- Anti-allergic substances from the rhizomes of Dioscorea membranacea
-
Extracts of five species of Thai medicinal plants, locally known as Hua-Khao-Yen, were screened for anti-allergic activities using RBL-2H3 cells. Of the five species studied, the ethanolic extract of Dioscorea membranacea exhibited potent inhibitory activity against β-hexosaminidase release as a marker of degranulation in RBL-2H3 cells, with an IC50 value of 37.5 μg/mL. Eight compounds were isolated from this crude ethanolic extract, [two naphthofuranoxepins (1, 2), one phenanthraquinone (3), three steroids (4-6), and two steroidal saponins (7, 8)], and tested for their anti-allergic activities. The results showed that dioscorealide B (2) possessed the highest activity with an IC50 value of 5.7 μM, followed by dioscoreanone (3, IC50 = 7.7 μM), dioscorealide A (1, IC50 = 27.9 μM), and diosgenin (9, IC50 = 29.9 μM). Structure-activity relationship studies of naphthofuranoxepins on anti-allergic activity revealed that the hydroxylation at position 8 conferred higher activity than methoxylation. For diosgenin derivatives, the aglycone was found to possess higher activity than the diglucosylated molecule; whereas substitution with rhamnoglucosides apparently results in loss of activity. Furthermore, effects of dioscorealide A, dioscorealide B, and dioscoreanone on antigen-induced release of TNF-α and IL-4 in the late phase reaction were also examined.
- Tewtrakul, Supinya,Itharat, Arunporn
-
-
Read Online
- FUROSTANOL GLYCOSIDES FROM TRIGONELLA FOENUM-GRAECUM SEEDS
-
Two new furostanol glycosides, trigofoenosides F and G, have been isolated as their methyl esters from the methanolic extract of Trigonella foenum-graecum seeds (Leguminosae).The structures of the original glycosides have been determined as (25R)-furost-5-en-3β,22,26-triol, 3-O-α-L-rhamnopyranosyl(1->2)β-D-glucopyranosyl(1->6)β-D-glucopyranoside; 26-O-β-D-glucopyranoside and (25R)-furost-5-en-3β,22,26-triol, 3-O-α-L-rhamnopyranosyl(1->2)4)>β-D-glucopyranosyl(1->6)β-D-glucopyranoside; 26-O-β-D-glucopyranoside, respectively.Key Word Index - Trigonella foenum-graecum; Leguminosae (Fabaceae); fenugreek; furostanol glycosides.
- Gupta, Rajesh K.,Jain, Dharam C.,Thakur, Raghunath S.
-
-
Read Online
- Spirostanol glycosides from Asparagus plumosus
-
Three spirostanol glycosides were isolated from a methanol extract of the leaves of Asparagus plumosus and characterized.
- Sati,Pant
-
-
Read Online
- Bivalent furostene carbamates as antiproliferative and antiinflammatory agents
-
Breast cancer is the most prevalent cancer in women affecting about 12% of world's female population. It is a multifactorial disease, mostly invasive in nature. Diosgenin and related compounds are potent antiproliferative agents. Carbamate derivatives have been synthesized at C26 of furostene ring after opening spiroketal bond (F-ring) of diosgenin. Compound 10 possessed significant antiproliferative activity against human breast cancer cells by arresting the population at G1 phase of cell division cycle and induced apoptosis. Induction of apoptosis was observed through the caspase signalling cascade by activating caspase-3. Moreover, carbamate 10 exhibited moderate antiinflammatory activity by decreasing the expression of cytokines, TNF-α and IL-6 in LPS-induced inflammation in primary macrophage cells. Furthermore, compound 10 significantly reduced Ehrlich ascites carcinoma significantly in mice. It was well tolerated and safe in acute oral toxicity in Swiss albino mice. The concomitant anticancer and antiinflammatory properties of carbamate 10 are important and thus, can further be optimized for a better anti-breast cancer candidate.
- Pathak, Nandini,Fatima, Kaneez,Singh, Sneha,Mishra, Divya,Gupta, Amit Chand,Kumar, Yogesh,Chanda, Debabrata,Bawankule,Shanker, Karuna,Khan, Feroz,Gupta, Atul,Luqman, Suaib,Negi, Arvind S.
-
-
- New furostanol glycosides from Polygonatum multiflorum (L.) All
-
The phytochemical investigation of the whole plant of Polygonatum multiflorum resulted in the isolation of two new steroidal glycosides, polmultoside A (4) and polmultoside B (5), along with three known glycosides protobioside (1), protodeltonin (2) and huangjiangsu A (3). The structures of the isolated compounds have been elucidated by extensive 1D (1H, 13C) and 2D (COSY, HSQC, HMBC) NMR spectral data analysis, as well as high-resolution mass determinations.
- Gvazava, Lili,Nebieridze, Vazha,Ganzera, Markus,Skhirtladze, Alexander
-
-
- From organocatalysed desilylations to high-yielding benzylidenations of electron-deficient benzaldehydes
-
A new type of organoprecatalyst (MeSCH2Cl/KI) for desilylation and benzylidenation reactions has been designed. Both reactions are user friendly and high yielding (71->99%) and have fast reaction rates. The desilylation of iodo silyl ethers was achieved with no sequential etherification side reactions like those seen for reactions when using TBAF. In the application of the catalytic system to a 6-TBDMS ether of a glucoside, glucoside benzylidenations using electron-deficient benzaldehydes were achieved in 87% yield compared with the previously reported yields of 69-77%. Altogether, 14 benzylidenation reactions were realised using silyloxy alcohols and electrondeficient benzaldehydes instead of their activated acetal forms. In terms of reaction rates and yields, the order of the benzylidenations is p-fluorobenzaldehyde > benzaldehyde > p-anisaldehyde, and a possible mechanism is discussed. These experiments have preliminarily differentiated this cost-effective catalytic system from the classic Lewis acids.
- Niu, Qun,Xing, Linlin,Li, Chunbao
-
p. 358 - 364
(2017/06/19)
-
- Novel steroidal glycosides from the bulbs of lilium pumilum
-
Examination of the bulbs of Lilium pumilum (Liliaceae) led to the isolation of four novel steroidal glycosides (1-4) with a 2,3,4-trisubstituted β-D-glucopyranosyl unit. In 1 and 3, the α-L-arabinopyranosyl moiety is linked to C-3 of the inner trisubstituted β-D-glucopyranosyl group and is present as an usual 4C1 conformation. In contrast, in 2 and 4, the α-L-arabinopyranosyl moiety, which is attached to C-4 of the inner trisubstituted β-D-glucopyranosyl group, is present as a 1C4 conformation. The structures of the new steroidal glycosides were determined based on the results of spectroscopic analyses, including two-dimensional (2D) NMR data and hydrolysis.
- Matsuo, Yukiko,Takaku, Reina,Mimaki, Yoshihiro
-
p. 16255 - 16265
(2015/12/01)
-
- Unexpected fragmentation of 16β-acetoxy-22-oxocholestanes on the action of methylenetriphenylphosphorane
-
Treatment of 16β-acetoxy-22-oxocholestanes with methylenetriphenylphosphorane results in the cleavage of C22-C23 bond and formation of bisnorcholanic (22→16)-lactones. The analogous fragmentation also partially proceeds on ButOK action.
- Valiullina, Zuleykha R.,Khasanova, Lidiya S.,Selezneva, Natalya K.,Gimalova, Fanuza A.,Pivnitsky, Kasimir K.,Miftakhov, Mansur S.
-
p. 272 - 273
(2015/02/05)
-
- Electrochemical synthesis of glycoconjugates from activated sterol derivatives
-
Several derivatives of cholesterol and other 3β-hydroxy- Δ5-steroids were prepared and tested as sterol donors in electrochemical reactions with sugar alcohols. The reactions afforded glycoconjugates with sugar linked to a steroid moiety by an ether bond. Readily available sterol diphenylphosphates yielding up to 54% of the desired glycoconjugate were found to be the best sterol donors.
- Tomkiel, Aneta M.,Kowalski, Jan,P?oszyńska, Jolanta,Siergiejczyk, Leszek,?otowski, Zenon,Sobkowiak, Andrzej,Morzycki, Jacek W.
-
-
- Pathways of biotransformation of zingiberen newsaponin from Dioscorea zingiberensis C. H. Wright to diosgenin
-
A new steroidal saponin-β-glucosidase from Aspergillus flavus that specifically hydrolyzed the terminal β-d-glucosyl group at the C-3 position of zingiberen newsaponin, deltonin and trillin from Dioscorea zingiberensis C. H. Wright (DZW) was purified, and characterized. The optimal temperature and pH for the new steroidal saponin-β-glucosidase was 50 C and pH 5.0. The steroidal saponin-β-glucosidase was stable at 30-60 C, and retained more than 80% activity. Further, the purified protein was analyzed by ESI-Q-TOF proteomic analyzer. The results indicated that this enzyme is a β-glucosidase of the type glycosidase hydrolase 3 (GH3). Using a combination of the steroidal saponin-β-glucosidase and steroidal saponin-α-1,2-rhamnosidase from Curvularia lunata obtained previously in our lab, the saponins zingieren newsaponin and deltonin could be converted to diosgenin. The pathways of converting zingiberen newsaponin and deltonin into diosgenin by the two key enzymes were elucidated in this study.
- Huang, Hongzhi,Zhao, Min,Lu, Li,Tan, Dawei,Zhou, Wenbin,Xiong, Chengqi,Zhao, Yang,Song, Xinbo,Yu, Liyan,Ma, Baiping
-
-
- Steroidal glycosides from the bulbs of Fritillaria meleagris and their cytotoxic activities
-
Steroidal glycosides (1-18), including 10 new compounds (1-10), were isolated from the bulbs of Fritillaria meleagris (Liliaceae). The structures of the new compounds were determined by two-dimensional (2D) NMR analysis, and by hydrolytic cleavage followed by spectroscopic and chromatographic analysis. The isolated compounds and their aglycones were evaluated for cytotoxic activity against HL-60 human promyelocytic leukemia cells and A549 human lung adenocarcinoma cells. Morphological observation and flow cytometry analysis showed that 5β-spirostanol glycoside (2) and a cholestane derivative (17a) induced apoptotic cell death in HL-60 cells through different mechanisms of action. Furthermore, the (22R)-spirosolanol glycoside (11) selectively induced apoptosis in A549 cells without affecting the caspase-3 activity level.
- Matsuo, Yukiko,Shinoda, Daisuke,Nakamaru, Aina,Mimaki, Yoshihiro
-
p. 670 - 682
(2013/07/05)
-
- An efficient and recyclable catalyst for the cleavage of tert-butyldiphenylsilyl ethers
-
An efficient, chemoselective, and environment-friendly method for the deprotection of tert-butyldiphenylsilyl ethers mediated by triflic acid supported on silica gel is reported. A wide range of tert-butyldiphenylsilyl ethers derived from carbohydrate and saponin residues can be smoothly cleaved in the presence of various types of other protecting groups in good to excellent yields in acetonitrile. This heterogeneous reaction does not require aqueous workup, and the supported catalyst can be readily recycled.
- Yan, Shiqiang,Ding, Ning,Zhang, Wei,Wang, Peng,Li, Yingxia,Li, Ming
-
experimental part
p. 6 - 20
(2012/07/13)
-
- Furostanol saponins from the rhizomes of Dioscorea japonica and their effects on NGF induction
-
The rhizome of Dioscorea japonica is a food and medicinal source known as 'San Yak' in Korea. Two new furostanol saponins, coreajaponins A (1) and B (2), together with 10 known compounds (3-12) were isolated from the rhizomes of D. japonica. Their structures were determined by spectroscopic methods, including 1D and 2D NMR techniques, HRMS, and chemical methods. Nerve growth factor (NGF), a crucial factor for neuronal survival and differentiation, can potentially improve neurodegenerative diseases and diabetic polyneuropathy. We evaluated the effects of isolates (1-12) on NGF induction in a C6 rat glioma cell line. Coreajaponin B (2) upregulated NGF content without significant cell toxicity, as did 6, 8, 9, and 11.
- Kim, Ki Hyun,Kim, Min Ah,Moon, Eunjung,Kim, Sun Yeou,Choi, Sang Zin,Son, Mi Won,Lee, Kang Ro
-
supporting information; experimental part
p. 2075 - 2078
(2011/05/02)
-
- Cytotoxic steroidal saponins from the rhizomes of Tacca integrifolia
-
Three new steroid saponins (3β,25R)-spirost-5-en-3-yl 6-deoxy-α-L-mannopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4) -6-deoxy-α-L-mannopyranosyl-(1→3)]-β-D-glucopyranoside (1), (3β,22R,25R)-26-(β-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl 6-deoxy-α-L-mannopyranosyl-(1→2)-[6-deoxy-α-L-mannopyranosyl- (1→3)]-β-D-glucopyranoside (3), and (3β,22R,25R)-26-(β-D- glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl 6-deoxy-α-L-mannopyranosyl- (1→2)-[β-D-glucopyranosyl-(1→4)-6-deoxy-α-L-mannopyranosyl- (1→3)]-β-D-glucopyranoside (5), as well as the new pregnane glycoside (3β,16β)-3-{[6-deoxy-α-L-mannopyranosyl-(1→2) -[6-deoxy-α-L-mannopyranosyl-(1→3)]-β-D-glucopyranosyl]-oxy} -20-oxopregn-5-en-16-yl (4R)-5-(β-D-glucopyranosyloxy)-4-methylpentanoate (6), were isolated from the rhizomes of Tacca integrifolia together with two known (25R) configurated steroid saponins (3β,25R)-spirost-5-en-3-yl 6-deoxy-α-L-mannopyranosyl-(1→2)-[6-deoxy-α-L-mannopyranosyl- (1→3)]-β-D-glucopyranoside (2) and (3β,22R,25R)-26-(β-D- glucopyranosyloxy)-22-methoxyfurost-5-en-3-yl 6-deoxy-α-L-mannopyranosyl- (1→2)-[6-deoxy-α-L-mannopyranosyl-(1→3)]-β-D- glucopyranoside (4). The cytotoxic activity of the isolated compounds was evaluated in HeLa cells and showed the highest cytotoxicity value for compound 2 with an IC50 of 1.2±0.4 μm. Intriguingly, while compounds 1-5 exhibited similar cytotoxic properties between 1.2±0.4 (2) and 4.0±0.6 μm (5), only compound 2 showed a significant microtubule-stabilizing activity in vitro.
- Shwe, Htay Htay,Aye, Mye,Sein, Myint Myint,Htay, Khin Than,Kreitmeier, Peter,Gertsch, Juerg,Reiser, Oliver,Heilmann, Joerg
-
experimental part
p. 610 - 622
(2011/07/30)
-
- KHSO4-SiO2-MeOH An efficient selective solid-supported system for deprotection of alcohols from esters
-
KHSO4-SiO2 can efficiently deprotect alcohols from esters through transesterification in methanol under mild condition. Esters of aromatic alcohols are easily transesterified at room temperature compared to the corresponding aliphatic or alicyclic alcohol. NAcetyl compounds and ethers are resistant to the reagent under the above condition. The method is very useful for preparation of biodiesel methyl ricinoleate from castor oil.
- Goswami, Amrit,Das, Ram N.,Borthakur, Naleen
-
p. 1893 - 1895
(2008/09/19)
-
- Deoxygenation of aliphatic acetate derivatives using electrogenerated organic amalgams
-
An electrochemical deoxygenation reaction of aliphatic acetates has been developed, using electrogenerated organic amalgams (R4N-Hg). This methodology led us to obtain the deoxygenated product and the alcohol in a 1:1 ratio with total transform
- Fragoso-Luna, Lizeth M.,Frontana-Uribe, Bernardo A.,Cárdenas, Jorge
-
p. 1151 - 1155
(2007/10/03)
-
- New steroidal glycosides from Balanites aegyptiaca
-
Five new steroidal glycosides were isolated from the roots of Balanites aegyptiaca, a widely used African medicinal plant. On the basis of spectroscopic and chemical evidence, their structures were determined as (3β,12α,14β, 16β)-12-hydroxycholest-5-ene-3,16-diyl bis(β-D-glucopyranoside) (1), (3β,20S,22R,25R)- and (3β,20S,22R,25S)-26-(β-D-glucopyranosyloxy)-22-methoxyurost -5-en-3-yl βD-xylopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 4)[α-L-rhamnopyranosyl-(1 → 2)]-β-D-glucolpyranoside (2 and 3, resp.), and (3β,20S,22R,25S)- and (3β,20S,22R,25S)-spirost-5-en-3-yl 3β-D-xylopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1→4)[α-L-rhamnopyranosyl-(1 → 2)]-β-D-glucopyranoside (4 and 5, resp.).
- Farid, Huda,Haslinger, Ernst,Kunert, Olaf,Wegner, Christian,Hamburger, Matthias
-
p. 1019 - 1026
(2007/10/03)
-
- Spirostanols obtained by cyclization of pseudosaponin derivatives and comparison of anti-platelet agglutination activities of spirostanol glycosides
-
Naturally occurring saponins 3 and 4 have a normal type F ring and α- arranged CH3-21 group. Treatments of pseudosaponin peracetates 18 and 19 derived from 3 and 4, respectively, with alcoholic KOH, followed by acidification with acetic acid, gave spirostanols 20 and 22 having iso type F rings as major products. Structural analyses of sapogenins and saponins derived from pseudo derivatives 11, 12, 18 and 19 were performed by comparisons of their 1H-NMR spectral data and the X-ray analytical data of 3-O-p-bromobenzoyl sarsasapogenin 7, 3-O-acetyl diosgenin 13 and saponin 20. The mechanisms of ring-closure reaction of the side chain at C-22 of pseudosapogenins and pseudosaponins were deduced using stereomodels of the spirostanols derived from 11 under various reaction conditions. Inhibitory activities of saponin diglycosides 3, 4, 20, 21 and 25 on human platelet agglutinations induced by ADP and ristocetin were compared. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
- Tobari, Akihiko,Teshima, Mutsumi,Koyanagi, Junich,Kawase, Masami,Miyamae, Hiroshi,Yoza, Kenji,Takasaki, Akihiko,Nagamura, Yoich,Saito, Setsuo
-
p. 511 - 527
(2007/10/03)
-
- Medicinal foodstuffs. VIII.1 Fenugreek seed. (2) : Structures of six new furostanol saponins, trigoneosides IVa, Va, Vb, VI, VIIb, and VIIIb, from the seeds of indian trigonella foenum-graecum L
-
Following the characterization of trigoneosides Ia, Ib, IIa, IIb; IIIa, and IIIb, seven new steroidal saponins called trigoneosides IVa, Va, Vb, VI, VIIb, VIIIb, and IX were isolated from a medicinal foodstuff fenugreek seed, the seeds of Trigonella foenum-graecum L. (Leguminosae) originating from India. The structures of trigoneosides IVa, Va, Vb, VI, VIIb, and VIIIb were elucidated on the basis of chemical and physicochemical evidence.
- Yoshikawa, Masayuki,Murakami, Toshiyuki,Komatsu, Hajime,Yamahara, Johji,Matsuda, Hisashi
-
p. 397 - 405
(2007/10/03)
-
- A new furostanol saponin with six sugars from the bulbs of Allium sphaerosephalon structural elucidation by modern NMR techniques
-
A new bisdesmosidic furostanol saponin with six monosaccharides (1) was isolated from the bulbs of Allium sphaerosephalon. The structure was determined by the concerted use of modern NMR techniques. The corresponding spirostanol saponin (2) of 1 showed cytotoxic activity against leukemia MOLT-4 cells, while 1 was inactive.
- Mimaki, Yoshihiro,Satou, Tadaaki,Kuroda, Minpei,Kameyama, Aiko,Sashida, Yutaka,Li, Hong-Yu,Harada, Nobuyuki
-
p. 431 - 432
(2007/10/03)
-
- TRANSFORMATIONS OF SOLASODINE AND DERIVATIVES OF HECOGENIN BY CUNNINGHAMELLA ELEGANS
-
Incubation of (25R)-5α-spirostane-3β,12β-diol (rickogenin) with the fungus Cunninghamella elegans led to the formation of (25R)-7β,12β-dihydroxy-5α-spirostan-3-one, (25R)-5α-spirostan-3β,7β,12β-triol and (25R)-5α-spirostan-3β,7α,12α-triol.Incubation of (25R)-5α-spirostan-3,12-dione (hecogenone) with the same fungus gave rise to (25R)-5α-spirostan-3,7,12-trione.When the (22R,25R)-spirosolane, solasod-5-en-3β-ol (solasodine) was incubated with C. elegans, solasod-5-ene-3β,7β-diol, solasod-5-ene-3β,7α-diol and 3β-hydroxysolasod-5-en-7-one were produced.In contrast, incubation of solasodine with Penicillium patulum gave solasod-4-en-3-one and the 6-methylsalicylic acid salt of solasodine.
- Patel, Asmita V.,Blunden, Gerald,Crabb, Trevor A.
-
p. 125 - 134
(2007/10/02)
-
- STEROID GLYCOSIDES OF THE ROOTS OF Capsicum annuum. II. THE STRUCTURE OF THE CAPSICOSIDES
-
Two tigogenin glycosides and two diosgenin glycosides have been isolated from a methanolic extract of the roots of bush red pepper.An aattempt to isolate the individual spirostanol glycosides directly was unsuccessful.These compounds have very similar structures.For their separation, acetylation and epoxidation of the double bond of the aglycon, diosgenin, in the corresponding glycosides was performed.The derivatives obtained were purified by chromatography.To establish the complete chemical structure of each capsicoside we used both chemical and physical methods:complete and partial acid hydrolysis, methylation followed by methanolysis, IR spectroscopy, mass spectroscopy, etc.It was shown that capsicoside A2 is (25R)-5α-spirostan-3β-ol 3-O-β-D-galactopyranoside, capsicoside B2 is (25R)-5α-spirostan-3β-ol 3-O-4)-β-D-galactopyranoside>, capsicoside A3 is (25R)-spirost-5-en-3β-ol 3-O-β-D-galactopyranoside, and capsicoside B3 is identical with funkioside C.
- Gutsu, E. V.,Kintya, P. K.,Lazur'evskii, G. V.
-
p. 202 - 205
(2007/10/02)
-
- STRUCTURE CHARACTERIZATION OF HAEMOSTATIC DIOSGENIN GLYCOSIDES FROM PARIS POLYPHYLLA
-
Key Word Index - Paris polyphylla; Liliaceae; polyphyllin D; pariphyllin; yunnan paiyao; haemostatic and cytotoxic diosgenin glycosides. - From Paris polyphylla var. chinensis Hare (Liliaceae), four diosgenin glycosides with haemostatic effects were isolated.The structure of the major component was elucidated by chemical and spectroscopic methods as 3-(Rha -> 2Glu)>-Ara -> 4Glu)>-β-D-glucopyranosyl)-25(R)-spirost-5-en-3β-ol.This saponin was found to be identical to three previously reported compounds to which other structures were originally assigned, namely the major component from P. polyphylla Smith, the major cytotoxic component of yunnan paiyao, and polyphyllin D from P. polyphylla grown in the Himalaya region.
- Ma, James C. N.,Lau, F. W.
-
p. 1561 - 1566
(2007/10/02)
-
- A FUROSTANOL GLUCURONIDE FROM SOLANUM LYRATUM
-
A new furostanol glucuronide and three known glycosides, SL-0, aspidistrin and methyl proto-aspidistrin, were isolated from the fresh immature berries of Solanum lyratum.The structure of the new compound was characterized as 26-O-β-D-glucopyranosyl-(22ξ,25R)-3β,22,26-trihydroxyfurost-5-ene 3-O-α-L-rhamnopyranosyl-(1 -> 2)- 3)>-β-D-glucopyranoside. Key Word Index - Solanum lyratum; Solanaceae; furostanol glucuronide.-24β-ethyl-5α-cholesta-7,trans-22,25(27)-trien-3β-ol; spinasteryl-β-D-glucopyranoside.
- Yahara, Shoji,Murakami, Naomi,Yamasaki, Masaki,Hamada, Toshiyuki,Kinjo, Jun-ei,Nohara, Toshihiro
-
p. 2748 - 2750
(2007/10/02)
-
- Studies on the Constituents of Palmae Plants. II. The Constituents of Rhapis exelsa Henry and R. humilis Bl.
-
Further studies have been done on the constituents of the stems, underground parts and leaves of two Palmae plants, Rhapis exelsa Henry and R. humilis Bl.We isolated and identified dioscin, Pb, deltonin, methyl proto-dioscin, methyl proto-Pb and methyl proto-deltonin from the stems, dioscin, methyl proto-dioscin and methyl proto-Pb from the underground parts, and saponaretin (= isovitexin), methyl proto-dioscin, methyl proto-Pb and methyl proto-rhapissaponin from the leaves of R. exelsa.On the other hand we isolated and identified prosapogenin A of dioscin, dioscin, deltonin, methyl proto-prosapogenin A of dioscin, methyl proto-dioscin and methyl proto-deltonin from the stems, dioscin, methyl proto-prosapogenin A of dioscin, methyl proto-dioscin and methyl proto-Pb from the underground parts, and saponaretin, vitexin, isoorientin, methyl proto-prosapogenin A of dioscin, methyl proto-dioscin and methyl proto-Pb from the leaves of R. humilis.Methyl proto-rhapissaponin is a new furostanol saponin and its structure has been established to be 26-O-β-D-glucopyranosyl 22-O-methyl-25(R)-furost-5-en-3β,22,26-triol 3-O-4)-α-L-rhamnopyranosyl(1->4)-α-L-rhamnopyranosyl(1->4)>-2)>-β-D-glucopyranoside.This is the second report of the isolation of steroidal saponins from Palmae plants, and the results are interesting from the standpoint of chemotaxonomy. Keywords - Rhapis exelsa; Rhapis humilis; Palmae; steroidal saponin; furostanol oligoside; diosgenin; flavone glycoside; flavone C-glycoside; methyl proto-rhapissaponin
- Hirai, Yasuaki,Sanada, Shuichi,Ida, Yoshiteru,Shoji, Junzo
-
p. 4003 - 4011
(2007/10/02)
-
- STEROID GLYCOSIDES OF THE SEEDS OF Solanum melongena. STRUCTURES OF MELONGOSIDES A, B, E, F, AND H
-
Three chromatographically individual fractions, each containing tigogenin glycosides and diosgenin glycosides have been isolated by chromatography on a silica gel column from a methanolic extract of eggplant seeds.To separate the mixture of two difficultly separable glycosides into individual components, each fraction was acetylated and epoxidated, and the derivatives obtained were separated chromatographically.The tigogenin glycoside peracetates isolated were saponified, and the diosgenin epoxide glycoside acetates were de-epoxidated and saponified, to give the individual glycosides, melongosides A, B, E, F, and H.The complete chemical structure of each melongoside has been shown with the aid of acid hydrolysis, methylation, and periodate oxidation followed by a study of the products obtained.
- Kintya, P. K.,Shvets, S. A.
-
p. 575 - 578
(2007/10/02)
-
- Afromontoside. A New Cytotoxic Principle from Dracaena afromontana
-
A new cytotoxic principle, steroidal saponin afromontoside (1), has been isolated from a methanolic extract of the twigs of Dracaena afromontana.It was shown to be (25R)-furost-5-ene-3β,22α,26-triol 26-O-α-L-rhamnopyranoside 3-O-(4)>-β-D-glucopyranoside) by spectral and chemical methods.The aglycone of afromotoside, diosgenin, as well as dihydrodiosgenin and severall structurally related compounds have been shown to be cytotoxic to cultured KB cells.
- Reddy, K. Sambi,Shekhani, Mohammed S.,Berry, David E.,Lynn, David G.,Hecht, Sidney M.
-
p. 987 - 992
(2007/10/02)
-
- Comparative Studies on the Constituents of Ophiopogonis Tuber and Its Congeners. II. Studies on the Constituents of the Subterranean Part of Ophiopogon planiscapus NAKAI. (1)
-
Seven steroidal glycosides, tentatively named glycosides A, B(1), C(2), D(3), E(4), F(5), and G(6), were isolated from the methanol extract of the subterranean part of Ophiopogon planiscapus NAKAI (Liliaceae).The structures of these glycosides were established as so-called β-sitosterol-β-D-glucopyranoside, diosgenin 3-O-α-L-rhamnopyranosyl(12)-β-D-glucopyranoside (=prosapogenin A of dioscin) (1), diosgenin 3-O-2)>-4)>-β-D-glucopyranoside (=deltonin) (2), 26-O-β-D-gucopyranosyl-22-hydroxyfurost-5-ene-3β,26-diol 3-O-α-L-rhamnopyranosyl(12)-β-D-glucopyranoside (3), ruscogenin 1-O-α-L-rhamnopyranosyl(12)-4-O-sulfo-α-L-arabinopyranoside (4), 26-O-β-D-glucopyranosyl-22-hydroxyfurost-5-ene-3β,26-diol 3-O-2)>-4)>-β-D-glucopyranoside (=22-hydroxyl form of deltoside) (5) and 26-O-β-D-glucopyranosyl-22-hydroxyfurost-5-ene-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(12)-4-O-sulfo-α-L-arabinopyranosides (6), respectively.The relationship of steroidal glycosides of Ophiopogon japonicus KER-GAWLER, O. planiscapus NAKAI and Liriope platyphylla WANG et TANG, which are considered to be the plants of origin of the crude drug, Ophiopogonis Tuber, is also discussed.This is believed to be the first report of steroidal glycosides having a sulfate group on the sugar moiety.Keywords - Ophiopogonis Tuber; Ophiopogon planiscapus; Liliaceae; spirostanol glycoside; furostanol glycoside; sulfated steroidal glycoside; diosgenin; ruscogenin
- Watanabe, Yoshiaki,Sanada, Shuichi,Ida, Yoshiteru,Shoji, Junzo
-
p. 3486 - 3495
(2007/10/02)
-
- Comparative Studies on the Constituents of Ophiopogonis Tuber and Its Congeners. I. Studies of the Constituents of the Subterranean Part of Liriope platyphylla Wang et Tang.
-
Eight steroidal glycosides, tentatively named glycosides A(1), B(2), C(3), D(4), E(5), F(6), G(7) and H(8), were isolated from the methanol extract of the subterranean part of Liriope platyphylla Wang et Tang (Liliaceae).The structures of these glycosides were established as ruscogenin 3-O-α-L-rhamnopyranoside (1), 25(S)-ruscogenin 1-O-β-D-fucopyranosido-3-O-α-L-rhamnopyranoside (2), 25(S)-ruscogenin 1-O-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranoside (3), ruscogenin 3-O-β-D-glucopyranosyl(1->3)-α-L-rhamnopyranoside (4), a mixture of 3-O-2)>3)>-β-D-glucopyranosides of diosgenin and yamogenin (=a mixture of ophiopogonin D' and its 25(S)-isomer, 5), a mixture of 3-O-β-chacotriosides of diosgenin and yamogenin (= a mixture of dioscin and its 25(S)-isomer, 6), ruscogenin 1-sulfate 3-O-α-L-rhamnopyranoside (7), and 26-O-β-D-glucopyranosyl-22-O-methylfurost-5-ene-3β,26-diol 3-O-β-chacotrioside (=methyl proto-dioscin, 8).
- Watanabe, Yoshiaki,Sanada, Shuichi,Ida, Yoshiteru,Shoji, Junzo
-
p. 1980 - 1990
(2007/10/02)
-
- A NEW STEROID GLYCOSIDE, TACCAOSIDE, FROM Tacca cheancer
-
A new steroid glycoside of the spirostan series - taccaoside (I) - has been isolated from an ethanolic extract of the roots of Tacca cheancer (family Taccaceae).An acid hydrolysate was found to contain the aglycone diosgenin (II) and the sugars D-glucose and L-rhamnose in a ratio of 1:2.By methyletion and hydrolysis of the permethylete (IV) it has been established that the two terminal L-rhamnose residues are attached at C-2 and C-3 of the D-glucose molecule which, in its turn, substitutes the hydroxy group at C-3 of diosgenin.Glycoside (I) has the structure of (25R)-spirost-5-en-3β-ol 3-O-2)>3)>-β-D-glucopyranoside>.
- Ngok, Fam Khoang,Kel'ginbaev, A. N.,Gorovits, M. B.,Abubakirov, N. K.
-
p. 262 - 264
(2007/10/02)
-