The stereochemistry of 1 was elucidated by using NOEDS. The fragmentation pattern observed in the EIMS spectrum (the base peak at m/z 151 and the fragments at m/z 280, 272, 152, 137 and 123), and its UV spectrum, which showed an alkaline bathochromic shift of absorption maxima, both suggest a pinoresinol-type lignan containing at least one phenolic group. The HR EIMS spectrum showed the molecular ion peak at m/z 374.1896 which fits the molecular formula C 20H 22O 7, as expected for a lignan. In this paper, a novel di-hydroxylated pinoresinol-type lignan is described.Ĭompound 1 showed the characteristic reaction (black spots) for pinoresinol-type lignans on TLC plates when sprayed with H 2SO 4 and heated.
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Instead, two compounds with a lignan skeleton were isolated and their chemical structures were determined by using NMR ( 1H and 13C) spectroscopy including NOE experiments. In contrast, this study did not reveal the presence of either valepotriates or alkaloids. Several phytochemical studies carried out on Valeriana and on other taxonomically related plant genera such as Fraxinus 5, Eucomia 6 and Olea 7, 8 have reported the presence of pinoresinol derivatives, valepotriates and alkaloids as major components in the plant extracts. Frequently, lignan type compounds have been involved in these biological activities 1- 4. Valeriana carnosa is an annual shrub which grows on the islands spread along the Patagonian canals of Chile (66º 25- 73º 40 W 48º 36-56º 30 S), where rain falls for over 300 days of the year, and this plant has been used for years by ancient local natives and nowadays because of the particular medicinal properties attributed to it (antioxidant, antihypertensive, vasodilative, anti-stress, among others).
![how to draw boat conformation on chem draw how to draw boat conformation on chem draw](https://i.ytimg.com/vi/DRfbc110EKg/maxresdefault.jpg)
Uno de estos metabolitos es el 1-hidroxipinoresinol ( 1), el cual fue previamente aislado desde plantas de los géneros Olea y Fraxinus y el otro ( 2) se identificó como un compuesto nuevo y fue caracterizado mediante técnicas espectroscópicas de RMN- 1H (incluyendo experimentos de ENO) y RMN- 13C y espectrometría de masas. The other one ( 2) was identified as a novel compound and was characterised by using 1H (including NOE experiments), and 13C-NMR spectroscopic techniques and mass spectrometry.Īdemás del conocido éster metílico del ácido cafeico, se aislaron dos lignanos del tipo del pinoresinol utilizando plantas enteras de Valeriana carnosa Sm. One of these metabolites isġ-hydroxypinoresinol ( 1), which has previously been isolated from the genera Olea and Fraxinus.
![how to draw boat conformation on chem draw how to draw boat conformation on chem draw](https://i.ytimg.com/vi/R8I6NS-xoGA/maxresdefault.jpg)
In addition to the known caffeoyl methyl ester, two pinoresinol type lignans were isolated from the whole plant of Valeriana carnosa Sm. Universidad de Magallanes, Casilla 113-D, Punta Arenas, Chile Departamento de Ciencias y Recursos Naturales, Facultad de Ciencias,