Two new tryptophan derivatives from the seed kernels of Entada rheedei

Effects on cell viability and HIV infectivity

L. K. Nzowa, R. B. Teponno, L. A. Tapondjou, L. Verotta, Zhaohao Liao, David Graham, Mary Christine Zink, L. Barboni

Research output: Contribution to journalArticle

Abstract

Two new tryptophan derivatives, N-sulfonyl-L-tryptophan (tryptorheedei A) (1) and 3-(N-sulfonylindolyl)-D-lactic acid (tryptorheedei B) (2) together with the known 5-O-β-D-glucopyranosyl-2-hydroxyphenylacetic acid (3), 1-O-methylglucopyranoside, entadamide A, homogentisic acid and 3-O-β-D-glucopyranosyl-β-sitosterol, were isolated from the seed kernels of Entada rheedei (Mimosaceae). Their structures were established using 1D and 2D NMR spectroscopy, mass spectrometry and by comparison with spectroscopic data reported in the literature. Compounds 1 and 2 showed no toxicity to TZM and Human PBMC cells. Both compounds 1 and 2 were found to promote early infection events in HIV, likely by inhibiting the enzyme indolamine 2,3-dioxygenase (IDO) and preventing tryptophan depletion. Inhibition of IDO acutely in HIV infection inhibits viral replication, but chronic activation of IDO leads to immune impairment in AIDS. IDO is also the gatekeeper enzyme for kynurenine metabolism, a pathway involved in serotonin and melatonin biosynthesis and the regulation of glutamate and dopamine levels in the brain. Therefore inhibition of IDO might explain both the reported medicinal and neuropsychiatric effects of E. rheedei.

Original languageEnglish (US)
Pages (from-to)37-42
Number of pages6
JournalFitoterapia
Volume87
Issue number1
DOIs
StatePublished - Jun 2013

Fingerprint

Indoleamine-Pyrrole 2,3,-Dioxygenase
Tryptophan
Cell Survival
Seeds
HIV
Methylglucosides
Homogentisic Acid
Kynurenine
Melatonin
Enzymes
HIV Infections
Glutamic Acid
Lactic Acid
Dopamine
Mass Spectrometry
Serotonin
Acquired Immunodeficiency Syndrome
Magnetic Resonance Spectroscopy
Brain
Infection

Keywords

  • Entada rheedei
  • HIV infection
  • Mimosaceae
  • Tryptophan derivatives

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

Cite this

Two new tryptophan derivatives from the seed kernels of Entada rheedei : Effects on cell viability and HIV infectivity. / Nzowa, L. K.; Teponno, R. B.; Tapondjou, L. A.; Verotta, L.; Liao, Zhaohao; Graham, David; Zink, Mary Christine; Barboni, L.

In: Fitoterapia, Vol. 87, No. 1, 06.2013, p. 37-42.

Research output: Contribution to journalArticle

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