Lavandulifolioside: A New Phenylpropanoid Glycoside from Stachys lavandulifolia

✍ Scribed by Arif Ahmet Başaran; İhsan Çaliş; Clemens Anklin; Sansei Nishibe; Otto Sticher

• Publisher: John Wiley and Sons
• Year: 1988
• Tongue: German
• Weight: 391 KB
• Volume: 71
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19880710612

✦ Synopsis

A new phenylpropanoid glycoside has been isolated from the methanolic extract of the aerial parts of Stachys lauandulifolia (Lamiaceae), lavandulifolioside (1). On the basis of chemical and spectral data the structure of the new compound 1 has been elucidated as p-

1. Introduction.

-Stachys lavandulifolia VAHL oar. lavandulifolia (Lamiaceae) is known as 'hairy tea' in Turkey. Since it is used as a herbal tea in the vicinities of Antalya (South Anatolia), it was investigated for its essential oil [l].

Caffeic acid esters such as chlorogenic and quinic acids are important substances from the point of view of chemotaxonomic studies, and their distribution in the Lamiaceae Family at the generic level has considerable value [2]. In respect of this consideration, we have further studied the water-soluble constituents of Stachys lavandulifolia.

After a series of chromatographic separations of the methanolic extract, we isolated the fractions rich in two phenylpropanoid glycosides (caffeic-acid sugar esters). These compounds were purified by using reversed-phase vacuum liquid chromatography (RP-VLC), resulting in lavandulifolioside (l), a new phenylpropanoid glycoside and an already known glycoside, acteoside (2). We describe here the structural elucidation of the new substance, lavandulifolioside (1).

2. Results and

Discussion. -Lavandulifolioside (1) was obtained as an amorphous substance with the mol.wt. 756.71 g (calc. for C,,H,O,,): Positive-ion FAB-MS: 757 ( [ M + HI'). Negative-ion FAB-MS: 755 ([M -HI-). [E]: = 40.3 (c = 0.595, H,O).

Its UV spectrum exhibited peaks at 203,219 (sh), 242 (sh), 291 (sh), 333 nm, confirming its polyphenolic nature. IR bands (cm-') for OH groups (3400, br.), an a,p-unsaturated ester (o"(C=O) 1685,o"(C=C) 1620), and aromatic rings (1600, 1510) were observed.

The 'H-NMR spectrum (Table 1) exhibited signals belonging to caffeic acid and