Ecdysteroids from Leuzea carthamoides

Girault, Jean‐Pierre; Lafont, René; Varga, E.; Hajdú, Zoltán; Herke, Ibolya; Szendrei, K.

doi:10.1016/0031-9422(88)84085-8

Cited by 51 publications

(31 citation statements)

References 11 publications

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“…The double quantum filter correlation spectroscopy (DQF COSY) experiment on 1 indicated the presence of partial structures written in bold lines (Fig. 1), and in the heteronuclear multiple bond connectivity spectroscopy (HMBC) experiment, long-range correlations were observed between the following protons and carbons: H-12 and C-9, 14, 18; H- 25) except for the signals due to the terminal side chain part (C-25-C-27), while the proton and carbon signals due to the glycoside moiety were superimposable on those of ecdysterone 25-O-b-D-glucopyranoside. 24 Inhibitory Effects of Constituents on Melanogenesis in B16 Melanoma 4A5 Cells Melanin production is principally responsible for skin color, and melanin pigmentation is a major defense mechanism against ultraviolet rays from the sun.…”

Section: )mentioning

confidence: 99%

Brazilian Natural Medicines. IV. New Noroleanane-Type Triterpene and Ecdysterone-Type Sterol Glycosides and Melanogenesis Inhibitors from the Roots of Pfaffia glomerata

et al. 2010

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The Amaranthaceae plant, Pfaffia (P.) glomerata, which is so-called as Brazil ginseng in Japan, is widely cultivated in South American countries such as Brazil, Ecuador, and Panama. The roots of this plant are used as a Brazilian folk medicine for a tonic and treatment of diabetes. The extract from the roots of P. glomerata has been reported to possess gastroprotective, 2) anti-oxidant, 3) and anti-inflammatory effects.4) On the other hand, ecdysterone has been characterized as the principal constituent from the roots.5,6) However, chemical and pharmacological studies on the roots of P. glomerata have not been investigated sufficiently yet. During the course of characterization studies on the bioactive constituents of Brazilian natural medicines, 1,7-10) the ethyl acetate (EtOAc) and 1-butanol (1-BuOH) soluble fractions of the roots of P. glomerata were found to show inhibitory effects on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. From the EtOAc and 1-BuOH soluble fractions, we have isolated a new noroleanane-type triterpene, pfaffianol A (1), two new noroleanane-type triterpene glycosides, pfaffiaglycosides A (2) and B (3), and three ecdysterone-type sterol glycosides, pfaffiaglycosides C (4), D (5), and E (6), with eight known constituents. Furthermore, we examined the inhibitory effects of the fractions and principal constituents on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. In this paper, we describe the isolation and structure elucidation of the new constituents The ethyl acetate and 1-butanol soluble fractions of the roots of Pfaffia glomerata were found to show inhibitory effects on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. From the ethyl acetate and 1-butanol soluble fractions, we isolated a new noroleanane-type triterpene, pfaffianol A, its glycosides, pfaffiaglycosides A and B, and ecdysterone-type sterol glycosides, pfaffiaglycosides C, D, and E, together with eight known constituents. The structures of new constituents were determined on the basis of physicochemical and chemical evidence. Among them, pfaffianol A (IC 50 ‫؍‬ ‫44؍‬ m mM) and pfaffoside C (IC 50 ‫؍‬ ‫29؍‬ m mM) substantially inhibited melanogenesis without cytotoxic effects. The inhibitory effects were stronger than that of reference compound, arbutin (IC 50 ‫؍‬ ‫471؍‬ m mM).

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Section: )mentioning

confidence: 99%

Brazilian Natural Medicines. IV. New Noroleanane-Type Triterpene and Ecdysterone-Type Sterol Glycosides and Melanogenesis Inhibitors from the Roots of Pfaffia glomerata

et al. 2010

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“…Part of fraction E-3-2 (200 mg) was isolated and purified by pre-HPLC (pre-ODS, 15 × 250 mm, ACN-H 2 O, 15:85) to yield ecdysterone (2, 30 mg), 25-R inokosterone (3, 10 mg) and 25-S inokosterone (4, 12 mg). Their structures were elucidated by comparison of their spectral data (UV, MS, 1 H NMR and 13 C NMR) with literature values (Zhu et al, 2004;Coll et al, 1994;Giranlt et al, 1988). The structures were shown in Fig.…”

Section: Extraction and Isolation Of Phytoecdysones In Rabmentioning

confidence: 99%

Simultaneous qualitation and quantification of four phytoecdysones in Radix Achyranthis Bidentatae by high‐performance liquid chromatography with diode array detection

et al. 2007

Biomedical Chromatography

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A high-performance liquid chromatographic method with diode array detection was developed and validated to simultaneously identify and quantify four phytoecdysones,i.e., polypodine B (1), ecdysterone (2), 25-R inokosterone (3) and 25-S inokosterone (4), in Radix Achyranthis Bidentatae. The analysis was performed using a C(18) column with 6% tetrahydrofuran aqueous and acetonitrile isocratic elution, and the detection was carried out by DAD at 242 nm. The identities of the analytes were determined by comparing the retention time and UV spectrum with those of reference compounds. The validation of the method included linearity, sensitivity, recovery and stability. All calibration curves of the four phytoecdysones showed good linear regression (r(2) >or= 0.9993). The limit of detection (S/N = 3) and limit of quantification (S/N = 10) were less than 7.5 and 12.3 ng, respectively. The method provided desirable repeatability with overall intra- and inter-day variations of less than 4.67%. The obtained recoveries varied between 95.1 and 104.4% while the relative standard deviations were below 4.85% (n = 3). The analysis results indicated that the contents of the investigated phytoecdysones in Radix Achyranthis Bidentatae from different locations were highly variant, and the genuine crude drug indigenous to Henan province did not possess the highest concentration of phytoecdysones.

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“…5). The known compounds ajuforrestins A (3) and B (4) [8], 20-hydroxyecdysone (5) [9][10][11], polypodin B (6) [9,12], ajugalactone (7) [4], 8-O-acetylharpagid (8) [13,14], and N- [2-hydroxy-(nonadecanoyl-tricosanoyl)]-4-hydroxytrans-8-sphingenine (10) [5] were identified by their spectral data and by comparison with previously reported data. Apigenin (9), ␤-sitosterol (11), and daucosterol (12) were identified by their spectral data and by co-TLC with authentic samples.…”

Section: O-␤-d-glucopyranosyl-(2s3s4r 8e)-2-[(2r)-2-hydroxyh-mentioning

confidence: 99%

“…In order to find the active compounds of this folk medicine, a phytochemical investigation was carried out on the aqueous ethanolic extract of E. wallchii. This study led to the isolation of a new phytoecdysteroid 28-epi-cyasterone (1A), a new glycoceramide eriophytonoide (2), and 11 known compounds, cyasterone (1B), ajuforrestins A (3) and B (4), 20-hydroxyecdysone (5), polypodin B (6), ajugalactone (7), 8-O-acetylharpagid (8), apigenin (9), N- [2- (10), ␤-sitosterol (11), and daucosterol (12). Their structures were elucidated on the basis of spectral and chemical evidence.…”

Section: Introductionmentioning

confidence: 99%

Phytoecdysteroids and glycoceramides from Eriophyton wallchii

Luo

et al. 2004

Steroids

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Ecdysteroids from Leuzea carthamoides

Cited by 51 publications

References 11 publications

Brazilian Natural Medicines. IV. New Noroleanane-Type Triterpene and Ecdysterone-Type Sterol Glycosides and Melanogenesis Inhibitors from the Roots of Pfaffia glomerata

Brazilian Natural Medicines. IV. New Noroleanane-Type Triterpene and Ecdysterone-Type Sterol Glycosides and Melanogenesis Inhibitors from the Roots of Pfaffia glomerata

Simultaneous qualitation and quantification of four phytoecdysones in Radix Achyranthis Bidentatae by high‐performance liquid chromatography with diode array detection

Phytoecdysteroids and glycoceramides from Eriophyton wallchii

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