Phenylbutanoid and taxane-like metabolites from needles of Taxus brevifolia

Chu, Alex; Furlan, Maysa; Davin, Laurence B.; Zajíček, Jaroslav; Towers, G.H.N.; Soucy-Breau, Chantal; Rettig, Steven J.; Croteau, Rodney; Lewis, Norman

doi:10.1016/s0031-9422(00)90475-8

Cited by 35 publications

(21 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Tripodantoside is the main antibacterial compound found in T. acutifolius infusion. This substance has an unusual phenylbutanoid structure (Chu et al 1993). To the best of our knowledge, this is the first report on the purification and identification of this compound in an angiosperm species and the first report on its antibacterial activity.…”

Section: Discussionmentioning

confidence: 83%

See 1 more Smart Citation

Purification and identification of antibacterial phenolics fromTripodanthus acutifoliusleaves

Soberón

Sgariglia

Sampietro

et al. 2010

Journal of Applied Microbiology

View full text Add to dashboard Cite

Aims: To perform an activity‐guided purification, identification and quantification of antibacterial compounds from Tripodanthus acutifolius infusion. To validate the antibacterial activity of purified substances. Methods and Results: Bioautographic methods were employed as screening assays for purifying bioactive substances. Purification procedures included sephadex LH‐20 column chromatography and reverse phase HPLC. Identification was achieved by spectroscopic methods (UV‐Vis, MS, NMR and polarimetry) and chromatographic assays (paper chromatography and HPLC). Antibacterial activity was studied by microdilution, colony count and photometric assays, Sytox green stain and transmission electron microscopy (TEM). Four glycoflavonoids (rutin, nicotiflorin, hyperoside and isoquercitrin) and an unusual phenylbutanoid glycoside (tripodantoside) were purified and identified. Tripodantoside was found at 6·59 ± 0·82 g per 100 g of dry leaves. The flavonoids showed bactericidal effect at a concentration of 4 mg ml−1 against Staphylococcus aureus and Pseudomonas aeruginosa strains from American Type Culture Collection, while tripodantoside was almost four times more active than those compounds, with a minimum bactericidal concentration = 1·024 mg ml−1 against these strains. Tripodantoside aglycone showed bacteriolytic effects on the assayed strains, causing evident damages on cell wall and membrane, while tripodantoside did not exhibit those effects. Conclusions: The antibacterial activity of T. acutifolius infusion would be partially attributed to the purified glycoflavonoids and mainly to tripodantoside. Significance and Impact: The high extraction yield and the antibacterial activity exhibited by tripodantoside makes this chemical structure of interest to support further studies dealing with chemical modifications to increase the antibacterial activity or to seek another activities.

show abstract

Section: Discussionmentioning

confidence: 83%

“…Tripodantoside is the main antibacterial compound found in T. acutifolius infusion. This substance has an unusual phenylbutanoid structure (Chu et al. 1993).…”

Section: Discussionmentioning

confidence: 99%

Purification and identification of antibacterial phenolics fromTripodanthus acutifoliusleaves

Soberón

Sgariglia

Sampietro

et al. 2010

Journal of Applied Microbiology

View full text Add to dashboard Cite

show abstract

“…The optical rotation of compound 1 was [α] D 25 + 51.6 ( c 0.025, CHCl 3 ). After comparing these data with previously reported data in the literature (Chu et al, ), the compound was identified as ( S )‐4‐(3‐hydroxybutyl)phenol [(+)‐rhododendrol] (Figure ).…”

Section: Resultsmentioning

confidence: 61%

Isolation and identification of two phytotoxic compounds from the medicinal plant Cassia alata L.

Das

Iwasaki

Suenaga

et al. 2020

Weed Biology and Management

View full text Add to dashboard Cite

Cassia alata (Caesalpiniaceae), an ornamental shrub, has many biological properties such as antifungal and antibacterial activities. Several bioactive and phytotoxic compounds have already been isolated from C. alata. Phytotoxic substances from plants have drawn attention as an alternative biological approach to control weeds. Thus, we conducted this research to explore other phytotoxic compounds in C. alata leaves. Aqueous methanol extracts of C. alata leaves strongly inhibited the seedling growth of broccoli, cabbage, cress, radish and rapeseed, in which the level of inhibition correlated with concentration. Two active compounds were isolated through chromatographies and identified using spectral data as (S)‐4‐(3‐hydroxybutyl)phenol [(+)‐rhododendrol] and (E)‐4‐((1R,4R)‐4‐hydroxy‐2,6,6‐trimethylcyclohex‐2‐en‐1‐yl)but‐3‐en‐2‐one [3‐hydroxy‐α‐ionone]. These two active compounds inhibited the growth of cress seedlings in a concentration‐dependent manner. The required concentrations for 50% growth inhibition (I50 value) of cress seedlings were 192.0–296.1 μM for (+)‐rhododendrol and 132.4–195.3 μM for 3‐hydroxy‐α‐ionone. These results indicate that the two phytotoxic compounds play a part in the phytotoxic activity of C. alata leaves.

show abstract

“…After interpretation of the 2D-NMR data, its structure was revised to 11(15 ! 1)abeo-taxane and further confirmed by Xray-crystallographic analysis [89] [90]. Taxuspine Q (12) bears a rare tigloyloxy group at C(10).…”

mentioning

confidence: 67%

“…Thus, there were some misidentified cases, and brevifoliol was such an example. Brevifoliol was originally regarded as a normal 6/8/6-ring taxane [17] [89]. After interpretation of the 2D-NMR data, its structure was revised to 11(15 !…”

mentioning

confidence: 99%