Bryophyllum pinnatum is a succulent perennial plant native to Madagascar which is used in anthroposophical medicine to treat psychiatric disorders and as a tocolytic agent to prevent premature labour. We performed a metabolite profiling study in order to obtain a comprehensive picture of the constituents in B. pinnatum leaves and to identify chromatographic markers for quality control and safety assessment of medicinal preparations. Preliminary HPLC-PDA-ESIMS analyses revealed that flavonoid glycosides were the main UV-absorbing constituents in the MeOH extract of B. pinnatum. Two phenolic glucosides, syringic acid -D-glucopyranosyl ester (1) and 4'-O--D-glucopyranosyl-cis-p-coumaric acid (2), as well as nine flavonoids (3-11) including kaempferol, quercetin, myricetin, acacetin, and diosmetin glycosides were unambiguously identified by 1H and 2D NMR analysis after isolation from a MeOH extract. The flavonol glycosides quercetin 3-O--L-arabinopyranosyl-(1 → 2)--L-rhamnopyranoside 7-O--D-glucopyranoside (3) and myricetin 3-O--L-arabinopyranosyl-(1 → 2)--L-rhamnopyranoside (4) were new natural products. With the aid of HPLC-PDA-APCIMS and authentic references isolated from the related species B. daigremontianum, the presence of four bufadienolides, bersaldegenin-1-acetate (12), bryophyllin A (13), bersaldegenin-3-acetate (14), and bersaldegenin-1,3,5-orthoacetate (15) AbstractBryophyllum pinnatum is a succulent perennial plant native to Madagascar which is used in anthroposophical medicine to treat psychiatric disorders, and as a tocolytic agent to prevent premature labour. We performed a metabolite profiling study in order to obtain a comprehensive picture of the constituents in B. pinnatum leaves, and to identify chromatographic markers for quality control and safety

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Scheme 1. Framework of polyenes (above) with even number of p-centres and polymethines (below) with odd number of p-centres. A = acceptor, D = donor.Scheme 3. Synthesised merocyanine derivatives. For better comparison of experimental and theoretical data a common atom numbering system was used, which is different from IUPAC numbering. Hex = hexyl.

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