BIOMAT Database Logo BIOMAT Database Logo

In vitro leishmanicidal activity of benzophenanthridine alkaloids from Bocconia pearcei and related compounds. 2010

Hiroyuki Fuchino, and Marii Kawano, and Kanami Mori-Yasumoto, and Setsuko Sekita, and Motoyoshi Satake, and Tsutomu Ishikawa, and Fumiyuki Kiuchi, and Nobuo Kawahara
Research Center for Medicinal Plant Resources, National Institute of Biomedical Innovation, 1-2 Hachimandai, Tsukuba, Ibaraki, Japan. fuchino@nibio.go.jp

Leishmanicidal activities of benzophenanthridine alkaloids isolated from fruits of Bocconia pearcei and their derivatives were examined. Seven benzophenanthridine compounds were isolated from the methanolic extracts of B. pearcei. Among them, dihydrosanguinarine showed the most potent leishmanicidal activities (IC(50) value: 0.014 microg/ml, respectively). To examine the structure-activity relationship of the benzophenanthridine skeleton, the leishmanicidal activities for 32 synthetic samples were examined. The existence of bulky groups at the C(7)-C(8) position was found to enhance the activity. On the other hand, the bulkiness at the C(2)-C(3) position on the D-ring, a carbonyl group at C-6, substitution at C-6 and cleavage or saturation of the C(5)-C(6) bond reduced activity. A methyl group on nitrogen of the C-ring was thought to be necessary for significant activity.

UI MeSH Term Description Entries
D007891 Leishmania A genus of flagellate protozoa comprising several species that are pathogenic for humans. Organisms of this genus have an amastigote and a promastigote stage in their life cycles. As a result of enzymatic studies this single genus has been divided into two subgenera: Leishmania leishmania and Leishmania viannia. Species within the Leishmania leishmania subgenus include: L. aethiopica, L. arabica, L. donovani, L. enrietti, L. gerbilli, L. hertigi, L. infantum, L. major, L. mexicana, and L. tropica. The following species are those that compose the Leishmania viannia subgenus: L. braziliensis, L. guyanensis, L. lainsoni, L. naiffi, and L. shawi. Leishmania (Leishmania),Leishmania (Viannia),Leishmania leishmania,Leishmania viannia,Leishmania leishmanias,Leishmania viannias,Leishmanias,Leishmanias (Leishmania),Leishmanias (Viannia),leishmanias, Leishmania,viannias, Leishmania
D010936 Plant Extracts Concentrated pharmaceutical preparations of plants obtained by removing active constituents with a suitable solvent, which is evaporated away, and adjusting the residue to a prescribed standard. Herbal Medicines,Plant Extract,Extract, Plant,Extracts, Plant,Medicines, Herbal
D005638 Fruit The fleshy or dry ripened ovary of a plant, enclosing the seed or seeds. Berries,Legume Pod,Plant Aril,Plant Capsule,Aril, Plant,Arils, Plant,Berry,Capsule, Plant,Capsules, Plant,Fruits,Legume Pods,Plant Arils,Plant Capsules,Pod, Legume,Pods, Legume
D000470 Alkaloids Organic nitrogenous bases. Many alkaloids of medical importance occur in the animal and vegetable kingdoms, and some have been synthesized. (Grant & Hackh's Chemical Dictionary, 5th ed) Alkaloid,Plant Alkaloid,Plant Alkaloids,Alkaloid, Plant,Alkaloids, Plant
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D000981 Antiprotozoal Agents Substances that are destructive to protozoans. Schizonticides,Agents, Antiprotozoal
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D053119 Benzophenanthridines Compounds of four rings containing a nitrogen. They are biosynthesized from reticuline via rearrangement of scoulerine. They are similar to BENZYLISOQUINOLINES. Members include chelerythrine and sanguinarine.
D021261 Parasitic Sensitivity Tests Tests that demonstrate the relative effectiveness of chemotherapeutic agents against specific parasites. Drug Sensitivity Tests, Helminth,Drug Sensitivity Tests, Parasitic,Drug Sensitivity Tests, Protozoal,Helminth Drug Sensitivity Tests,Parasite Sensitivity Tests,Protozoa Drug Sensitivity Tests,Protozoal Drug Sensitivity Tests,Parasite Sensitivity Test,Parasitic Sensitivity Test,Sensitivity Test, Parasite,Sensitivity Test, Parasitic,Sensitivity Tests, Parasite,Test, Parasite Sensitivity,Test, Parasitic Sensitivity,Tests, Parasite Sensitivity,Tests, Parasitic Sensitivity

Related Publications

Hiroyuki Fuchino, and Marii Kawano, and Kanami Mori-Yasumoto, and Setsuko Sekita, and Motoyoshi Satake, and Tsutomu Ishikawa, and Fumiyuki Kiuchi, and Nobuo Kawahara
Identification of benzophenanthridine alkaloids from Bocconia arborea by gas chromatography-mass spectrometry.
January 2002, Phytochemical analysis : PCA,
Hiroyuki Fuchino, and Marii Kawano, and Kanami Mori-Yasumoto, and Setsuko Sekita, and Motoyoshi Satake, and Tsutomu Ishikawa, and Fumiyuki Kiuchi, and Nobuo Kawahara
Two antimicrobial alkaloids from Bocconia arborea.
August 1999, Journal of ethnopharmacology,
Hiroyuki Fuchino, and Marii Kawano, and Kanami Mori-Yasumoto, and Setsuko Sekita, and Motoyoshi Satake, and Tsutomu Ishikawa, and Fumiyuki Kiuchi, and Nobuo Kawahara
Antiinflammatory activity of quaternary benzophenanthridine alkaloids from Chelidonium majus.
October 1981, Planta medica,
Hiroyuki Fuchino, and Marii Kawano, and Kanami Mori-Yasumoto, and Setsuko Sekita, and Motoyoshi Satake, and Tsutomu Ishikawa, and Fumiyuki Kiuchi, and Nobuo Kawahara
Benzophenanthridine alkaloids from Corydalis flabellata.
March 2002, Planta medica,
Hiroyuki Fuchino, and Marii Kawano, and Kanami Mori-Yasumoto, and Setsuko Sekita, and Motoyoshi Satake, and Tsutomu Ishikawa, and Fumiyuki Kiuchi, and Nobuo Kawahara
Leishmanicidal activity of some stilbenoids and related heterocyclic compounds.
August 2001, Bioorganic & medicinal chemistry letters,
Hiroyuki Fuchino, and Marii Kawano, and Kanami Mori-Yasumoto, and Setsuko Sekita, and Motoyoshi Satake, and Tsutomu Ishikawa, and Fumiyuki Kiuchi, and Nobuo Kawahara
Aporphine alkaloids from Guatteria spp. with leishmanicidal activity.
July 2003, Planta medica,
Hiroyuki Fuchino, and Marii Kawano, and Kanami Mori-Yasumoto, and Setsuko Sekita, and Motoyoshi Satake, and Tsutomu Ishikawa, and Fumiyuki Kiuchi, and Nobuo Kawahara
Structure-activity relationship of benzophenanthridine alkaloids from Zanthoxylum rhoifolium having antimicrobial activity.
January 2014, PloS one,
Hiroyuki Fuchino, and Marii Kawano, and Kanami Mori-Yasumoto, and Setsuko Sekita, and Motoyoshi Satake, and Tsutomu Ishikawa, and Fumiyuki Kiuchi, and Nobuo Kawahara
Inhibition of reverse transcriptase activity by benzophenanthridine alkaloids.
January 1979, Lloydia,
Hiroyuki Fuchino, and Marii Kawano, and Kanami Mori-Yasumoto, and Setsuko Sekita, and Motoyoshi Satake, and Tsutomu Ishikawa, and Fumiyuki Kiuchi, and Nobuo Kawahara
Inhibition of reverse transcriptase activity by benzophenanthridine alkaloids.
January 1979, Journal of natural products,
Hiroyuki Fuchino, and Marii Kawano, and Kanami Mori-Yasumoto, and Setsuko Sekita, and Motoyoshi Satake, and Tsutomu Ishikawa, and Fumiyuki Kiuchi, and Nobuo Kawahara
Leishmanicidal, antiplasmodial and cytotoxic activity of indole alkaloids from Corynanthe pachyceras.
August 2000, Planta medica,
Copied contents to your clipboard!