Hai-Yan Tian

Jinan University (Guangzhou, China), Shengcheng, Guangdong, China

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Publications (36)75.53 Total impact

  • [Show abstract] [Hide abstract]
    ABSTRACT: A new quassinoid, bruceene A (1) along with seventeen known quassinoids (2-18) was isolated from the fruits of Brucea javanica. The structure of 1 was elucidated by extensive spectroscopic methods, and was further confirmed by single-crystal X-ray diffraction analysis. Isolation of similar quassinoids 1-3 as those in genus Ailanthus from genus Brucea, indicated the close chemotaxonomic relationship between these two genera, which further supported the phylogenetic study by DNA analysis. Compounds 5, 7, 10 and 12 with a 3-hydroxy-3-en-2-one moiety showed potent inhibitory activities against the MCF-7 and MDA-MB-231 cells with IC50 values in the ranges 0.063-0.182μM and 0.081-0.238μM, respectively; while glycosidation at 3-OH significantly decreased the cytotoxicity. It was also found that the most potent compound 7 induced apoptosis in MCF-7 cells via the intrinsic mitochondrial apoptotic pathway. Copyright © 2015. Published by Elsevier B.V.
    Fitoterapia 06/2015; 105. DOI:10.1016/j.fitote.2015.06.004 · 2.22 Impact Factor
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    ABSTRACT: Twelve new bufadienolides (1-12), along with fourteen known analogues (13-26) were isolated from the skins of Bufo bufo gargarizans Cantor. Their chemical structures were elucidated on the basis of NMR, HRESIMS and X-ray diffraction analysis. Compound 1 was an unusual bufadienolide with 3,19-epoxy moiety and A/B trans ring junction. Compounds 2-4 were rare bufadienolides possessing 10-H or 10-carboxyl units. All the isolated compounds were tested for their cytotoxic effects on HepG2, A549 and HeLa cells. Six new compounds (2, 3, 5, 6, 10 and 12) displayed significant anti-proliferative activities with IC50 values ranging from 0.049 to 1.856μM. Arenobufagin (24) exhibited the most potent cytotoxic activity with IC50 value 0.011μM. In addition, the present data provided more insight into the structure-activity relationships of bufadienolides. Copyright © 2015. Published by Elsevier B.V.
    Fitoterapia 05/2015; 105. DOI:10.1016/j.fitote.2015.05.013 · 2.22 Impact Factor
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    ABSTRACT: Three new 6,6-spiroketal polyketides, streptospirodienoic acids A (1), B (2) and streptospirodienoate A (3), were obtained from the fermentation broth of Streptomycetes sp. (no. 0950134). Their structures were constructed by one 6,6-spiroketal core coupled with hexadienoic acid, in which the starter unit might be 2-methylpropionyl-CoA. Their chemical structures were determined by detailed analyses of UV, IR, HRESIMS, 1D, 2D-NMR spectroscopic data and the X-ray crystallography technique. The biosynthetic pathway for 1 and 2 was proposed. Compound 3 showed moderate cytotoxic activity against HCT-116 cells (IC50 = 5.2 μM), while compounds 1 and 2 showed no activity (IC50 > 10.0 μM).
    RSC Advances 11/2014; 4(108). DOI:10.1039/C4RA10672E · 3.84 Impact Factor
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    ABSTRACT: Five new cardenolide lactates (1-5) and one new dioxane double linked cardenolide glycoside (17) along with 15 known compounds (6-16 and 18-21) were isolated from the ornamental milkweed Asclepias curassavica. Their structures were elucidated by extensive spectroscopic methods (IR, UV, MS, 1D- and 2D-NMR). The molecular structures and absolute configurations of 1-3 and 17 were further confirmed by single-crystal X-ray diffraction analysis. Simultaneous isolation of dioxane double linked cardenolide glycosides (17-21) and cardenolide lactates (1-5) provided unique chemotaxonomic markers for this genus. Compounds 1-21 were evaluated for the inhibitory activities against DU145 prostate cancer cells. The dioxane double linked cardenolide glycosides showed the most potent cytotoxic effect followed by normal cardenolides and cardenolide lactates, while the C21 steroids were non-cytotoxic. Enzymatic assay established a correlation between the cytotoxic effects in DU145 cancer cells and the Ki for the inhibition of Na+,K+-ATPase. Molecular docking analysis revealed relatively strong H-bond interactions between the bottom of the binding cavity and compounds 18 or 20, and explained why the dioxane double linked cardenolide glycosides possessed higher inhibitory potency on Na+,K+-ATPase than the cardenolide lactate.
    Organic & Biomolecular Chemistry 09/2014; 12(44). DOI:10.1039/C4OB01545B · 3.49 Impact Factor
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    ABSTRACT: One new stenine-type alkaloid, tuberostemonine D (1), together with five known stenine-type alkaloids (2-6) and two known stemoninine-type alkaloids (7 and 8), were isolated from the roots of Stemona tuberosa, which provided chemotaxonomic clues for the close relationship between genera Stemona and Stichoneuron.
    Chinese Chemical Letters 09/2014; DOI:10.1016/j.cclet.2014.03.051 · 1.18 Impact Factor
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    ABSTRACT: Five new sesquiterpenoids Nardosinanone A-E (1-5), were isolated from the extract of Nardostachys chinensis, and their structures were determined by extensive spectroscopic analysis. Compound I featured a nardosinane sesquiterpenoid with an unusual tricyclic skeleton. Compounds 2-4 were new nardosinane sesquiterpenoids bearing a rare 10,11-epoxy group. The absolute configurations were determined by single-crystal X-ray diffraction analysis, ECD calculation method, the CD analysis of the in situ formed [Rh-2(OCOCF3)(4)] complex, and the CD data analysis based on the octane rule of cyclohexanone.
    Tetrahedron 07/2014; 70(30):4507–4511. DOI:10.1016/j.tet.2014.05.010 · 2.82 Impact Factor
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    ABSTRACT: Background Natural products present in low quantity in herb medicines constitute an important source of chemical diversity. However, the isolation of sufficient amounts of these low abundant constituents for structural modification has been a challenge for several decades and subsequently halts research on the utilization of this important source of chemical entities for drug discovery and development. And, pro-angiogenic therapies are being explored as options to treat cardio-cerebral vascular diseases and wound healing recently. The present study investigates the pro-angiogenic potential of tanshinone derivatives produced by one-pot synthesis using zebrafish model. Methodology/Principal Findings In order to address the difficulty of chemical modification of low abundant constituents in herb medicines, a novel one-pot combinatorial modification was used to diversify a partially purified tanshinone mixture from Salvia miltiorrhiza. This led to the isolation of ten new imidazole-tanshinones (Compounds 1–10) and one oxazole-tanshinone (Compound 11), the structures of which were characterized by spectroscopic methods in combination with single-crystal X-ray crystallographic analysis. The angiogenesis activities of the new tanshinone derivatives were determined in an experimental model of chemical-induced blood vessels damage in zebrafish. Of all the tested new derivatives, compound 10 exhibited the most potent vascular protective and restorative activity with an EC50 value of 0.026 µM. Moreover, the mechanism underlying the pro-angiogenesis effect of 10 probably involved the VEGF/FGF-Src-MAPK and PI3K-P38 signalling pathways by gene expression analysis and a blocking assay with pathways-specific kinase inhibitors. Conclusions/Significance Taken together, our study demonstrated the more distinctive pro-angiogenic properties of 10 than other tanshinones and revealed 10 has potential for development as a pro-angiogenic agent for diseases associated with insufficient angiogenesis. Our results highlighted the great potential of adopting a newly modified one-pot approach to enhance the chemical diversity and biological activities of constituents from natural products regardless of their abundances.
    PLoS ONE 07/2014; 9(7):e100416. DOI:10.1371/journal.pone.0100416 · 3.53 Impact Factor
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    ABSTRACT: Three new C-3 dehydrated bufadienolides were isolated from the venom of Bufo bufo gargarizans. Their structures were elucidated as 5 beta,12 beta-12,14-dihydroxy-11-oxobufa-3,20,22-trienolide (1), 5 beta,12 beta-12,14-dihydroxy-11-oxobufa-2,20,22-trienolide (2), and 5 beta,12 alpha-12,14-dihydroxy-11-oxobufa-2,20,22-trienolide (3) on the basis of extensive spectroscopic analysis, especially 1D NMR and 2D NMR data. In addition, all three compounds were tested for their cytotoxic activities against A549 and HepG2 cancer cell lines. Compounds 2 and 3 showed significant cytotoxicities with IC50 values less than 10 mu mol/L on both cancer cells.
    Chinese Chemical Letters 07/2014; 25(7). DOI:10.1016/j.cclet.2014.02.006 · 1.18 Impact Factor
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    ABSTRACT: Hellebrigenin, one of bufadienolides belonging to cardioactive steroids, was found in skin secretions of toads and plants of Helleborus and Kalanchoe genera. In searching for natural constituents with anti-hepatoma activities, we found that hellebrigenin, isolated from traditional Chinese medicine Venenum Bufonis, potently reduced the viability and colony formation of human hepatocellular carcinoma cells HepG2, and went on to explore the underlying molecular mechanisms. Our results demonstrated that hellebrigenin triggered DNA damage through DNA double-stranded breaks and subsequently induced cell cycle G2/M arrest associated with up-regulation of p-ATM (Ser(1981)), p-Chk2 (Tyr(68)), p-CDK1 (Tyr(15)) and Cyclin B1, and down-regulation of p-CDC25C (Ser(216)). It was also found that hellebrigenin induced mitochondrial apoptosis, characterized by Bax translocation to mitochondria, disruption of mitochondrial membrane potential, release of cytochrome c into cytosol and sequential activation of caspases and PARP. In addition, Akt expression and phosphorylation were inhibited by hellebrigenin, whereas Akt silencing with siRNA significantly blocked cell cycle arrest but enhanced apoptosis induced by hellebrigenin. Activation of Akt by human insulin-like growth factor I (hIGF-I) could obviously attenuate hellebrigenin-induced cell death. In summary, our study is the first to report the efficacy of hellebrigenin against HepG2 and elucidated its molecular mechanisms including DNA damage, mitochondria collapse, cell cycle arrest and apoptosis, which will contribute to the development of hellebrigenin into a chemotherapeutic agent in the treatment of liver cancer.
    Chemico-Biological Interactions 06/2014; DOI:10.1016/j.cbi.2014.06.003 · 2.98 Impact Factor
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    ABSTRACT: Two new bufadienolide glycosides (1 and 2) with an A/B trans ring fusion together with nine known compounds (3–11) were isolated from the rhizomes of Helleborus thibetanus. The structures of new compounds were elucidated by extensive spectroscopic analyses in combination with single-crystal X-ray diffraction. The bufadienolides 1 and 3–6 exhibited potent cytotoxic activities against the prostate cancer cells.
    Natural Product Research 06/2014; 28(12). DOI:10.1080/14786419.2014.891200 · 1.23 Impact Factor
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    ABSTRACT: The title compound, C24H33NO4·H2O, the reaction product of de-acetyl-cinobufagin with ammonium acetate, consists of three cyclo-hexane rings (A, B and C), one five-membered ring (D), one six-membered lactone ring (E) and an epoxide ring (F). The stereochemistry of the ring junctures are A/B cis, B/C trans, C/D cis and D/F cis. Cyclo-hexane rings A, B and C have normal chair conformations. The five-membered ring D adopts an envelope conformation (with the C atom bearing the lactone ring as the flap) and the lactone ring E is planar. In the crystal, hy-droxy and water O-H⋯O and amine N-H⋯O hydrogen bonds involving carbonyl, hy-droxy and water O-atom acceptors link the mol-ecules into a three-dimensional network.
    Acta Crystallographica Section E Structure Reports Online 06/2014; 70(Pt 6):o651-2. DOI:10.1107/S1600536814010046 · 0.35 Impact Factor
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    ABSTRACT: A new cyclodepsipeptide cordycecin A (1), together with four known ones beauvericin E (2), beauvericin J (3), beauvericin (4), and beauvericin A (5) were isolated from the ascocarps and insect-body portions of fungus Cordyceps cicadae. Their structures were identified by NMR and MS analyses. The absolute configuration of 1 was confirmed by crystal X-ray diffraction. Compounds 2-5 exhibited a significant inhibitory effect on HepG2 and HepG2/ADM cells with IC50 values ranging from 2.40±0.37 to 14.48±1.68μM. Interestingly, compounds 3-5 showed cytotoxic activity against multiple drug resistant HepG2 cell line (HepG2/ADM) with IC50 value 25-fold more sensitive to doxorubicin.
    Fitoterapia 05/2014; 97. DOI:10.1016/j.fitote.2014.05.010 · 2.22 Impact Factor
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    ABSTRACT: To investigate the chemical constituents of medicinal plant Uncaria hirsuta, three new monoterpenoid alkaloids, named hirsutanines A-C (1-3), were isolated. Their structures with absolute configurations were elucidated by means of NMR, X-ray diffraction and CD analysis. Compound 3 was the first dimeric monoterpenoid alkaloid obtained from genus Uncaria.
    Natural product research 04/2014; DOI:10.1080/14786419.2014.901320 · 1.23 Impact Factor
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    ABSTRACT: Twelve compounds were isolated from the venom of Bufo bufo gargarizans. On the basis of their physical and chemical properties and spectral data, their structures were identified as resibufagenin (1), bufotalin (2), desacetylcinobufagin (3), 19-oxodesacetylcinobufotalin (4), cinobufotalin (5), 1beta-hydroxylbufalin (6), 12alpha-hydroxybufalin (7), bufotalinin (8), Hellebrigenin (9), telocinobufagin (10), hellebrigenol (11) and cinobufagin-3-hemisuberate methyl ester (12), respectively. Compounds 7 and 12 are new natural products.
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    ABSTRACT: Bufalin possesses a strong anti-cancer effect, but the cardiac toxicity targeting the Na(+), K(+)-ATPase limits its application. Here, two bufalin derivatives, bufadienolactam (1) and secobufalinamide (2), were synthesised by treating bufalin with ammonium acetate in dimethylformamide solution. Their structures were elucidated by extensive spectroscopic methods. The structure of compound 2 was further confirmed by single-crystal X-ray diffraction analysis. Compounds 1 and 2 expressed strong inhibitory activities against androgen-dependent prostate cancer cells (IC50 values about 10 μM), but only weak inhibition on Na(+), K(+)-ATPase (Ki about 70 μM), indicating that they might be potential anti-prostate cancer agents without severe cardiac toxicity.
    Natural product research 01/2014; 28(11). DOI:10.1080/14786419.2014.881363 · 1.23 Impact Factor
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    ABSTRACT: Chaetoglobosin Y (1), was isolated from the endolichenic fungal strain Chaetomium globosum (No. 64-5-8-2), along with related six known cytochalasans, chaetoglobosin Fex (2), chaetoglobosin E (3), isochaetoglobosin D (4), chaetoglobosin G (5), cytoglobosin B (6), and cytoglobosin C (7). Their structures were determined by detailed spectroscopic analyses and comparison with those of the closely related compounds previously reported. The cytotoxicity to HCT-116 cell line of 2-7 was evaluated in vitro with doxorubicin as positive control.
    Fitoterapia 01/2014; 93. DOI:10.1016/j.fitote.2013.12.022 · 2.22 Impact Factor
  • Fitoterapia 01/2014; 97:23–27. · 2.22 Impact Factor
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    ABSTRACT: Molecular docking studies have shown that Δ(8,14)-anhydrobufalin (1) exhibited more potent binding affinity on androgen receptor (AR) than Δ(14,15)-anhydrobufalin (2) and bufalin (3). To validate the docking results, compounds 1 and 2 were synthesized. The AR competitive binding assay indicated that the IC50 values of 1-3 were 1.9, >50 and >50 μM (relative binding affinity), respectively, which confirmed that our theoretical binding mode was reliable and predictable. Furthermore, compound 1 was found to show more potent inhibitory activity against the androgen dependent LNCaP cancer cells than the androgen independent PC3 cancer cells, but exhibited less inhibition on the Na(+)/K(+) ATPase as compared with the parent compound 3. To the best of our knowledge, compound 1 represented the first AR antagonist derived from bufadienolide discovered through a series of combined approaches of molecular docking and actual experimental validation.
    Chemico-biological interactions 11/2013; DOI:10.1016/j.cbi.2013.10.020 · 2.98 Impact Factor
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    ABSTRACT: Five new C23 steroids (1-5) together with five known bufadienolides (6-10) were isolated from the venom of Bufo bufo gargarizans (ChanSu in Chinese). The structures of the new steroids were elucidated by extensive spectroscopic methods in combination with X-ray diffraction analysis. Among these C23 steroids, only compound 3 showed cytotoxicities against HepG2 and A549 cancer cells, with respective IC50 values of 26.8 ± 8.3 and 45.6 ± 2.5 μM. In contrast, the bufadienolides (7-10) displayed potent inhibitory activities against these cancer cells, with respective IC50 values in the ranges 0.5-5.5 and 0.6-6.5 μM, but relatively less cytotoxicity on normal mouse spleen cells. In addition, the Na(+)/K(+)-ATPase inhibitory activities of 2, 5, and 7 revealed that the lactone moiety of a bufadienolide was important for the inhibitory activity.
    Journal of Natural Products 09/2013; 76(10). DOI:10.1021/np400174f · 3.95 Impact Factor
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    ABSTRACT: The title compound, C22H29NO4, a stemona alkaloid, is composed of two lactone rings (A and E), a six-membered ring (B), a pyrrole ring (C) and a seven-membered ring (D). The five-membered rings A and E exhibit envelope conformations (C atoms as flaps) while ring C is planar. Ring B exhibits a twist-chair conformation due to fusion with pyrrole ring C while ring D adopts a chair conformation. The junction between rings A and B is cis. In the crystal, weak C-H⋯O inter-actions involving the two carbonyl groups, a methyl-ene and a methyl group give rise to a three-dimensional network.
    Acta Crystallographica Section E Structure Reports Online 09/2013; 69(Pt 9):o1369-70. DOI:10.1107/S1600536813021077 · 0.35 Impact Factor

Publication Stats

95 Citations
75.53 Total Impact Points

Institutions

  • 2011–2015
    • Jinan University (Guangzhou, China)
      • School of Medicine
      Shengcheng, Guangdong, China
  • 2010–2014
    • University of Jinan (Jinan, China)
      Chi-nan-shih, Shandong Sheng, China