Genomes and Genes
Summary: Group of alkaloids containing a benzylpyrrole group (derived from TRYPTOPHAN)
- Kong K, Enquist J, McCallum M, Smith G, Matsumaru T, Menhaji Klotz E, et al. An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B. J Am Chem Soc. 2013;135:10890-3 pubmed publisher..The synthesis is convergent and employs a stereoselective intermolecular nitrone cyloaddition reaction as a key step. ..
- Nugroho A, Hirasawa Y, Piow W, Kaneda T, Hadi A, Shirota O, et al. Antiplasmodial indole alkaloids from Leuconotis griffithii. J Nat Med. 2012;66:350-3 pubmed publisher..Its structure was elucidated by various spectroscopic means such as NMR and MS, and also by chemical means. Antiplasmodial activity against Plasmodium falciparum 3D7 of indole alkaloids isolated from L. griffithii was investigated.
- Chen H, Bai J, Fang Z, Yu S, Ma S, Xu S, et al. Indole alkaloids and quassinoids from the stems of Brucea mollis. J Nat Prod. 2011;74:2438-45 pubmed publisherSeven new indole alkaloids, bruceollines H-N (1-7), three new quassinoids, yadanziolides T-V (10-12), and four known analogues, bruceolline E (8), bruceolline F (9), bruceine D (13), and yadanziolide B (14), were isolated from an ethanol ..
- Finefield J, Frisvad J, Sherman D, Williams R. Fungal origins of the bicyclo[2.2.2]diazaoctane ring system of prenylated indole alkaloids. J Nat Prod. 2012;75:812-33 pubmed publisher..2.2]diazaoctane ring system. Furthermore, the diverse fungal origin of these natural products is closely examined and, in many cases, updated to reflect the currently accepted fungal taxonomy. ..
- Du F, Li X, Li C, Shang Z, Wang B. Cristatumins A-D, new indole alkaloids from the marine-derived endophytic fungus Eurotium cristatum EN-220. Bioorg Med Chem Lett. 2012;22:4650-3 pubmed publisherFour new indole alkaloids, namely, cristatumins A-D (1-4), along with six known congeners (5-10) were identified from the culture extract of Eurotium cristatum EN-220, an endophytic fungus isolated from the marine alga Sargassum ..
- Rocha E Silva L, Montoia A, Amorim R, Melo M, Henrique M, Nunomura S, et al. Comparative in vitro and in vivo antimalarial activity of the indole alkaloids ellipticine, olivacine, cryptolepine and a synthetic cryptolepine analog. Phytomedicine. 2012;20:71-6 pubmed publisherb>Indole alkaloids ellipticine (1), cryptolepine triflate (2a), rationally designed 11-(4-piperidinamino)cryptolepine hydrogen dichloride (2b) and olivacine (3) (an isomer of 1) were evaluated in vitro against Plasmodium falciparum and in ..
- Takeda M, Takahashi M, Hara N, Matsumoto S. Glial cell line-derived neurotrophic factor modulates the excitability of nociceptive trigeminal ganglion neurons via a paracrine mechanism following inflammation. Brain Behav Immun. 2013;28:100-7 pubmed publisher..GDNF paracrine mechanism could be important as a therapeutic target for trigeminal inflammatory hyperalgesia. ..
- Saikia S, Takemoto D, Tapper B, Lane G, Fraser K, Scott B. Functional analysis of an indole-diterpene gene cluster for lolitrem B biosynthesis in the grass endosymbiont Epichloë festucae. FEBS Lett. 2012;586:2563-9 pubmed publisher..festucae and in cells of Penicillium paxilli containing copies of these genes under the control of a P. paxilli biosynthetic gene promoter. We propose a biosynthetic scheme to account for this metabolic diversity. ..
- Chen M, Shao C, Fu X, Xu R, Zheng J, Zhao D, et al. Bioactive indole alkaloids and phenyl ether derivatives from a marine-derived Aspergillus sp. Fungus. J Nat Prod. 2013;76:547-53 pubmed publisherTwo new prenylated indole alkaloids, 17-epi-notoamides Q and M (1 and 2), and two new phenyl ether derivatives, cordyols D and E (9 and 13), together with 10 known compounds (3-8, 10-12, 14) were isolated from a marine-derived Aspergillus ..
- Bian Z, Marvin C, Martin S. Enantioselective total synthesis of (-)-citrinadin A and revision of its stereochemical structure. J Am Chem Soc. 2013;135:10886-9 pubmed publisher..The successful synthesis of citrinadin A led to a revision of the stereochemical structure of the core substructure of the citrinadins. ..
- Du R, Li E, Cao Y, Song Y, Tan R. Fumigaclavine C inhibits tumor necrosis factor ? production via suppression of toll-like receptor 4 and nuclear factor ?B activation in macrophages. Life Sci. 2011;89:235-40 pubmed publisher..FC attenuated TNF? via the TLR4-NF?B signaling transduction pathway, suggesting that this alkaloid might serve as a promising molecule for anti-inflammatory treatment of atherosclerosis. ..
- Mansoor T, Ramalho R, Mulhovo S, Rodrigues C, Ferreira M. Induction of apoptosis in HuH-7 cancer cells by monoterpene and beta-carboline indole alkaloids isolated from the leaves of Tabernaemontana elegans. Bioorg Med Chem Lett. 2009;19:4255-8 pubmed publisherThree known (1-3) and a novel (4) monoterpene indole alkaloids have been isolated from the methanol extract of leaves of Tabernaemontana elegans and their structures were elucidated by a series of spectroscopic experiments, involving NMR, ..
- Pauletti P, Cintra L, Braguine C, da Silva Filho A, Silva M, Cunha W, et al. Halogenated indole alkaloids from marine invertebrates. Mar Drugs. 2010;8:1526-49 pubmed publisherThis review discusses the isolation, structural elucidation, and biological activities of halogenated indole alkaloids obtained from marine invertebrates...
- Cook K, Hilton S, Mecinovic J, Motherwell W, Figg W, Schofield C. Epidithiodiketopiperazines block the interaction between hypoxia-inducible factor-1alpha (HIF-1alpha) and p300 by a zinc ejection mechanism. J Biol Chem. 2009;284:26831-8 pubmed publisher..The results have implications for the design of selective ETPs and for the interaction of ETPs with other zinc ion-binding protein targets involved in gene expression. ..
- Ge H, Yu Z, Zhang J, Wu J, Tan R. Bioactive alkaloids from endophytic Aspergillus fumigatus. J Nat Prod. 2009;72:753-5 pubmed publisher..Furthermore, 14-norpseurotin (4) significantly induced neurite outgrowth of rat pheochromocytoma cells (PC12) at a 10.0 microM concentration. ..
- Lim K, Hiraku O, Komiyama K, Koyano T, Hayashi M, Kam T. Biologically active indole alkaloids from Kopsia arborea. J Nat Prod. 2007;70:1302-7 pubmedNine new indole alkaloids, rhazinoline (1), 19(S)-methoxytubotaiwine (2), 19(R)-methoxytubotaiwine (3), kopsamidine A (4), kopsamidine B (5), kopsinidine A (6), kopsinidine B (7), paucidactine C (8), and pericine N-oxide (9), in addition ..
- Kochanowska A, Rao K, Childress S, El Alfy A, Matsumoto R, Kelly M, et al. Secondary metabolites from three Florida sponges with antidepressant activity. J Nat Prod. 2008;71:186-9 pubmed publisherBrominated indole alkaloids are a common class of metabolites reported from sponges of the order Verongida...
- Wu P, Hsu Y, Jao C. Indole alkaloids from Cephalanceropsis gracilis. J Nat Prod. 2006;69:1467-70 pubmedPurification of CHCl3 and EtOAc solubles of the MeOH extract of Cephalanceropsis gracilis afforded seven new indole alkaloids, cephalinones A (1), B (2), C (3), and D (4) and cephalandoles A (5), B (6), and C (7), besides eight known ..
- Zhang H, Wang X, Lin L, Ding J, Yue J. Indole alkaloids from three species of the Ervatamia genus: E. officinalis, E. divaricata, and E. divaricata Gouyahua. J Nat Prod. 2007;70:54-9 pubmedSix new indole alkaloids, 14,15-didehydro-10,11-dimethoxy-16-epivincamine (1), 14,15-didehydro-10-hydroxy-11-methoxy-16-epivincamine (2), 14,15-didehydro-10,11-dimethoxyvincamine (3), 14,15-didehydro-10-hydroxy-11-methoxyvincamine (4), 19,..
- Tsukamoto S, Kato H, Greshock T, Hirota H, Ohta T, Williams R. Isolation of notoamide E, a key precursor in the biosynthesis of prenylated indole alkaloids in a marine-derived fungus, Aspergillus sp. J Am Chem Soc. 2009;131:3834-5 pubmed publisherNotoamide E was identified to be a short-lived precursor in the biosynthesis of prenylated indole alkaloids in the mussel-derived Aspergillus sp...
- Carroll A, Hyde E, Smith J, Quinn R, Guymer G, Forster P. Actinophyllic acid, a potent indole alkaloid inhibitor of the coupled enzyme assay carboxypeptidase u/hippuricase from the leaves of Alstonia actinophylla (Apocynaceae). J Org Chem. 2005;70:1096-9 pubmed..84 microM. Actinophyllic acid possesses a unique 2,3,6,7,9,13c-hexahydro-1H-1,7,8-(methanetriyloxymethano)pyrrolo[1',2':1,2]azocino[4,3-b]indole-8(5H)-carboxylic acid skeleton. ..
- Frederich M, Tits M, Angenot L. Potential antimalarial activity of indole alkaloids. Trans R Soc Trop Med Hyg. 2008;102:11-9 pubmed..Among the natural products, indole alkaloids represent an interesting class of compounds...
- Sichaem J, Surapinit S, Siripong P, Khumkratok S, Jong Aramruang J, Tip Pyang S. Two new cytotoxic isomeric indole alkaloids from the roots of Nauclea orientalis. Fitoterapia. 2010;81:830-3 pubmed publisherA pair of new isomeric indole alkaloids, naucleaorals A (1) and B (2) were isolated from the roots of Nauclea orientalis...
- Youssef D. Hyrtioerectines A-C, cytotoxic alkaloids from the red sea sponge hyrtioserectus. J Nat Prod. 2005;68:1416-9 pubmed..Hyrtioerectines A-C were moderately cytotoxic. ..
- Carroll A, Avery V. Leptoclinidamines A-C, indole alkaloids from the Australian ascidian Leptoclinides durus. J Nat Prod. 2009;72:696-9 pubmed publisherThree new indole alkaloids, leptoclinidamines A-C (1-3), were isolated from the Australian ascidian Leptoclinides durus. Their structures were determined by analysis of 2D NMR spectra...
- Loris E, Panjikar S, Ruppert M, Barleben L, Unger M, Schübel H, et al. Structure-based engineering of strictosidine synthase: auxiliary for alkaloid libraries. Chem Biol. 2007;14:979-85 pubmed..condensation between tryptamine and secologanin, leading to the synthesis of about 2000 monoterpenoid indole alkaloids in higher plants...
- Tamura M, Koyama R, Ikegaya Y, Matsuki N, Yamada M. K252a, an inhibitor of Trk, disturbs pathfinding of hippocampal mossy fibers. Neuroreport. 2006;17:481-6 pubmed..Similar defasciculation was observed with an inhibitor of MEK, which is one of the signaling molecules downstream of Trk. This study suggests for the first time that Trk and the MEK pathway are required for mossy fiber pathfinding. ..
- Imlach W, Finch S, Dunlop J, Meredith A, Aldrich R, Dalziel J. The molecular mechanism of "ryegrass staggers," a neurological disorder of K+ channels. J Pharmacol Exp Ther. 2008;327:657-64 pubmed publisher..Our study therefore reveals a new role for the accessory BK beta4 subunit in motor control. The beta4 subunit could be considered as a potential target for treatment of ataxic conditions in animals and in humans. ..
- Lopez C, Claude B, Morin P, Max J, Pena R, Ribet J. Synthesis and study of a molecularly imprinted polymer for the specific extraction of indole alkaloids from Catharanthus roseus extracts. Anal Chim Acta. 2011;683:198-205 pubmed publisher..MIP) for catharanthine and vindoline have been synthesized in order to specifically extract these natural indole alkaloids from Catharanthus roseus by solid-phase extraction (SPE)...
- Kawamura N, Kawamura K, Manabe M, Tanaka T. Inhibition of brain-derived neurotrophic factor/tyrosine kinase B signaling suppresses choriocarcinoma cell growth. Endocrinology. 2010;151:3006-14 pubmed publisher..Thus, autocrine signaling of the BDNF/TrkB system is important for human choriocarcinoma cell growth, and inhibition of BDNF/TrkB signaling in these cells could provide a novel therapy for patients with choriocarcinoma...
- Miller K, Williams R. Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids. Chem Soc Rev. 2009;38:3160-74 pubmed publisher..Detailed herein are a number of synthetic disconnections including intramolecular S(N)2' cyclizations, biomimetic Diels-Alder reactions, radical cyclizations, and cationic cascade reactions...
- Bao B, Sun Q, Yao X, Hong J, Lee C, Sim C, et al. Cytotoxic bisindole alkaloids from a marine sponge Spongosorites sp. J Nat Prod. 2005;68:711-5 pubmed..Compounds 1, 4, 5, and 11 showed moderate to significant cytotoxicity against five human tumor cell lines, and compounds 1-5 showed weak antibacterial activity against clinically isolated methicillin-resistant strains. ..
- Hirasawa Y, Arai H, Zaima K, Oktarina R, Rahman A, Ekasari W, et al. Alstiphyllanines A-D, indole alkaloids from Alstonia macrophylla. J Nat Prod. 2009;72:304-7 pubmed publisher..Alkaloids 1-4 showed moderate antiplasmodial activity against Plasmodium falciparum and vasorelaxant activity against phenylephrine-induced contraction of isolated rat aorta. ..
- Segraves N, Crews P. Investigation of brominated tryptophan alkaloids from two thorectidae sponges: Thorectandra and Smenospongia. J Nat Prod. 2005;68:1484-8 pubmed..Compounds 1, 3-8, 10, and 11 were found to inhibit the growth of Staphylococcus epidermidis with either weak or moderate MICs. ..
- Tsukamoto S, Kato H, Samizo M, Nojiri Y, Onuki H, Hirota H, et al. Notoamides F-K, prenylated indole alkaloids isolated from a marine-derived Aspergillus sp. J Nat Prod. 2008;71:2064-7 pubmed publisherSix new prenylated indole alkaloids, named notoamides F-K (8-13), were isolated from a marine-derived Aspergillus sp. Their structures, including absolute configurations, were elucidated by spectroscopic methods...
- Zhao Y, Li Z, Zhou X, Cai Z, Gong X, Zhou C. Quality evaluation of Evodia rutaecarpa (Juss.) Benth by high performance liquid chromatography with photodiode-array detection. J Pharm Biomed Anal. 2008;48:1230-6 pubmed publisher..The total contents of evodiamine and rutaecarpine in different samples were calculated and the blending method proposed was demonstrated to be very useful in saving resources and in guiding rational herb use...
- Macabeo A, Krohn K, Gehle D, Read R, Brophy J, Cordell G, et al. Indole alkaloids from the leaves of Philippine Alstonia scholaris. Phytochemistry. 2005;66:1158-62 pubmed..isolated from the (pH 5) alkaloid extract of Philippine Alstonia scholaris leaves together with the known indole alkaloids 19,20-(E)-vallesamine (3), angustilobine B N4-oxide (4), 20(S)-tubotaiwine (5), and 6,7-seco-angustilobine B (..
- Deng P, Ye F, Cai W, Tan G, Hu C, Deng H, et al. Stimulation of calcitonin gene-related peptide synthesis and release: mechanisms for a novel antihypertensive drug, rutaecarpine. J Hypertens. 2004;22:1819-29 pubmed..These results suggest, for the first time, that the hypotensive effect of Rut is mediated by stimulation of CGRP synthesis and release via activation of VR1 in the phenol-induced hypertensive rat. ..
- Higuchi K, Kawasaki T. Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. Nat Prod Rep. 2007;24:843-68 pubmedThis review covers the literature on simple indole alkaloids and those with a nonrearranged monoterpenoid unit. Newly isolated alkaloids, structure determinations, total syntheses and biological activities are included.
- Baggio C, De Martini Otofuji G, de Souza W, de Moraes Santos C, Torres L, Rieck L, et al. Gastroprotective mechanisms of indole alkaloids from Himatanthus lancifolius. Planta Med. 2005;71:733-8 pubmedThe indole alkaloids mixture (AlkF) obtained from the barks of Himatanthus lancifolius (Muell. Arg.) Woodson was evaluated for gastroprotective properties in rodents...
- Yu J, Tan G, Deng P, Xu K, Hu C, Li Y. Involvement of CGRP in the inhibitory effect of rutaecarpine on vasoconstriction induced by anaphylaxis in guinea pig. Regul Pept. 2005;125:93-7 pubmed
- Pasquali G, Porto D, Fett Neto A. Metabolic engineering of cell cultures versus whole plant complexity in production of bioactive monoterpene indole alkaloids: recent progress related to old dilemma. J Biosci Bioeng. 2006;101:287-96 pubmedMonoterpene indole alkaloids (MIAs) are a large class of plant alkaloids with significant pharmacological interest. The sustained production of MIAs at high yields is an important goal in biotechnology...
- Medeiros M, Prado L, Fernandes V, Figueiredo S, Coppede J, Martins J, et al. Antimicrobial activities of indole alkaloids from Tabernaemontana catharinensis. Nat Prod Commun. 2011;6:193-6 pubmed..aeruginosa the MIC of MMV ranged from 0.08 to 0.31 mg/mL. The chromatography analysis of the EB2 fraction revealed the presence of indole alkaloids, including MMV, possibly responsible for the observed antimicrobial activity.
- Takeda M, Kitagawa J, Nasu M, Takahashi M, Iwata K, Matsumoto S. Glial cell line-derived neurotrophic factor acutely modulates the excitability of rat small-diameter trigeminal ganglion neurons innervating facial skin. Brain Behav Immun. 2010;24:72-82 pubmed publisher..We therefore conclude that a local release of GDNF from TRG neuronal soma and/or nerve terminals may regulate normal sensory function, including nociception. ..
- Runguphan W, O Connor S. Metabolic reprogramming of periwinkle plant culture. Nat Chem Biol. 2009;5:151-3 pubmed publisher..This work demonstrates the power of genetic engineering to retailor the structures of complex alkaloid natural products in plant culture. ..
- Meinke P, Colletti S, Fisher M, Wyvratt M, Shih T, Ayer M, et al. Discovery of the development candidate N-tert-butyl nodulisporamide: a safe and efficacious once monthly oral agent for the control of fleas and ticks on companion animals. J Med Chem. 2009;52:3505-15 pubmed publisher..Tissue distribution studies in mice using [(14)C]-labeled 3 indicate that adipose beds serve as ligand depots, contributing to the long terminal half-lives of these compounds. ..
- Chen Z, Hu G, Li D, Chen J, Li Y, Zhou H, et al. Synthesis and vasodilator effects of rutaecarpine analogues which might be involved transient receptor potential vanilloid subfamily, member 1 (TRPV1). Bioorg Med Chem. 2009;17:2351-9 pubmed publisher..The vasodilator effects of these compounds were evaluated and the structure-activity relationship was elucidated for the first time. The results suggested a new direction of valuable TRPV1 agonist as anti-hypertensive drugs. ..
- Baran P, Hafensteiner B, Ambhaikar N, Guerrero C, Gallagher J. Enantioselective total synthesis of avrainvillamide and the stephacidins. J Am Chem Soc. 2006;128:8678-93 pubmed..A full account of our successful efforts to convert stephacidin A into stephacidin B via avrainvillamide is presented. Finally, the first analogues of these natural products have been prepared and evaluated for anticancer activity. ..
- Szabó L. Rigorous biogenetic network for a group of indole alkaloids derived from strictosidine. Molecules. 2008;13:1875-96 pubmedStrictosidine, the precursor of more than 2,500 indole alkaloids, was isolated from four species of three plant families...
- Hong Y, Lee W, Lee S, Son J, Kim H, Nam J, et al. Synthesis and biological properties of benzo-annulated rutaecarpines. Biol Pharm Bull. 2010;33:1704-9 pubmed..Benzo-annulation on ring A led to significant increase of inhibitory activity against topo II while annulations on ring E increased inhibitory activity against topo I. ..