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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The Minor Iridoid Glucosides of Barleria lupulina: Isolation, Crystal Structure and Plant Growth-Inhibiting Properties of 6-O-Acetylshanzhiside Methyl Ester

LT Byrne, JM Sasse, BW Skelton, A Suksamrarn and AH White

Australian Journal of Chemistry 40(5) 785 - 794
Published: 1987

Abstract

The minor iridoid glucosides present in the aerial parts of Barleria lupulina Lindl. ( Acanthaceae ) have been identified as ipolamiidoside (7) and the new compound 6-O-acetylshanzhiside methyl ester (3). The structure of (3) was determined by spectroscopic and chemical methods, and was confirmed by a single-crystal X-ray structure determination. Crystals of (3) are orthorhombic P212121, a 43.75(1), b 8.151(3), c 5.695(2) Å, Z 4. The crystal structure was determined at 295 K from diffractometer data [I528 reflections with I > 3σ(I)] and refined to a residual of 0.043.

Shanzhiside methyl ester (1) and its 6-Oacetyl (3), 8-Oacetyl (2) and 6,8-O,O-diacetyl (4) derivatives, all of which occur in Barleria lupulina, have been found to inhibit the growth of wheat embryos.

https://doi.org/10.1071/CH9870785

© CSIRO 1987

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