The Conversion of [12-2H3]-Labelled Velutinal in Injured Fruit Bodies of Lactarius vellereus. Further Insight into the Biosynthesis of the Russulaceae Sesquiterpenes.

Hansson, Tiiu; Pang, Zijie; Sterner, Olov; Jaud, J.; Négrel, Jean Claude; Chanon, Michel; Striley, Cindy; Weidlein, Johann; Nasiri, Ahmad; Okada, Yoshito

doi:10.3891/acta.chem.scand.47-0403

Cited by 13 publications

(7 citation statements)

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“…A novel group of tricyclic sesquiterpenes with a lactarane structure are one of the most well‐studied group of secondary compounds isolated from Russulaceae, which impart the characteristic sharp or acrid taste of sporocarps (Sterner et al ., ). These compounds are considered part of a chemical defense system that is enzymatically activated by physical trauma to the fungus, which then converts dialdehydes into iso‐vellerol or vellerol to deter mycophagy by both insects and small mammals (Bergman et al ., ; Daniewski et al ., ; Hansson et al ., ). The presence of such a defense system seems to be in contrast to the lifestyle of sequestrate species of Russulaceae that rely on animal vectors for dispersal.…”

Section: Genomic Content Of Russulaceaementioning

confidence: 97%

Russulaceae: a new genomic dataset to study ecosystem function and evolutionary diversification of ectomycorrhizal fungi with their tree associates

et al. 2018

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The family Russulaceae is considered an iconic lineage of mostly mushroom-forming basidiomycetes due to their importance as edible mushrooms in many parts of the world, and their ubiquity as ectomycorrhizal symbionts in both temperate and tropical forested biomes. Although much research has been focused on this group, a comprehensive or cohesive synthesis by which to understand the functional diversity of the group has yet to develop. Interest in ectomycorrhizal fungi, of which Russulaceae is a key lineage, is prodigious due to the important roles they play as plant root mutualists in ecosystem functioning, global carbon sequestration, and a potential role in technology development toward environmental sustainability. As one of the most species-diverse ectomycorrhizal lineages, the Russulaceae has recently been the focus of a dense sampling and genome sequencing initiative with the Joint Genome Institute aimed at untangling their functional roles and testing whether functional niche specialization exists for independent lineages of ectomycorrhizal fungi. Here we present a review of important studies on this group to contextualize what we know about its members' evolutionary history and ecosystem functions, as well as to generate hypotheses establishing the Russulaceae as a valuable experimental system.

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Section: Genomic Content Of Russulaceaementioning

confidence: 97%

Russulaceae: a new genomic dataset to study ecosystem function and evolutionary diversification of ectomycorrhizal fungi with their tree associates

et al. 2018

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“…2 This is followed by an enzymatic β-elimination of the epoxide in 6a to yield the proposed intermediate 8a, that spontaneously would be converted to isovelleral (1). 3,4 The formation of 8a, which should be highly unstable, was never demonstrated, but feeding the injured mushroom tissue methylvelutinal (6b), obtained by solvolysis of 6c in methanol, resulted in the formation of 8b, which could be isolated and characterized.…”

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confidence: 99%

“…To a solution of the crude acetal in acetone (10 ml) was added a solution of dimethyldioxirane (3.9 mmol, 65 ml, ∼0.06M in acetone) at 0°C. The solvent was removed after 1 h and the residue was re-dissolved in Et 2 (4). n-BuLi (0.61 ml, 1.51 mmol, 2.5 M in hexane) was added to a solution of diisopropyl amine (0.21 ml, 1.51 mmol) in THF (10 ml) at -78°C.…”

Section: -Methoxytetrahydro-1ah-cyclopropa[d]oxireno[h][2]benzofuranmentioning

confidence: 99%

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Synthesis of biomimetic precursors of isovelleral analogues

Röme¹,

Arzel²,

Johansson³

et al. 2008

Arkivoc

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Based on how the mushroom Lactarius vellereus converts an inactive precursor into the cytotoxic dialdehyde isovelleral (1) via a cyclic enol ether, as part of a binary chemical defense system that protects the fruit bodies against parasites, a synthetic way to obtain analogous dialdehydes masked in the same way has been developed. As isovelleral analogues (e.g. 2 and 3) possess extremely potent cytotoxic activity, but display low selectivity as their biological activity is linked to their reactivity, suitably masked isovelleraloids that are converted to the corresponding dialdehyde under specific conditions, may constitute a way to utilize these potent compounds. Specifically, compounds 4 and 5, biomimetic precursors of the isovelleral analogues 2 and 3, but trapped as the stable methyl acetals, have been prepared.

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“…Ця реакція є ензиматичною і відповідні перетворення не відбуваються іn vitro. Гриби різних видів Lactarius утворюють структурно відмінні сесквітерпени [5]. Так, за ушкоджен ня базидіом L. rufus і L. quietus утворюється тільки ізовелерал, у L. bertillonii -велерал, L. vellereus -ізовелерал і велерал, L. piperatus і L. torminosus -усі форми велералу і піпердіалу, L. necator -велерал і епіпіпердіал [4].…”

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Identification of components of the milky juice of Lactarius pergamenus (Fr.)Fr fungi by gas-liquid chromatography/mass spectrometry

Tsivinska¹

2013

Ukr.Biochem.J.

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Запропоновано метод розділення метанольного екстракту базидіом Lactarius pergamenus і дослідження фракції, екстрагованої гексаном, яка згідно з результатами попередніх досліджень виявляє найвищу антипроліферативну та протигрибкову активність. основну увагу приділено фракціонуванню та аналізу методом газорідинної хроматографії/мас-спектрометрії (ГРХ-Мс) екстрагованої гексаном фракції 1.4. ключову роль у розділенні цієї фракції відіграло застосування діоксану, який добре змішується як з полярними, так і неполярними розчинниками (гексаном, хлороформом, метанолом, водою). Зроблено висновок про повний хімічний склад гексанової фракції метанольного екстракту висушених базидіом Lactarius pergamenus. Показано, що ця фракція на 38% складається з вищих жирних кислот та їхніх похідних, на 29%-із фталатів, на 13%-із сесквітерпенів, на 2%-з альдегідів і на 18%-з інших сполук (вуглеводи, спирти, похідні гідразину та неідентифіковані сполуки). така сукупність речовин дозволяє утворити стійку емульсію молочного соку, який захищає плодове тіло гриба від бактеріальних і грибкових інфекцій та від поїдання ссавцями і комахами. к л ю ч о в і с л о в а: базидіоми гриба Lactarius pergamenus, екстракція метанолом, гексановий екстракт, хроматографія на силікагелі, газорідинна хроматографія/мас-спектрометрія.

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The Conversion of [12-2H3]-Labelled Velutinal in Injured Fruit Bodies of Lactarius vellereus. Further Insight into the Biosynthesis of the Russulaceae Sesquiterpenes.

Cited by 13 publications

References 0 publications

Russulaceae: a new genomic dataset to study ecosystem function and evolutionary diversification of ectomycorrhizal fungi with their tree associates

Russulaceae: a new genomic dataset to study ecosystem function and evolutionary diversification of ectomycorrhizal fungi with their tree associates

Synthesis of biomimetic precursors of isovelleral analogues

Identification of components of the milky juice of Lactarius pergamenus (Fr.)Fr fungi by gas-liquid chromatography/mass spectrometry

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