Contents lists available at ScienceDirect Phytochemistry Letters journal homepage: www.elsevier.com/locate/phytol Aromatic rutinosides from the aerial roots of Pandanus tectorius Poolsak Sahakitpichan a , Nitirat Chimnoi a , Wassapol Thamniyom a , Somsak Ruchirawat a , Tripetch Kanchanapoom a,b, * a Chulabhorn Research Institute, Kamphaeng Phet 6, Talat Bang Khen, Lak Si, Bangkok, 10210, Thailand b Faculty of Pharmaceutical Sciences, Khon Kaen University, Khon Kaen, 40002, Thailand ARTICLEINFO Keywords: Pandanus tectorius Pandanaceae aromatic rutinosides 2-hydroxy-phenylethanoid glycoside ABSTRACT Three new aromatic rutinosides, including 2-methoxy-4-methylphenyl 1-O-rutinoside (1), 3,5-dimethoxy-4-hy- droxyphenyl1-O-rutinoside(3)and(S)-2-hydroxy-2-phenylethyl1-O-rutinoside(6)wereisolatedfromthefresh aerial roots of Pandanus tectorius. Additionally, the 12 known compounds were identified; 2-methoxy-4-hydro- xymethylphenyl 1-O-rutinoside, cuneataside D, benzyl rutinoside, 2-phenethyl rutinoside, viridoside, 7,8-threo- 7-methoxysyringylglycerol, 7,8-erythro-7-methoxysyringylglycerol, methyl caffeate, 3,5-di-O-caffeoyl-quinic acid 1-methyl ether, 4,5-di-O-caffeoyl-quinic acid 1-methyl ether, 3,4-di-O-caffeoyl-epi-quinic acid methyl ester andhedyotolD7"-O-β-D-glucopyranoside. The structure determinations were considered based on the physical data and the spectroscopic evidence including 1D and 2D NMR experiments. 1. Introduction Pandanus tectorius (Thainame:Ka-Ra-Ket)isamemberofthefamily Pandanaceae. This species has been reported to treat several medical conditions such as leprosy, diabetes mellites, hypertension and urinary tract ailments. In Thailand, P. tectorius is used as traditional medicine; the decoction of the aerial roots has been used for diuretic purposes. Pandanus species are well-known plants containing essential oils, ter- penes, sterols, lignans, coumarins, caffeoylquinic acids, flavonoids, phenolic compounds (Vahirua-Lechat et al., 1996; Takayama et al., 1999; Tan et al., 2008; Liu et al., 2013; Hoa et al., 2014; Mai et al., 2015; Nguyen et al., 2016). This article described the isolation and structure identification of three new aromatic rutinosides (1, 3 and 6, Fig. 1) and the 12 known compounds (2, 4, 5, 7-15) from the water soluble fraction of the methanol extract of the fresh aerial roots of P. tectorius origin from Thailand. 2. Results and discussion The three new aromatic rutinosides (1, 3 and 6) and 12 known com- pounds (2, 4, 5, 7-15) were isolated from the methanol extract of fresh aerial roots of P. tectorius. The known compounds were identified as 2- methoxy-4-hydroxymethylphenyl 1-O-rutinoside (2)(Chang et al., 2002), cuneataside D (4)(Chang and Case 2005), benzyl rutinoside (5) (Kawahara et al., 2005), 2-phenethyl rutinoside (7)(Hase et al., 1995), viridoside (8)(Yousef et al., 2006), 7,8-threo-7-methoxysyringylglycerol (9)(Shi et al., 2010), 7,8-erythro-7-methoxysyringylglycerol (10)(Huang et al., 2014), methyl caffeate (11)(van Dyck et al., 2000), 3,5-di-O-caf- feoyl-quinic acid 1-methyl ether (12), 4,5-di-O-caffeoyl-quinic acid 1-me- thyl ether (13),(Aboul Ela et al., 2012), 3,4-di-O-caffeoyl-epi-quinic acid methylester(14)(Mijangos-Ramosetal.,2018)andhedyotolD7"-O-β-D- glucopyranoside (15)(Yin et al., 2016) by comparison of physical data with literature values and from spectroscopic evidence. Compound 1 was obtained as an amorphous powder. The de- termined molecular formula was C 20 H 30 O 11 by using high resolution electrospray time-of-flight (HR-ESI-TOF) mass spectrometric analysis. The 1 H NMR spectrum displayed the presence of a 1,2,4-trisubstituted aromatic ring system from the chemical shifts at δ H 6.72 (1H, dd, J = 8.2, 1.7 Hz), 6.82 (1H, d, J =1.7 Hz) and 7.01 (1H, d, J =8.2 Hz); a methyl singlet signal at δ H 2.23; and one methoxyl group at δ H 3.84. Theothertwoanomericprotonsignalsatδ H 4.77(1H,d, J =7.4Hz)for aβ-D-glucopananosylmoiety;andδ H 4.69(1H,d, J =1.5Hz)foranα- L-rhamnopyranosyl unit were also presented. These chemical shifts were similar to those of 2-methoxy-4-hydroxymethylphenyl 1-O-ruti- noside (2), except for the presence of a methyl signal instead of a hy- droxymethyl group at C-4 position. The assignment was confirmed by the HMBC experiment, in which the significances of multiple correla- tions were observed from 1) H 3 -7 (δ H 2.23) to C-3 (δ C 114.6), C-4 (δ C 134.2)andC-5(δ C 122.5);2)2-OCH 3 (δ H 3.84)toC-2(δ C 150.6);3)H- 1'(δ H 4.77)toC-1(δ C 145.7);and4)H-1"(δ H 4.69)toC-6'(δ C 67.8)as shownin Fig.2.Therefore,thiscompoundwasidentifiedas2-methoxy- 4-methylphenyl 1-O-rutinoside. https://doi.org/10.1016/j.phytol.2020.04.008 Received 13 February 2020; Received in revised form 8 April 2020; Accepted 14 April 2020 ⁎ Corresponding author. E-mail address: trikan@kku.ac.th (T. Kanchanapoom). Phytochemistry Letters 37 (2020) 47–50 1874-3900/ © 2020 Phytochemical Society of Europe. Published by Elsevier Ltd. All rights reserved. T