Oleanen and stigmasterol derivatives from Ambroma augusta

Alam, Mohammad Mahboob; Chopra, Neeraj; Ali, Mohammed; Niwa, Masayuki

doi:10.1016/0031-9422(95)00774-1

Cited by 74 publications

(51 citation statements)

References 6 publications

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“…1, 15.5, 16.8, 18.0, 23.4 and 18.4 were assigned to the methyl groups. The spectral data of compound 59 were in close Ombuna et al 691 agreement with those of 3β-sitosterol, whose structure is shown below (Alam et al, 1996).…”

Section: Compoundsupporting

confidence: 68%

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Stem bark extracts of Erythrina excelsa (BAK) and their biological activities

Ombuna¹,

Machocho²,

Keru³

et al. 2016

J. Med. Plants Res.

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The species is known from Southern Nyanza, Migori in Kenya. The extraction of the stem bark was done sequentially using organic solvents starting with the least polar; n-hexane then dichloromethane, ethyl acetate and finally the most polar methanol. Antibacterial and antifungal activities of the crude extract and that of isolated compounds from the stem bark of E. excelsa were investigated. The crude extracts had substantial activity against the tested micro-organisms. Methanol extract was highly active with inhibition zones of 15 mm against S. aureus and 14 mm against both B. subtillis and E. coli. Ethyl acetate and dichloromethane had mild activity. In antifungal test, methanol extract had highest activity of 15 mm against A. niger and 13 mm against C. albicans. Dichloromethane extract was also active with inhibition zones of 14 mm against A. niger and 12 mm against C. albicans while ethyl acetate had mild activity. A total of five compounds were isolated; glutinosalactone A (1), glutinosalactone B (2), lupinifolin (3), sitosterol (4) and 3β-stigimasterol (5). The compounds were active against the bacterial and fungal test strains used. Glutinosalactone A (1) had an activity of 15 mm against A. niger, 11 mm against both B. subtillis and S. aureas. Glutinosalactone B (2) had a high activity of 11 mm in both B. subtillis and C. albicans. and lupinifolin (3) had mild activity of 9 mm against both A. niger and C. albicans. Stigimasterol and sitosterol had mild activity of 8 mm against A. niger.

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Section: Compoundsupporting

confidence: 68%

“…Three signals at δ 36.1, 36.5 and 42.3 were associated with the three quaternary carbon atoms. The spectral data compared closely to that of 3β-stigmasterol, whose proposed structure is shown below (Alam et al, 1996). This compound is being reported from E. excelsa for the first time.…”

supporting

confidence: 54%

Stem bark extracts of Erythrina excelsa (BAK) and their biological activities

Ombuna¹,

Machocho²,

Keru³

et al. 2016

J. Med. Plants Res.

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“…Glucosylation may improve the solubility of the compound into water and express a relatively high potency. Stigamasterol glucoside was isolated from various natural resources, such as Cassia petersiana, 9) Atriplex nummularia, 10) Thalassodendron ciliatum, 11) Cissus javana 12) and Ambroma augusta as a biologically active compound, 13) along with various biological cytotoxic, anti-inflammatory, anti-bacterial and antisalmonellal activities. Although stigamasterol glucoside was previously isolated from P. urinaria, 14) this is the first report to clarify its anti-5α-reductase activity.…”

Section: )mentioning

confidence: 99%

“…The chemical structure was elucidated by analysis of NMR and MS spectra data compared with data reported previously. 13) …”

Section: Cell Culture and Inhibitory Assay For Lncap Cell Growthmentioning

confidence: 99%

Screening of Euphorbiaceae Plant Extracts for Anti-5α-reductase

Kamei

Noguchi

Matsuda

et al. 2018

Biological & Pharmaceutical Bulletin

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In our research program to find novel agents for alopecia from natural plant resources, we screened Euphorbiaceae plant extracts using an anti-5α-reductase assay. Among the samples tested, the extract of Phyllanthus urinaria showed the most potent activity with 24.3 and 64.6% inhibition at 50 and 200 µg/mL against the enzyme, respectively. The extract also suppressed the androgen activity of dihydrotestosterone in LNCaP cell line. These results show that the extract of P. urinaria may be a multi-potent agent for androgen-derived alopecia. We tested for activity on a hair regrowth model using mice. The extract of P. urinaria showed hair regrowth activity at 5 mg/mouse/d administration. Furthermore, the active principle for anti-5α-reductase activity was determined as stigmasterol glucoside from activity-guided fractionation and the IC 50 was 27.2 µM. These results suggest that extract of P. urinaria may be a promising candidate anti-alopecia agent.Key words 5α-reductase; androgen receptor; Euphorbiaceae; Phyllanthus urinaria; stigmasterol glucoside Hair loss is a major cosmetic problem in the prime of manhood, and may reduce QOL and lead to serious depression. Hair loss is mainly attributable to a change in testosterone level. Testosterone is a hormone in males that is dehydrolyzed to dihydrotestosterone by 5α-reductase, which is a more potent androgen than testosterone. Dihydrotestosterone strongly binds to androgen receptor and the complex migrates to the nucleus. This migration enhances the mRNA transcription of the anti-proliferative factor, transforming growth factor β (TGF-β) and suppresses the proliferation of hair follicle cells. Alopecia attributed to androgen is known as androgenetic alopecia and is recognized as a disease. Medical therapy for androgenetic alopecia is available; however, an alternative medicine for androgenetic alopecia using affordable self-care agents has long been awaited. In our research program to investigate hair growth agents from natural plant resources, we discovered that extracts from the flower of Pueraria lobata, 1) the leaves of Rosmarius officinalis2) and the rhizome of Panax ginseng 3) were effective for hair growth via their inhibition of 5α-reductase.In our research program to find effective plant materials from natural resources, we focused on Euphorbiaceae plants, which possess various active components and biological activities. [4][5][6] In addition, Euphorbiaceae plants have been said to be effective for burns to the skin since ancient times, which indicates cell proliferation activity. Thus, if a plant material extract has both cell proliferating and anti-5α-reductase activities, it may be a suitable agent for hair growth. In these circumstances, we screened 10 plant extracts for anti-5α-reductase activity and the active principles were determined.We selected plant samples randomly from Euphorbiaceae plants for screening as follows; whole plant of Phyllanthus urinaria, root of Glochidion eriocarpum, whole plant of Speranskia tuberculate, leaf of Breynia patens, wh...

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“…The compounds were identified by comparison of their NMR data with those reported in the literature (Alam et al, 1996;Ayres et al, 2009;Daniewski et al, 1996;Nyasse et al, 1988 143.5, 122.9, 121.6, 118.4, 117.4, 74.8, 39.8, 39.4, 37.5, 32.8, 31.5, 28.0, 24.8, 24.4, 23.9, 22.7, 21.5, 20.6, 19.7, 12.5, 11.8, 11.3 122.0, 100.9, 78.9, 77.9, 77.1, 75.6, 69.8, 61.5, 56.5, 55.8, 50.0, 45.6, 42.1, 39.5, 38.4, 37.0, 36.5, 35.9, 33.7, 31.6, 31.4, 29.3, 28.9, 28.0, 25.8, 24.0, 22.9, 20.9, 19.5, 19.0, 18.7, 18.5, 11.6, 11.4. mustakone 203.4, 120.8, 171.4, 55.8, 54.7, 45.6, 22.8, 35.9, 57.8, 32.4, 19.6, 20.6, 20.5, 24.3 Different letters in the same column differ at 5% probability by Tukey test. SE = standard error.…”

Section: Isolation Of the Constituents Of Active Extractmentioning

confidence: 99%

Effect of extracts of Trichilia silvatica C. DC., on development and reproduction parameters of Spodoptera frugiperda (J. E. Smith) (Lepidoptera: Noctuidae)

Freitas¹,

Formagio²,

Pereira³

et al. 2014

Afr. J. Biotechnol.

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The objective of this study was to evaluate the effects of the methanolic extracts from the leaves, bark and flowers of Trichilia silvatica on Spodoptera frugiperda. Also, it was use in evaluating the total phenolic and flavonoid content of methanolic extracts. We also reported chemical study on the most active extract. Corn leaves were immersed in a 1% methanolic extract solution and fed to second instars of S. frugiperda. The extract of the T. silvatica (LTS) leaves decreased the viability of the larva, prolonged larval duration, affected the pupal biomass, decreased the period of oviposition and the number of eggs as well as affected the egg viability. The methanolic extract of the T. silvatica (BTS) bark decreased the larval viability, oviposition period, number of eggs and egg viability. The flower extract of T. silvatica (FTS) decreased the larval viability and period of oviposition. In relation to the constituent contents, the methanolic extract of the leaves showed highest total phenol (233.37 mg gallic acid/g of extract) and flavonoid (53.17 mg quercetin/g of extract) content. The chemical study of the FTS resulted in α-tocopherol, sitosterol 3-O-glucopyranoside, mustakone and N-metilproline. Our results indicate that the extracts affected the biology of S. frugiperda, with LTS being the most promising.

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Oleanen and stigmasterol derivatives from Ambroma augusta

Cited by 74 publications

References 6 publications

Stem bark extracts of Erythrina excelsa (BAK) and their biological activities

Stem bark extracts of Erythrina excelsa (BAK) and their biological activities

Screening of Euphorbiaceae Plant Extracts for Anti-5α-reductase

Effect of extracts of Trichilia silvatica C. DC., on development and reproduction parameters of Spodoptera frugiperda (J. E. Smith) (Lepidoptera: Noctuidae)

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