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Phytochemical Study of Stem and Leaf of Clausena Lansium

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Phytochemical Study of Stem and Leaf of Clausena Lansium molecules Article Phytochemical Study of Stem and Leaf of Clausena lansium Wenwen Peng 1,2,*, Xiaoxiang Fu 2, Yuyan Li 2, Zhonghua Xiong 2, Xugen Shi 2, Fang Zhang 2, Guanghua Huo 1 and Baotong Li 3,* 1 Jiangxi Key Laboratory for Conservation and Utilization of Fungal Resources, Jiangxi Agricultural University, Nanchang 330045, China 2 College of Agriculture, Jiangxi Agricultural University, Nanchang 330045, China 3 School of Land Resources and Environment, Jiangxi Agricultural University, Nanchang 330045, China * Correspondence: [email protected] (W.P.); [email protected] (B.L.) Academic Editors: Jianbo Xiao, Yanbo Zhang and Hui Ni Received: 23 July 2019; Accepted: 26 August 2019; Published: 28 August 2019 Abstract: Clausena lansium Lour. Skeels (Rutaceae) is widely distributed in South China and has historically been used as a traditional medicine in local healthcare systems. Although the characteristic components (carbazole alkaloids and coumarins) of C. lansium have been found to possess a wide variety of biological activities, little attention has been paid toward the other components of this plant. In the current study, phytochemical analysis of isolates from a water-soluble stem and leaf extract of C. lansium led to the identification of 12 compounds, including five aromatic glycosides, four sesquiterpene glycosides, two dihydrofuranocoumarin glycosides, and one adenosine. All compounds were isolated for the first time from the genus Clausena, including a new aromatic glycoside (1), a new dihydrofuranocoumarin glycoside (6), and two new sesquiterpene glycosides (8 and 9). The phytochemical structures of the isolates were elucidated using spectroscopic analyses including NMR and MS. The existence of these compounds demonstrates the taxonomic significance of C. lansium in the genus Clausena and suggests that some glycosides from this plant probably play a role in the anticancer activity of C. lansium to some extent. Keywords: Clausena lansium; aromatic glycosides; sesquiterpene glycosides; dihydrofuranocoumarin glycosides 1. Introduction The genus Clausena (Rutaceae) is comprised of approximately 30 species that are scattered throughout the subtropical and tropical regions, including China, Vietnam, Indonesia, Malaysia, and the Philippines [1,2]. There are approximately 10 species as well as 2 varieties in China, which appear in Southern China. Clausena lansium Lour. Skeels (Rutaceae), belonging to the genus Clausena of the family Rutaceae, is a fruit tree and a species of strongly scented evergreen tree growing in South China [1,2]. C. lansium is famous for their fruits, which are usually very popular tropical, health-promoting fruits, while their roots, stems, leaves, and seeds have also been extensively applied in folk medicine or traditional Chinese medicine for the treatments of abdominal pain, malaria, cold, dermatopathy, and snake bites [2,3]. Various biological studies, on the alkaloids, coumarins, and sesquiterpenes from this plant have reported the neuroprotective [4,5], antitumor [6,7], hepatoprotective [8], anti-inflammatory [9], antifungal [10], antioxidant [11], antiobesity [12], nematicidal [13], antimicrobial [14], and hypoglycemic [15] effects of the C. lansium. In our previous studies, some carbazole alkaloids [16] and coumarins [17] were separated from the stem and leaf of C. lansium. As a part of our ongoing research into the natural products possessing structural and biological diversity from C. lansium, a systematic phytochemical study on the stem and leaf of C. lansium Molecules 2019, 24, 3124; doi:10.3390/molecules24173124 www.mdpi.com/journal/molecules Molecules 2019, 24, 3124 2 of 11 Molecules 2019, 24, x FOR PEER REVIEW 2 of 11 was accordingly carried out. The investigation resulted in the separation and characterization of five lansium was accordingly carried out. The investigation resulted in the separation and characterization aromatic glycosides (1–5), two dihydrofuranocoumarin glycosides (6,7), four sesquiterpene glycosides of five aromatic glycosides (1–5), two dihydrofuranocoumarin glycosides (6,7), four sesquiterpene (8–11), and one adenosine (12) (Figure1). All compounds were isolated for the first time from the glycosides (8–11), and one adenosine (12) (Figure 1). All compounds were isolated for the first time genus Clausena, including a new aromatic glycoside (1), a new dihydrofuranocoumarin glycoside (6), from the genus Clausena, including a new aromatic glycoside (1), a new dihydrofuranocoumarin and two new sesquiterpene glycosides (8 and 9). The molecular structures of new compounds were glycoside (6), and two new sesquiterpene glycosides (8 and 9). The molecular structures of new established using comprehensive spectroscopic studies. The known compounds were determined compounds were established using comprehensive spectroscopic studies. The known compounds by comparing their experimental data with those described in the literature. The existence of these were determined by comparing their experimental data with those described in the literature. The compounds demonstrates the taxonomic significance of C. lansium in the genus Clausena and suggests existence of these compounds demonstrates the taxonomic significance of C. lansium in the genus that some glycosides from this plant probably play a role in the anticancer activity of C. lansium to Clausena and suggests that some glycosides from this plant probably play a role in the anticancer some extent. activity of C. lansium to some extent. 4 5 3 HO 6 2 1 7 HO O 6' OCH3 5' O O O OH O O HO O 4' 1' HO HO O O O 2' O O 3' OH OH HO 5'' O OH OH O 1'' 4'' 3'' OH OH OH OH OH OH OH OH OH OH 2'' OH OH 1 2 3 4 HO 2'' 5 4 HO 3' 6 4a COOCH 3 3 3'' 1'' 2' 2 O O O 7 8a O O O O O 6''' O O O HO O OH HO OH OH 5''' O O 4''' OH 1''' OH OH OH OH OH 2''' OH OH OH OH 5 6 7 O O 2 O 2 O 3 1 3 1 4 4 7 8 10 8 10 NH 9 9 2 5 5 6 OH OH 7 OH HO N N O 6' O 6' O O N HO HO HO HO N OH 5' 5' O O O O O 4' OH 1' 4' OH 1' OH OH 2' 2' HO 3' HO 3' HO HO OH OH OH OH HO OH 10 12 8 9 11 FigureFigure 1. 1. TheThe chemical chemical structures structures of of compounds compounds 11––1212 fromfrom the the stem stem and and leaf leaf of of ClausenaClausena lansium. lansium. 2.2. Results Results and and Discussion Discussion 2.1. Elucidation of Chemical Structures of Four New Compounds 1,6,8,9 2.1. Elucidation of Chemical Structures of Four New Compounds 1,6,8,9 Claulanaroside (1) was obtained as a white amorphous powder, and its elemental composition Claulanaroside (1) was obtained as a white amorphous powder, and its elemental composition + was determined to be C18H26O10 by HRESIMS m/z: 425.1623 (Calculated for: [C18H26O10 + Na] , was determined to be C18H26O10 by HRESIMS m/z: 425.1623 (Calculated for: [C18H26O10 + Na]+, 425.1628) with 6 degrees of unsaturation. The Infrared Radiation (IR) spectrum exhibited absorptions 425.1628) with 6 degrees of unsaturation. The Infrared Radiation (IR) spectrum exhibited absorptions for hydroxyl groups (3441 and 1062 cm 1) and the aromatic ring (1618, 1547, and 1498 cm 1). The 1H for hydroxyl groups (3441 and 1062 cm−−1) and the aromatic ring (1618, 1547, and 1498 cm−−1). The 1H NMR data of 1 (Table1) showed clear signals for five aromatic protons ( δH 7.31 (2H, d, J = 7.2 Hz), NMR data of 1 (Table 1) showed clear signals for five aromatic protons (δH 7.31 (2H, d, J = 7.2 Hz), 7.23 (2H, m), and 7.18 (1H, d, J = 7.3)), indicating a monosubstituted benzene ring in 1. The 13C-NMR spectroscopic data (Table 1) showed the presence of a six-carbon sugar (δC 100.8, 77.2, 76.6, 76.5, 70.3, Molecules 2019, 24, 3124 3 of 11 Molecules 2019, 24, x FOR PEER REVIEW 3 of 11 and7.23 61.4), (2H, m),a five-carbon and 7.18 (1H, sugar d, J(δ=C 109.3,7.3)),indicating 79.2, 77.6, a73.9, monosubstituted and 64.6), a benzene benzene ring ring (δC in 137.6,1. The 127.8,13C-NMR 127.8, 127.9, 127.9, and 127.3) and an oxymethylene (δC 70.4). Coupled with the above evidence, comparison spectroscopic data (Table1) showed the presence of a six-carbon sugar ( δC 100.8, 77.2, 76.6, 76.5, 70.3, of the 1H- and 13C NMR data of 1 and icariside F2 [18] implied that the aglycone of 1 was and 61.4), a five-carbon sugar (δC 109.3, 79.2, 77.6, 73.9, and 64.6), a benzene ring (δC 137.6, 127.8, methylbenzene and the C-7 position was glycosylated. Acid hydrolysis of 1 afforded D-glucose and 127.8, 127.9, 127.9, and 127.3) and an oxymethylene (δC 70.4). Coupled with the above evidence, Dcomparison-apiose, which of the were1H- anddetected13C NMR by dataderivatization of 1 and icarisideand HPLC F2 [ 18analysis] implied [19,20]. that the The aglycone anomeric of 1 configurationswas methylbenzene of monosaccharide and the C-7 position units waswere glycosylated. confirmed to Acid be β hydrolysis for the D of-glucose1 afforded and dD-glucose-apiose 3 accordingand d-apiose, to their which JH1-H2 were coupling detected constants by derivatization (7–8 and and2–3 HPLCHz, respectively) analysis [19 ,[18,21,22].20]. The anomericDetailed comparisonconfigurations of the of monosaccharideNMR data of 1 with units those were of confirmed icariside F2 to revealed be β for that the thed-glucose positions and of dthe-apiose β-D- apiofuranosyl linkage3 were different in 1 and icariside F2.
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