supplementary material

New Cytotoxic Lignan Glycosides from Phyllanthus glaucus
Shan Yua,b, Jun-Jiang Lva, Jian-Qiang Zhaoa,Yan Lia,Dong Wanga, Chong-Ren Yanga, Min
Xua,*, and Ying-Jun Zhang a,*
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming
Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of
University of the Chinese Academy of Sciences, Beijing 100049, P. R.China
Corresponding author contact details: Tel.: +86-871-6553235; fax: +86-871-65223235;
e-mail: (Ying-Jun ZHNAG), (Min XU)
New Cytotoxic Lignan Glycosides from Phyllanthus glaucus Wall
During the process of exploring bioactive lead compounds from Phyllanthus species,
diphyllin4-O-α-L-arabinopyranosyl-(1→3)-α-L-arabinopyranoside (1), and a phenolic
compound, 3,4,5-trimethoxybenzyl alcohol 7-O-α-L-arabinofuranosyl-(1→6)-β-Dglucopyranoside (2), were isolated from the methanol extract of the whole plants of
Phyllanthus glaucus Wall. ex Müll. Arg, together with 31 known compounds,
including 19 lignan derivatives (3-21), four phenylpropanoids (22-25), seven simple
phenolics (26-32) and one monoterpenoid (33). Their structures were determined on the
basis of the HR-ESI-MS, 1D and 2D NMR spectroscopic analysis, and pre-column
derivative/chiral HPLC analysis in case of 1 for the absolute configurations. All these
compounds were obtained from P. glaucus for the first time. Moreover, the known
lignan glycoside, phyllanthusmin C (5) showed in vitro cytotoxicities against HL-60,
MCF-7 and SW480 cells with IC50 values of 9.2 ± 0.2, 19.2 ± 1.7, and 20.5 ± 0.9,
Keywords: Phyllanthus glaucus Wall. ex Müll. Arg, glycoside, arylnaphthalene lignan,
Supplementary material
Identification of Compounds 3 - 33
Figure S1. 1H NMR spectrum for 1 in methanol-d4
Figure S213C NMR and DEPT spectra for 1 in methanol-d4
Figure S3. HSQC spectrum of compound 1in methanol-d4
Figure S4. HMBC spectrum of compound 1in methanol-d4
Figure S5. ROESY spectrum of compound 1in methanol-d4
Figure S6. QC-TOCSY spectrum for 1 in methanol-d4
Figure S7. 1H-1H COSY spectrum for 1 in methanol-d4
Figure S8. HR-ESI-MS for 1
Figure S9. 1H NMR spectrum for 2 in methanol-d4
Figure S10. 13C NMR and DEPT spectra for 2 in methanol-d4
Figure S11. HSQC spectrum for 2 in methanol-d4
Figure S12. HMBC spectrum for 2 in methanol-d4
Figure S13. QC-TOCSY spectrum for 2 in methanol-d4
Figure S14. HR-ESI-MS for 2
1.Identification of Compounds 3 - 33
The known compounds 3-33 were identified as 19 lignan derivatives, reticulatuside A (3) (Ma
et al. 2012), arabelline (4) (Al-Abed et al. 1990), phyllanthusmin C (5) (Wu & Wu 2006),
(-)-secoisolariciresinol (6) (Wang et al. 2000), (-)-isolariciresinol (7) (Jiang et al. 2001),
(-)-isolarisiresinol 9'-O-β-D-glucopyranoside (8) (Cai et al. 2009, Wen et al. 2012),
(-)-isolariciresinol 9-O-β-D-xylopyranoside (9) (Huang et al. 2007), (-)-lyoniresinol (10)
(Imai et al. 2013), rourinoside (11) (He et al. 2006), 7S,8S-threo-4,7,9,9'-tetrahydroxy-3,3'dimethoxy-8-O-4'-neolignan (12) (Matsuda & Kikuchi 1996), buddlenol D (13) (Li et al.
2013), ficusequilignan A (14) (Li et al. 2012), (-)-lariciresinol (15) (Devkota et al. 2012),
8S,8S'-5,5'-dimethoxylariciresiol (16) (Rahman et al. 2007), (-)-pinoresinol (17) (Calderón et
al. 2002), (-)-syringaresinol (18) (Ma et al. 2007, Xiong et al. 2011), (7S,8R)-cedrusin (19)
(Cho et al. 2014), (7R,8S)-dihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside (20)
(Matsuda et al. 1996), and (7R,8S)-dihydrodehydrodiconifenyl alcohol (21) (Fukuyama et
al.1996), four phenylpropanoids, (E)-isoconiferin (22) (Takano et al. 2006), salidroside I (23)
(Wu et al. 2013), coniferin (24) (Han et al. 2006) and 1-O-(β-D-glucopyranosyl)-2-[2methoxy-4-(ω-hydroxypropyl)-phenoxyl]-propan-3-ol (25) (Marinos et al. 1992), seven
simple phenolics, 3,4-dimethoxybenzyl alcohol-7-O-β-D-glucopyranoside (26) (Kanho et al.
2005), 3,4,5-trimethoxybenzyl alcohol-7-O-β-D-glucopyranoside (27) (Kanho et al. 2005),
3,4,5-trimethoxyphenyl-β-D-glucopyranoside (28) (Achenbach & Benirschke 1997), 3,4,5trihydroxybenzoic acid methyl ester (29) (Fiuza et al. 2004), ficusol (30) (Li & Kuo 1998),
bergenin (31) (Nunomura et al. 2009) and 11-O-(4'-O-methoxygalloyl)-bergenin (32) (Lee et
al. 2005), and one monoterpenoid, alangionoside J (33) (Otsuka et al. 1995).
Figure S1
H NMR spectrum for 1 in methanol-d4
Figure S2
C NMR and DEPT spectra for 1 in methanol-d4
Figure S3
HSQC spectrum for 1 in methanol-d4
Figure S4
HMBC spectrum for 1 in methanol-d4
Figure S5
ROESY spectrum for 1 in methanol-d4
Figure S6
QC-TOCSY spectrum for 1 in methanol-d4
Figure S7 1H-1H COSY spectrum for1 in methanol-d4
Figure S8 HR-ESI-MS for 1
Figure S9
H NMR spectrum for 2 in methanol-d4
Figure S10
C NMR and DEPT spectra for 2 in methanol-d4
Figure S11 HSQC spectrum for 2 in methanol-d4
Figure S12
HMBC spectrum for 2 in methanol-d4
Figure S13 QC-TOCSY spectrum for 2 in methanol-d4
Figure S14 HR-ESI-MS for 2
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