Phomactin E, F, and G: New Phomactin-group PAF Antagonists from a Marine Fungus Phoma sp.

Sugano, Michihiro; Sato, Aiya; Iijima, Yasuteru; Furuya, Kouhei; Kuwano, Harumitsu; Hata, Tadashi

doi:10.7164/antibiotics.48.1188

Cited by 91 publications

(60 citation statements)

References 5 publications

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“…(Chen et al 1996); antimalarial: hypothemycin and aigialomycin D activity at IC50 values of 2.2 and 6.6 μg/ml , while bostrycin showed weak activity (Trisuwan et al 2010); cytotoxic (penochalasins A-C most potent against P388 leukemia cell line (Numata et al 1996;Iwamoto et al 1999), while trichdenones A-C are mildly cytotoxic (Amagata et al 1998), communesins A and B are cytotoxic alkaloids from a Penicillium sp. (Numata et al 1993(Numata et al , 1996, paeciloxocin A against HepG2 cell line (Wen et al 2010), pentostatin A-D, nigrosporanene A against MCF-7 and Vero cells (IC50 values of 9.37, 5.42 μg/mL, respecvtively) (Rukachaisirikul et al 2010); Xylaria psidii and strain KT31 (a sterile algicolous strain from Kappaphycus alvarezii) showed strong cytoxic activity at IC50 values of 4 μg/mL and 1.5 μg/mL, respectively (Tarman et al 2011); platelet activating factor PAF) antagonists: phomactins are a new class pf specific PAF antagonsis (Sugano et al 1995). Other uses of metabolites from marine fungi are dicussed by Verbist et al (2000).…”

Section: Bioactive Compoundsmentioning

confidence: 99%

Fifty years of marine mycology

Jones

2011

Fungal Diversity

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Marine fungi have been widely studied over the past millennium and considerable progress has been made in documenting their phylogeny, biodiversity, ultrastructure, ecology, physiology and their ability to cause decay of lignocellulosic compounds. These studies have generated a wealth of publications and this review will focus primarily on research undertaken since 1995. During this period new topics have attracted marine mycologists especially: algicolous and manglicolous fungi, deep sea fungi, planktonic fungi, endophytes of marine plants, and the screening of taxa for new chemical structures and bioactive compounds. This review will also highlight areas that warrant further investigation, including surveys for marine fungi in Africa, artic waters and south America, more detailed studies of their physiology and biochemistry, and to determine the marine origin of so called "marine derived" fungi.

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Section: Bioactive Compoundsmentioning

confidence: 99%

Fifty years of marine mycology

Jones

2011

Fungal Diversity

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“…The sustainable fermentative microbial production of the macrocycle can be combined with further chemical or enzymatic derivations. It therefore represents a decisive step on the way to sustainable synthesis of bioactive cembranoid-and verticillene-type diterpenoids (16)(17)(18)(19)(20).…”

Section: Carbocation Cascade Mechanism: Steering Effect Of R580-pp I mentioning

confidence: 99%

“…However, the nature of the deprotonating base directing formation of T remains elusive. Monocyclic and bicyclic carbocations postulated to form during taxadiene formation, structurally resemble the macrocyclic core of other bioactive diterpenoids (16)(17)(18)(19)(20). The molecular mechanism of TXS, which can be considered as template for all class I terpene synthases, may therefore improve a general understanding of terpene synthase mechanisms.…”

mentioning

confidence: 99%

Identification of amino acid networks governing catalysis in the closed complex of class I terpene synthases

Schrepfer

Buettner

Goerner

et al. 2016

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

119

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Class I terpene synthases generate the structural core of bioactive terpenoids. Deciphering structure-function relationships in the reactive closed complex and targeted engineering is hampered by highly dynamic carbocation rearrangements during catalysis. Available crystal structures, however, represent the open, catalytically inactive form or harbor nonproductive substrate analogs. Here, we present a catalytically relevant, closed conformation of taxadiene synthase (TXS), the model class I terpene synthase, which simulates the initial catalytic time point. In silico modeling of subsequent catalytic steps allowed unprecedented insights into the dynamic reaction cascades and promiscuity mechanisms of class I terpene synthases. This generally applicable methodology enables the active-site localization of carbocations and demonstrates the presence of an active-site base motif and its dominating role during catalysis. It additionally allowed in silico-designed targeted protein engineering that unlocked the path to alternate monocyclic and bicyclic synthons representing the basis of a myriad of bioactive terpenoids.computational biology | closed complex modeling | protein engineering | terpene synthases | terpene synthase catalysis

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“…Prior investigations have demonstrated that phomactins are potent PAF antagonists that inhibit the binding of PAF to its receptors (Sugano et al, 1995(Sugano et al, , 1996. Others have shown that there are both intracellular and extracellular PAF receptor expression, and endogenously produced PAF acts as an intracellular messenger for eicosanoid production in guinea pig peritoneal macrophages (Stewart et al, 1990).…”

Section: Discussionmentioning

confidence: 98%

“…Phomactins, which are natural products isolated from the culture broth of the fungus Phoma sp., have been found to be active PAF antagonists (Chu et al, 1993;Sugano et al, 1995). These compounds characteristically bear a unique bicyclopentadecane carbon skeleton.…”

Section: Introductionmentioning

confidence: 98%