- Four new pregnane glycosides from Gymnema latifolium and their α-glucosidase and α-amylase inhibitory activities
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Four new pregnane glycosides, gymlatifosides A - D (1 ? 4) and one known pregnane glycoside, verticilloside J (5) were isolated from the leaves of Gymnema latifolium Wall. ex Wight. Their chemical structures were elucidated on the basis of extensive spectroscopic methods, including 1D, 2D NMR, HR-ESI-MS, and in comparison with the reported data. All these compounds were tested for α-glucosidase and α-amylase inhibitory activities. Compound 5 exhibited the most anti α-glucosidase activity with inhibitory percentage of 37.8 ± 1.5% at the concentration of 200 μM. Compounds 1–4 showed moderate anti α-glucosidase activity with inhibitory percentage ranging from 7.0 to 30.1%. In addition, all compounds 1–5 showed moderate/weak anti α-amylase activity in the investigated test.
- Yen, Duong Thi Hai,Trang, Do Thi,Tai, Bui Huu,Doan, Vu Van,Yen, Pham Hai,Nhiem, Nguyen Xuan,Van Minh, Chau,Hoang Duc, Manh,Park, SeonJu,Hyuk Lee, Jae,Kim, Sun Yeou,Kim, Seung Hyun,Kiem, Phan Van
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supporting information
p. 4460 - 4467
(2020/03/03)
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- New calogenin pregnane glycoside derivative from Huernia saudi- arabica and its Lipase and α-Glucosidase Inhibitory Activities
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As ongoing investigation of Huernia saudi-arabica D.V.Field (Asclepiadaceae), a new steroidal pregnane glycoside (Huernioside A) was isolated from dichloromethane fraction (DCM); it was identified as 3β, 11, 14β, 20(R)-tetrahydroxy-pregna-5,9(11)-diene-3-O-β-D-thevetopyranosyl-(1-4)-β-D-cymaropyranoside(HCP) through analysis of 1D, 2D NMR besides ESI-MS data. The alcoholic extract of the aerial part (ALE), DCM and HCP showed inhibitory potential against pancreatic lipase compared to orilstat. Among the tested samples, the ALE and HCP exhibited a promising pancreatic lipase inhibitory commotion through IC50 values of 0.61 ± 0.15, 1.23 ± 0.07 mg/ml (equivalent to 88.8 μM), respectively. HCP was prevailed to have a mixed mode of inhibition as exposed by enzyme kinetic studies. Hydrophobic interactions were the major forces involved in ligand enzyme interactions. In contrast, moderate α-glucosidase inhibitory activities were evidenced for ALE and HCP (% inhibition: 24.8 ± 1.8 and 26.6 ± 2.5, respectively) compared to acarbose. This investigation is the first to report on the possible in vitro anti-obesity and anti-diabetic impact of H. saudi-arabica.
- AbdElSattar, Essam,El Sayed, Abeer Mohamed,Khalil, Mohammed Nabil
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- Melanogenesis inhibitory pregnane glycosides from Cynanchum atratum
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Bioassay-guided fractionation of the methanolic extract from the roots of Cynanchum atratum has resulted in the isolation of three new pregnane glycosides (1–3) along with four known compounds (4–7). Their structures were identified by analysis of the spectroscopic data including extensive 2D NMR. All of the isolates were evaluated for their potential to inhibit the melanin production in α-melanocyte stimulating hormone (α-MSH)-activated B16 melanoma cells. Of these, compounds 4–7 dose-dependently inhibited the melanin production with the IC50 values ranging from 4 μM to 33 μM.
- Jin, Qinghao,Han, Xiang Hua,Yun, Cheong-Yong,Lee, Chul,Lee, Jin Woo,Lee, Dongho,Lee, Mi Kyeong,Jung, Sang-Hun,Hong, Jin Tae,Kim, Youngsoo,Hwang, Bang Yeon
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supporting information
p. 1252 - 1256
(2018/03/12)
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- Two new 14, 15-secopregnane-type steroidal glycosides from the roots of Cynanchum limprichtii
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Two new steroidal glycosides 1 and 2, along with three known ones (3–5), were isolated from the 95% ethanol extract of the roots of Cynanchum limprichtii Schltr. The structure of the new compounds was elucidated as 3-O-α-L-diginopyranosyl-(1→4)-β-D-digito
- Liu, Jia-chuan,Yu, Li-li,Chen, Shao-fei,Lu, Xiao-jie,Zhao, Dan,Wang, Hai-feng,Chen, Gang,Pei, Yue-hu
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p. 261 - 267
(2017/10/06)
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- New C21 steroidal glycosides from the roots of Cynanchum stauntonii and their protective effects on hypoxia/reoxygenation induced cardiomyocyte injury
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Phytochemical investigations from the roots of Cynanchum stauntonii led to obtain four new C21 steroidal glycosides (1–4) and one known compound stauntoside F (5). Their chemical structures were characterized by sophisticated analyses of IR, HR
- Lei, Qiao-Shi,Zuo, Yi-Han,Lai, Chang-Zhi,Luo, Jin-Fang,Pang, Shu-Wen,Zhou, Hua,Yao, Xin-Sheng,Tang, Jin-Shan
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p. 1716 - 1722
(2017/07/27)
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- C21 steroidal glycosides from Cynanchum stauntonii induce apoptosis in HepG2 cells
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Two new (1–2) and three known (3–5) C21 steroidal glycosides were isolated from Cynanchum stauntonii. Their structures were elucidated on the basis of 1D and 2D-NMR spectroscopic data as well as HRTOFMS analysis. The cytotoxicity of the compoun
- Che, Chun-Tao,Ma, Lin,Wang, Lei,Wei, Yu-Jian,Wu, Zheng-Feng,Ye, Wen-Cai,Yin, Zhi-Qi,Yu, Shu-Le,Zhang, Jian,Zhang, Qing-Wen,Zhao, Ming
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- New Sweet-Tasting C21-Pregnane Glycosides from Pericarps of Myriopteron extensum
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Ten novel C21 pregnane glycosides, extensumside C-L (1-10), were isolated as highly sweet-tasting substances from the edible pericarps of Myriopteron extensum (Wight) K. Schum by sensory-guided fractionation and purification. Their structures were determined through 1D and 2D NMR, such as HSQC, HMBC, 1H-1H COSY, HSQC-TOCSY, and ROESY, as well as other spectroscopic analysis combined with chemical evidence. These compounds shared the same aglycone, 3β,16α-dihydroxy-pregn-5-en-20-one, and contained the deoxysugar chain and the glucose chain which were linked to C-3 and C-16 of the aglycone, respectively. The sweetness potency was evaluated by a human sensory panel test and preliminary structure-taste relationship was discussed. The sweetness intensities of these compounds are between 50 and 400 times greater than that of sucrose. Furthermore, quantitation analyses of compounds 1, 3, 4, and 6 in different parts of M. extensum indicated that the concentrations of these sweet components in the pericarps are obviously higher than those in stems and roots.
- Sun, Guo,Dai, Qin,Zhang, Hong-Xia,Li, Zhi-Jian,Du, Zhi-Zhi
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p. 9381 - 9389
(2016/12/23)
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- Hirundigenin type C21 steroidal glycosides from Cynanchum stauntonii and their anti-inflammatory activity
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Six new hirundigenin-type C21 steroidal glycosides, namely hirundigosides E-J (1-6), were obtained from the dried roots of Cynanchum stauntonii. Their chemical structures were elucidated by analyses of HR ESI-TOF MS, 1D, 2D-NMR, and X-ray cryst
- Lai, Chang-Zhi,Liu, Hai-Bin,Liu, Jian-Xin,Ouyang, Qin,Pang, Shu-Wen,Zhou, Hua,Tian, Hai-Yan,Liu, Liang,Yao, Xin-Sheng,Tang, Jin-Shan
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p. 59257 - 59268
(2016/07/06)
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- Nine new steroidal glycosides from the roots of Cynanchum stauntonii
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Nine new steroidal glycosides, named as stauntosides C-K (2, 5, 7-10, 13, 14, and 16), along with seven known compounds (1, 3, 4, 6, 11, 12, and 15) were isolated from the 95% ethanol extract of the roots of Cynanchum stauntonii. The structures of these new compounds were elucidated on the basis of extensive spectroscopic analyses, mainly 1D and 2D NMR, and HRESI-MS, and qualitative chemical methods. Their significance in terms of the chemotaxonomy of C. stauntonii is discussed.
- Yu, Jin-Qian,Deng, An-Jun,Qin, Hai-Lin
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- Two secopregnane-type steroidal glycosides from Cynanchum stauntonii (Decne.) Schltr.ex Levl.
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Two new steroid glycosides, stauntosaponins A (1) and B (2), were isolated from Cynanchum stauntonii (Decne.) Schltr.ex Levl. (Asclepiadaceae) together with five known compounds, anhydrohirundigenin monothevetoside, glaucogenin C mono-d-thevetoside, hirundoside A, cynatratoside A, and glaucogenin C. Stauntosaponins A and B were formulated as 3-O-β-d-oleandropyranosyl-14, 16: 15, 20: 18, 20-triepoxy-14, 15-secopregn-4, 6, 8(14)-triene (1) and 3-O-β-d-thevetopyranosyl-14, 16: 15, 20: 18, 20-triepoxy-14, 15-secopregn-4, 6, 8(14)-triene (2). Compounds 1 and 2 showed moderate inhibitory activities against Na+/K+-ATPase with IC 50 values of 21 and 29 μM, respectively, whereas ouabain as a positive control displayed an IC50 value of 3.5 μM.
- Shibano, Makio,Misaka, Ayaka,Sugiyama, Kayoko,Taniguchi, Masahiko,Baba, Kimiye
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experimental part
p. 304 - 308
(2012/07/27)
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- Five new pregnane glycosides from the stems of Marsdenia tenacissima
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Activity-guided fractionation of the stems of Marsdenia tenacissima led to the isolation of five new pregnane glycosides, namely marstenacissides E (1), F (2), G (3), H (4), and I (5). Their structures were determined on the basis of 1H and 13C NMR, COSY, TOCSY, ROESY, and FABMS experiments.
- Xia, Zeng-Hua,Mao, Shi-Long,Lao, Ai-Na,Uzawa, Jun,Yoshida, Shigeo,Fujimoto, Yasuo
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experimental part
p. 477 - 485
(2011/07/08)
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- New hedgehog/GLI-signaling inhibitors from Adenium obesum
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The aberrant hedgehog (Hh)/GLI signaling pathway causes the formation and progression of a variety of tumors. We recently constructed a cell-based screening system to search for Hh/GLI signaling inhibitors from natural resources. Using our screening system, Adenium obesum was found to include Hh/GLI signaling inhibitors from our tropical plant extract libraries. Bioassay-guided fractionation of this plant extract led to the isolation of 17 cardiac glycosides (1-17), including 3 new compounds (4, 9, 16). These compounds showed strong inhibitory activities, especially the IC50 of 17 is 0.11 μM. The inhibition of GLI-related protein expression with 3, 9, 11, 15 and 17 was observed in human pancreatic cancer cells (PANC1), which express Hh/GLI components aberrantly. The expressions of GLI-related proteins PTCH and BCL2 were clearly inhibited. These compounds also showed selective cytotoxicity against two cancer cell lines, with less effect against normal cells (C3H10T1/2). RT-PCT examinations showed that Ptch mRNA expression by 3, 11, 15 and 17 was inhibited.
- Arai, Midori A.,Tateno, Chikashi,Koyano, Takashi,Kowithayakorn, Thaworn,Kawabe, Seiichiro,Ishibashi, Masami
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experimental part
p. 1133 - 1139
(2011/04/15)
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- Pregnane glycosides from Hoodia gordonii
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Hoodia gordonii is a 'weight loss' herb, which has gained popularity in the western countries as an appetite suppressant dietary supplement. Phytochemical study of its aerial parts led to isolation of seven pregnane glycosides (hoodigosides W-Z, hoodistan
- Shukla, Yatin J.,Pawar, Rahul S.,Ding, Yuanqing,Li, Xing-Cong,Ferreira, Daneel,Khan, Ikhlas A.
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experimental part
p. 675 - 683
(2010/02/17)
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- Triterpene glycosides from Antarctic sea cucumbers. 1. Structure of liouvillosides A1, A2, A3, B1, and B2 from the sea cucumber Staurocucumis liouvillei: New procedure for separation of highly polar glycoside fractions and taxonomic revision
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Five new triterpene glycosides, liouvillosides A1 (1), A 2 (2), A3 (3), B1 (4), and B2 (5), have been isolated from the Antarctic sea cucumber Staurocucumis liouviellei along with the known liouvilloside A (6), isolated earlier from the same species, and hemoiedemosides A (7) and B (8), isolated earlier from the Patagonian sea cucumber Hemioedema spectabilis. The isolation was carried out using a new chromatographic procedure including application of ion-pair reversed-phase chromatography followed by chiral chromatography on a cyclodextrin ChiraDex column. The structures of the new glycosides were elucidated using extensive NMR spectroscopy (1H and 13C NMR spectrometry, DEPT, 1H-1H COSY, HMBC, HMQC, and NOESY), ESI-FTMS, and CID MS/MS, and chemical transformations. Glycosides 1-3 are disulfated tetraosides and glycosides 4 and 5 are trisulfated tetraosides. Glycosides 2 and 3 contain 3-O-methylquinovose, found for the first time as a natural monosaccharide in sea cucumber glycosides. On the basis of analyses of glycoside structures a taxonomic revision is proposed.
- Antonov, Alexandr S.,Avilov, Sergey A.,Kalinovsky, Anatoly I.,Anastyuk, Stanislav D.,Dmitrenok, Pavel S.,Evtushenko, Evgeny V.,Kalinin, Vladimir I.,Smirnov, Alexey V.,Taboada, Sergi,Ballesteros, Manuel,Avila, Conxita,Stonik, Valentin A.
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experimental part
p. 1677 - 1685
(2009/07/18)
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