A distinctive flavonoid chemistry for the anomalous genus Biebersteinia

Greenham, Jenny; Vassiliades, Dionyssios D.; Harborne, Jeffrey B.; Williams, Christine A.; Eagles, John M.; Grayer, Renée J.; Veitch, Nigel C.

doi:10.1016/s0031-9422(00)00355-1

Cited by 27 publications

(10 citation statements)

References 8 publications

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“…The placement of Biebersteinia in Sapindales, rather than Geraniales, agrees with the flavonoid composition of B. orphanidis, which resembles that of Rutaceae in certain uncommon methylated flavones, including sudachitin (Greenham et al 2001). The flavonoid profile of B. orphanidis differs from the profiles of the central Asian species B. odora and B. heterostemon in containing six closely related flavone methyl ethers, with dihydroxy, dimethoxy A-ring substitution (Greenham et al 2001).…”

Section: Discussionsupporting

confidence: 67%

“…The flavonoid profile of B. orphanidis differs from the profiles of the central Asian species B. odora and B. heterostemon in containing six closely related flavone methyl ethers, with dihydroxy, dimethoxy A-ring substitution (Greenham et al 2001). Also, fatty acids in B. orphanidis leaves are of the C 18:3 type, a type not found in Geraniacae, but present in Sapindaceae (Tzakou et al 2001).…”

Section: Discussionmentioning

confidence: 80%

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Placing Biebersteiniaceae, a herbaceous clade of Sapindales, in a temporal and geographic context

Muellner

Vassiliades²,

Renner³

2007

Plant Syst. Evol.

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Abstract. Biebersteiniaceae comprise a single genus with four species of perennial herbs occurring from central Asia to Greece. A previous molecular phylogenetic study placed one of the species in an isolated position in Sapindales, while morphological studies had placed Biebersteinia in or near Geraniaceae, albeit doubtfully. We tested the monophyly and placement of the family with data from the chloroplast genes rbcL and atpB obtained for all four species, other major clades of Sapindales and outgroups for a total of up to 114 taxa. Parsimony, Bayesian, and likelihood analyses place Biebersteinia in Sapindales, possibly as sister to the other eight families. Strict and relaxed molecular clocks constrained with fossils of Biebersteinia and up to eight other Sapindales suggest that the Biebersteinia crown group diversified in the Oligocene and Miocene, while the stem lineage dates back to the Late Paleocene. Ages for other sapindalean families are earlier than those obtained in more sparsely sampled analyses, although estimates for Burseraceae agree surprisingly well. Ancestral area analyses suggest that Biebersteinia expanded from the eastern part of its range (i.e. Tibet and Inner Mongolia) to the west, although analyses are hampered by the unclear sister group relationships.

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Section: Discussionsupporting

confidence: 67%

Section: Discussionmentioning

confidence: 80%

Placing Biebersteiniaceae, a herbaceous clade of Sapindales, in a temporal and geographic context

Muellner

Vassiliades²,

Renner³

2007

Plant Syst. Evol.

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“…6). On the other hand, it is even more interesting to consider whether a 7-O-demethylation is involved in the production of NEV in other species, such as H. annuus (Asteraceae) (55), Limnophila aromatica (Plantaginaceae) (56), Lysionotus pauciflorus (Gesneriaceae) (57), and Biebersteinia orphanidis (family unassigned) (58). To date, there are no data regarding the formation of lipophilic flavones in any of the above species.…”

Section: Discussionmentioning

confidence: 99%

The Roles of a Flavone-6-Hydroxylase and 7-O-Demethylation in the Flavone Biosynthetic Network of Sweet Basil

Berim

Gang

2013

Journal of Biological Chemistry

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Background: Late steps of lipophilic flavone biosynthesis in mints are unknown. Results: CYP82D monooxygenases catalyze 6-hydroxylation of 7-O-methylated precursor, whose 7-methyl group is subsequently removed by demethylation in basil but not in peppermint. Conclusion: Flavone biosynthesis in basil involves an unusual loop. Significance: Novel mechanisms elucidated in basil suggest a new hypothesis for similar metabolic networks in other plants.

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“…Thus far, isolation of an alkaloid, vasicinone, and number of polysaccharides and peptide substances has been reported [5]. Flavonoids including 7-glucosides of apigenin, luteolin, and tricetin, as well as the 7-rutinoside of apigenin and luteolin have been isolated from its leaves which in part are responsible for antioxidant and antihemolytic activities [6-8]. Recently, essential oil composition of B. multifida was studied which exhibited that the main components were (E)-nerolidol, phytol, 6,10,14-trimethyl-2- pentadecanone and hexadecanoic acid [9].…”

Section: Introductionmentioning

confidence: 99%

Coumarin compounds of Biebersteinia multifida roots show potential anxiolytic effects in mice

et al. 2013

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BackgroundTraditional preparations of the root of Biebersteinia multifida DC (Geraniaceae), a native medicinal plant of Irano-Turanian floristic region, have been used for the treatment of phobias as anxiolytic herbal preparation.MethodsWe utilized the phobic behavior of mice in an elevated plus-maze as a model to evaluate the anxiolytic effect of the plant extract and bio-guided fractionation was applied to isolate the active compounds. Total root extract, alkaline and ether fraction were administered to mice at different doses 30 and 90 min prior to the maze test. Saline and diazepam were administered as negative and positive controls, respectively. The time spent in open and closed arms, an index of anxiety behavior and entry time, was measured as an index of animal activity.ResultsThe total root extract exhibited anxiolytic effect which was comparable to diazepam but with longer duration. This sustained effect of the crude extract was sustained for 90 min and was even more after injection of 45 mg/kg while the effect of diazepam had been reduced by 90 min. The anxiolytic effect factor was only present in the alkaline fraction and displayed its effect at lower doses than diazepam while pure vasicinone as the previously known alkaloid did not shown anxiolytic effect. The effect of the alkaline fraction was in a dose dependent manner starting at 0.2 mg/kg with a maximum at 1.0 mg/kg. Bio-guided fractionation using a variety of chromatographic methods led to isolation and purification of three coumarin derivatives from the bioactive fraction, including umbelliferone, scopoletin, and ferulic acid.ConclusionFor the first time, bio-guided fractionation of the root extract of B. multifida indicates significant sustained anxiolytic effects which led to isolation of three coumarin derivatives with well-known potent MAO inhibitory and anti-anxiety effects. These data contribute to evidence-based traditional use of B. multifida root for anxiety disorders.

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A distinctive flavonoid chemistry for the anomalous genus Biebersteinia

Cited by 27 publications

References 8 publications

Placing Biebersteiniaceae, a herbaceous clade of Sapindales, in a temporal and geographic context

Placing Biebersteiniaceae, a herbaceous clade of Sapindales, in a temporal and geographic context

The Roles of a Flavone-6-Hydroxylase and 7-O-Demethylation in the Flavone Biosynthetic Network of Sweet Basil

Coumarin compounds of Biebersteinia multifida roots show potential anxiolytic effects in mice

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