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1.
Chem Pharm Bull (Tokyo) ; 37(11): 2991-4, 1989 Nov.
Article in English | MEDLINE | ID: mdl-2632044

ABSTRACT

Three new quassinoids, javanicins A, C and D, were isolated from the bark of Picrasma javanica (Simaroubaceae). The structures were established on the basis of spectroscopic data and chemical evidence.


Subject(s)
Glaucarubin/analogs & derivatives , Glaucarubin/analysis , Phenanthrenes/analysis , Plants, Medicinal/analysis , Quassins , Chemical Phenomena , Chemistry , Indonesia , Molecular Conformation , Plant Extracts
2.
J Nat Prod ; 52(2): 398-401, 1989.
Article in English | MEDLINE | ID: mdl-2746262

ABSTRACT

Yadanziosides M [3] and P [1] were isolated from Brucea antidysenterica. Their structures were elucidated by spectral data. Bruceantinoside B reported previously was reinvestigated and revealed to be a mixture of yadanzioside P and bruceantinoside C [2]. The structure of yadanzioside P was found to be identical to that of bruceantinoside B.


Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Glaucarubin/isolation & purification , Phenanthrenes/isolation & purification , Quassins , Antineoplastic Agents, Phytogenic/analysis , Glaucarubin/analogs & derivatives , Glaucarubin/analysis , Magnetic Resonance Spectroscopy
5.
J Nat Prod ; 49(3): 440-4, 1986.
Article in English | MEDLINE | ID: mdl-3760884

ABSTRACT

Two new quassinoids, 13, 18-dehydro-6 alpha-senecioyloxychaparrin (4) and 12-dehydro-6 alpha-senecioyloxychaparrin (5), have been isolated from Simaba multiflora fruits. Their structures were deduced from spectral data. 1H-13C 2-D chemical-shift correlation nmr was applied to the structural elucidation of the antileukemic quassinoid 4.


Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Glaucarubin/isolation & purification , Phenanthrenes/isolation & purification , Plants, Medicinal/analysis , Quassins , Animals , French Guiana , Glaucarubin/analogs & derivatives , Glaucarubin/analysis , Glaucarubin/pharmacology , Leukemia, Experimental/drug therapy , Magnetic Resonance Spectroscopy , Mice
7.
Anal Biochem ; 136(1): 145-56, 1984 Jan.
Article in English | MEDLINE | ID: mdl-6711803

ABSTRACT

A microtitration plate enzyme-linked immunosorbent assay has been developed for quassin and closely related seco-triterpenes. The method is much more sensitive than conventional chromatographic techniques and enables the routine analysis of large numbers of samples with a detection limit of 5 ng quassin. Antibody production was elicited by injecting a conjugate of iso-quassinic acid linked to bovine serum albumin into rabbits. Important features of the technique are (a) the use of a double-antibody, noncompetitive enzyme-linked immunosorbent assay for a low-molecular-weight, nonantigenic compound using microtitration plates; and (b) that the initial incubation of samples with primary antiserum can be carried out in buffer containing up to 20% (v/v) methanol with minimal loss of sensitivity. The structural requirements for recognition of the hapten by the antiserum are considered based on the levels of cross-reaction found with a wide range of other quassinoids.


Subject(s)
Glaucarubin/analysis , Phenanthrenes/analysis , Quassins , Chemical Phenomena , Chemistry , Cross Reactions , Enzyme-Linked Immunosorbent Assay/methods , Glaucarubin/analogs & derivatives , Methanol
8.
J Pharm Sci ; 72(11): 1282-4, 1983 Nov.
Article in English | MEDLINE | ID: mdl-6417321

ABSTRACT

A series of quassinoids were observed to be potent inhibitors of induced inflammation and arthritis in rodents. Brusatol afforded the most potent activity followed by brucein-D. A 3-hydroxy-delta 3-2-oxo moiety in brusatol or a 1-hydroxy-delta 3-2-oxo moiety in brucein-D, as well as a C-15 ester-bearing delta-lactone ring in brusatol and C-11 and C-12 free hydroxyl groups are required in both quassinoids for potent anti-inflammatory activity. Preliminary studies indicate that one of the modes of action of quassinoids as anti-inflammatory agents is to stabilize lysosomal membranes, reducing the release of hydrolytic enzymes that cause damage to surrounding tissues.


Subject(s)
Anti-Inflammatory Agents/pharmacology , Glaucarubin/pharmacology , Phenanthrenes/pharmacology , Quassins , Animals , Arthritis, Experimental/drug therapy , Glaucarubin/analogs & derivatives , Glaucarubin/analysis , Liver/enzymology , Lysosomes/enzymology , Male , Mice , Oxidative Phosphorylation/drug effects , Prostaglandin-Endoperoxide Synthases/metabolism , Rats , Rats, Inbred Strains , Structure-Activity Relationship
9.
J Nat Prod ; 44(3): 279-84, 1981.
Article in English | MEDLINE | ID: mdl-7264678

ABSTRACT

The structure of soularubinone 3, a new antileukemic quassinoid isolated from the leaves of Soulamea tomentosa (Brongn, and Gris), has been established by spectral and chemical methods. It has been shown to be the C-15 beta-hydroxy-isovaleric ester of glaucarubolone. Soularubinone shows significant antineoplastic activity against mouse leukemia P-388 and inhibits cell transformation induced by Rous sarcoma virus. The known quassinoid chaparrinone I has also been isolated.


Subject(s)
Antineoplastic Agents, Phytogenic/analysis , Glaucarubin/analysis , Phenanthrenes/analysis , Quassins , Animals , Cell Transformation, Neoplastic/drug effects , Chemical Phenomena , Chemistry, Physical , Glaucarubin/analogs & derivatives , Glaucarubin/pharmacology , Leukemia P388/drug therapy , Magnetic Resonance Spectroscopy , Mice
10.
J Nat Prod ; 43(4): 503-9, 1980.
Article in English | MEDLINE | ID: mdl-7431025

ABSTRACT

The South American Simaba cuspidata Spruce and North Indian Ailanthus grandis Prain were investigated as sources of potentially useful antineoplastic agents. Both of these Simaroubaceae plant species were found to produce 6 alpha-tigloyloxychaparrinone (4a) and the new quassinoid 6 alpha-tigloyloxychaparrin (3b). The latter structure was determined by interpretation of spectral data and oxidation to 6 alpha-tigloyloxychaparrinone (4a). While both glycol 3b and alpha-ketol 4a were found to significantly inhibit growth of the murine P388 lymphocytic leukemia cell line, only the alpha-ketol (4a) inhibited growth of the corresponding in vivo system.


Subject(s)
Antineoplastic Agents, Phytogenic/analysis , Lactones/analysis , Phenanthrenes/analysis , Plants, Medicinal/analysis , Quassins , Animals , Chemical Phenomena , Chemistry , Glaucarubin/analogs & derivatives , Glaucarubin/analysis , Glaucarubin/pharmacology , Leukemia P388/drug therapy , Mice , Oxidation-Reduction
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