BIOMAT Database Logo BIOMAT Database Logo

Five novel mono-tetrahydrofuran ring acetogenins from the seeds of Annona muricata. 1996

M J Rieser, and Z M Gu, and X P Fang, and L Zeng, and K V Wood, and J L McLaughlin
AgrEvo Research Center, Pikeville, North Carolina 27863, USA.

Bioactivity-directed fractionation of the seeds of Annona muricata L. (Annonaceae) resulted in the isolation of five new compounds: cis-annonacin (1), cis-annonacin-10-one (2), cis-goniothalamicin (3), arianacin (4), and javoricin (5). Three of these (1-3) are among the first cis mono-tetrahydrofuran ring acetogenins to be reported. NMR analyses of published model synthetic compounds, prepared cyclized formal acetals, and prepared Mosher ester derivatives permitted the determinations of absolute stereochemistries. Bioassays of the pure compounds, in the brine shrimp test, for the inhibition of crown gall tumors, and in a panel of human solid tumor cell lines for cytotoxicity, evaluated relative potencies. Compound 1 was selectively cytotoxic to colon adenocarcinoma cells (HT-29) in which it was 10,000 times the potency of adriamycin.

UI MeSH Term Description Entries
D008175 Lung Neoplasms Tumors or cancer of the LUNG. Cancer of Lung,Lung Cancer,Pulmonary Cancer,Pulmonary Neoplasms,Cancer of the Lung,Neoplasms, Lung,Neoplasms, Pulmonary,Cancer, Lung,Cancer, Pulmonary,Cancers, Lung,Cancers, Pulmonary,Lung Cancers,Lung Neoplasm,Neoplasm, Lung,Neoplasm, Pulmonary,Pulmonary Cancers,Pulmonary Neoplasm
D010941 Plant Tumors A localized proliferation of plant tissue forming a swelling or outgrowth, commonly with a characteristic shape and unlike any organ of the normal plant. Plant tumors or galls usually form in response to the action of a pathogen or a pest. (Holliday, P., A Dictionary of Plant Pathology, 1989, p330) Crown Gall,Galls, Plant,Plant Galls,Crown Galls,Gall, Crown,Gall, Plant,Galls, Crown,Plant Gall,Plant Tumor,Tumor, Plant,Tumors, Plant
D010946 Plants, Medicinal Plants whose roots, leaves, seeds, bark, or other constituent parts possess therapeutic, tonic, purgative, curative or other pharmacologic attributes, when administered to man or animals. Herbs, Medicinal,Medicinal Herbs,Healing Plants,Medicinal Plants,Pharmaceutical Plants,Healing Plant,Herb, Medicinal,Medicinal Herb,Medicinal Plant,Pharmaceutical Plant,Plant, Healing,Plant, Medicinal,Plant, Pharmaceutical,Plants, Healing,Plants, Pharmaceutical
D001943 Breast Neoplasms Tumors or cancer of the human BREAST. Breast Cancer,Breast Tumors,Cancer of Breast,Breast Carcinoma,Cancer of the Breast,Human Mammary Carcinoma,Malignant Neoplasm of Breast,Malignant Tumor of Breast,Mammary Cancer,Mammary Carcinoma, Human,Mammary Neoplasm, Human,Mammary Neoplasms, Human,Neoplasms, Breast,Tumors, Breast,Breast Carcinomas,Breast Malignant Neoplasm,Breast Malignant Neoplasms,Breast Malignant Tumor,Breast Malignant Tumors,Breast Neoplasm,Breast Tumor,Cancer, Breast,Cancer, Mammary,Cancers, Mammary,Carcinoma, Breast,Carcinoma, Human Mammary,Carcinomas, Breast,Carcinomas, Human Mammary,Human Mammary Carcinomas,Human Mammary Neoplasm,Human Mammary Neoplasms,Mammary Cancers,Mammary Carcinomas, Human,Neoplasm, Breast,Neoplasm, Human Mammary,Neoplasms, Human Mammary,Tumor, Breast
D004354 Drug Screening Assays, Antitumor Methods of investigating the effectiveness of anticancer cytotoxic drugs and biologic inhibitors. These include in vitro cell-kill models and cytostatic dye exclusion tests as well as in vivo measurement of tumor growth parameters in laboratory animals. Anticancer Drug Sensitivity Tests,Antitumor Drug Screens,Cancer Drug Tests,Drug Screening Tests, Tumor-Specific,Dye Exclusion Assays, Antitumor,Anti-Cancer Drug Screens,Antitumor Drug Screening Assays,Tumor-Specific Drug Screening Tests,Anti Cancer Drug Screens,Anti-Cancer Drug Screen,Antitumor Drug Screen,Cancer Drug Test,Drug Screen, Anti-Cancer,Drug Screen, Antitumor,Drug Screening Tests, Tumor Specific,Drug Screens, Anti-Cancer,Drug Screens, Antitumor,Drug Test, Cancer,Drug Tests, Cancer,Screen, Anti-Cancer Drug,Screen, Antitumor Drug,Screens, Anti-Cancer Drug,Screens, Antitumor Drug,Test, Cancer Drug,Tests, Cancer Drug,Tumor Specific Drug Screening Tests
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000972 Antineoplastic Agents, Phytogenic Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. Antineoplastics, Botanical,Antineoplastics, Phytogenic,Agents, Phytogenic Antineoplastic,Botanical Antineoplastics,Phytogenic Antineoplastic Agents,Phytogenic Antineoplastics
D012639 Seeds The encapsulated embryos of flowering plants. They are used as is or for animal feed because of the high content of concentrated nutrients like starches, proteins, and fats. Rapeseed, cottonseed, and sunflower seed are also produced for the oils (fats) they yield. Diaspores,Elaiosomes,Embryos, Plant,Plant Embryos,Plant Zygotes,Zygotes, Plant,Diaspore,Elaiosome,Embryo, Plant,Plant Embryo,Plant Zygote,Seed,Zygote, Plant
D014407 Tumor Cells, Cultured Cells grown in vitro from neoplastic tissue. If they can be established as a TUMOR CELL LINE, they can be propagated in cell culture indefinitely. Cultured Tumor Cells,Neoplastic Cells, Cultured,Cultured Neoplastic Cells,Cell, Cultured Neoplastic,Cell, Cultured Tumor,Cells, Cultured Neoplastic,Cells, Cultured Tumor,Cultured Neoplastic Cell,Cultured Tumor Cell,Neoplastic Cell, Cultured,Tumor Cell, Cultured
D015107 4-Butyrolactone One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent. 1,4-Butanolide,4-Hydroxybutyric Acid Lactone,Furanone, tetrahydro-2-,gamma-Butyrolactone,Dihydro-2(3H)-furanone,1,4 Butanolide,4 Butyrolactone,4 Hydroxybutyric Acid Lactone,Furanone, tetrahydro 2,Lactone, 4-Hydroxybutyric Acid,gamma Butyrolactone

Related Publications

M J Rieser, and Z M Gu, and X P Fang, and L Zeng, and K V Wood, and J L McLaughlin
Three new anti-proliferative Annonaceous acetogenins with mono-tetrahydrofuran ring from graviola fruit (Annona muricata).
June 2014, Bioorganic & medicinal chemistry letters,
M J Rieser, and Z M Gu, and X P Fang, and L Zeng, and K V Wood, and J L McLaughlin
Two new mono-tetrahydrofuran ring acetogenins, annomuricin E and muricapentocin, from the leaves of Annona muricata.
April 1998, Journal of natural products,
M J Rieser, and Z M Gu, and X P Fang, and L Zeng, and K V Wood, and J L McLaughlin
Muricoreacin and murihexocin C, mono-tetrahydrofuran acetogenins, from the leaves of Annona muricata.
September 1998, Phytochemistry,
M J Rieser, and Z M Gu, and X P Fang, and L Zeng, and K V Wood, and J L McLaughlin
Cytotoxic mono-tetrahydrofuran ring acetogenins from leaves of Annona montana.
December 2001, Planta medica,
M J Rieser, and Z M Gu, and X P Fang, and L Zeng, and K V Wood, and J L McLaughlin
Five new monotetrahydrofuran ring acetogenins from the leaves of Annona muricata.
November 1996, Journal of natural products,
M J Rieser, and Z M Gu, and X P Fang, and L Zeng, and K V Wood, and J L McLaughlin
Annonaceous acetogenins of the seeds from Annona muricata.
January 2001, Journal of Asian natural products research,
M J Rieser, and Z M Gu, and X P Fang, and L Zeng, and K V Wood, and J L McLaughlin
Four mono-tetrahydrofuran ring acetogenins, montanacins B-E, from Annona montana.
August 2000, Chemical & pharmaceutical bulletin,
M J Rieser, and Z M Gu, and X P Fang, and L Zeng, and K V Wood, and J L McLaughlin
New adjacent Bis-tetrahydrofuran Annonaceous acetogenins from Annona muricata.
March 2003, Planta medica,
M J Rieser, and Z M Gu, and X P Fang, and L Zeng, and K V Wood, and J L McLaughlin
Novel cytotoxic annonaceous acetogenins from Annona muricata.
July 2001, Journal of natural products,
M J Rieser, and Z M Gu, and X P Fang, and L Zeng, and K V Wood, and J L McLaughlin
Bioactive single-ring acetogenins from seed extracts of Annona muricata.
February 1993, Planta medica,
Copied contents to your clipboard!