Steroidal Saponins from the Rhizomes of Polygonatum sibiricum

Son, Kun Ho; Chul, Jae; Kang, Sam Sik

doi:10.1021/np50068a010

Cited by 55 publications

(28 citation statements)

References 11 publications

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“…The crude can be seen such as a potential source of useful drug in table 4 Saponins in Anredera cordifolia plant as Binahong, exhibit a variety of biological activities, and saponins compound in plants widely used in foods, medicines and cosmetics (Waller and Yamasaki, 1966), in other plants research by Ono et al (1988) and Son and Do (1990), among them, a steroidal saponins is known to have a hypoglycemic activity (Kato and Miura, 1994). In fact, saponins in rhizome of plant species are used for diabetes in folk medicine (Jeong and Jim Wong, 2005) .The Saponin compounds are very important for the role of activities substances in this Binahong plant for the human health, the result of saponins compound from leaves, stem and tubers of Binahong plant, the determine of Saponin in this plant, is domineer compound…”

Section: Resultsmentioning

confidence: 99%

Determination of Saponin Compound from Anredera cordifolia (Ten) Steenis Plant (Binahong) to Potential Treatment for Several Diseases

Astuti

Sakinah²,

B.M³

et al. 2011

JAS

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Saponin has various types; it can be bond with glycosides that form soapy lathers when mixed and agitated with water, and have been used to treat diabetes; liver, hepatitis, cardiovascular as high blood pressure, high cholesterol, and physical stress. In this study describe of saponins compound in Binahong, one of medicinal plant investigated from these plant probably contribute to the effectiveness the above plant for treatment several diseases. The sample were dried by oven (60 o C) to be powder and extracted with solvents. After that used qualitative and quantitative test. The result of Binahong plant contains saponins compound on all a part of the Binahong plant, are positive indicate of presence of saponins triterpenoid and steroid. . Moreover crude of saponins substances from Leaves (28.14±0.22), Stems (3.65±011) and Tubers (43.15±0.10) of mg/g. The research showed of the Binahong plant, importance of the distribution of determination of saponins compound from plant, has a potential to treatment for several diseases

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Section: Resultsmentioning

confidence: 99%

Determination of Saponin Compound from Anredera cordifolia (Ten) Steenis Plant (Binahong) to Potential Treatment for Several Diseases

Astuti

Sakinah²,

B.M³

et al. 2011

JAS

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“…A comparison of the 13 C-NMR spectra of 1 and 3b,19a,23,30-tetrahydroxyurs-12-en-28-oic acid (30-hydroxyrotundic acid) 28-O-glucoside 44) showed the expected downfield shifts for absorption due to C-20 (ϩ28.4 ppm) and C-30 (ϩ3.8 ppm), and upfield shifts for C-18 (Ϫ4.8 ppm), C-22 (Ϫ5.0 ppm), and C-29 (Ϫ4.7 ppm) due to the g-gauche effect exerted by the b-oriented hydroxyl group at C-20. [45][46][47] The NMR data of rings C/D/E in 1 were similar to those of kudinolic acid (3b,19a,20b-trihydroxyurs-12-en-28-oic acid) isolated from the leaves of Ilex kudincha. 48) This was further corroborated by the heteronuclear multiple bond correlation (HMBC) spectrum, in which the proton signal at The coupling constants allowed the identification of a bquinovosyl (6-deoxyglucosyl) unit.…”

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confidence: 55%

A New Polyoxygenated Triterpene and Two New Aeginetic Acid Quinovosides from the Roots of Rehmannia glutinosa

et al. 2011

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Rehmanniae Radix is the fresh or dry root of Rehmannia glutinosa LIBOSCH. (Scrophulariaceae). As officially listed in the Korean Pharmacopoeia, this herbal drug is to be used in dried form or after processing.1) The dry roots of R. glutinosa have been used in traditional Chinese medicine as an antipyretic and hemostatic.2,3) A number of chemical constituents with diverse structures, including iridoids, [4][5][6][7][8][9][10][11][12][13] ionone glucosides, 14,15) sesquiterpenes, 16,17) phenylethanoid glycosides, 18,19) norcarotenoids, 20,21) cerebrosides, 12) carbohydrates, and others, [22][23][24][25][26] have been isolated from this plant. During our ongoing studies of bioactive constituents used in traditional Chinese medicines, we characterized the 70% EtOH extracts of the roots of Paeonia lactiflora [27][28][29][30][31] and Astragalus membranaceus, [32][33][34][35] and the aerial parts of Lonicera japonica, [36][37][38][39][40][41] and several constituents have been isolated and characterized from these extracts. In the continuing search for new chemical and biomarkers from the medicinal plant R. glutinosa for quality control studies of related herbal medicines, a new polyoxygenated triterpene and two aeginetic acid quinovosides, together with other known components, were isolated. In the present investigation, we report the isolation and structure elucidation of a minor polyoxygenated triterpene named glutinolic acid (1) and two new aeginetic acid quinovosides (2, 3) from the roots of R. glutinosa cultivated in Korea. Results and DiscussionThe dried roots of R. glutinosa were crushed and extracted with 70% EtOH. The concentrated extract was suspended in H 2 O and successively extracted with EtOAc and BuOH. The EtOAc extract was added to 90% aqueous MeOH and extracted with hexane to give hexane and 90% MeOH extracts. The 90% MeOH extract was subjected to sequential column chromatography over silica gel, MCI gel and RP-18 gel to yield a new minor polyoxygenated triterpene named glutinolic acid (1) and two new aeginetic acid quinovosides (2, 3).Glutinolic acid (1) C-NMR data for 1 revealed the presence of one oxymethine carbon at d 71.3, two oxymethylene carbons at d 68.7 and 66.3, two oxygenated quaternary carbons at d 74.9 and 76.6, a carboxylic acid carbon at d 183.0, and an olefinic double bond (d 129.5, 139.5) supporting a pentahydroxy-urs-12-en-oic acid skeleton bearing an a-hydroxyl at C-19. Regarding the two hydroxyl groups and a carboxylic acid group on the D/E rings, two methyl groups on the D/E rings were transformed into the COOH and one CH 2 OH group, respectively. The latter group and the remaining hydroxyl group on the D/E rings were assigned at C-20 due to its quaternary nature. A comparison of the 13 C-NMR spectra of 1 and 3b,19a,23,30-tetrahydroxyurs-12-en-28-oic acid (30-hydroxyrotundic acid) 28-O-glucoside 44) showed the expected downfield shifts for absorption due to C-20 (ϩ28.4 ppm) and C-30 (ϩ3.8 ppm), and upfield shifts for C-18 (Ϫ4.8 ppm), C-22 (Ϫ5.0 ppm), and C-29 (Ϫ4.7 ppm) due to t...

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“…The MeOH-eluted and MeOH-H 2 O (6:4)-eluted fractions were then subjected to silica gel and octadecylsilanized (ODS) silica gel column chromatography (CC) and reversed-phase preparative high-performance liquid chromatography (HPLC) to obtain compounds 1 – 15 ( Figure 1 ). The structures of the known compounds 1 – 3 and 7 – 9 were identified as (25 S )-spirost-5-en-3β-yl O -β- d -glucopyranosyl-(1→2)- O -[β- d -xylopyranosyl-(1→3)]- O -β- d -glucopyranosyl-(1→4)-β- d -galactopyranoside ( 1 ) [ 5 ], (25 S )-14α-hydroxyspirost-5-en-3β-yl O-β- d -glucopyranosyl-(1→2)- O -[β- d -xylopyranosyl-(1→3)]- O -β- d -glucopyranosyl-(1→4)-β- d -galactopyranoside ( 2 ) [ 5 ], (25 R )-spirost-5-en-3β-yl O -α-L-rhamnopyranosyl-(1→4)-β- d -glucopyranoside ( 3 ) [ 6 ], (25 S )-26-[(β- d -glucopyranosyl)oxy]-22α-hydroxyfurost-5-en-3β-ol ( 7 ) [ 7 ], (25 S )-26-[(β- d -glucopyranosyl)oxy]-22α-hydroxyfurost-5-en-3β-yl O -β- d -glucopyranosyl-(1→2)- O -[β- d -xylopyranosyl-(1→3)]- O -β- d -glucopyranosyl-(1→4)-β- d -galactopyranoside ( 8 ) [ 8 ], and (25 S )-26-[(β- d -glucopyranosyl)oxy]-14α,22α-hydroxyfurost-5-en-3β-yl O -β- d -glucopyranosyl-(1→2)- O -[β- d -xylopyranosyl-(1→3)]- O -β- d -glucopyranosyl-(1→4)-β- d -galactopyranoside ( 9 ) [ 9 ], respectively.…”

Section: Resultsmentioning

confidence: 99%

Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity

Matsuo

Shinoda

Nakamaru

et al. 2017

IJMS

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Phytochemical examination of Convallaria majalis (Liliaceae) whole plants yielded 15 steroidal glycosides (1–15), including nine new compounds (4–6, 10–15) with a lycotetrose unit. The structures of the new compounds were determined using two-dimensional Nuclear magnetic resonance (NMR) analyses and chemical methods. The isolated compounds were evaluated for cytotoxicity against HL-60 human promyelocytic leukemia cells, A549 human lung adenocarcinoma cells, and HSC-4 and HSC-2 human oral squamous cell carcinoma cell lines. Of these, (25S)-spirost-5-en-3β-yl O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside (1) exhibited cytotoxic activity against HL-60, A549, HSC-4, and HSC-2 cells with IC50 values ranging from 0.96 to 3.15 μM. The corresponding furostanol glycoside of 1, (25S)-26-[(β-d-glucopyranosyl)oxy]-22α-hydroxyfurost-5-en-3β-yl O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside (8), was cytotoxic to the adherent cell lines of A549, HSC-4, and HSC-2 cells with IC50 values of 2.97, 11.04, and 8.25 μM, respectively. The spirostanol lycotetroside (1) caused necrotic cell death in A549 cells in a dose-dependent manner. Alternatively, the furostanol lycotetroside (8) induced apoptotic cell death in A549 cells in a time-dependent manner, as was evident by morphological observations and flow cytometry analyses.

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Steroidal Saponins from the Rhizomes of Polygonatum sibiricum

Cited by 55 publications

References 11 publications

Determination of Saponin Compound from Anredera cordifolia (Ten) Steenis Plant (Binahong) to Potential Treatment for Several Diseases

Determination of Saponin Compound from Anredera cordifolia (Ten) Steenis Plant (Binahong) to Potential Treatment for Several Diseases

A New Polyoxygenated Triterpene and Two New Aeginetic Acid Quinovosides from the Roots of Rehmannia glutinosa

Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity

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