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,*
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
China
b
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: zhangyj@mail.kib.ac.cn (Ying-Jun ZHNAG), xumin@mail.kib.ac.cn (Min XU)
New Cytotoxic Lignan Glycosides from Phyllanthus glaucus Wall
During the process of exploring bioactive lead compounds from Phyllanthus species,
two
new
glycosides
including
an
arylnaphthalene
lignan,
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,
respectively.
Keywords: Phyllanthus glaucus Wall. ex Müll. Arg, glycoside, arylnaphthalene lignan,
phenolics,cytotoxicity
Supplementary material
Content
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
Reference
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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
1
H NMR spectrum for 1 in methanol-d4
Figure S2
13
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
1
H NMR spectrum for 2 in methanol-d4
Figure S10
13
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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