Occurrence of fusicoccanes in plants and fungi

Muromtsev, G. S.; Voblikova, V. D.; Kobrina, N. S.; Koreneva, V.M.; Krasnopolskaya, Tatyana S.; Sadovskaya, V. L.

doi:10.1007/bf00210706

Cited by 49 publications

(37 citation statements)

References 62 publications

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“…It has a unique dicyclopenta[a,d]cyclooctane skeleton (5-8-5 ring system) with a ␥-lactone ring bridging one of the five-membered rings and the eight-membered ring. Similar 5-8-5 tricyclic terpenoids (ophiobolanes and fusicoccanes) are found in fungi and plants (27). However, to our knowledge, any derivative that has a lactone ring is novel.…”

Section: Resultsmentioning

confidence: 59%

“…However, to our knowledge, any derivative that has a lactone ring is novel. Fusicoccane-type cyclic diterpenes are biologically synthesized from geranylgeranyl diphosphate by two-step cyclization catalyzed by terpene cyclases (27,28). Fusicoccins can act as activators of H ϩ -ATPases in plants by modifying the function of 14-3-3 proteins and also exhibit unique biological activity (i.e., anticancer activity) in animal cells (28).…”

Section: Resultsmentioning

confidence: 99%

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Evidence for biological nitrification inhibition inBrachiariapastures

Subbarao

Nakahara²,

Hurtado³

et al. 2009

Proc. Natl. Acad. Sci. U.S.A.

427

420

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Nitrification, a key process in the global nitrogen cycle that generates nitrate through microbial activity, may enhance losses of fertilizer nitrogen by leaching and denitrification. Certain plants can suppress soil-nitrification by releasing inhibitors from roots, a phenomenon termed biological nitrification inhibition (BNI). Here, we report the discovery of an effective nitrification inhibitor in the root-exudates of the tropical forage grass Brachiaria humidicola (Rendle) Schweick. Named ''brachialactone,'' this inhibitor is a recently discovered cyclic diterpene with a unique 5-8-5-membered ring system and a ␥-lactone ring. It contributed 60 -90% of the inhibitory activity released from the roots of this tropical grass. Unlike nitrapyrin (a synthetic nitrification inhibitor), which affects only the ammonia monooxygenase (AMO) pathway, brachialactone appears to block both AMO and hydroxylamine oxidoreductase enzymatic pathways in Nitrosomonas. global warming ͉ nitrogen pollution ͉ nitrous oxide emissions ͉ root exudation ͉ climate change M ost modern agricultural systems are based on large inputs of inorganic nitrogen (N), with ammonium (NH 4 ϩ ) being the primary N source (1, 2). Also, current crop management practices result in the development of highly nitrifying soil environments (3, 4). Nitrification results in the transformation of the relatively immobile NH 4 ϩ to highly mobile nitrate (NO 3 Ϫ ), making inorganic N susceptible to losses through leaching of NO 3 Ϫ and/or gaseous N emissions, potentially initiating a cascade of environmental and health problems (1, 2, 5, 6). Nitrous oxide (N 2 O) is one of the three major biogenic greenhouse gases contributing to global warming, produced primarily from denitrification processes in agricultural systems (5, 7). Also, assimilation of NO 3 Ϫ by plants can result in further N 2 O emissions directly from plant canopies (8). The low agronomic N-use efficiency (NUE) found in many agricultural systems is largely the result of N losses associated with nitrification (i.e., N losses from NO 3 Ϫ leaching and denitrification) (9-11). Most plants have the ability to assimilate both NH 4 ϩ and NO 3 Ϫ (12); therefore, nitrification does not need to be a dominant process in the N cycle for efficient N use.Nitrification is low in some forest and grassland soils (13-17). Since the early 1960s, some tropical grasses have been suspected of having the capacity to inhibit nitrification (18-21). However, this concept remained controversial due to the lack of direct evidence showing such inhibitory effects or the identification of specific inhibitors (22).We adopted a very sensitive bioassay using a recombinant luminescent Nitrosomonas europaea to detect biological nitrification inhibition (BNI) in plant-soil systems with the inhibitory activity of roots expressed in allylthiourea units (ATU) (23). Using this methodology, we were able to show that certain plants release nitrification inhibitors from their roots (23-26). Such BNI capacity appears to be relatively widespread among...

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Section: Resultsmentioning

confidence: 59%

Section: Resultsmentioning

confidence: 99%

Evidence for biological nitrification inhibition inBrachiariapastures

Subbarao

Nakahara²,

Hurtado³

et al. 2009

Proc. Natl. Acad. Sci. U.S.A.

427

420

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“…Although a large number of fusicoccane diterpenes with various bioactivities have been characterised from plants and fungi (Muromtsev et al 1994;de Boer & de Vries-van Leeuwen 2012), trichocitrin (1) represents the first Trichoderma-derived and furan-bearing fusicoccane diterpene. As shown in Figure 2, a plausible biogenetic pathway is proposed for 1.…”

Section: Resultsmentioning

confidence: 99%

Trichocitrin, a new fusicoccane diterpene from the marine brown alga-endophytic fungus Trichoderma citrinoviride cf-27

Liang

Miao

Song

et al. 2016

Natural Product Research

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“…In 1980 we obtained the first evidence for the existence of endogenous FC in higher plants [7]. Then, combining HPLC and GC/MS analysis, we managed to demonstrate the presence of endogenous FC A (1-10 pmol/kg) in headed cabbage leaves and in maize roots and cobs [8,9].…”

Section: Introductionmentioning

confidence: 96%

“…Fusicoccin was discovered by Ballio in 1964 [5]. (ii) Analysis of the literature [6] shows that the typical core of the FC molecule is not at all unique, but is widely encountered among both fungal and plant metabolites. Hence the enzymic systems making this peculiar group of diterpenoids are rather common.…”

Section: Introductionmentioning

confidence: 99%