(+)-lyoniresinol nmr

(+)-lyoniresinol

(6R,7R,8S)-8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)- 1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-ol

 JP2010150152

A lignan that is tetralin substituted by a 4-hydroxy-3,5-dimethoxy group at position 4, hydroxymethyl groups at positions 2 and 3, methoxy groups at positions 5 and 7 and a hydroxy group at position 6. Isolated from Machilus robusta and Sinocalamus affinis, it exhibits antineoplastic activity.


m.p(℃) 176-179

IR(cm-¹)
(KBr) 3380 (OH), 1598, 1490, 1463, 1295, 1195 (aromatic -CH=CH-)

UV(nm)
λmax 219, 278

MS
EIMS m/z 420 [M]+


1H NMR data

(300 MHz, CDCl3 + CD3OD) δ: 6.48 (1H, s, H-8), 6.32 (2H, s, H-2´, 6´), 4.11 (1H, d, J = 6.3 Hz, H-4), 3.84 (3H, s, 7-OCH3), 3.74 (6H, s, 3´, 5´-OCH3), 3.59 (1H, dd, J = 5.4, 11.1 Hz, H-2a), 3.56 (2H, t, H-3a), 3.46 (1H, dd, J = 5.4, 11.1 Hz, H-2a), 2.64 (1H, dd, J = 5.4, 15.0 Hz, H-1), 2.54 (1H, br d, J = 15.0 Hz, H-1), 1.99 (1H, m, H-3), 1.65 (1H, m, H-2)

13 C NMR

75 MHz, CDCl3 + CD3OD) 
δ: 147.8 (C-3´, 5´), 

147.4 (C-5), 

146.5 (C-7), 

138.6 (C-6), 

137.9 (C-1´),

133.5 (C-4´), 

129.4 (C-9), 

125.6 (C-10), 

107.0 (C-8), 

106.1 (C-6´, 2´), 

66.7 (C-2a), 

63.9 (C-3a), 

60.0 (5-OCH3),

56.4 (3´, 5´-OCH3), 

49.1 (C-3), 
42.5 (C-4), 

40.6 (C-2), 
33.4 (C-1)

Xiong L, Zhu C, Li Y, Tian Y, Lin S, Yuan S, Hu J, Hou Q, Chen N, Yang Y, Shi J (2011) Lignans and neolignans from Sinocalamus affinis and their absolute configurations. Journal of natural products 74, 1188-1200 [PubMed:21469695] [show Abstract]

Li Y, Cheng W, Zhu C, Yao C, Xiong L, Tian Y, Wang S, Lin S, Hu J, Yang Y, Guo Y, Yang Y, Li Y, Yuan Y, Chen N, Shi J (2011) Bioactive neolignans and lignans from the bark of Machilus robusta. Journal of natural products 74, 1444-1452 [PubMed:21627109] [show Abstract]