Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure-activity correlations with related alkaloids
| Autor: | Akihiro Aoshima, Yuh Pan Chen, Yasumasa Ikeshiro, Hiroshi Furukawa, Masataka Itoigawa, Toshihiro Fujioka, Kunihide Mihashi, Kuo Hsiung Lee, Susan L. Morris-Natschke, L. Mark Cosentino, Yoshiki Kashiwada |
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| Rok vydání: | 2004 |
| Předmět: |
Nuciferine
Stereochemistry Anti-HIV Agents Clinical Biochemistry Pharmaceutical Science Pharmacognosy Nelumbo Biochemistry Cell Line chemistry.chemical_compound Structure-Activity Relationship Alkaloids Tetrahydroisoquinolines Drug Discovery Animals Aporphine Benzylisoquinoline Molecular Biology biology Molecular Structure Alkaloid Organic Chemistry biology.organism_classification Isoquinolines Plant Leaves chemistry HIV-1 Molecular Medicine Quercetin Coclaurine |
| Zdroj: | Bioorganicmedicinal chemistry. 13(2) |
| ISSN: | 0968-0896 |
| Popis: | (+)-1(R)-Coclaurine (1) and (-)-1(S)-norcoclaurine (3), together with quercetin 3-O-beta-D-glucuronide (4), were isolated from the leaves of Nelumbo nucifera (Nymphaceae), and identified as anti-HIV principles. Compounds 1 and 3 demonstrated potent anti-HIV activity with EC50 values of 0.8 and0.8 microg/mL, respectively, and therapeutic index (TI) values of125 and25, respectively. Compound 4 was less potent (EC50 2 microg/mL). In a structure-activity relationship study, other benzylisoquinoline, aporphine, and bisbenzylisoquinoline alkaloids, including liensinine (14), negferine (15), and isoliensinine (16), which were previously isolated from the leaves and embryo of Nelumbo nucifera, were evaluated for anti-HIV activity. Compounds 14-16 showed potent anti-HIV activities with EC50 values of0.8 microg/mL and TI values of9.9,8.6, and6.5, respectively. Nuciferine (12), an aporphine alkaloid, had an EC50 value of 0.8 microg/mL and TI of 36. In addition, synthetic coclaurine analogs were also evaluated. Compounds 1, 3, 12, and 14-16 can serve as new leads for further development of anti-AIDS agents. |
| Databáze: | OpenAIRE |
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