Antibiotic Substances from the Heart Wood of Thuja plicata D. Don. II. The Constitution of y-Thujaplicin.

Erdtman, H.; Gripenberg, Jarl; Laaksonen, Terttu

doi:10.3891/acta.chem.scand.02-0625

Cited by 52 publications

(19 citation statements)

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“…The thujaplicins, dolabrin, and thujaplicinol ("tropolones") are toxic to coho salmon fry (Peters 1974, Peters et al 1976) and guppies (Erdtman and Gripenberg 1948b). They are also largely responsible for the high natural durability of western redcedar wood (Barton 1973b).…”

Section: Productsmentioning

confidence: 99%

“…Dark-colored heartwood near the center of a redcedar tree is low in both thujapliciris and resistance; light-colored heartwood near the periphery is high in both (van der Kamp 1975). The thujaplicins are highly toxic to a great variety of wood-destroying fungi (Erdtman and Gripenberg 1948b, Roff and Atkinson 1954, Roff and Whittaker 1959, Rudman 1962, Freydl 1963. Indeed, thujaplicins are about as active as pent ac h lo ro p he n o I (Re n ne rf e I t 1 948) -concentrations of 0.001-0.002 percent inhibit fungus growth (Rennerfelt and Nacht 1955).…”

Section: Extractives and Decaymentioning

confidence: 99%

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Western redcedara literature review.

Minore¹

1983

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Section: Productsmentioning

confidence: 99%

Section: Extractives and Decaymentioning

confidence: 99%

Western redcedara literature review.

Minore¹

1983

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“…It has been proposed that the oxygen atoms are equivalent and the hydroxyl hydrogen is symmetrically situated with respect to the two oxygen atoms as in (Ib) (Dewar, 1945;Nozoe, 1949;Erdtman & Gripenberg, 1948).…”

Section: Molecular Geometrymentioning

confidence: 99%

The crystal and molecular structure of tropolone

Shimanouchi¹,

Sasada²

1973

Acta Crystallogr Sect B

102

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Tropolone, C7H602, crystallizes in space group P21/e, with a= 7.135, b---12.178, c= 7.122 A, fl= 99.63 ° and Z= 4. The crystal structure was solved by the symbolic addition procedure and refined by the leastsquares method to give the final R value of 0.054 for the 853 observed reflexions. The molecule is essentially planar and exhibits a slight degree of bond alternation in the seven-membered ring. The hydroxyl group makes a bifurcated hydrogen bond with carbonyl oxygen atoms, of which one branch is intramolecular and the other intermolecular. The latter intermolecular branches form a hydrogenbonded dimer. These characteristic hydrogen bonds seem to play a role in increasing the contribution from the dipolar ionic forms to the ground state of the tropolone molecule.

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“…La présence de tropolones naturelles du type a, b et d thujaplicine avait déjà été mise en évidence dans le bois de Red Cedar en 1948 [5,6]. Dans la présente étude, la b-thujaplicine a été identifiée pour la première fois dans des cals et des cultures de suspensions cellulaires de Thuja plicata Donn.…”

Section: Discussionunclassified

“…En 1948, Erdtman et Gripenberg [5,6] On peut remarquer en outre l'existence d'un épaule-ment à 280 nm, caractéristique de la présence de substances phénoliques. Ces dernières seraient vraisemblablement responsables de la coloration brune des cals observable après 2 mois de croissance, résultant d'une activité polyphénoloxydasique ou peroxydasique.…”

Section: Caractérisation Spectrale Des Extraits Etoac à Partir Des Caunclassified

Biosynth�se de tropolones dans les cals et les suspensions cellulaires � partir d'�bauches foliaires de plantules de Thuja plicata Donn

Haluk¹,

Roussel-Bousta²

2003

Ann. For. Sci.

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Résumé -Nous avons développé des cultures cellulaires de Thuja plicata Donn à partir de cals provenant d'ébauches foliaires de plantules cultivés sur milieu de Gamborg B5 enrichi en saccharose ou en glucose, complémenté de benzylaminopurine (BAP) et d'acide 1-naphtalène acétique (NAH) comme régulateurs de croissance. La synthèse de novo de la b-thujaplicine, tropolone naturelle majoritaire dans de nombreuses espèces de Cupressacées, est accélérée en présence d'éliciteur du type extrait de levure. L'extraction des tropolones intracellulaires est réalisée par broyage des cellules en présence d'acétate d'éthyle. La culture des cals en présence d'éliciteur et de saccharose à 2 % conduit à un rendement plus intéressant en tropolones (6,5 mg g -1 de cal frais) comparativement à celui sans éliciteur (1,75 mg). L'utilisation de glucose à 2 % améliore également les rendements en tropolones (3,15 mg sans éliciteur et 8,1 mg avec éliciteur par g de cal frais). Les cultures de suspensions cellulaires de Thuja plicata réalisées à partir de cals montrent que la vitesse d'agitation de l'agitateur orbitalaire influence la biosynthèse des tropolones (maximum de 5,1 mg g -1 de cellules fraîches à 120 rpm au bout de 14 jours de croissance contre 2 mg à 80 et 180 rpm). red cedar / tropolones / b-thujaplicine / éliciteurs / cals / suspensions cellulairesAbstract -Biosynthesis of tropolones from callus and suspension-cultured cells initiated from young seedlings of Thuja plicata Donn. Thuja plicata callus and cell cultures have been cultured in Gamborg B5 medium supplemented with saccharose or glucose, 1-naphtalene acetic acid (NAA) and benzylaminopurine (BAP) as growth regulators. The addition of elicitor as yeast extract to callus culture of Thuja plicata leads to an increase in the production of tropolones, typical heartwood constituents of Cupressus species. Calli cultured in a medium supplemented with saccharose 2% and yeast extract accumulate tropolones in about 6.5 mg g -1 cell fresh weight, which is easily extracted from callus culture with ethylacetate. Without elicitation, the content of tropolones was only 1.75 mg g -1 cell fresh weight. In a medium supplemented with glucose, the content of tropolone increases (8.1 mg with elicitation and 3.15 mg without elicitation). Cell cultures obtained from calli show an effect of the rotary shaker speed on the tropolones production (5.1 mg g -1 at 120 rpm agitation and only 2 mg at 80 or 180 rpm). red cedar / tropolones / b-thujaplicine / elicitors / callus / cell culture

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Antibiotic Substances from the Heart Wood of Thuja plicata D. Don. II. The Constitution of y-Thujaplicin.

Cited by 52 publications

References 0 publications

Western redcedara literature review.

Western redcedara literature review.

The crystal and molecular structure of tropolone

Biosynth�se de tropolones dans les cals et les suspensions cellulaires � partir d'�bauches foliaires de plantules de Thuja plicata Donn

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Antibiotic Substances from the Heart Wood of Thuja plicata D. Don. II. The Constitution of y-Thujaplicin.

Cited by 52 publications

References 0 publications

Western redcedar&#151;a literature review.

Western redcedar&#151;a literature review.

The crystal and molecular structure of tropolone

Biosynth�se de tropolones dans les cals et les suspensions cellulaires � partir d'�bauches foliaires de plantules de Thuja plicata Donn

Contact Info

Product

Resources

About

Western redcedara literature review.

Western redcedara literature review.