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ABSTRACT: Phytochemical investigation of the fresh tubers of Ophiopogon japonicus led to the isolation of two new furostanol saponins (1 and 2) together with two known steroidal saponins (3 and 4). Comprehensive spectroscopic analysis allowed the chemical structures of two new compounds to be elucidated as (25R)-26-O-[β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl]-5-ene-furost-1β,3β,22α,26-tetraol-3-O-α-l-rhamnopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-glucopyranoside (1, ophiopogonin P) and (25R)-26-O-[β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl]-5-ene-furost-1β,3β,22α,26-tetraol-3-O-α-l-rhamnopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-glucopyranoside (2, ophiopogonin Q). Furostanol saponins with the disaccharide chain linked at C-26 hydroxy group of the aglycone have been rarely reported from natural sources.
Journal of Asian natural products research 04/2013; · 0.61 Impact Factor
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ABSTRACT: Ultra high-performance liquid chromatography (UHPLC) coupled with hybrid quadrupole time-of-flight mass spectrometry (Qtof MS(E)) was used to rapidly separate and identify steroidal saponins from the crude extract of the seeds of Trigonella foenum-graecum (TFG). By using the UHPLC/Qtof MS(E) data acquisition strategy, both intact precursor and fragment ion information were obtained from a single injection. Fragmentation rules for five major groups of saponins from TFG are summarized, and possible fragmentation pathways are proposed. Accurate mass measurements of molecular ions and fragment ions as well as retention times permitted the identification or tentative identification of a total of ninety-five saponins based on comparison with reference standards. This included twenty-two pairs of isomers. Thirty of these saponins were identified for the first time.
Journal of pharmaceutical and biomedical analysis 02/2013; 74:257-67. · 2.45 Impact Factor
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ABSTRACT: Two new kaurene diterpenoid glycosides, named Graecumoside A (1) and B (2), were isolated from fenugreek seeds, along with three known flavonoid-C-glycosides, isoorientin (3), isovitexin (4) and vitexin (5). By combined analyses of 1D- and 2D-NMR, and MS spectroscopy, the structures of two new compounds were elucidated as 3-O-β- D-glucopyranosyl kaur-5, 16-dien-3β, 6, 13β-trihydroxy-7-oxo-18-oic acid methyl ester and 3-O-β-neohesperidosyl kaur-5, 16-dien-3β, 6, 13β-trihydroxy-7-oxo-18-oic acid methyl ester, respectively. The kaurene diterpenoid glycosides were first isolated and identified from fenugreek seeds.
Natural product research 09/2012; · 1.01 Impact Factor
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ABSTRACT: Three new steroidal saponins, parisyunnanosides G-I (1-3), one new C(21) steroidal glycoside, parisyunnanoside J (4), and three known compounds, padelaoside B (5), pinnatasterone (6), and 20-hydroxyecdyson (7), were isolated from the rhizomes of Paris polyphylla Smith var. yunnanensis. Compounds 1 and 3 have unique trisdesmoside structures that include a C-21 β-d-galactopyranose moiety. All compounds were evaluated for their cytotoxicity against human CCRF leukemia cells.
Journal of Natural Products 06/2012; 75(6):1201-5. · 3.13 Impact Factor
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Tao Zhang,
Li-Ping Kang,
He-Shui Yu,
Yi-Xun Liu,
Yang Zhao, Cheng-Qi Xiong,
Jie Zhang,
Peng Zou,
Xin-Bo Song,
Chao Liu,
Bai-Ping Ma
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ABSTRACT: Eight novel steroidal saponins, ophiopogonins H-O (1-8), along with seven known steroidal saponins (9-15) were isolated from the tubers of Ophiopogon japonicus. The structures of these new compounds were determined by detailed spectroscopic analysis, including extensive 1D and 2D NMR data, and the analysis of hydrolytic reaction products. For the first time, rare furostanol saponins with disaccharide moiety linked at position C-26 of the aglycone were reported to be isolated from a natural source.
Steroids 04/2012; 77(12):1298-305. · 2.83 Impact Factor
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Li-ping Kang,
Kate Yu,
Yang Zhao,
Yi-xun Liu,
He-shui Yu,
Xu Pang, Cheng-qi Xiong,
Da-wei Tan,
Yue Gao,
Chao Liu,
Bai-ping Ma
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ABSTRACT: Steroidal saponins in Rhizoma Paridis attract scientific attentions for their structural diversity and significant bioactivities. In this work, an ultra performance liquid chromatography coupled with a hybrid quadrupole time-of-flight mass spectrometry (UPLC/Q-TOF MS) was used to rapidly separate and identify steroidal saponins from the extract of the rhizome of Paris polyphylla var. yunnanensis (PPY). The fragment ions from glycosidic and cross-ring cleavages offered a wealth of structural information that is indicative to the aglycones, sugar types and the connecting sequence of sugar units. Based on the exact mass information, the fragmentation characteristics, and the LC retention times of 21 reference steroidal saponin standards, 98 constituents were tentatively identified with their structures proposed, which covered more than 30 types of steroidal aglycones. The 98 constituents consist of 22 pairs of structural isomers, and 40 steroidal glycosides that are identified for the first time from the nature.
Journal of pharmaceutical and biomedical analysis 03/2012; 62:235-49. · 2.45 Impact Factor
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Li-ping Kang,
Jie Zhang,
Yue Cong,
Bin Li, Cheng-qi Xiong,
Yang Zhao,
Da-wei Tan,
He-shui Yu,
Zu-yin Yu,
Yu-wen Cong,
Chao Liu,
Bai-ping Ma
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ABSTRACT: Five new steroidal glycosides, timosaponin J ( 1), timosaponin K ( 2), (25 S)-karatavioside C ( 5), timosaponin L ( 6), and (25 S)-officinalisnin-I ( 8), together with eight known steroidal saponins, timosaponin E (1) ( 3), purpureagitosid ( 4), timosaponin BII ( 7), timosaponin B III ( 9), anemarrhenasaponin I ( 10), anemarrhenasaponin III ( 11), anemarrhenasaponin A (2) ( 12), and timosaponin A III ( 13), were isolated from the rhizomes of Anemarrhena asphodeloides. Their structures were elucidated on the basis of spectroscopic and chemical evidence. The aglycones of compounds 1 and 2 are new aglycones. Compounds 1- 13 were evaluated for their platelet aggregation activities, and compound 13 exhibited the strongest inhibitory effect on adenosine diphosphate (ADP)-induced platelet aggregation.
Planta Medica 02/2012; 78(6):611-6. · 2.15 Impact Factor
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ABSTRACT: Five new glucosylated steroidal glycosides, cantalasaponin I-B(1) (1), I-B(2) (2), I-B(3) (3), I-B(4) (4) and I-B(5) (5), were isolated and purified from the transformed product of the cantalasaponin I by using Toruzyme 3.0 l as biocatalyst. Their structures were elucidated on the basis of high-resolution electrospray ionization mass spectrometry, one-dimensional ((1) H and (13) C NMR) and two-dimensional [COSY, heteronuclear single-quantum correlation (HSQC), HMBC and HSQC-TOCSY] NMR spectral analyses and chemical evidence.
Magnetic Resonance in Chemistry 01/2012; 50(1):79-83. · 1.44 Impact Factor
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Xu Pang,
Yue Cong,
He-Shui Yu,
Li-Ping Kang,
Bing Feng,
Bing-Xing Han,
Yang Zhao, Cheng-Qi Xiong,
Da-Wei Tan,
Wei Song,
Bin Liu,
Yu-Wen Cong,
Bai-Ping Ma
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ABSTRACT: Nine spirostanol saponins (1-9) and seven mixtures of 25 R and 25 S spirostanol saponin isomers (10-16) were obtained from the seeds of Trigonella foenum-graecum after enzymatic hydrolysis of the furostanol saponin fraction by β-glucosidase. Their structures were determined by NMR and MS spectroscopy. Among them, 1- 4, 6, 8, and 9 were new compounds and five, 11B, 12A, 13B, 14A, and 14B, were new structures observed from seven mixtures. In addition, the inhibitory effects of all saponins on rat platelet aggregation were evaluated.
Planta Medica 11/2011; 78(3):276-85. · 2.15 Impact Factor
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ABSTRACT: In order to clarify the chemical constituents in Qiliqiangxin capsule, a rapid ultra-performance liquid chromatography/orthogonal acceleration time-of-flight mass spectrometry (UPLC-Q-TOF/MS(E)) method was established. Forty peaks were identified on line using this method. The herbal sources of these peaks were assigned. The results implied that triterpenoid saponins, flavonoid glycosides, C21-steroids and phenolic acids were included in the main components of Qiliqiangxin capsule. The method is simple and rapid for elucidation of the constituents of Qiliqiangxin capsule and the results are useful for the quality control of Qiliqiangxin capsule.
Yao xue xue bao = Acta pharmaceutica Sinica 10/2011; 46(10):1231-6.
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He-Shui Yu,
Bai-Ping Ma,
Li-Ping Kang,
Tao Zhang,
Feng-Juan Jiang,
Jie Zhang,
Peng Zou,
Yang Zhao, Cheng-Qi Xiong,
Da-Wei Tan,
Xin-Bo Song,
Kate Yu
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ABSTRACT: Two new spirostanol saponins, named kingianoside H (1) and kingianoside I (2), were isolated from the processed rhizomes of Polygonatum kingianum, along with a known triterpenoid saponin ginsenoside-Rc (3), four known spirostanol saponins Tg (4), (5), polygonatoside C(1) (6) and ophiopogonin C' (7). The structures of the new compounds were elucidated by detailed spectroscopic analyses, including 1D and 2D NMR techniques and chemical methods. Compounds 3 and 5 were first reported from the genus Polygonatum. Compounds 4, 6 and 7 are reported for the first time from the processed Polygonatum kingianum.
Chemical & pharmaceutical bulletin 10/2009; 57(9):1011-4. · 1.70 Impact Factor
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He-Shui Yu,
Jie Zhang,
Li-Ping Kang,
Li-Feng Han,
Peng Zou,
Yang Zhao, Cheng-Qi Xiong,
Da-Wei Tan,
Xin-Bo Song,
Kate Yu,
Bai-Ping Ma
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ABSTRACT: Further studies on the fresh rhizomes of Polygonatum kingianum led to the isolation of one new spirostanol saponin (25R)-kingianoside G (1), and two pairs mixture of 25R and 25S stereoisomeric spirostanol saponins (25R, S)-pratioside D1 (2a, 2b) and (25R, S)-kingianoside A (3a, 3b), among them 2b and 3b were new spirostanol saponins, together with another two known compounds, disporopsin (4) and daucosterol (5). The structures of the new saponins were determined by detailed analysis of their 1D and 2D NMR spectra, and chemical evidences.
CHEMICAL & PHARMACEUTICAL BULLETIN 02/2009; 57(1):1-4. · 1.59 Impact Factor
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ABSTRACT: Four triterpenoid saponins were isolated from Albizziae cortex, and a complete assignment of their (1)H and (13)C NMR spectra was carried out using 1D and 2D NMR ((1)H-(1)H COSY, HSQC, HMBC, and HSQC-TOCSY) methods. Their (1)H NMR assignments were reported for the first time and some of their (13)C NMR spectral data reported in literature were corrected.
Magnetic Resonance in Chemistry 09/2008; 46(11):1059-65. · 1.44 Impact Factor
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ABSTRACT: A mixture of a pair of stereoisomeric new spirostanol saponins (1a and 1b) and a new cholestane saponin (2) were isolated from the rhizome of Paris pollyphylla Smith var. yunnanensis. Their structures were elucidated as (25R)-spirost-5-en-3beta, 7beta-diol-3-O-alpha-L-arabinofuranosyl-(1 --> 4)-[alpha-L-rhamnopyranosyl-(1 --> 2)]-beta-D-glucopyranoside (1a), (25R)-spirost-5-en-3beta, 7alpha-diol-3-O-alpha-L-arabinofuranosyl-(1 --> 4)-[alpha-L-rhamnopyranosyl-(1 --> 2)]-beta-D-glucopyranoside (1b) and 26-O-beta-D-glucopyranosyl-(25R)-Delta(5(6), 17(20))-dien-16, 22-dione-cholestan-3beta, 26-diol-3-O-alpha-L-arabinofuranosyl-(1 --> 4)-[alpha-L-rhamnopyranosyl-(1 --> 2)]-beta-D-glucopyranoside (2) by a combination of HR-ESI-MS, FAB-MS, 1D and 2D NMR techniques (including (1)H-NMR, (13)C-NMR, (1)H--(1)H COSY, HSQC, HMBC and NOESY).
Magnetic Resonance in Chemistry 10/2007; 45(9):739-44. · 1.44 Impact Factor
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ABSTRACT: To investigate the chemical constituents of the rhizomes of Anemarrhena asphodeloides Bunge.
The compounds were separated by means of solvent extraction, chromatography on absorbent resin SP825 and silica gel C18 repeatedly, and their structures were elucidated on the basis of chemical methods and spectral analyses (FAB-MS, 1H NMR, 13C NMR, 1H-1H COSY).
Six steroidal saponins were isolated from the rhizomes of Anemarrhena asphodeloides Bunge. They were identified as (25S)-26-O-beta-D-glucopyranosyl-22-hydroxy-5beta-furostane-2beta, 3beta, 26-triol-3-O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-galactopyranoside (timosaponin N, 1), timosaponin E1 (2), (25S)-26-O-beta-D-glucopyranosyl-22-methoxy-5beta-furostane-2beta, 3beta, 26-triol-3-O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-galactopyranoside (timosaponin O, 3) , timosaponin E2 (4), (25R) -26-O-beta-D-glucopyranosyl-22-hydroxy-5alpha-furostane-2alpha, 3beta, 26-triol-3-O-beta-D-glucopyranosyl-(1 --> 2)-[beta-D-xylpyranosyl-(1 --> 3)]-beta-D-glucopyranosyl-(1 --> 4)-beta-D-galactopyranoside (purpureagitosid, 5) and marcogenin-3-O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-galactopyranoside (6).
Compound 1 and compound 3 are new compounds, and compound 5 was isolated from the rhizomes of Anemarrhena asphodeloides Bunge for the first time.
Yao xue xue bao = Acta pharmaceutica Sinica 06/2006; 41(6):527-32.
