Calopins and Cyclocalopins − Bitter Principles fromBoletus calopus and Related Mushrooms

Hellwig, Veronika; Dasenbrock, Johannes; Gräf, Claudia; Kahner, Lydia; Schumann, Susanne; Steglich, Wölfgang

doi:10.1002/1099-0690(200209)2002:17<2895::aid-ejoc2895>3.0.co;2-s

Cited by 31 publications

(25 citation statements)

References 10 publications

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“…Caloboletus , typified by C.calopus (Pers.) Vizzini, is mainly characterized by yellow tubes, yellow or more rarely orange to red pores changing to blue when injured, bitter taste of the context due to the presence of calopin and cyclocalopin (Hellwig et al 2002; Vizzini 2014; Zhao et al 2014a; Wu et al 2016a; Zhang et al 2017). Until now, four species, including C.panniformis (Taneyama & Har.…”

Section: Resultsmentioning

confidence: 99%

New and noteworthy boletes from subtropical and tropical China

Chai¹,

Liang²,

Xue³

et al. 2019

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The morphology, ecology, and phylogenetic relationships of specimens of the family Boletaceae from subtropical and tropical China were investigated. Four species, Butyriboletushuangnianlaii, Lanmaoamacrocarpa, Neoboletusmultipunctatus, and Sutoriussubrufus, are new to science. Chalciporusradiatus and Caloboletusxiangtoushanensis are redescribed. Caloboletusguanyui is proposed to replace Boletusquercinus Hongo, an illegitimate later homonym. The recently described Tylopiluscallainus is synonymized with the Japanese Boletusvirescens, and the new combination T.virescens (Har. Takah. & Taneyama) N.K. Zeng et al. is proposed. Moreover, Neoboletus is treated as an independent genus based on evidence from morphology and molecular phylogenetic data in the present study, and many previously described taxa of Sutorius are recombined into Neoboletus: N.ferrugineus (G. Wu et al.) N.K. Zeng et al., N.flavidus (G. Wu & Zhu L. Yang) N.K. Zeng et al., N.hainanensis (T.H. Li & M. Zang) N.K. Zeng et al., N.obscureumbrinus (Hongo) N.K. Zeng et al., N.rubriporus (G. Wu & Zhu L. Yang) N.K. Zeng et al., N.sanguineoides (G. Wu & Zhu L. Yang) N.K. Zeng et al. , N.sanguineus (G. Wu & Zhu L. Yang) N.K. Zeng et al., and N.tomentulosus (M. Zang et al.) N.K. Zeng et al.

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Section: Resultsmentioning

confidence: 99%

New and noteworthy boletes from subtropical and tropical China

Chai¹,

Liang²,

Xue³

et al. 2019

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“…For instance, the fungivorous opossum avoids most species which exhibit a bitter and pungent taste to humans 27. The characteristic bitter taste of Boletus calopus and Boletus radicans is mainly caused by the sesquiterpenoid O ‐acetylcyclocalopin A ( 11 ) 28. The fungus Sarcodon scabrosus contains several bitter diterpenes, such as sarcodonin A ( 12 ) 29.…”

Section: Constitutive Chemical Defencementioning

confidence: 99%

Chemical Defence Strategies of Higher Fungi

Spiteller

2008

Chemistry A European J

116

107

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Like plants, fungi have evolved a variety of defence strategies in order to protect themselves against feeding mammals, insects and infection with parasitic fungi. In contrast to plants little is known on the chemical ecology of fruiting bodies of higher fungi, particularly those defence mechanisms which are induced upon wounding have only occasionally been recognised. Methods both for the detection of permanently present defence compounds and for the elucidation of wound-activated chemical defence mechanisms are discussed in this concept paper.

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“…The compound was first isolated in 2002 from Boletus calopus by Steglich and co-workers. 148 Concurrently, the same group reported the synthesis of a model compound to assign the absolute configuration of 170, 149 and in 2003 they achieved the total synthesis of 170 by utilising an ene reaction as the key step (Scheme 24). 150 For the synthesis of 170, the catechol 178 was used as starting material.…”

Section: Syn Thesismentioning

confidence: 99%

Synthesis of Secondary Metabolites from Higher Fungi

Reck

Spiteller

2015

Synthesis

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Higher fungi are a promising source of new bioactive natural products with great structural diversity, ranging from polyketides to terpenoids and alkaloids. Many of these structures are a challenge for synthetic organic chemists who have been inspired to develop new total syntheses. Nevertheless, reviews covering syntheses of fungal natural products are lacking. One aim of this review is to close this gap and to present a selection of more recent syntheses of fungal secondary metabolites from different structural classes. Secondly, this review intends to demonstrate that there are many more motivations for the synthesis of natural products than to confirm a proposed structure or to report the first total synthesis of a new natural product. Thirdly, this review is intended to stimulate the interest of organic chemists in the synthesis of fungal natural products. 1

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Calopins and Cyclocalopins − Bitter Principles fromBoletus calopus and Related Mushrooms

Cited by 31 publications

References 10 publications

New and noteworthy boletes from subtropical and tropical China

New and noteworthy boletes from subtropical and tropical China

Chemical Defence Strategies of Higher Fungi

Synthesis of Secondary Metabolites from Higher Fungi

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