Janthitrems B and C, two principal indole-diterpenoids produced by Penicillium janthinellum

Penn, Julia; Swift, Richard J.; Wigley, Lucy J.; Mantle, Peter G.; Bilton, John N.; Sheppard, Richard N.

doi:10.1016/0031-9422(93)85153-i

Cited by 27 publications

(31 citation statements)

References 2 publications

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“…Members of the terpene-indole alkaloid family such as the paspalines 53 and the janthitrems 54 – 56 are potent mycotoxins and exhibit insecticidal and tremorgenic activity 57 . The structurally related penitrems additionally act as feeding deterrents and modulators of ion channels in various insects 58 – 60 .…”

Section: Resultsmentioning

confidence: 99%

Chemical warfare between leafcutter ant symbionts and a co-evolved pathogen

et al. 2018

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Acromyrmex leafcutter ants form a mutually beneficial symbiosis with the fungus Leucoagaricus gongylophorus and with Pseudonocardia bacteria. Both are vertically transmitted and actively maintained by the ants. The fungus garden is manured with freshly cut leaves and provides the sole food for the ant larvae, while Pseudonocardia cultures are reared on the ant-cuticle and make antifungal metabolites to help protect the cultivar against disease. If left unchecked, specialized parasitic Escovopsis fungi can overrun the fungus garden and lead to colony collapse. We report that Escovopsis upregulates the production of two specialized metabolites when it infects the cultivar. These compounds inhibit Pseudonocardia and one, shearinine D, also reduces worker behavioral defenses and is ultimately lethal when it accumulates in ant tissues. Our results are consistent with an active evolutionary arms race between Pseudonocardia and Escovopsis, which modifies both bacterial and behavioral defenses such that colony collapse is unavoidable once Escovopsis infections escalate.

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Section: Resultsmentioning

confidence: 99%

Chemical warfare between leafcutter ant symbionts and a co-evolved pathogen

et al. 2018

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“…A fermentation system for studying the indole source in lolitrem biosynthesis in the context of its tryptophan-derived co-metabolite ergovaline (5) would be attractive, but is probably not yet available in sufficient product yield. However, several model systems are available in addition to that for nodulisporic acid (7) in the particular Nodulisporium sp., namely paxilline (11) alone in P. paxilli (Ibba et al, 1987), penitrem A (2) and pennigritrem (12) together in P. nigricans (Penn et al, 1992), penitrem A (2) and nigrifortine (18) together in P. nigricans (Laws and Mantle, 1985;Mantle et al, 1984), and janthitrems alone in P. janthinellum (Penn et al, 1993). Experiments conducted with 13 C and 14 C in parallel could also aid clarification of tryptophan's role as an indole source.…”

Section: Patterns Of Biosynthesis In Fungimentioning

confidence: 96%

The role of tryptophan as a biosynthetic precursor of indole-diterpenoid fungal metabolites: Continuing a debate

Mantle

2009

Phytochemistry

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“…Toxins causing tremorgenic effects in mice include penitrem (Penicillium crustosum and P. aurantiogriseum) and paspalitrem (also produced by Penicillium spp. and Claviceps paspali) [174][175][176][177][178][179]. Fusarium verticilliodes also produces mycotoxins such as fusarins [180][181][182], moniliformin [150,183], fusaric acid, fusaproliferin and beauvericin.…”

Section: Other Neurotropic Mycotoxinsmentioning

confidence: 99%