Antiviral activity of natural and semi-synthetic chromone alkaloids.
The activity against human immunodeficiency virus (HIV) and herpes simplex virus (HSV), of the non-polar fraction of a methanolic extract of the rootbark of Schumanniophyton magnificum was found to be present in a fraction containing the chromone secondary amine schumannificine 1. Other chromone alkaloids present in the plant were isolated and tested for inhibition of HIV and HSV infections in C8166 and Vero cells, respectively. Acyl and methyl derivatives were prepared and tested. Of all the compounds tested, schumannificine 1 displayed the greatest activity against HIV, whereas potent anti-HSV activity was observed for a number of its derivatives. The presence of a piperidine ring and unsubstituted hydroxy groups on the molecules seems to favour the anti-HIV activity. The anti-HIV activity is considered to be due to irreversible binding to gp120 rather than inhibition of reverse transcriptase or protease.
Houghton
P J
PJ
Department of Pharmacy, King's College London, UK.
Woldemariam
T Z
TZ
Khan
A I
AI
Burke
A
A
Mahmood
N
N
D000470:Alkaloids / Q000302:isolation & purification / Q000494:pharmacology*; D000818:Animals; D000998:Antiviral Agents / Q000302:isolation & purification / Q000494:pharmacology*; D002522:Chlorocebus aethiops; D002867:Chromones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D015699:HIV Envelope Protein gp120; D016333:HIV Protease; D054303:HIV Reverse Transcriptase; D015497:HIV-1 / Q000187:drug effects; D018259:Herpesvirus 1, Human / Q000187:drug effects; D006801:Humans; D010944:Plants / Q000737:chemistry; D011753:Pyrones / Q000737:chemistry / Q000494:pharmacology; D012194:RNA-Directed DNA Polymerase / Q000187:drug effects; D013329:Structure-Activity Relationship; D014709:Vero Cells
D000470:Alkaloids; D000998:Antiviral Agents; D002867:Chromones; D015699:HIV Envelope Protein gp120; D011753:Pyrones; C092909:schumannificine; D054303:HIV Reverse Transcriptase; D012194:RNA-Directed DNA Polymerase; D016333:HIV Protease