Two New Flavonol Glycosides and a Metabolite Profile of Bryophyllum pinnatum, a Phytotherapeutic Used in Obstetrics and Gynaecology

Abstract

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

Bryophyllum pinnatum and Related Species Used in Anthroposophic Medicine: Constituents, Pharmacological Activities, and Clinical Efficacy

“…Thirteen bufadienolides (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13), including three glycosides, have been reported from B. pinnatum, B. delagoense, B. daigremontianum, and the hybrid B. daigremontianum x tubiflorum (l " Table 1, Fig. 1), mostly in conjunction with various bioactivities such as insecticidal and cytotoxic properties [11][12][13][14][15][16][17][18][19][20][21][22][23].…”

“…1), mostly in conjunction with various bioactivities such as insecticidal and cytotoxic properties [11][12][13][14][15][16][17][18][19][20][21][22][23]. A characteristic structural feature is the 1,3,5-orthoacetate function, which is present in about half of these compounds.…”

“…They include numerous flavonol derivatives , mainly quercetin and kaempferol glycosides, as well as a few flavone glycosides, such as acacetin, luteolin, and diosmetin glycosides (36-40) (l " Table 2, Fig. 2) [13,[25][26][27][28][29][30][31][32][33][34][35][36]. In addition, epigallocatechin-3-Osyringate (41) [36] and an ethenylamino-substituted anthocyanidin with a biogenetically unlikely structure [37] have been reported.…”

“…A lignan glycoside, bryophylluside (51), was isolated from the herbs of B. pinnatum [26]. Phenolic acid derivatives identified in B. pinnatum include gallic acid [36], syringic acid β-D-glucopyranosyl ester, 4′-O-β-D-glucopyranosyl-cis-p-coumaric acid [13], and, according to a previous review, ferulic acid, syringic acid, caffeic acid, p-coumaric acid, protocatechuic acid, 4-hydroxy-3-methoxy-cinnamic acid, and p-hydroxybenzoic acid [2]. 4-OEthylgallic acid, syringic acid, vanillic acid, methyl gallate, 3,4-dimethoxyphenol, phloroglucinol, and 3,4-dihydroxyallylbenzene were reported in B. delagoense [38].…”

“…3). B. pinnatum was shown to contain large amounts of malic acid [13]. Other carboxylic acids include, according to a previous review, oxalic acid, citric acid, isocitric acid, cinnamic acid, succinic acid, oxaloacetate, and phosphoenolpyruvate [2].…”