Two new diphenylmethyl-substituted xanthones, named muchimangins K (1) and L (2), have been isolated from the roots of Securidaca longepedunculata (Polygalaceae) collected in the Democratic Republic of Congo. Their structures were established by analyses of the spectral data, including 2D NMR spectra, to be l,3,6,8-tetrahydroxy-2,5-dimethoxy-4-[l-(2,4,5-trimethoxyphenyl)-1-phenylmethyl]xanthone (1) and l,3,6-trihydroxy-4,7-dimethoxy-2-[l-(2,4,5-trimethoxyphenyl)-1-phenylmethyl]xanthone (2).
AyensuES. (1978) Medicinal Plants of West Africa. Reference Publications, Inc., Algonac, 218–220.
2.
ScandolaM, GamesDE, CostaC, AllegriG, BertazzoA, CurcurutoO, TraldiP. (1994) Structural study of alkaloids from Securidaca longipedunculata roots. II. Isolation and characterization by supercritical fluid chromatography/mass spectrometry. Journal of Heterocyclic Chemistry, 31, 219–224.
3.
CostaC, BertazzoA, AllegriG, CurcurutoO, TraldiP. (1992) Indole alkaloids from the roots of an African plant Securidaca longipedunculata. I. Isolation by column chromatography and preliminary structural characterization by mass spectrometry. Journal of Heterocyclic Chemistry, 29, 1641–1647.
4.
Mitaine-OfferAC, PénezN, MiyamotoT, DelaudeC, MirjoletJF, DuchampO, Lacaille-DuboisMA. (2010) Acylated triterpene saponins from the roots of Securidaca longepedunculata. Phytochemistry, 71, 90–94.
5.
StevensonPC, DayarathnaTK, BelmainSR, VeitchNC. (2009) Bisdesmosidic saponins from Securidaca longepedunculata roots: evaluation of deterrency and toxicity to coleopteran storage pests. Journal of Agricultural & Food Chemistry, 57, 8860–8867.
6.
GaleffiC, FedericiE, MsonthiJD, Marini-BettoloGB, NicolettiM. (1990) Research on African medicinal plants. Part XVIII. New xanthones from Ectiadiopsis oblongifolia and Securidaca longipedunculata. Fitoterapia, 61, 79–81.
7.
AwaleS, LuJ, KalauniSK, KurashimaY, TezukaY, KadotaS, EsumiH. (2006) Identification of arctigenin as an antitumor agent having the ability to eliminate the tolerance of cancer cells to nutrient starvation. Cancer Research, 66, 1751–1757.
8.
AwaleS, NakashimaEMN, KalauniSK, TezukaY, KurashimaY, LuJ, EsumiH, KadotaS. (2006) Angelmarin, a novel anti-cancer agent able to eliminate the tolerance of cancer cells to nutrient starvation. Bioorganic & Medicinal Chemistry Letters, 16, 581–583.
9.
LiF, AwaleS, TezukaY, EsumiH, KadotaS. (2010) Study on the constituents of Mexican propolis and their cytotoxic activity against PANC-1 human pancreatic cancer cells. Journal of Natural Products, 73, 623–621.
10.
WinNN, AwaleS, EsumiH, TezukaY, KadotaS. (2007) Bioactive secondary metabolites from Boesenbergia pandurata of Myanmar and their preferential cytotoxicity against human pancreatic cancer PANC-1 cell line in nutrient-deprived medium. Journal of Natural Products, 70, 1582–1587.
11.
DibweDF, AwaleS, KadotaS, TezukaY. (2012) Damnacanthal from the Congolese medicinal plant Garcinia huillensis has a potent preferential cytotoxicity against human pancreatic cancer PANC-1 cells. Phytotherapy Research, 26, 1920–1926.
12.
DibweDF, AwaleS, KadotaS, MoritaH, TezukaY. (2013) Heptaoxygenated xanthones as anti-austerity agents from Securidaca longepedunculata. Bioorganic & Medicinal Chemistry, 21, 7663–7668.
DibweDF, AwaleS, KadotaS, MoritaH, TezukaY. (2014) Muchimangins E and F: novel diphenylmethyl-substituted xanthones from Securidaca longepedunculata Tetrahedron Letters, 55, 1916–1919.
15.
DibweDF, AwaleS, KadotaS, MoritaH, TezukaY. (2014) Muchimangins G-J: fully-substituted xanthones with a diphenylmethyl substituent, from Securidaca longepedunculata Journal of Natural Products, in press. DOI: 10.1021/np5000445.
LannangAM, LontsiD, NgounouFN, SondengamBL, NkengfackAE, van HeerdenFR, AssobJCN. (2006) Securidacaxanthone A, a heptaoxygenated xanthone from Securidaca longepedunculata. Fitoterapia, 77, 199–202.
18.
IkeyaY, SugamaK, OkadaM, MitsuhashiH. (1991) Two xanthones from Polygala tenuifolia. Phytochemistry, 30, 2061–2065.