Glepidotin C: A minor antimicrobial bibenzyl from Glycyrrhiza lepidota

Gollapudi, Rao; Telikepalli, Hanumaiah; Keshavarz-Shokri, Ali; Velde, David Vander; Mitscher, Lester A.

doi:10.1016/0031-9422(89)80394-2

Cited by 17 publications

(11 citation statements)

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“…7) Chemical constituents of the leaves of G. lepidota were elucidated to isolate flavonoids and stilbenoids, [8][9][10] including two flavanones, pinocembrin and glabranin, 8) which are species-specific constituents in the leaves of G. glabra. 11,12) In addition, there have been two preliminary reports about the isolation of saponins from the underground parts of G. lepidota, 13,14) but their data have not yet been published.…”

Section: )mentioning

confidence: 99%

“…5,6) It is reported that G. lepidota crosses in different combinations with species of the glycyrrhizin-producing species (G. glabra and G. uralensis) and macedonoside C-producing species (G. echinata and G. pallidiflora), suggesting that this American species occupies an intermediate position between the two groups. 7) Chemical constituents of the leaves of G. lepidota were elucidated to isolate flavonoids and stilbenoids, [8][9][10] including two flavanones, pinocembrin and glabranin, 8) which are species-specific constituents in the leaves of G. glabra. 11,12) In addition, there have been two preliminary reports about the isolation of saponins from the underground parts of G. lepidota, 13,14) but their data have not yet been published.…”

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Phylogenetic Relationship of Glycyrrhiza lepidota, American Licorice, in Genus Glycyrrhiza Based on rbcL Sequences and Chemical Constituents

Hayashi

Miwa

Inoue

2005

Biological & Pharmaceutical Bulletin

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The roots and stolons of three Glycyrrhiza species, i.e. Glycyrrhiza glabra L., Glycyrrhiza uralensis FISCH. and Glycyrrhiza inflata BATAL., contain large amounts of glycyrrhizin (1), an oleanane-type triterpene saponin, which is a well-recognized natural sweetener and pharmaceutical.1,2) Three other Glycyrrhiza species, i.e. Glycyrrhiza echinata L., Glycyrrhiza macedonica BOISS. et ORPH. and Glycyrrhiza pallidiflora MAXIM., however, do not produce glycyrrhizin but produce macedonoside C (2) as a major triterpene saponin.3,4) To elucidate the phylogenetic relationship of these six Glycyrrhiza plants, we determined the nucleotide sequences of a chloroplast gene for the large subunit of ribulose-1,5-bisphosphate carboxylase/oxygenase (rbcL).4) Based on these rbcL sequences, the six Glycyrrhiza species were divided into two groups: the three glycyrrhizin-producing species: G. glabra, G. uralensis, and G. inflata, and the three macedonoside Cproducing species: G. echinata, G. macedonica and G. pallidiflora, indicating that the phylogenetic relationship deduced from their rbcL sequences is in accordance with the similarity of their chemical constituents. 4)Glycyrrhiza lepidota (NUTT.) PURSH, American licorice, is the only member of the genus native to North America, 5) and its aerial and underground parts were used by native North Americans medicinally. 5,6) It is reported that G. lepidota crosses in different combinations with species of the glycyrrhizin-producing species (G. glabra and G. uralensis) and macedonoside C-producing species (G. echinata and G. pallidiflora), suggesting that this American species occupies an intermediate position between the two groups.7) Chemical constituents of the leaves of G. lepidota were elucidated to isolate flavonoids and stilbenoids, [8][9][10] including two flavanones, pinocembrin and glabranin, 8) which are species-specific constituents in the leaves of G. glabra. 11,12) In addition, there have been two preliminary reports about the isolation of saponins from the underground parts of G. lepidota, 13,14) but their data have not yet been published. Thus, we first attempted to characterize saponins from the stolons of this species, and then determined its rbcL sequence to elucidate the phylogenetic relationship of G. lepidota among the genus Glycyrrhiza. RESULTS AND DISCUSSION Isolation and Characterization of Saponins fromStolons of G. lepidota Air-dried stolons of G. lepidota collected in Canada were extracted with 70% ethanol, and the extract was subjected to a series of reverse-phase silica gel (ODS) column chromatography, Sephadex LH-20 column chromatography and preparative HPLC to afford two known compounds, 3 and 4, and they were identified as macedonoside A (3) 3) and licorice saponin H2 (4) 15) by comparison of their spectral data with published data. The isolation and structural elucidation of compounds 3 and 4 was also preliminarily reported by Mizutani et al.,13) but their data have not yet been published. Table 1 shows the contents of four saponins, glycyrrhizin (1),...

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Phylogenetic Relationship of Glycyrrhiza lepidota, American Licorice, in Genus Glycyrrhiza Based on rbcL Sequences and Chemical Constituents

Hayashi

Miwa

Inoue

2005

Biological & Pharmaceutical Bulletin

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“…st [129] 121 Gancaonin P 5,7,3¢,4¢-tetrahydroxy-6-prenylflavonol … l … … … … … … … … … … … … … [86] 122…”

Section: Resultsunclassified

Phenolic compounds of the genera Glycyrrhiza L. and Meristotropis Fisch. et Mey. (review)

Ammosov

Литвиненко

2007

Pharm Chem J

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“…They have also reported the antimicrobial activity of flavonoids obtained from G. lepidota, but the potency is not particularly high (360,361). NAMBA et al reported that isoglycyrol (168), glycyrol (169), glycycoumarin (172) and glycyrin (248) isolated from G. uralensis have potent antibacterial action against a cariogenic bacterium, Streptococcus mutans (330).…”

Section: Biological Activities Of Phenolic Constituentsmentioning

confidence: 95%

“…An optically active dihydrostilbene having a 2-hydroxy-3-methyl-3-butenyl group, glepidotin C (299), has been isolated together with two prenylated flavonoids (glepidotins A and B) from the whole plant of G. lepidota (American or wild licorice) by MnSCHER et al (360,361). The structure of glepidotin A was postulated to be that shown in formula 300 (5,7-dihydroxy-8-prenylflavonol) because the naturally occurring compound was different from a presumed 5,7-dihydroxy-6-prenylflavonol (301) whose synthesis had been reported earlier by JAIN and ZUTSHI (362).…”

Section: Phenolic Compounds From Whole Plantsmentioning

confidence: 99%