy-linalool Stefano Serra and Davide De Simeis Enhanced Production of -Guaiene, a Bicyclic Sesquiterpene Accumulated in Agarwood, by Coexpression of -Guaiene Synthase and Farnesyl Diphosphate Synthase Genes in Escherichia coli Takahiro Kato, Jung-Bum Lee, Futoshi Taura and Fumiya Kurosaki Germacrene Analogs are Anti-androgenic on Androgen-dependent Cells Jukkarin Srivilai, Nantaka Khorana, Neti Waranuch, Wudtichai Wisuitiprot, Nungruthai Suphrom, Apichart Suksamrarn and Kornkanok Ingkaninan Terpenoids from the Fermented Broths of Coprinellus radians Ming-Shian Lee, Che-Jen Hsiao, Yu-Ming Ju, Yueh-Hsiung Kuo, Ruo-Kai Lin and Tzong-Huei Lee On the Allylic Oxidation of Ent-kaurenic Acid Methyl Ester with Lead Tetra-acetate Julio Rojas, Rosa Aparicio and Alfredo Usubillaga Antioxidants from Annatto Seeds as Possible Inhibitory Agents of the Hepatotoxicity Induced by the Antitumor Agent Cisplatin Lucéia Fátima Souza, Niara da Silva Medeiros, Paula Cilene Pereira dos Santos, Carlos Henrique Pagno, Cleice Dalla Nora, Erna Vogt de Jong and Alessandro de Oliveira Rios Cytotoxic Activity of Some Lupeol Derivatives Barbara Bednarczyk-Cwynar, Tomasz Więcaszek and Piotr Ruszkowski In vitro Anticancer Activities of Some Triterpene Glycosides from Holothurians of Cucumariidae, Stichopodidae, Psolidae, Holothuriidae and Synaptidae families Sergey N. Fedorov, Sergey A. Dyshlovoy, Alexandra S. Kuzmich, Larisa K. Shubina, Sergey A. Avilov, Alexandra S. Silchenko, Ann M. Bode, Zigang Dong and Valentin A. Stonik Regulusosides A, B, and C, Three New Polyhydroxysteroid Glycosides from the Starfish Pentaceraster regulus Alla A. Kicha, Natalia V. Ivanchina, Timofey V. Malyarenko, Anatoly I. Kalinovsky, Pavel S. Dmitrenok, Evgeny A. Pislyagin and Ekaterina A. Yurchenko Aphelasteroside F, a new Asterosaponin from the Far Eastern Starfish Aphelasterias japonica Roman S. Popov, Natalia V. Ivanchina, Anatoly I. Kalinovsky, Sofiya D. Kharchenko, Alla A. Kicha, Timofey V. Malyarenko, Svetlana P. Ermakova and Pavel S. Dmitrenok Unusual Steroid Constituents from the Tropical Starfish Leiaster sp. Timofey V. Malyarenko, Alla A. Kicha, Natalia V. Ivanchina, Anatoly I. Kalinovsky, Pavel S. Dmitrenok and Valentin A. Stonik Absolute Configuration and Body Part Distribution of the Alkaloid 6-epi-Monanchorin from the Marine Polychaete Chaetopterus variopedatus Larisa K. Shubina, Tatyana N. Makarieva, Vladimir A. Denisenko, Pavel S. Dmitrenok, Sergey A. Dyshlovoy, Gunhild von Amsberg, Valery P. Glazunov, Artem S. Silchenko, Inna V. Stonik, Hyi-Seung Lee, Yeon-Ju Lee and Valentin A. Stonik N-Demethylaaptanone, A new Congener of Aaptamine Alkaloids from the Vietnamese Marine Sponge Aaptos aaptos Natalia K. Utkina and Vladimir A. Denisenko Influence of the Metabolites of the Marine Algicolous Fungus Penicillium sp. on Seedling Root Growth of Agricultural Plants Mikhail M. Anisimov, Elena L. Chaikina, Olga F. Smetanina and Anton N. Yurchenko Gramine-derived Bromo-alkaloids Activating NF-B-dependent Transcription from the Marine Hydroid Abietinaria abietina Alla G. Guzii, Tatyana N. Makarieva, Sergey N. Fedorov, Vladimir A. Denisenko, Pavel S. Dmitrenok, Aleksandra S. Kuzmich, Vladimir B. Krasokhin, Hyi-Seung Lee, Yeon-Ju Lee and Valentin A. Stonik Inhibitory Effect of Three Diketopiperazines from Marine-derived Bacteria on Secretory Group IIA Phospholipase A2 Hyukjae Choi, Sae-Kwang Ku and Jong-Sup Bae Multifunctional Monoamine Oxidases and Cholinesterases Inhibitory Effects, as well as UPLC-DAD-MS Chemical Profile of Alkaloid Fractions Obtained from Species of the Palicoureeae Tribe Luiz Carlos Klein-Júnior, Carolina dos Santos Passos, Juliana Salton, Fernanda Gobbi de Bitencourt, Luís Funez, Jean Paulo de Andrade, Jonathan Parra Villalobos, Sérgio Augusto de Loreto Bordignon, André Luís Gasper, Yvan Vander Heyden and Amélia Teresinha Henriques Flavonoids from the Bark of Artocarpus integer var. silvestris and their Anti-inflammatory Properties Masuri Kama Kamaruddin Shah, Hasnah Mohd Sirat, Shajarahtunnur Jamil and Juriyati Jalil A Novel Biflavonoid from Rhus leptodictya Tshifhiwa Matamela, Ivan R. Green and Fanyana M. Mtunzi A New Flavonoid from Camellia sinensis Fermented Tea Ayaka Usui, Azusa Nakamura, Manami Era, Yosuke Matsuo, Takashi Tanaka and Kanji Ishimaru Continued inside backcover
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