scispace - formally typeset

Journal ArticleDOI

(−)-Maglifloenone, a novel spirocyclohexadienone neolignan and other constituents from Magnolia liliflora

01 Jan 1982-Phytochemistry (Pergamon)-Vol. 21, Iss: 3, pp 747-750

TL;DR: This is the first report of two neolignans of spirocyclohexadienone skeleton and of taspine from the Magnoliaceae family and the second report of the natural occurrence of futoenone.

AbstractA new neolignan designated (−)-maglifloenone and the known one futoenone, both of which contain the rarely occurring spirocyclohexadienone skeleton, have been isolated together with the tetrahydrofuranolignan (+)-veraguensin, an optically inactive tertiary base taspine and β-sitosterol from the leaves and twigs of Magnolia liliflora. The structure and stereochemistry of (−)-maglifloenone have been deduced from the spectral data and the mass fragmentation of (−)-maglifloenone and futoenone have been rationalized. This is the first report of two neolignans of spirocyclohexadienone skeleton and of taspine from the Magnoliaceae family and the second report of the natural occurrence of futoenone.

...read more


Citations
More filters
Journal ArticleDOI
TL;DR: The results obtained in this study support the role of essential oil and the leaf extracts derived from M. liliflora as a remarkable approach to inhibit the growth of food spoilage and foodborne pathogens.
Abstract: The aim of this study was to examine the chemical composition of the essential oil isolated from the floral parts of Magnolia liliflora Desr. by hydrodistillation, and to test the efficacy of essential oil and various leaf extracts against a diverse range of microorganisms comprising food spoilage and foodborne pathogenic bacteria. The chemical composition of essential oil was analyzed by GC-MS. It was determined that 52 compounds, which represented 78.07% of total oil, were present in the oil. The oil contained mainly levoxine (15.59%), methylcyclopropane (24.26%), 2-beta-pinene (5.3%), caryophyllene oxide (4.01%), and beta-caryophyllene (1.7%). The oil (1000 ppm/disc) and leaf extracts (1500 ppm/disc) exhibited promising antibacterial effects against the tested pathogens as a diameter of zones of inhibition (9 to 18 and 7 to 12 mm) and MIC values (125 to 1000 and 500 to 3000 microg/mL), respectively. Also, the oil had a potent detrimental effect on the viable count of the tested bacteria. The results obtained in this study support the role of essential oil and the leaf extracts derived from M. liliflora as a remarkable approach to inhibit the growth of food spoilage and foodborne pathogens.

75 citations

Patent
06 Jan 1995
Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i.e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase. Also disclosed is a method to treat disorders mediated by PAF and/or leukotrienes that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier, to a patient in need of such therapy.

46 citations

Journal ArticleDOI
TL;DR: Members of the Annonaceae have the particularity to elaborate a broad spectrum of natural products that have displayed anti-bacterial, anti-fungal, and anti-protozoal effects and have been used for the treatment of medical conditions, such as skin diseases, intestinal worms, inflammation of the eyes, HIV, and cancer.
Abstract: One of the rich sources of lead compounds is the Angiosperms. Many of these lead compounds are useful medicines naturally, whereas others have been used as the basis for synthetic agents. These are potent and effective compounds, which have been obtained from plants, including anti-cancer (cytotoxic) agents, anti-malaria (anti-protozoal) agents, and anti-bacterial agents. Today, the number of plant families that have been extensively studied is relatively very few and the vast majorities have not been studied at all. The Annonaceae is the largest family in the order Magnoliales. It includes tropical trees, bushes, and climbers, which are often used as traditional remedies in Southeast Asia. Members of the Annonaceae have the particularity to elaborate a broad spectrum of natural products that have displayed anti-bacterial, anti-fungal, and anti-protozoal effects and have been used for the treatment of medical conditions, such as skin diseases, intestinal worms, inflammation of the eyes, HIV, and cancer. These special effects and the vast range of variation in potent compounds make the Annonaceae unique from other similar families in the Magnoliales and the Angiosperms in general. This paper attempts to summarize some important information and discusses a series of hypotheses about the effects of Annonaceae compounds.

36 citations

Patent
24 Aug 1992
Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes, 2,4-diaryl pyrrolidines, and 2,5-diaryl pyrrolidines are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i.e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase. A method to treat disorders mediated by PAF or leukotrienes is also disclosed, that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.

35 citations

Journal ArticleDOI
Abstract: A chloroform extract of fresh leaves of Magnolia liliflora contained the four new phenolic neolignans, liliflodione [a bicyclo(3,2,1)octanoid], liliflol A and B (dihydrobenzofuranoids) and liliflone (a hexahydrobenzofuranoid), along with seven known neolignans. The absolute structures of the new compounds were elucidated by means of chemical and spectral studies.

29 citations


References
More filters
Journal ArticleDOI
TL;DR: Pharmacological properties of the extracts from the magnolia cortex (the bark of Magnolia obovata THUNB.) were examined with special reference to their central nervous system action.
Abstract: Pharmacological properties of the extracts from the magnolia cortex (the bark of Magnolia obovata THUNB.) were examined with special reference to their central nervous system action. The ether extract of the magnolia (1g/kg i.p.) markedly depressed the spontaneous activity of mice and chicks, while the water extract (1g/kg i.p.) procuced prompt paralysis of respiration. Distinct muscle weakness was found after administraction of the ether extract, through the clinging power test on the wire net, and was different from the effect of the water extract. The ether extract supressed convulsion produced by strychnine, picrotoxin, or pentetrazol. Tremor by oxotremorine was also blocked by the ether extract. Pentetrazol infusion technique was employed for the elucidation of the mode of this drug action. Depressive effect of the ether extract was also exerted on the crossed extensor reflex of the chick spinal cord.

19 citations

Journal ArticleDOI
Abstract: Three uncommon lignans calopiptin ( 1 ), galgravin ( 2 ) and veraguensin ( 3 ) were isolated from M. acuminata root-bark, along with a novel bis -phenylpropide, acuminatin ( 4 ) which was characterized by physical and chemical methods.

19 citations

Journal ArticleDOI
Abstract: The α,α?-diaryl-β,β-dimethyltetrahydrofurenoid lignan, calopiptin, from Piptocalyx moorei has been converted by demethylenation and methylation into veraguensin, now also isolated from Trimenia papuana (both species, family Trimeniaceae). Ozonolysis yields (-)-2,3-dimethylsuocinic acid which establishes the absolute trans configuration of the methyl groups. The benzylic proton giving a signal at low field from the other in the p.m.r, spectrum is assigned as trans to the adjacent methyl group by shielding and spin-decoupling arguments. The signal moves to even lower field on nitration of one of the aryl groups, identified as 3,4-dimethoxyphenyl by competitive nitration experiments and high-resolution mass spectrometry. Calopiptin is 2R-(3,4-dimethoxyphenyl)-3S,4S-dimethyl-5S-(3,4-methylenedioxyphenyl)tetrahydrofuran.

14 citations