Cytotoxic polyisoprenes and glycosides of long-chain fatty alcohols from Dimocarpus fumatus

Voutquenne, Laurence; Lavaud, Catherine; Massiot, Georges; Sévenet, Thierry; Hadi, Hamid A.

doi:10.1016/s0031-9422(98)00483-x

Cited by 84 publications

(38 citation statements)

References 16 publications

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“…Twelve known compounds, morelloflavone (1) (Li et al, 2002), morelloflavone-7"-sulphate (2) (Li et al, 2002), guttiferone A (3) (Gustafson et al, 1992), sargaol (2-geranyl-6-hydroxy-2,8-dimethylchromene) (4) (Numuta et al, 1992;Voutquenne et al, 1999), isojacareubin (5) (Helesbeux et al, 2004), 6-deoxyisojacareubin (6) (Ishiguro et al, 1993) and the common triterpenoids, betulin, betulin aldehyde, lupeol, lupenone, euphol and stigmasterol were isolated in this investigation The structures of the isolated compounds were established using NMR spectroscopy and mass spectrometry and by comparison against literature data as referenced above.…”

Section: Resultsmentioning

confidence: 99%

Non-toxic melanin production inhibitors from Garcinia livingstonei (Clusiaceae)

Mulholland

Mwangi

Dlova³

et al. 2013

Journal of Ethnopharmacology

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Section: Resultsmentioning

confidence: 99%

Non-toxic melanin production inhibitors from Garcinia livingstonei (Clusiaceae)

Mulholland

Mwangi

Dlova³

et al. 2013

Journal of Ethnopharmacology

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“…(0.0010%), L-phenylalanine 37) (0.0018%), thymidine 37) (0.0026%), and sitosterol 3b-O-b-D-glucopyranoside 29,38) (0.0046%). The EtOAc-soluble fraction was also subjected to normal-phase and reversed-phase silica gel column chromatography and repeated HPLC to give apigenin 23) (3, 0.0021%), luteolin 23) (7, 0.0069%), quercetin 23) (13, 0.0060%), (ϩ)-pinoresinol 39) (16, 0.0004%), (ϩ)-syringaresinol 40) (18, 0.0004%), (Ϫ)-secoisolariciresinol 41) (20, 0.0007%), (Ϫ)-arctigenin 27) (21, 0.038%), 22 (0.054%), 3-methoxy-4-hydroxyphenylethanol 42) (0.0021%), (Ϫ)-2-oxoisodauc-5-en-12-al 43) (0.0002%), (ϩ)-glutinol 44) (0.0006%), a-amyrin 45) (0.0086%), lupeol 45) (0.0074%), clionasterol 46) (0.0026%), azelaic acid 37) (0.0024%), linolenic acid 37) (0.027%), linoleic acid 37) (0.065%), oleic acid 37) (0.0093%), hexadecanoic acid 37) (0.075%), octadecanoic acid 37) (0.0092%), eicosanoic acid 37) (0.0028%), docosanoic acid 37) (0.0025%), tricosanoic acid 37) (0.0007%), and eicosanol 37) (0.0011%).…”

mentioning

confidence: 99%

Bioactive Constituents from Chinese Natural Medicines. XV. Inhibitory Effect on Aldose Reductase and Structures of Saussureosides A and B from Saussurea medusa

et al. 2005

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The Compositae plant, Saussurea medusa MAXIM., is a rare perennial medicinal herb growing in the northwestern parts of China (e.g., Tibet, Xinjiang, Qinghai, Gansu, Yunnan, and Sichuan provinces). The whole plant or aerial parts of S. medusa, popularly known as "Xuelianhua ( )", has been commonly used in both traditional Chinese medicine and Tibetan folk medicine as a remedy for rheumatic arthritis, menoxenia, gynopathy, traumatic bleeding, and headache.2-4) Several lignan, neolignan, flavonoid, terpenoid, and chlorophyll constituents have previously been isolated from S. medusa [5][6][7][8][9][10] and their pharmacologic activities such as anti-tumor-promoting, 5) immunosuppressive 6) and cellprotecting activities 7) were also reported. In the course of our studies on bioactive constituents from Chinese natural medicines, [11][12][13][14][15][16][17] we found that the 80% aqueous acetone extract from the whole plant of S. medusa showed a potent inhibitory effect on rat lens aldose reductase (IC 50 ϭ1.4 mg/ml). In this paper, we report the isolation and structure elucidation of two new megastigmane glycosides, saussureosides A (1) and B (2), together with 13 flavonoids (3-15), four lignans (16)(17)(18)(19) and three neolignans (20)(21)(22), three quinic acids (23-25), and 24 other known constituents.The 80% aqueous acetone extract from the whole plant of S. medusa was partitioned into an EtOAc-H 2 O (1 : 1, v/v) mixture to furnish the EtOAc-soluble fraction and aqueous layer. The aqueous layer was extracted with n-butanol (n-BuOH) to give n-BuOH and H 2 O-soluble fractions. The n-BuOH-soluble fraction, which was the most active fraction (IC 50 ϭ0.8 mg/ml), was subjected to normal-phase and reversed-phase silica gel column chromatography and repeated HPLC to give saussureosides A (1, 0.0007%) and B (2, 0.0038%), apigenin (0.0011%). Structure of Saussureosides A (1) and B (2) Saussureoside A (1) was isolated as a white powder with negative optical rotation ([a] D 24 Ϫ45.0°). In the UV spectrum of 1, an absorption maximum was observed at 229 (log e 4.07) nm, while the IR spectrum of 1 showed absorption bands at 1684, 1671, and 1260 cm Ϫ1 assignable to a,b-unsaturated carbonyl, olefin, and epoxide functions and strong absorption bands at 3410 and 1078 cm Ϫ1 suggestive of a glycoside moiety. In the positive-ion FAB-MS of 1, a quasimolecular ion peak was observed at m/z 425 (MϩNa) The 80% aqueous acetone extract from the whole plant of Saussurea medusa MAXIM. was found to inhibit rat lens aldose reductase (IC 50 ‫4.1؍‬ m mg/ml). From this extract, flavonoids, lignans, and quinic acid derivatives were isolated together with two new ionone glycosides, saussureosides A and B. Their absolute stereostructures were elucidated on the basis of chemical and physicochemical evidence including the application of modified Mosher's method. In addition, some isolates were found to show an inhibitory effect on aldose reductase.

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“…Compounds 2-6 were identified by interpretation of their spectral data, mainly FAB-MS and 2D-NMR (COSY, NOESY, HMBC, HMQC), as well by comparison with literature data as soyacerebroside I (2), 15) adenosine (3), 16) b-sitosterol (4), 17) palmitic acid (5), 16) and 1-O-palmitoyl-2-Ooleoyl-glycero-3-phosphocholine or 1-O-oleoyl-2-O-palmitoyl-glycero-3-phosphocholine (6), 13) respectively. Soyacerebroside I (2) has been previously isolated from Glycine max (Leguminoseae), 18) Prunus jamasakura (Rosaceae), 19) and Dimocarpus fumatus and Longan arillus (Sapindaceae).…”

Section: A New Phenanthrene Glycoside and Other Constituents From Diomentioning

confidence: 99%

“…Soyacerebroside I (2) has been previously isolated from Glycine max (Leguminoseae), 18) Prunus jamasakura (Rosaceae), 19) and Dimocarpus fumatus and Longan arillus (Sapindaceae). 15,20) Plant cerebrosides are of interest because they have been shown to be cytotoxic, 21) anti-ulcerogenic, 22) and hepatoprotective. 23) To our knowledge, the isolation of 2 from Dioscorea opposita is the first account of the isolation of a cerebroside from the Dioscoreaceae family.…”

Section: A New Phenanthrene Glycoside and Other Constituents From Diomentioning

confidence: 99%