A saponin-rich extract of Phytolacca dioica L. berries, its acid hydrolysate, and its major aglycone, phytolaccagenin, were assayed for antifungal activity against ATCC standard cultures of Candida albicans and Cryptococcus neoformans, and against clinical isolates of these fungi. The activity of the extract was either low or negligible, but the hydrolysate, containing the sapogenins, including phytolaccagenin, and also pure phytolaccagenin, showed promising antifungal potency. Hydrolysis of a natural product extract is shown to be a useful modification leading to improved bioactivity.
SegalBH, HerbrechtR, StevensDA, Ostrosky-ZeichnerL, SobelJ, ViscoliC, WalshTJ, MaertensJ, PattersonTF, PerfectJR, DupontB, WingardJR, CalandraT, KauffmanCA, GraybillJR, BadenLR, PappasPG, BennettJE, KontoyiannisDP, CordonnierC, VivianiMA, BilleJ, AlmyroudisNG, WheatLJ, GraningerW, BowEJ, HollandSM, KullbergBJ, DismukesWE, De PauwBE. (2008) Defining responses to therapy and study outcomes in clinical trials of invasive fungal diseases: Mycoses Study Group and European Organization for Research and Treatment of Cancer consensus criteria. Clinical and Infectious Diseases, 47, 674–683.
2.
PfallerMA, DiekemaDJ. (2007) Epidemiology of invasive candidiasis: a persistent public health problem. Clinical and Microbiology Reviews, 20, 133–163.
3.
MathewB, NathM. (2009) Recent approaches to antifungal therapy for invasive mycoses. ChemMedChem, 4, 310–323.
PattersonTF. (2005) Advances and challenges in management of invasive mycoses. Lancet, 366, 1013–1025.
6.
MaregesiS, PietersL, NgassapaO, ApersS, VigerhoetsR, CosP, VandenBerghe D, VlietinkA. (2008) Screening of some Tanzanian medicinal plants from Bunda district for antibacterial, antifungal and antiviral activities. Journal of Ethnopharmacology, 119, 58–66.
7.
CosP, VlietinkA, VandenBerghe D, MaesL. (2006) Anti-infective potential of natural products: how to develop a stronger in vitro “proof-of-concept”. Journal of Ethnopharmacology, 106, 290–302.
8.
AgrawalSK, SinghS, VermaS, KumarS. (2000) Antifungal activity of anthraquinone derivatives from Rheum emodi. Journal of Ethnopharmacology, 72, 43–46.
9.
DanelutteAP, LagoaJH, YoungMC, KatoMJ. (2003) Antifungal flavanones and prenylated hydroquinones from Piper crassinervium Kunth. Phytochemistry, 64, 555–559.
10.
MalheirosA, CechinelFilho V, SchmittC, YunesR, EscalanteA, SvetazL, ZacchinoS, DelleMonache F. (2005) Antifungal activity of drimane sesquiterpenes from Drymis brasiliensis using bioassay-guided fractionation. Journal of Pharmacy and Pharmaceutical Sciences, 8, 335–339.
11.
SteinA, AlvarezS, AvanciniC, ZacchinoS, vonPoser G. (2006) Antifungal activity of some coumarins obtained from species of Pterocaulon (Asteraceae). Journal of Ethnopharmacology, 107, 95–98.
12.
AgüeroM, AlvarezS, LunaL, FeresinG, DeritaM, TapiaA, ZacchinoS. (2007) Antifungal activity of Zuccagnia punctata Cav. Evidences for the mechanism of action. Planta Medica, 73, 1074–1080.
SpargS, LightM, Van StadenJ. (2004) Biological activities and distribution of plant saponins. Journal of Ethnopharmacology, 94, 239–243.
16.
FrancisG, KeremZ, MakkarHPS. (2002) The biological action of saponins in animal systems: a review. The British Journal of Nutrition, 88, 587–605.
17.
KimN, DesjardinsA, WuC, KinghornD. (1999) Activity of triterpenoid glycosides from the root bark of Mussaenda macrophylla against two oral pathogens. Journal of Natural Products, 62, 1379–1384.
YiY. (1991) A triterpenoid saponin from Phytolacca esculenta. Phytochemistry, 30, 2552–2554.
20.
YiY. (1991) A triterpenoid and its saponin from Phytolacca esculenta. Phytochemistry, 30, 4179–4181.
21.
HaraguchiM, MotidomeM, GottliebO. (1988) Chemical study of the saponins of Phytolacca thyrsiflora. Acta Amazonica18, 443–448.
22.
WooW, KangS. (1977) The structure of phytolaccoside G. Journal of the Pharmaceutical Society of Korea, 21, 159–162.
23.
YiY, DaiF. (1991) A new triterpenoid and its glycoside from Phytolacca esculenta. Planta Medica, 57, 162–164.
24.
SlacaninI, MarstonA, HostettmannK. (1988) High-performance liquid chromatographic determination of molluscicidal saponins from Phytolacca dodecandra. Journal of Chromatography, 448, 265–274.
25.
YiY. (1992) Two new saponins from the roots of Phytolacca esculenta. Planta Medica, 58, 89–101.
26.
EscalanteAM, SantecchiaCB, LópezSN, GattusoMA, GutiérrezRavelo A, DelleMonache F, GonzálezSierra M, ZacchinoSA(2002) Isolation of antifungal saponins from Phytolacca tetramera, an Argentinean species in critical risk. Journal of Ethnopharmacology, 82, 29–34.
27.
SolimanHSM, SimonA, TóthG, DuddeckH (2001) Identification and structure determination of four triterpene saponins from some Middle-East plants. Magnetic Resonance in Chemistry, 39, 567–576.
28.
Santander-AndradeP. (1978) Fruit saponins of Phytolacca dioica (ombú). MSc Thesis, Faculty of Sciences, University of Chile.
29.
SpengelSM, LuterbacherS, SchaffnerW. (1995) New aspects on the chemotaxonomy of Phytolacca dodecandra with regard to the isolation of phytolaccagenin, phytolaccagenic acid and their glycosides. Planta Medica, 61, 385–386.
30.
StraussA, SpengelSM, SchaffnerW. (1995) Saponins from root cultures of Phytolacca acinosa. Phytochemistry, 38, 861–865.
31.
WooWS, KangSS. (1975) The occurrence and chemistry of Phytolacca triterpenoids. Journal of the Pharmaceutical Society of Korea, 19, 189–208.
SugaY, MaruyamaY, KawanishiS, ShojiJ. (1978) Studies on the constituents of Phytolaccaceous plants. I. On the structures of phytolaccasaponin B, E, and G from the roots of Phytolacca americana. Chemical and Pharmaceutical Bulletin, 26, 520–525.
34.
KobayashiA, HagiharaK, KajiyameS, KanzakiH, KawazuK. (1995) Antifungal compounds induced in the dual culture with Phytolacca americana callus and Botrytis fabae. Zeitschrift für Naturforschung C, 50, 398–402.
35.
EscalanteA, GattusoA, PérezP, ZacchinoS. (2008) Evidence for the mechanism of action of the antifungal phytolaccoside B isolated from Phytolacca tetramera Hauman. Journal of Natural Products, 71, 1720–1725.
36.
PeláezF, CabellosA, PlatasG, DiezM, González del ValA, BasilioA, MartánI, VicenteF, BillsG, GiacobbeR, SchwartzE, OnishiJ, MeinzM, AbruzzoG, FlatteryA, KongL, KurtzM. (2000) The discovery of enfumafungin, a novel antifungal compound produced by an endophytic Hormonema species, biological activity and taxonomy of the producing organisms. Systematic and Applied Microbiology, 23, 333–343.
37.
LópezSN, RamalloIA, GonzálezSierra M, ZacchinoSA, FurlánRLE. (2007) Chemically engineered extracts as an alternative source of bioactive natural product-like compounds. Proceedings of the National Academy of Sciences USA, 104, 441–444.
38.
SalazarMO, RamalloIA, MicheloniO, GonzálezSierra M, FurlánRLE. (2009) Chemically engineered extracts: bioactivity alteration through sulfonylation. Bioorganic and Medicinal Chemistry Letters, 19, 5067–5070.
39.
SinghN. (2003) Treatment of opportunistic mycoses: how long is long enough?The Lancet Infectious Diseases, 3, 703–708.
40.
Clinical and Laboratory Standards Institute (CLSI), formerly National Committee for Clinical Laboratory Standards (NCCLS). (2002) Reference method for broth dilution antifungal susceptibility testing of yeasts and filamentous fungi, approved standard. Vol 22, 2nd ed. NCCLS, Wayne, PA, 1–29.
41.
ErnstE, RolingE, PetzoldR, KeeleD, KlepserM. (2002) In vitro activity of micafungin (FK-463) against Candida spp.: microdilution, time-kill, and postantifungal-effect studies. Antimicrobial Agents and Chemotherapy, 46, 3846–3853.
42.
WagnerH.BladtS. (1996) Plant Drug Analysis. A Thin Layer Chromatography Atlas, 2nd ed. Springer Verlag (Berlin), 305–326; 335-340; 359.
43.
WrightLR, ScottEM, GormanSP. (1983) The sensitivity of mycelium, arthrospores, and microconidia of Trichophyton mentagrophytes to imidazoles determined by in vitro tests. Journal of Antimicrobial Chemotherapy, 12, 317–327.
44.
RahalisonL, HamburgerM, HostettmannK, MonodM, FrenkE. (1991) A bioautographic agar overlay method for the detection of antifungal compounds from higher plants. Phytochemical Analysis, 2, 199–203.
