![(25R)-26-O-β-D-glucopyranosyl-furosta-5,20(22)-diene-1β,3β,26-triol 1-O-[α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranoside]](/Databaselist/images/loading.webp)
472-11-7Relevant academic research and scientific papers
Synthesis of (25R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)- [β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside
Liu, Meizheng,Yu, Biao,Wu, Xiangyang,Hui, Yongzheng,Fung, Kwok-Pui
, p. 745 - 754 (2000)
The synthesis of (25R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)- [β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside, a saponin from the tuber of Liriope muscari (Decne.) Bailey, is described.
Steroidal glycosides from Ruscus ponticus
Napolitano, Assunta,Muzashvili, Tamar,Perrone, Angela,Pizza, Cosimo,Kemertelidze, Ether,Piacente, Sonia
, p. 651 - 661 (2011)
A comparative metabolite profiling of the underground parts and leaves of Ruscus ponticus was obtained by an HPLC-ESIMSn method, based on high-performance liquid chromatography coupled to electrospray positive ionization multistage ion trap mass spectrometry. The careful study of HPLC-ESIMSn fragmentation pattern of each chromatographic peak, in particular the identification of diagnostic product ions, allowed us to get a rapid screening of saponins belonging to different classes, such as dehydrated/or not furostanol, spirostanol and pregnane glycosides, and to promptly highlight similarities and differences between the two plant parts. This approach, followed by isolation and structure elucidation by 1D- and 2D-NMR experiments, led to the identification of eleven saponins from the underground parts, of which two dehydrated furostanol glycosides and one new vespertilin derivative, and nine saponins from R. ponticus leaves, never reported previously. The achieved results highlighted a clean prevalence of furostanol glycoside derivatives in R. ponticus leaves rather in the underground parts of the plant, which showed a wider structure variety. In particular, the occurrence of dehydrated furostanol derivatives, for the first time isolated from a Ruscus species, is an unusual finding which makes unique the saponins profile of R. ponticus.
A SPIROSTANOL GLYCOSIDE FROM THE RHIZOMES OF OPHIOPOGON INTERMEDIUS
Rawat, M. S. M.,Negi, D. S.,Panwar, M. S.,Pant, G.
, p. 3326 - 3327 (1988)
A new ruscogenin glycoside has been characterized from the rhizomes of Ophiopogon intermedius.Key Word Index - Ophiopogon intermedius; Haemodoraceae; rhizomes; spirostanol glycoside; ruscogenin; spermicidal potential.
New neuritogenic steroidal saponin from Ophiopogon japonicus (Thunb.) Ker-Gawl
Qu, Yuan,Zhang, Yang,Pei, Liang,Wang, Yan,Gao, Lijuan,Huang, Qianming,Ojika, Makoto,Sakagami, Youji,Qi, Jianhua
, p. 1201 - 1204 (2011)
A new steroidal saponin was isolated from Ophiopogon japonicus. This saponin possesses a modification by 2-hydroxy-3-methylvalerylation of the hydroxyl group at C-4' of the sugar, linked to C-1 of the aglycone. It exhibited significant neuritogenic activity for PC12 cells. The structure-activity relationship revealed the aglycone, rather than the sugar moieties and acylation, to be important for the neuritogenic activity.
First total synthesis of 25(R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside, an Ophiopogonis saponin from the tuber of Liriope muscari (Decne.)
Liu, Meizheng,Yu, Biao,Hui, Yongzheng
, p. 415 - 418 (1998)
The first total synthesis of 25(R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside (1), an Ophiopogonis saponin with strong anti-inflammatory and immunopharmacological activities from the tuber of Liriope muscari (Decne.), is described. The glycosylation of a highly hindered alcohol by Schmidt's 'inverse procedure' is demonstrated.
Steroidal glycosides from the underground parts of Dracaena thalioides and their cytotoxic activity
Tang, Liying,Wang, Zhuju,Wu, Hongwei,Yokosuka, Akihito,Mimaki, Yoshihiro
, p. 102 - 110 (2015/02/19)
Six spirostanol glycosides (1-6) and 12 known compounds (7-18) were isolated from the underground parts of Dracaena thalioides (Agavaceae). Their structures were determined by spectroscopic analysis, including 2D NMR spectroscopic data, and chemical transformations. The isolated compounds were evaluated for cytotoxic activity against HL-60 human leukemia cells. Compounds 1, 3-6, and 8-18 showed cytotoxicity against HL-60 cells, of which 10, a bisdesmosidic spirostanol derivative, showed potent cytotoxicity against HL-60 cells with an IC50 value of 0.38 μM and induced apoptosis in HL-60 cells.
Steroidal glycosides from the bulbs of Ornithogalum thyrsoides
Kuroda, Minpei,Mimaki, Yoshihiro,Ori, Kazutomo,Sakagami, Hiroshi,Sashida, Yutaka
, p. 1690 - 1696 (2007/10/03)
Phytochemical analyses have been carried out on the fresh bulbs of Ornithogalum thyrsoides with particular attention to the steroidal glycoside constituents, resulting in the isolation of four new spirostanol saponins and seven new cholestane glycosides, together with three known steroidal compounds. The structures of the new glycosides were determined on the basis of their spectroscopic data, including 2D NMR spectroscopy, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activities against HL-60 human promyelocytic leukemia cells and HSC-2 human oral squamous cell carcinoma cells.
STEROIDS OF THE SPIROSTAN AND FUROSTAN SERIES FROM PLANTS OF THE GENUS Allium. XXI. STRUCTURE OF ALLIOSPIROSIDE A AND ALLIOFUROSIDE A FROM Allium cepa
Kravets, S. D.,Vollerner, Yu. S.,Gorovits, M. B.,Shashkov, A. S.,Abubakirov, N. K.
, p. 174 - 181 (2007/10/02)
Two new steroid glycosides have been isolated from the generative organs (pericarps and peduncles) of Allium cepa L.: alliospiroside A and alliofuroside A.According to chemical transformations and spectral characteristics, alliospiroside A has the structure of (25S)-spirost-5-ene-1β,3β-diol 1-O- 2)-α-L-arabinopyranoside>.The structure of (25S)-furost-5-ene-1β,3β,22α,26-tetraol 20-O-β-D-glucopyranoside 1-O- 2)-α-L-arabinopyranoside> has been established for alliofuroside A.
Comparative Studies on the Constituents of Ophiopogonis Tuber and Its Congeners. III. Studies on the Constituents of the Subterranean Part of Ophiopogon ohwii Okuyama and O. jaburan (Kunth) Lodd.
Watanabe, Yoshiaki,Sanada, Shuichi,Ida, Yoshiteru,Shoji, Junzo
, p. 3994 - 4002 (2007/10/02)
Six steroidal glycosides tentatively named glycosides O-1, O-2 (1), O-3 (2), O-4 (3), O-5 (4) and O-6 (5), were isolated from the subterranean part of Ophiopogon ohwii Okuyama (Liliaceae) and another six steroidal glycosides, tentatively named glycosides J-1, J-2 (6), J-3 (7), J-4 (8), J-5 (9) and J-6 (10), were isolated from the subterranean part of O. jaburan (Kunth) Lodd.Glycosides O-1 and J-1 were identified as so-called β-sitosterol β-D-glucopyranoside.The structures of 1-10 were established as ophiopogonin B (1), Ophiopogonin D (2), ruscogenin 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranoside (3), ruscogenin 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-α-L-arabinopyranoside (=glycoside E of O. planiscapus Nakai) (4), 26-O-β-D-glucopyranosyl 22-hydroxy-25(R)-furost-5-en-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranoside (5), ophiopogonin D (=glycoside O-3 (2)) (6), a mixture of 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranosido-3-O-β-D-glucopyranosides of ruscogenin and neoruscogenin (7), neoruscogenin 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-α-L-arabinopyranosido-3-O-β-D-glucopyranoside (8), a mixture of 26-O-β-D-glucopyranosyl 22-hydroxy-25(R)-furost-5-en-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranosido-3-O-β-D-glucopyranoside and 26-O-β-D-glucopyranosyl 22-hydroxyfurost-5,25(27)-dien-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranosido-3-O-β-D-glucopyranoside (9), and 26-O-β-D-glucopyranosyl 22-hydroxyfurost-5,25(27)-dien-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-α-L-arabinopyranosido-3-O-β-d-glucopyranoside (10).It is interesting that the main saponins, ophiopogonins B and D, found in Ophiopogonis Tuber (obtained from O. japonicus Ker-Gawler) were also found in O. ohwii (Okuyama and the latter saponin was also found in O. jaburan (Kunth) Lodd.Further, several steroidal glycosides carrying sulfate on the sugar moiety were found in Liliaceous plants belonging to the genus Ophiopogon. Keywords - Ophiopogonis Tuber; Ophiopogon ohwii; Ophiopogon jaburan; Liliaceae; spirostanol glycoside; furostanol glycoside; sulfated steroidal glycoside
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.
Watanabe, Yoshiaki,Sanada, Shuichi,Ida, Yoshiteru,Shoji, Junzo
, p. 1980 - 1990 (2007/10/02)
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).
