Article

The Exploration of whitening and sun screening compounds in bengkoang roots (Pachyrhizus erosus)

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Abstract

Bengkoang roots (Phacyrhizus erosus) have been used as cosmetics materials, primarily as sun screening and skin whitening materials. Indonesia is a tropical country, which has high sunlight intensities every day. Sunlight, primarily the ultraviolet ray, causes several damages on skin; for examples, sunburn, cancer, and hyperpigmentation. Therefore, the Indonesian people need sun screening and skin whitening preparations to avoid the negative effects of ultraviolet. Up to now, active compounds in bengkoang roots which have skin whitening and sun screening activity have not been discovered yet. Therefore, the study on isolation, structure elucidation, antioxidative and anti-tyrosinase assay of active compounds in bengkoang roots has been conducted. The isolation of active compounds has been carried out by Soxhlet extraction using solvents (petroleum ether, ethyl acetate and butanol) followed by fractionated using column chromatography. The structures of the compounds were elucidated using 1D and 2D NMR spectroscopy and mass spectrometry. 13 compounds were isolated. All compounds have an antioxidative activity with the exceptions of ß-sitosterol and stigmasterol. Three isoflavonoids (i.e. daidzein; daidzein-7-O-ß-glucopyranose; 5-Hydroxy-daidzein-7-O-ß-glucopyranose), and a pterocarpan (i. e. (8,9)-Furanyl-pterocarpan-3-ol) were isolated from the ethyl acetate extract. All compounds showed tyrosinase inhibitory activity with IC50 values from 4.38 to 22.20 mM. The other compounds, i. e. 2-Butoxy-2,5-bis(hydroxymethyl)-tetrahydrofurane from the butanol extract and 4-2-(Furane-2-nyl)ethyl)-2-methyl-2,5-dihydrofurane-3-carbaldehyde from the ethyl acetate after hydrolysis extract have the tyrosinase inhibitory activity with IC50 values of 1.21 mM and 0.20 mM, respectively. Based on the results, it can be concluded that bengkoang root can be used as sun screening and skin whitening materials for cosmetics preparations, because the bengkoang root posseses many compounds which have UV absorption, antioxidative and tyrosinase inhibitory activities. Die Wurzeln der Bengkoang (Phacyrhizus erosus) werden im Bereich der Kosmetik, speziell zum Schutz vor UV-Strahlung und zum Bleichen der Haut, verwendet. Indonesien ist ein tropisches Land, in dem täglich die Sonne scheint. Die Sonnenstrahlung, insbesondere die UV-Strahlung hat negative Auswirkungen, wie z. B. Sonnenbrand, Krebserzeugung und Hyperpigmentation. Deshalb brauchen die Menschen in Indonesien „sunscreen and whitening“-Kosmetik zum Schutz der Haut vor der Sonneneinstrahlung. Bis heute gibt es keine wissenschaftlichen Beweise, ob Bengkoang Wirkstoffe enthält, die die UV-Strahlung absorbieren und die Haut bleichen können. Ziel der Arbeit war die Suche nach Substanzen mit diesem Eigenschaften. Deshalb stand die Isolierung und Strukturaufklärung von Inhaltstoffen aus Bengkoang-Wurzeln sowie die Analyse der UV-Absorptionsfähigkeit und Analyse der Hautbleichungs-Fähigkeit der gefundenen Verbindungen im Mittelpunkt der Arbeit. Die Hautbleichungs-Fähigkeit wurde durch die Analyse der antioxidativen Aktivität und Tyrosinase-Inhibitor-Aktivität getestet. Aus Extrakten unterschiedlicher Polarität wurden Sekundärstoffe durch unterschiedliche chromatographische Trenn-Methoden (Säulenchromatographie mit verschiedenen stationären Phasen) isoliert, deren Struktur mittels Massen-spektrometrie und ein- und zweidimensionalen Kernresonanz-Spektroskopie-Experimente aufgeklärt würde. Insgesamt wurden 13 Naturstoffe isoliert, von denen 11 die antioxidative Aktivität haben. Nur ß-Sitosterol und Stigmasterol zeigten keine die antioxidative Aktivität. Drei Verbindungen der Isoflavonoid-Gruppe, nämlich Daidzein, Daidzein-7-O-ß-glucopyranose, 5-hydroxy-daidzein-7-O-ß-glucopyranose und eine Verbindung der Pterocarpan-Gruppe, nämlich (8,9)-Furanyl-pterocarpan-3-ol, wurde aus dem Essigsäureethylacetat-Extrakt isoliert. Alle haben starke Tyrosinase-Inhibitions-Aktivität mit IC50-Werten von 4.38 mM bis 22.20 mM. Die andere Verbindungen, nämlich 2-Butoxy-2,5-bis(hydroxymethyl)-tetrahydrofuran aus dem Butanol-Extrakt und 4-(2-(Furan-2-nyl)ethyl)-2-methyl-2,5-dihydrofuran-3-carbaldehyd aus dem Essigsäureethylacetat-Extrakt-nach- Hydrolyse, haben eine Tyrosinase-Inhibitions-Aktivität mit IC50-Werten von 1.21 mM und 0.20 mM. Zusammenfassend kann festgestellt werden, dass Bengkoang viele aktive Verbindungen im Bereich der UV Absorption, antioxidative Aktivität und Tyrosinase-Inhibitions-Aktivität haben. Deshalb kann Bengkoang für Kosmetik, speziell als Material, das vor UV-Strahlung schützt und die Haut bleicht, verwendet werden.

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... Bengkoang is a species of genus Pachyrizus and grows in Indonesia, and has been used as one of traditional cosmetics for sunscreen and whitening cosmetics (Lukitaningsih et al., 2013). This plant content 86-90% water and phenolic compound (Lukitaningsih, 2009). In addition, Bengkoang also contains saponin serving as natural "sunscreen" in preventing skin damage caused by free-radical excitement as the result of absorption of ultra-violet rays (Sandler, 2005). ...
... All compounds used in this experiment have been isolated according to the procedure in Lukitaningsih (2009). The determination of the tyrosinase inhibition type of isolated compounds was carried out according to Chen and Kubo (2002) with a little modification. ...
Article
Full-text available
In Indonesia, Bengkoang (Phacyrhizus erosus) have been used as one of cosmetics especially as sun screening and skin whitening materials. Six active compounds in Bengkoang with antioxidant and skin whitening activities have been isolated, namely daidzein, daidzin, genistin, (8,9)-furanyl-pterocarpan-3-ol, 4-(2-(furane-2-yl)ethyl)-2-methyl-2,5-dihydro-furane-3-carbaldehyde and 2-butoxy-2,5-bis(hydroxymethyl)-tetrahydrofurane-3,4-diol. According to literatures, the type of their tyrosinase inhibitory activity has not yet reported. The determination of whitening activity of each compound was evaluated by the evaluation of Lineweaver-Burk plot. The result showed that five compounds had competitive inhibitory activity and 8,9-furanyl-pterocarpan-3-ol showed a non-competitive inhibition.
... Drug therapy such as proton pump inhibitors (PPIs) (omeprazole, lansoprazole, pantoprazole), H2-receptor antagonists (cimetidine, ranitidine, famotidine), and antacids are often used to treat gastric ulcers (Longo and Fauci 2010;Tarigan 2001). Proton pump inhibitors are chosen as the first choice of therapy because this class of medications has a very strong inhibitory effect on gastric acid secretion, resulting in an 80-90% reduction of the gastric's daily acid production. ...
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Gastroprotective is an effect caused by the compounds that have the capability of protecting the gastric mucosa. Peperomia pellucida L. plants contain alkaloids, flavonoids, saponins, tannins, and terpenoids, while Pachyrhizus erosus L. contains flavonoids, alkaloids, tannins, and saponins. Peperomia pellucida L. reportedly contains dillapiole compounds with a gastroprotective effect. Moreover, its isolation result from Pachyrhizus erosus L. indicates the presence of dulcitol, gentisic acid, and formononetin, which has antioxidant activity. This study aims to determine the gastroprotective effect of the combination of Peperomia pellucida L. and Pachyrhizus erosus L. extract on rats with gastric ulcer models by looking at the ulcer index, percentage of inhibition, and histopathology. The research method used in this study was by making a combination of Peperomia pellucida L. and Pachyrhizus erosus L. extract. The combined extract was then given to five treatment groups. Group I as a negative control, group II as a positive control was given sucralfate, groups III, IV, and V were given a combination of Peperomia pellucida L. and Pachyrhizus erosus L. extract of 100, 200, and 400 mg/kg BW. The treatment was given orally for 14 days, after 1 h of treatment on the 14th day, 96% ethanol induction was given orally at a dose of 5 mg/kg BW. The animal dissection was performed 24 h after the induction. The results from observations showed an increase in body weight before and after the treatment. The ulcer index produced by negative control, positive control in the treatment with doses of 100, 200, and 400 were 4.18; 2.98; 2.42; 2.04; and 1.07. This study showed that the combination of Peperomia pellucida L. and Pachyrhizus erosus L. extract has a gastroprotective effect.
... They have been used as skin whitening materials. Yet, the active compounds in bengkoang roots having skin whitening activity have not previously been investigated (Lukitaningsih, 2009). ...
Article
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In Indonesia, the roots of bengkoang (Phacyrhizus erosus) have been used as the excipient for sun screening and skin whitening paste. Since the active compounds exhibiting skin whitening or sun screening effect have not previously been studied, the aim of this study was to identify compounds with antioxidant and tyrosinase inhibitor activities. Soxhlet extraction was used as the method of isolation with petroleum ether as the solvent and it was followed by fractionation using ethyl acetate to obtain three isoflavonoids (i.e. daidzein (2); daidzein-7-O-ß-glucopyranose (3); 5-hydroxy-daidzein-7-O-ß-glucopyranose (4)), and a new pterocarpan (i. e. 8,9-furanyl-pterocarpan-3-ol (1)) which antioxidant activities (SC 50% values) of 2.11; 11.86; 0.69 and 7.86 respectively. All compounds showed tyrosinase inhibiting activities with IC 50 values of 4.38; 5.35; 7.49 and 22.20 mM, respectively for compound 4, 2, 1 and 3. These compounds can be used as antioxidant and skin whitening materials.
... erosus). The structure of this compound is similar to soy isoflavones [19] . On the basis of structure similarity, it is interesting to investigate the estrogenic effect of other phytoestrogens. ...
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Objective To investigate the estrogenic effect of (8,9)-furanyl-pterocarpan-3-ol (FPC) on growth of human breast cancer T47D cells and the interactions between the FPC and tamoxifen (TAM), on the growth of estrogen receptor-dependent breast cancer T47D cells. Methods The proliferation effect of FPC were conducted on T47D cells In vitro by MTT test. T47D cells were treated with FPC alone (0.01-200 μmol/L) or in combination with TAM 20 nmol/L. Furthermore, the expression of ERα or c-Myc were also determined by immunohistochemistry. Results The results indicated that administration of an anti-estrogen TAM showed growth inhibitory effect on T47D cells, wheraes co-administered with low concentration (less than 1 μmol/L) of FPC attenuated to promote cell proliferation. In contrast, the combination of TAM with higher doses (more than 20 μmol/L) of FPC showed growth inhibitory. This result was supported by immunocytochemistry studies that the administration of 20 nmol/L TAM down-regulated ER-α and c-Myc, but the combination of 20 nmol/L TAM and 1 μmol/L FPC robustly up-regulated expression of ER-α. Thus, the reduced growth inhibition of TAM 20 nmol/L by FPC 1 μmol/L on T47D cells may act via the modulation of ER-α. Conclusions The findings indicate and suggest that FPC had estrogenic activity at low concentrations and anti-estrogenic effect that are likely to be regulated by c-Myc and estrogen receptors. We also confirm that low concentration of FPC attenuated the growth-inhibitory effects of TAM on mammary tumor prevention. Therefore, the present study suggests that caution is warranted regarding the consumption of dietary FPC by breast cancer patients while on TMA therapy.
Conference Paper
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Introduction: Bengkuang (Pachyrizus erosus (L.) Urb) contains 86-90% water, phenol, and saponins. In substance fenolida Bengkuang effective in inhibiting the formation of melanin so pigmentation, due to sun can be reduced making it suitable for skin in the tropics such as Indonesia, including Bengkulu Province. Objective: In this study the gel was formulated and evaluate starch bengkuang formulation with varying HPMC is gelling agent. Method: This research is an experimental study. Gel made in 3 formulas at concentration of starch bengkuang every formula 5 gr with different HPMC F1,F2,F3 with a concentration of 3%,5%,7%. Results: Gel from starch bengkuang was evaluated for 3 weeks, from the research starch bengkuang with gelling agent HPMC can be formulated into gel preparations, Gel with a concentration of HPMC 3% in F1 is the best preparation. The form of moderately viscous, rose fragrant, homogeneous with a pH of 6 and the spread of 5-7 cm, not irritate the skin and From the results of visual observation there is no the growth of bacterial and fungi in the gel. Conclusion: Starch bengkuang with gelling agent HPMC preparation gel can be made in various concentrations. The physical properties gel a variation of the starch bengkuang does not affect the stability physical gel and has not change for storage. Keywords: starch bengkuang_Pachyrizus erosus_preparation gel_HPMC
Article
Abstrak Tantangan pertanian ke depan adalah peningkatan produksi pertanian, kelestarian lingkungan dan kesehatan masyarakat sebagai akibat meningkatnya jumlah penduduk dan kesadaran masyarakat akan pengaruh negatif yang ditimbulkan oleh penggunaan pupuk anorganik dan pestisida sintetik/kimia (anorganik). Sistem pertanian organik merupakan salah satu solusi yang diajukan untuk diterapkan pada sistem pertanian di masa yang akan datang. Sistem pertanian organik adalah sistem budidaya pertanian yang mengandalkan bahan-bahan alami tanpa menggunakan bahan kimia/sintesis (anorganik). Pemanfaatan pupuk organik dan pestisida nabati dalam usaha pertanian akan mengurangi resiko pencemaran lingkungan, meningkatkan efisiensi pemupukan, serta menekan pengaruh negatif dari penggunaan pupuk anorganik dan pestisida sintesik/kimia (anorganik). Prinsip dalam sistem pertanian organik adalah adanya keseimbangan siklus hara dan kesuburan tanah serta pengendalian hama dan penyakit secara terpadu. Untuk meningkatkan kesuburan tanah dan memenuhi kebutuhan pupuk organik di dalam menjaga keseimbangan siklus hara, serta mengurangi penggunaan pestisida nabati, peran legum seperti bengkuang (Pachyrrhizuz erosus L.) perlu dikaji lebih mendalam. Tanaman bengkuang sangat potensial dalam mendukung diterapkannya sistem pertanian organik karena; biomassa yang banyak dan mengandung nitrogen yang tinggi (3.42% - 3.51%), kemampuan hidup yang sangat luas di berbagai kondisi lahan karena bersimbiosis dengan bakteri Rhizobium dan Bradyrhizobium dalam menambat nitrogen (N2) udara dan bersimbiosis dengan cendawan mikoriza (AMF) yang dapat membantu penyerapan unsur hara terutama fosfor. Selain itu, kecuali umbi, bagian tanaman lainnya terutama pada biji bengkuang mengandung metabolit sekunder seperti rotenon yang bersifat insektisida. Dengan demikian maka bengkuang ini dapat dimanfaatkan sebagai bahan pupuk organik dan sebagai insektisida nabati dalam mendukung sistem pertanian organik. Kata Kunci: bengkuang(Pachyrrhizuz erosus L.), legum, rotenon, sistem pertanian organik Abstract The challenge of agriculture in the future is to increase agricultural production, environmental sustainability and public health as a result of increasing population and public awareness of the negative effects caused by the use of inorganic fertilizers and chemical/ synthetic pesticides. Organic farming system is one of the solutions proposed to be applied to agricultural systems in the future. Organic farming system is an agricultural cultivation system that relies on natural materials without using synthetic/chemicals (inorganic). Utilization of organic fertilizers and pesticides in agricultural businesses will reduce the risk of environmental pollution, improve fertilization efficiency, and reduce the negative effects of the use of inorganic fertilizers and chemical/synthetic pesticides. The principle in organic farming systems is the balance of nutrient cycling and soil fertility and integrated pest and disease control. To improve soil fertility and meet the needs of organic fertilizer in maintaining the balance of nutrient cycles, and reduce the use of synthetic chemical pesticides, the role of legumes such as yam bean (Pachyrrhizuz erosus L.) needs to be studied more deeply. Yam bean plants are very potential in supporting the implementation of organic farming systems because; a lot of high and nitrogen containing biomass (3.42% - 3.51%), a very broad life ability in various land conditions because it is symbiotic with Rhizobium and Bradyrhizobium bacteria in fixing nitrogen (N2) air and symbiosis with mycorrhizal fungi (AMF) which can help absorption of nutrients, especially phosphorus. Especially in jicama seeds contain secondary metabolites such as rotenone which are insecticides. Thus, this yam bean can be used as an organic fertilizer and as a organic/vegetable insecticide in supporting organic farming systems. Keywords: Yam bean (Pachyrrhizuz erosus L.), legumes, rotenon, organic farming systems
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