Chemical investigation of a sample of propolis originating from North-Western Cameroon led to the isolation of thirteen alk(en)ylphenols (1-13) (inseparable mixture) along with α-amyrin (14), β-amyrin (15), lupeol (16), cycloartenol (17), mangiferonic acid (18), ambonic acid (19), mangiferolic acid (20), ambolic acid (21), isomangiferolic acid (22) and nine alk(en)ylresorcinols (23-31) (inseparable mixture). All compounds were identified following analysis of their spectroscopic data and comparison with previously published reports. Compounds (8), (12), (13) and (30) are new natural products. GC-MS analysis carried out on the alk(en)ylphenol and alk(en)ylresorcinol mixtures (dimethyl disulphide trimethylsilyl derivatives) revealed the presence of saturated and mono-unsaturated compounds with side chain lengths ranging from C11 to C19 and C15 to C19, respectively. The position of the double bond in mono-unsaturated derivatives was established from the characteristic fragments resulting from the cleavage of the bond between the two methylthio-substituted carbons. The most abundant compound in each mixture was 3-(12'Z-heptadecenyl)-phenol (10) and 5-(12'Z-heptadecenyl)-resorcinol (29). This study is the first to report the presence of triterpenes (except for lupeol) and phenolic lipids, including eighteen compounds previously unreported in bee glue, in an African sample.
A new obtusafuran derivative, lawsonicin (1), and a new naphthaquinone, lawsonadeem (2), along with a known constituent, vomifoliol (3), were isolated from the aerial parts of Lawsonia alba and characterized by chemical transformation and spectroscopic experiments, including 2D‐NMR techniques.
Studies on the chemical constituents of the flowers of Azadirachta indica have led to the isolation of two new flavanones, flowerine (=5‐hydroxy‐7,4′‐dimethoxy‐8‐(3‐methylbut‐2‐enyl)flavan‐4‐one; 1) and flowerone (=5,7,8,4′‐tetrahydroxy‐3′‐(3‐methylbut‐3‐enyl)flavan‐4‐one; 2), and two new triterpenoids, O‐methylazadironolide (=7α‐(acetoxy)‐23ξ‐methoxy‐21,23‐epoxy‐24,25,26,27‐tetranorapotirucalla‐1,14,20(22)‐trien‐3,21‐dione; 3) and diepoxyazadirol (=(20S,23S,24R)‐7‐α‐(acetoxy)‐25‐hydroxy‐21,24 : 23,24‐diepoxyapotirucalla‐1,14‐dien‐3‐one; 4) along with the known triterpenoid trichilenone acetate (=7α‐(acetoxy)‐14,15 : 21,23‐diepoxy‐24,25,26,27‐tetranorapotirucalla‐1,20,22‐trien‐3‐one; 5), two known flavanones, nimbaflavone (=5,7‐dihydroxy‐4′‐methoxy‐8,3′‐bis(3‐methylbut‐2‐enyl)‐flavan‐4‐one; 6) and 3′‐prenylnaringenin (=5,7,4′‐trihydroxy‐3′‐(3‐methylbut‐2‐enyl) flavan‐4‐one; 7), and 4‐(2‐hydroxyethyl)phenol (8). Their structures have been elucidated through spectral studies, including 2D‐NMR experiments, and chemical transformation. Compounds 5, 7 and 8 are heretofore unreported from any part of tree, while 6 has been isolated earlier from leaves.
From the fruit coats of the medicinal plant Madhuca latifolia were isolated three new compounds, the triterpenoid madhucic acid ( 3b-(octanoyloxy)-11-oxoolean-12-en-28-oic acid; 1), the untypical isoflavone madhushazone ( 9-methoxy-7-(2,3,6-trimethoxyphenyl)- [1,3]dioxolo [4,5-g][1]benzopyran-8(8H)-one; 2), and a bis(isoflavone) named madhusalmone ( 5,14-dimethoxy-3,12-bis(3,4,5-trimethoxyphenyl)-1,6,8,10,15,17-hexaoxanaphtho[2',3': 6,7]cyclodeca[1,2-b]naphthalene-4,13(4H,13H)-dione; 3), as well as eight known constituents, and their structures were elucidated by spectral analysis, including 2D-NMR techniques.Introduction. ± Madhuca latifolia Syn. M. indica (Sapotaceae) is an important economic plant growing throughout the subtropical region of the Indo-Pak subcontinent [1]. The medicinal properties attributed to this plant are stimulant, demulcent, emollient, heating, and astringent [2]. The bark is a good remedy for itch, swellings, fractures, and snake-bite poisoning, internally employed in diabetes mellitus with much benefit [3]. Mahua oil is used for the treatment of skin diseases, rheumatism, headache, and as a laxative. Fruits are astringent and largely employed as a lotion in chronic ulcer, in acute and chronic tonsillitis and pharyngitis. . In view of the attributed medicinal properties, we investigated the fruit coats of M. indica, which resulted in the isolation and characterization of three new constituents: madhucic acid (1), a pentacyclic triterpenoid, madhushazone (2), an untypical isoflavone, and madhusalmone (3), a bis(isoflavone). Moreover, eight known constituents were isolated and identified by comparison of their physical and spectral data with those reported in the literature. These included b-amyrin acetate, hitherto unreported b-amyrin caprylate, 3b-(capryloxy)ursolic acid, a hydrocarbon (C 29 H 60 ), a triglyceride of palmito-dioleins, and three monoglycerides of stearic, oleic, and arachidic acid, respectively. These glycerides have previously been found in solid seed fats of the same species [15].
Studies on the chemical constituents of the flowers of Azadirachta indica have led to the isolation of two new flavanones, flowerine ( 5-hydroxy-7,4'-dimethoxy-8-(3-methylbut-2-enyl)flavan-4-one; 1) and flowerone ( 5,7,8,4'-tetrahydroxy-3'-(3-methylbut-3-enyl)flavan-4-one; 2), and two new triterpenoids, O-methylazadironolide ( 7a-(acetoxy)-23x-methoxy-21,23-epoxy-24,25,26,27-tetranorapotirucalla-1,14,20(22)-trien-3,21-dione; 3) and diepoxyazadirol ( (20S,23S,24R)-7-a-(acetoxy)-25-hydroxy-21,24 : 23,24-diepoxyapotirucalla-1,14-dien-3-one; 4) along with the known triterpenoid trichilenone acetate ( 7a-(acetoxy)-14,15 : 21,23-diepoxy-24,25,26,27-tetranorapotirucalla-1,20,22-trien-3-one; 5), two known flavanones, nimbaflavone ( 5,7-dihydroxy-4'-methoxy-8,3'-bis(3-methylbut-2-enyl)-flavan-4-one; 6) and 3'-prenylnaringenin ( 5,7,4'-trihydroxy-3'-(3-methylbut-2-enyl) flavan-4-one; 7), and 4-(2-hydroxyethyl)phenol (8). Their structures have been elucidated through spectral studies, including 2D-NMR experiments, and chemical transformation. Compounds 5, 7 and 8 are heretofore unreported from any part of tree, while 6 has been isolated earlier from leaves.
A new obtusafuran derivative, lawsonicin (1), and a new naphthaquinone, lawsonadeem (2), along with a known constituent, vomifoliol (3), were isolated from the aerial parts of Lawsonia alba and characterized by chemical transformation and spectroscopic experiments, including 2D-NMR techniques.
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