The natural occurrence of cis- and trans-cinnamylphenols

Gregson, Matthew; Kurosawa, Kazu; Ollis, W. D.; Redman, B. T.; Roberts, Richard J.; Sutherland, I. O.; Oliveira, Alaı́de Braga de; Eyton, W.B.; Gottlieb, O. R.; Dietrichs, H. H.

doi:10.1039/c19680001390

Cited by 12 publications

(8 citation statements)

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“…The identifications were supported by condensation of methoxy-p-quinol with cinnamyl alcohol in aq citric acid and distillation of the resulting (± )-obtusaquinol (22) which, through an abnormal Claisen rearrangement, gave racemic obtusafuran (method A, Table 2). …”

Section: -Aryl-3-methyl-l3-dihydrobenzofuransmentioning

confidence: 99%

The Flavonoids: Indispensable Additions to a Recent Coverage

Gottlieb

1977

Israel Journal of Chemistry

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While the flavonoids are biosynthetically and constitutionally a homogeneous group of compounds, the neoflavonoids, as presently defined, may be biosynthetically and are constitutionally a heterogeneous group. Biogenetic considerations which lead to these conclusions and reviews on occurrence, structural elucidation and synthesis are presented for 1,3‐diarylpropanes and flavans (flavonoids), as well as for cinnamylphenols and 2‐aryl‐3‐methylbenzofurans (neoflavonoids), with the purpose of providing addenda to the 1975 monograph, The Flavonoids, edited by Harborne, Mabry and Mabry for Chapman and Hall, London.

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Section: -Aryl-3-methyl-l3-dihydrobenzofuransmentioning

confidence: 99%

The Flavonoids: Indispensable Additions to a Recent Coverage

Gottlieb

1977

Israel Journal of Chemistry

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“…Machaerium is one of the largest tropical arboreal genera of Papilionoideae, with approximately 160 known taxa and popularly known as "jacarandás" (Plant, 2020;Bastos, 1987;Polido and Sartori, 2011). According to the literature, this genus is recognized by the occurrence of different class of natural products such as triterpenes, proanthocyanidins, cinnamylphenols, alkaloids, benzoquinones, steroids and the incisive presence of flavonoids (Ignoato et al, 2013;Kurosawa et al, 1978a, b;Ollis et al, 1978Ollis et al, , 1968Alves et al, 1966;Bento et al, 2018;Gregson et al, 1968;elSohly et al, 1999;Seo et al, 2001;Adrian et al, 2007;Santos et al, 2009;Oliveira et al, 1968;Braga et al, 1968). Based on previous studies involving the allelopathic activity of isovitexin and Machaerium eriocarpum leaf extract, associated with the absence of phytochemical studies of branch extract of this species, in this work the triterpene lupeol was isolated and its quantification was performed by HPLC-APCI-MS/MS and their allelopathic action.…”

Section: Introductionmentioning

confidence: 99%

The lupeol content in Machaerium species by HPLC-APCI-MS/MS and the allelopathic action

Tahira¹,

Tino²,

Bento³

et al. 2021

J. Hortic. For.

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The use of extracts from plants and/or allelopathic compounds from natural products can minimize the use of pesticides in agriculture. This is a chemical study of Machaerium eriocarpum branch extract and the evaluation of the allelopathic potential of Machaerium hirtum (Vell.) Stellfed and M. eriocarpum Benth (Fabaceae) leaves and branches extracts. The triterpene lupeol was isolated from the hydroethanolic extract of M. eriocarpum branches. The quantification of this compound in all extracts was performed by HPLC-APCI-MS/MS and the highest amount of lupeol was observed in the leaves extract of M. eriocarpum. Allelopathy tests were carried out against seeds of Sorghum bicolor L. (sorghum), evaluating the final percentage of germination, germination speed index (GSI), root growth and number of lateral roots. The leaves extracts of both species were effective in the inhibition of the root growth as well as of the lateral roots. The branches extract of M. hirtum showed inhibitory effect in the root growth and lateral roots only in 50 and 100 mg.L -1 doses. The lupeol showed mainly a strong inhibition of seed germination, root growth and lateral root appearance at 100 μM. This study showed the potentiality of Machaerium extracts and lupeol as bioherbicides.

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“…Changing the pH of the growth medium did not decrease the effectiveness of these two compounds in the pH range of 3 through 8. Both obtusastyrene and dihydro-obtusastyrene were rapidly bactericidal to Staphylococcus aureus and Bacillus cereus at 25 ,ug/ml.Obtusastyrene (4-cinnamylphenol) was originally extracted and identified from the heartwood of Dalbergia obtusa as a result of a phytochemical survey (1,4). The co-occurrence in other Dalbergia species of obtusastyrene with other neoflavanoid compounds has been reported (4).…”

mentioning

confidence: 99%

mentioning

confidence: 99%

“…Obtusastyrene (4-cinnamylphenol) was originally extracted and identified from the heartwood of Dalbergia obtusa as a result of a phytochemical survey (1,4). The co-occurrence in other Dalbergia species of obtusastyrene with other neoflavanoid compounds has been reported (4). In a search for the compounds responsible for the antimicrobial activity of Dalbergia nigra, two related neoflavanoid compounds, Dalbergione I and II, were found to be effective antimicrobials against gram-positive and -negative bacteria and acid-fast bacteria, plus some fungi (3).…”

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confidence: 99%

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Antimicrobial Properties of Natural Phenols and Related Compounds: Obtusastyrene and Dihydro-Obtusastyrene

King

Bayne

Jurd

et al. 1972

Antimicrob Agents Chemother

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Factors influencing the antimicrobial properties of obtusastyrene and dihydroobtusastyrene were studied. Both of these compounds were soluble in acetone, alcohol, and olive oil. In water, they were soluble at concentrations of 34 and 53 ,ug/ml, respectively. The minimal inhibitory concentrations against gram-positive bacteria and yeast were below 100 ,ug/ml. The compounds were not effective against gram-negative bacteria at 200 ,ug/ml or lower concentrations. With initial populations of cells greater than 106/ml, the concentrations of these compounds required to prevent growth were greater than with lower cell populations. Changing the pH of the growth medium did not decrease the effectiveness of these two compounds in the pH range of 3 through 8. Both obtusastyrene and dihydro-obtusastyrene were rapidly bactericidal to Staphylococcus aureus and Bacillus cereus at 25 ,ug/ml.Obtusastyrene (4-cinnamylphenol) was originally extracted and identified from the heartwood of Dalbergia obtusa as a result of a phytochemical survey (1,4). The co-occurrence in other Dalbergia species of obtusastyrene with other neoflavanoid compounds has been reported (4). In a search for the compounds responsible for the antimicrobial activity of Dalbergia nigra, two related neoflavanoid compounds, Dalbergione I and II, were found to be effective antimicrobials against gram-positive and -negative bacteria and acid-fast bacteria, plus some fungi (3).These results prompted us to survey the antimicrobial activity of obtusastyrene and related compounds. A report of this survey, performed by use of a replica-plating technique, has appeared (8). Obtusastyrene was found to be an effective antimicrobial agent against grampositive bacteria, yeasts, and molds in the range of 6 to 100 ,ug/ml. It was less effective against gram-negative bacteria. The minimal inhibitory concentration was not greatly influenced by the pH of the medium in the range from 3 to 7. This report describes further studies of obtusastyrene and its saturated side chain analogue dihydro-obtusastyrene (DH-obtusastyrene). MATERIAIS AND METHODSThe synthesis of obtusastyrene from phenol and cinnamyl alcohol has been reported (7, 8). DHobtusastyrene is prepared from obtusastyrene by hydrogenation of the side chain in the presence of palladium (Fig. 1).For culturing microorganisms, Trypticase Soy Broth or Agar with 2% added yeast extract (pH 7) was used except as noted below. This same broth was also used for serial dilutions. Routine incubation temperature was 28 C for 24 or 48 hr. Both antimicrobial agents were dissolved in acetone, and samples were added to the sterilized medium. Appropriate acetone controls were run in each experiment.Solubility values for the two compounds were calculated from spectrophotometric absorption curves at 254X for obtusastyreneand 274X for DH-obtusastyrene.

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The natural occurrence of cis- and trans-cinnamylphenols

Cited by 12 publications

References 0 publications

The Flavonoids: Indispensable Additions to a Recent Coverage

The Flavonoids: Indispensable Additions to a Recent Coverage

The lupeol content in Machaerium species by HPLC-APCI-MS/MS and the allelopathic action

Antimicrobial Properties of Natural Phenols and Related Compounds: Obtusastyrene and Dihydro-Obtusastyrene

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