H. Martin Garraffo, Ph.D.

Publications

A selection of recent and significant publications can be viewed below.

Molecular mechanisms of hypoxic responses via unique roles of Ras1, Cdc24 and Ptp3 in a human fungal pathogen Cryptococcus neoformans.
Chang YC, Khanal Lamichhane A, Garraffo HM, Walter PJ, Leerkes M, Kwon-Chung KJ.
PLoS Genet (2014 Apr) 10:e1004292. Abstract/Full Text
Histrionicotoxin alkaloids finally detected in an ant.
Jones TH, Adams RM, Spande TF, Garraffo HM, Kaneko T, Schultz TR.
J Nat Prod (2012 Nov 26) 75:1930-6. Abstract/Full Text
Alkaloids from single skins of the Argentinian toad Melanophryniscus rubriventris (ANURA, BUFONIDAE): An unexpected variability in alkaloid profiles and a profusion of new structures.
Garraffo HM, Andriamaharavo NR, Vaira M, Quiroga MF, Heit C, Spande TF.
Springerplus (2012 Dec) 1:51. Abstract/Full Text
Involvement of PDK1, PKC and TOR signalling pathways in basal fluconazole tolerance in Cryptococcus neoformans.
Lee H, Khanal Lamichhane A, Garraffo HM, Kwon-Chung KJ, Chang YC.
Mol Microbiol (2012 Apr) 84:130-46. Abstract/Full Text
Identification of a Cryptococcus neoformans cytochrome P450 lanosterol 14α-demethylase (Erg11) residue critical for differential susceptibility between fluconazole/voriconazole and itraconazole/posaconazole.
Sionov E, Chang YC, Garraffo HM, Dolan MA, Ghannoum MA, Kwon-Chung KJ.
Antimicrob Agents Chemother (2012 Mar) 56:1162-9. Abstract/Full Text
Alkaloids in the mite Scheloribates laevigatus: further alkaloids common to oribatid mites and poison frogs.
Saporito RA, Norton RA, Andriamaharavo NR, Garraffo HM, Spande TF.
J Chem Ecol (2011 Feb) 37:213-8. Abstract/Full Text
Sex-related differences in alkaloid chemical defenses of the dendrobatid frog Oophaga pumilio from Cayo Nancy, Bocas del Toro, Panama.
Saporito RA, Donnelly MA, Madden AA, Garraffo HM, Spande TF.
J Nat Prod (2010 Mar 26) 73:317-21. Abstract/Full Text
Caste-specific tyramides from Myrmicine ants.
Jones TH, Garraffo HM, Spande TF, Andriamaharavo NR, Gorman JS, Snyder AJ, Jeter AW, Torres JA, Snelling RR, Daly JW.
J Nat Prod (2010 Mar 26) 73:313-6. Abstract/Full Text
Roughing it: a mantellid poison frog shows greater alkaloid diversity in some disturbed habitats.
Andriamaharavo NR, Garraffo HM, Saporito RA, Daly JW, Razafindrabe CR, Andriantsiferana M, Spande TF.
J Nat Prod (2010 Mar 26) 73:322-30. Abstract/Full Text
Phantasmidine: an epibatidine congener from the ecuadorian poison frog Epipedobates anthonyi.
Fitch RW, Spande TF, Garraffo HM, Yeh HJ, Daly JW.
J Nat Prod (2010 Mar 26) 73:331-7. Abstract/Full Text
Efficient enantio- and diastereodivergent synthesis of poison-frog alkaloids 251O and trans-223B.
Toyooka N, Zhou D, Nemoto H, Tezuka Y, Kadota S, Andriamaharavo NR, Garraffo HM, Spande TF, Daly JW.
J Org Chem (2009 Sep 4) 74:6784-91. Abstract/Full Text
Heteroresistance to fluconazole in Cryptococcus neoformans is intrinsic and associated with virulence.
Sionov E, Chang YC, Garraffo HM, Kwon-Chung KJ.
Antimicrob Agents Chemother (2009 Jul) 53:2804-15. Abstract/Full Text
John William Daly, 1933-2008.
Garraffo HM.
Cell Mol Neurobiol (2009 Jun) 29:439-40. Abstract/Full Text
N-methyldecahydroquinolines: an unexpected class of alkaloids from Amazonian poison frogs (Dendrobatidae).
Daly JW, Ware N, Saporito RA, Spande TF, Garraffo HM.
J Nat Prod (2009 Jun) 72:1110-4. Abstract/Full Text
Epiquinamide: a poison that wasn't from a frog that was.
Fitch RW, Sturgeon GD, Patel SR, Spande TF, Garraffo HM, Daly JW, Blaauw RH.
J Nat Prod (2009 Feb 27) 72:243-7. Abstract/Full Text
Indolizidine 239Q and quinolizidine 275I. Major alkaloids in two Argentinian bufonid toads (Melanophryniscus).
Daly JW, Garraffo HM, Spande TF, Yeh HJ, Peltzer PM, Cacivio PM, Baldo JD, Faivovich J.
Toxicon (2008 Dec 15) 52:858-70. Abstract/Full Text
Individual and geographic variation of skin alkaloids in three species of Madagascan poison frogs (Mantella).
Daly JW, Garraffo HM, Spande TF, Giddings LA, Saporito RA, Vieites DR, Vences M.
J Chem Ecol (2008 Feb) 34:252-79. Abstract/Full Text
Facile synthesis of two diastereomeric indolizidines corresponding to the postulated structure of alkaloid 5,9E-259B from a Bufonid toad (Melanophryniscus).
Nelson A, Garraffo HM, Spande TF, Daly JW, Stevenson PJ.
Beilstein J Org Chem (2008 Jan 21) 4:6. Abstract/Full Text
Synthesis of poison-frog alkaloids 233A, 235U, and 251AA and their inhibitory effects on neuronal nicotinic acetylcholine receptors.
Toyooka N, Kobayashi S, Zhou D, Tsuneki H, Wada T, Sakai H, Nemoto H, Sasaoka T, Garraffo HM, Spande TF, Daly JW.
Bioorg Med Chem Lett (2007 Nov 1) 17:5872-5. Abstract/Full Text
Flexible synthetic routes to poison-frog alkaloids of the 5,8-disubstituted indolizidine-class I: synthesis of common lactam chiral building blocks and application to the synthesis of (-)-203A, (-)-205A, and (-)-219F.
Toyooka N, Zhou D, Nemoto H, Garraffo HM, Spande TF, Daly JW.
Beilstein J Org Chem (2007 Sep 28) 3:29. Abstract/Full Text
Oribatid mites as a major dietary source for alkaloids in poison frogs.
Saporito RA, Donnelly MA, Norton RA, Garraffo HM, Spande TF, Daly JW.
Proc Natl Acad Sci U S A (2007 May 22) 104:8885-90. Abstract/Full Text
Alkaloids in bufonid toads (melanophryniscus): temporal and geographic determinants for two argentinian species.
Daly JW, Wilham JM, Spande TF, Garraffo HM, Gil RR, Silva GL, Vaira M.
J Chem Ecol (2007 Apr) 33:871-87. Abstract/Full Text
Venom chemistry of the ant Myrmicaria melanogaster from Brunei.
Jones TH, Voegtle HL, Miras HM, Weatherford RG, Spande TF, Garraffo HM, Daly JW, Davidson DW, Snelling RR.
J Nat Prod (2007 Feb) 70:160-8. Abstract/Full Text
Flexible synthesis of poison-frog alkaloids of the 5,8-disubstituted indolizidine-class. II: Synthesis of (-)-209B, (-)-231C, (-)-233D, (-)-235B", (-)-221I, and an epimer of 193E and pharmacological effects at neuronal nicotinic acetylcholine receptors.
Kobayashi S, Toyooka N, Zhou D, Tsuneki H, Wada T, Sasaoka T, Sakai H, Nemoto H, Garraffo HM, Spande TF, Daly JW.
Beilstein J Org Chem (2007) 3:30. Abstract/Full Text
Geographic and seasonal variation in alkaloid-based chemical defenses of Dendrobates pumilio from Bocas del Toro, Panama.
Saporito RA, Donnelly MA, Garraffo HM, Spande TF, Daly JW.
J Chem Ecol (2006 Apr) 32:795-814. Abstract/Full Text
A revised structure for alkaloid 235C isolated from skin extracts of mantellid (Mantella) frogs of Madagascar.
Andriamaharavo NR, Andriantsiferana M, Stevenson PA, O'mahony G, Yeh HJ, Kaneko T, Garraffo HM, Spande TF, Daly JW.
J Nat Prod (2005 Dec) 68:1743-8. Abstract/Full Text
Alkaloids of anuran skin: antimicrobial function?
Macfoy C, Danosus D, Sandit R, Jones TH, Garraffo HM, Spande TF, Daly JW.
Z Naturforsch C (2005 Nov-Dec) 60:932-7. Abstract/Full Text
Alkaloids from amphibian skin: a tabulation of over eight-hundred compounds.
Daly JW, Spande TF, Garraffo HM.
J Nat Prod (2005 Oct) 68:1556-75. Abstract/Full Text
Biologically active substances from amphibians: preliminary studies on anurans from twenty-one genera of Thailand.
Daly JW, Noimai N, Kongkathip B, Kongkathip N, Wilham JM, Garraffo HM, Kaneko T, Spande TF, Nimit Y, Nabhitabhata J, Chan-Ard T.
Toxicon (2004 Dec 15) 44:805-15. Abstract/Full Text
Formicine ants: An arthropod source for the pumiliotoxin alkaloids of dendrobatid poison frogs.
Saporito RA, Garraffo HM, Donnelly MA, Edwards AL, Longino JT, Daly JW.
Proc Natl Acad Sci U S A (2004 May 25) 101:8045-50. Abstract/Full Text
A siphonotid millipede (Rhinotus) as the source of spiropyrrolizidine oximes of dendrobatid frogs.
Saporito RA, Donnelly MA, Hoffman RL, Garraffo HM, Daly JW.
J Chem Ecol (2003 Dec) 29:2781-6. Abstract/Full Text
Bioassay-guided isolation of epiquinamide, a novel quinolizidine alkaloid and nicotinic agonist from an Ecuadoran poison frog, Epipedobates tricolor.
Fitch RW, Garraffo HM, Spande TF, Yeh HJ, Daly JW.
J Nat Prod (2003 Oct) 66:1345-50. Abstract/Full Text
Evidence for an enantioselective pumiliotoxin 7-hydroxylase in dendrobatid poison frogs of the genus Dendrobates.
Daly JW, Garraffo HM, Spande TF, Clark VC, Ma J, Ziffer H, Cover JF Jr.
Proc Natl Acad Sci U S A (2003 Sep 16) 100:11092-7. Abstract/Full Text
Bioactive alkaloids of frog skin: combinatorial bioprospecting reveals that pumiliotoxins have an arthropod source.
Daly JW, Kaneko T, Wilham J, Garraffo HM, Spande TF, Espinosa A, Donnelly MA.
Proc Natl Acad Sci U S A (2002 Oct 29) 99:13996-4001. Abstract/Full Text
Synthesis of alkaloid 223A and a structural revision.
Toyooka N, Fukutome A, Nemoto H, Daly JW, Spande TF, Garraffo HM, Kaneko T.
Org Lett (2002 May 16) 4:1715-7. Abstract/Full Text
Evidence for biosynthesis of pseudophrynamine alkaloids by an Australian myobatrachid frog (pseudophryne) and for sequestration of dietary pumiliotoxins.
Smith BP, Tyler MJ, Kaneko T, Garraffo HM, Spande TF, Daly JW.
J Nat Prod (2002 Apr) 65:439-47. Abstract/Full Text
Structure of alkaloid 275A, a novel 1-azabicyclo[5.3.0]decane from a dendrobatid frog, Dendrobates lehmanni: synthesis of the tetrahydrodiastereomers.
Garraffo HM, Jain P, Spande TF, Daly JW, Jones TH, Smith LJ, Zottig VE.
J Nat Prod (2001 Apr) 64:421-7. Abstract/Full Text
Ammonia chemical ionization tandem mass spectrometry in structural determination of alkaloids. II. Tetraponerines from pseudomyrmecine ants.
Garraffo HM, Spande TF, Jain P, Kaneko T, Jones TH, Blum MS, Ali TM, Snelling RR, Isbell LA, Robertson HG, Daly JW.
Rapid Commun Mass Spectrom (2001) 15:1409-15. Abstract/Full Text
Alkaloids from frog skin: the discovery of epibatidine and the potential for developing novel non-opioid analgesics.
Daly JW, Garraffo HM, Spande TF, Decker MW, Sullivan JP, Williams M.
Nat Prod Rep (2000 Apr) 17:131-5. Abstract/Full Text
3-methyl-4-phenylpyrrole from the ants Anochetus kempfi and Anochetus mayri.
Jones TH, Flournoy RC, Torres JA, Snelling RR, Spande TF, Garraffo HM.
J Nat Prod (1999 Sep) 62:1343-5. Abstract/Full Text
Specificity of ascorbate analogs for ascorbate transport. Synthesis and detection of [(125)I]6-deoxy-6-iodo-L-ascorbic acid and characterization of its ascorbate-specific transport properties.
Rumsey SC, Welch RW, Garraffo HM, Ge P, Lu SF, Crossman AT, Kirk KL, Levine M.
J Biol Chem (1999 Aug 13) 274:23215-22. Abstract/Full Text
Ammonia chemical ionization tandem mass spectrometry in structure determination of alkaloids. I. Pyrrolidines, piperidines, decahydroquinolines, pyrrolizidines, indolizidines, quinolizidines and an azabicyclo[5.3.0]decane.
Garraffo HM, Spande TF, Jones TH, Daly JW.
Rapid Commun Mass Spectrom (1999) 13:1553-63. Abstract/Full Text
Occurrence and significance of decahydroquinolines from dendrobatid poison frogs and a myrmicine ant: use of 1H and 13C NMR in their conformational analysis
Spande TF, Jain P, Garraffo HM, Pannell LK, Yeh HJC, Daly JW, Fukumoto S, Imamura K, Tokuyama T, Torres JA, Snelling RR, Jones TH.
J Nat Prod (1999 Jan) 62:5-21. Abstract/Full Text
Absence of skin alkaloids in captive-raised Madagascan mantelline frogs (Mantella) and sequestration of dietary alkaloids.
Daly JW, Garraffo HM, Hall GS, Cover JF Jr.
Toxicon (1997 Jul) 35:1131-5. Abstract/Full Text
Pseudophrynaminol: a potent noncompetitive blocker of nicotinic receptor-channels.
Badio B, Garraffo HM, Padgett WL, Greig NH, Daly JW.
Biochem Pharmacol (1997 Mar 7) 53:671-6. Abstract/Full Text
Synthesis and nicotinic activity of epiboxidine: an isoxazole analogue of epibatidine.
Badio B, Garraffo HM, Plummer CV, Padgett WL, Daly JW.
Eur J Pharmacol (1997 Feb 26) 321:189-94. Abstract/Full Text
Alkaloid 223A: the first trisubstituted indolizidine from dendrobatid frogs.
Garraffo HM, Jain P, Spande TF, Daly JW.
J Nat Prod (1997 Jan) 60:2-5. Abstract/Full Text
A 1,4-disubstituted quinolizidine from a Madagascan mantelline frog (Mantella).
Jain P, Garraffo HM, Yeh HJ, Spande TF, Daly JW, Andriamaharavo NR, Andriantsiferana M.
J Nat Prod (1996 Dec) 59:1174-8. Abstract/Full Text
A new secotrinervitane diterpene isolated from soldiers of the Madagascan termite species, Nasutitermes canaliculatus.
Rabemanantsoa A, Ranarivelo Y, Andriantsiferana M, Tillequin F, Silverton JV, Garraffo HM, Spande TF, Yeh HJ, Daly JW.
J Nat Prod (1996 Sep) 59:883-6. Abstract/Full Text
Chemistry of venom alkaloids in someSolenopsis (Diplorhoptrum) species from Puerto Rico.
Jones TH, Torres JA, Spande TF, Garraffo HM, Blum MS, Snelling RR.
J Chem Ecol (1996 Jul) 22:1221-36. Abstract/Full Text