Yun-Bao Ma

Kunming University of Science and Technology, Yün-nan, Yunnan, China

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Publications (73)155.33 Total impact

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    ABSTRACT: Investigation on the fruits of Melia toosendan afforded seven new lignans (1-7), along with seventeen known compounds (8-24). The structures of the new compounds, involving four neo-lignans (1-4), two sesquilignans (5-6), and a nor-lignan (7), were elucidated based on extensive spectroscopic analyses (high-resolution electrospray ionization mass spectra, ultraviolet, infrared, one-dimensional and two-dimensional nuclear magnetic resonance). Compound 24 exhibited activity on melatonin receptor type 1 with an agonistic rate of 57.77 % at 1.02 mM according to the assay on HEK293 cell lines in vitro. Georg Thieme Verlag KG Stuttgart · New York.
    Planta Medica 06/2015; DOI:10.1055/s-0035-1546127 · 2.34 Impact Factor
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    ABSTRACT: The rhizome of Cyperus rotundus (C. rotundus) is a well-known traditional Chinese medicine to cure hepatitis in many formulae, but the active components responsible for hepatitis have not been elucidated. According to our bioassay on HepG2.2.15 cell line in vitro, the ethanol extract of C. rotundus demonstrated potent anti-HBV activity. This current study was designed to isolate and identify the anti-HBV active constituents from the rhizomes of C. rotundus. Bioactivity and LC-MS guided fractionation on the extract of C. rotundus using various chromatographic techniques including open-column, Sephadex LH-20 and semi-preparative high performance liquid chromatography led to the isolation and identification of thirty-seven sesquiterpenoids. Structural elucidation of the isolates was carried out by extensive spectroscopic analyses (UV, IR, HRMS, 1D- and 2D-NMR). The anti-HBV activity and cytotoxicity were evaluated on the HBV-transfected HepG2.2.15 cell line in vitro. The cytotoxicity effects of the isolates were assessed by a MTT assay. The secretions of HBsAg and HBeAg in the culture medium were detected by ELISA method, and the load of HBV DNA was quantified by real-time fluorescent PCR technique. Five new patchoulane-type sesquiterpenoids, namely cyperene-3, 8-dione (1), 14-hydroxy cyperotundone (2), 14-acetoxy cyperotundone (3), 3β-hydroxycyperenoic acid (4) and sugetriol-3, 9-diacetate (5), along with 32 known sesquiterpenoids were isolated from the active fractions of C. rotundus. Compounds 2 and 3 were the first cyperotundone-type sesquiterpenoids with a hydroxyl group at C-14 position. Nine eudesmane-type sesquiterpenoids (15-21 and 23-24) significantly inhibited the HBV DNA replication with IC50 values of 42.7±5.9, 22.5±1.9, 13.2±1.2, 10.1±0.7, 14.1±1.1, 15.3±2.7, 13.8±0.9, 19.7±2.1 and 11.9±0.6μM, respectively, of which, compounds 17, 21, 23 and 24 possessed high SI values of 250.4, 125.5,>259.6 and 127.5, respectively. Two patchoulane-type sesquiterpenoids (4 and 7) effectively suppressed the secretion of HBsAg in a dose-dependent manner with IC50 values of 46.6±14.3 (SI=31.0) and 77.2±13.0 (SI=1.7) μM, respectively. Compounds 2, 8, 12, 15, 17 and 25 possessed moderate activities against HBeAg secretion with IC50 values of 162.5±18.9 (SI=13.3), 399.2±90.0 (SI=10.6), 274.7±70.8 (SI=5.2), 313.9±87.5 (SI=7.2), 334.0±70.4 (SI=9.9) and 285.3±20.9 (SI=15.5) μM, respectively. This is the first study to reveal the anti-HBV constituents of C. rotundus, demonstrating that the eudesmane-type sesquiterpenoids might contribute to the anti-HBV activity of the rhizomes of Cyperus rotundus. Copyright © 2015. Published by Elsevier Ireland Ltd.
    Journal of ethnopharmacology 06/2015; 171. DOI:10.1016/j.jep.2015.05.040 · 2.94 Impact Factor
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    ABSTRACT: One unusual secoiridoid trimer, namely sweriyunnanlactone A (1), was isolated from Swertia yunnanensis under the guidance of LC–MS analysis. Sweriyunnanlactone A with a phenyl ring (ring F) was the first example of secoiridoid trimer featuring a C28 skeleton. Its structure was determined by extensive HRESIMS, 1D and 2D NMR spectroscopic data, and GIAO 13C NMR calculation. Compound 1 showed weak inhibition on HBV DNA replication with an IC50 value of 60.76 μM (SI = 12.6) on HepG 2.2.15 cell line in vitro.
    Tetrahedron Letters 04/2015; 56(17). DOI:10.1016/j.tetlet.2015.03.057 · 2.39 Impact Factor
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    ABSTRACT: Fifteen known compounds were isolated from Swertia delavayi by silica gel, Sephadex LH-20 and Rp-18 column chromatographies. Based on extensive spectroscopic analysis (MS, 1H, 13C-NMR), their structures were identified aserythrocentaurin (1), erythrocentaurindimethylacetal (2), sweroside (3), swertiamarin (4), gentiopicroside (5), swertiakoside A (6), 2'-O-acetylswertiamarin (7), 4'-O-[(Z) -coumaroyl] swertiamarin (8), 1,5,8-trihydroxy-3-methoxyxanthone (9), 8-O-β-D-glucopyranosyl-1-hydroxy-2,3, 5-trimethoxyxanthone (10), 8-O-[β-D-xyl- opyranosyl-(1 --> 6)-β-D-glucopyranosyl]-7,8-dihydroxy-3-methoxyxanthone (11), isovitexin (12), β-sitosterol (13), daucosterol (14), and oleanolic acid (15). Among them, ten ones (14, 7-11, 13) were obtained from S. delavayi for the first time. The isolates were evaluated for their anti-HBV activities in HepG 2. 2. 15 cell line in vitro. The results showed that compound 1, 2, 6, 7, 9 and 12 exhibited significant inhibitory activity on HBV DNA replication with IC50 values from 0.05 to 1.46 mmol x L(-1).
    Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 03/2015; 40(5):897-902.
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    ABSTRACT: Five new secoiridoid glycosides, swericinctosides A and B (1-2), 9-epi swertiamarin (3), 2'-O-m-hydroxybenzoyl swertiamarin (4), 4''-O-acetyl swertianoside E (5), and one unusual lactonic enol ketone, 3-(hydroxymethyl ene) dihydro-2H-pyran-2, 4(3H)-dione (6), together with three known compounds, swertiaside (7), swertianoside C (8) and decentapicrin B (9) were isolated from Swertia cincta. The structures of the new compounds were determined by extensive spectroscopic analyses including 1D and 2D NMR, HRESIMS, UV, IR and [α]D spectra. Anti-HBV assay on HepG 2.2.15 cell line in vitro demonstrated that compounds 1-9 possessed inhibitory activity on HBV DNA replication with IC50 values from 0.05 to 1.83mM, and compounds 1, 3, 5, 7 and 8 could inhibit the secretion of HBsAg with IC50 values from 0.24 to 1.06mM. Copyright © 2015. Published by Elsevier B.V.
    Fitoterapia 02/2015; 102. DOI:10.1016/j.fitote.2015.02.009 · 2.22 Impact Factor
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    ABSTRACT: p-Hydroxyacetophenone (p-HAP), as a main hepatoprotective and choleretic constituent of Artemisia capillaris, was revealed with anti-hepatitis B virus (HBV) effects in recent investigation. In addition to p-HAP, four derivatives of p-HAP were also isolated from A. capillaris by various chromatographic methods. Subsequent structural modification on p-HAP and its glycoside led to the synthesis of 28 additional derivatives, of which 13 compounds showed activity inhibiting hepatitis B surface antigen (HBsAg) secretion; and 18 compounds possessed inhibition on HBV DNA replication. The primary structure-activity relationships (SARs) suggested that the conjugated derivatives of p-HAP glycoside and substituted cinnamic acids (2a-2i) obviously enhanced the activity against HBV DNA replication with IC50 values ranged from 5.8 to 74.4μM. Copyright © 2015. Published by Elsevier Ltd.
    Bioorganic & Medicinal Chemistry Letters 02/2015; 25(7). DOI:10.1016/j.bmcl.2015.02.024 · 2.33 Impact Factor
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    ABSTRACT: Twenty-four derivatives of erythrocentaurin (ET) were synthesized and evaluated for their anti-HBV activities on HepG 2.2.15 cell line in vitro. Eight compounds 1, 2, 5, 8, 9, 1e, 1k, and 1m increased activity against HBV DNA replication with the SI values higher than 11. In particular, derivatives 1e and 1k exhibited the most potent inhibition on HBV DNA replication with the IC50 values of 0.026mM (SI>70.8) and 0.045mM (SI>36.0), respectively. The primary structure-activity relationships (SARs) of ET derivatives were summarized for exploring potent anti-HBV agents. Copyright © 2015 Elsevier Ltd. All rights reserved.
    Bioorganic & Medicinal Chemistry Letters 02/2015; 25(7). DOI:10.1016/j.bmcl.2015.02.009 · 2.33 Impact Factor
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    ABSTRACT: Three new secoiridoid aglycones of (-)-swermusic acid A (1) and B (3), and (-)-swerimuslatone A (2), and four new secoiridoid glycosides of 6'-O-formylsweroside (4), 6'-O-formylgentiopicroside (5), 6'-O-acetylamarogentin (6) and 6'-O-acetylamaronitidin (7), along with 40 known compounds (8-47) were isolated from Swertia mussotii. Their structures were elucidated on the basis of extensive spectroscopic analyses including MS, IR, UV, 1D- and 2D-NMR. 45 compounds from swertia mussotii were evaluated for their anti-HBV activity on the HepG 2.2.15 cell line in vitro inhibiting the secretions of HBsAg and HBeAg, as well as HBV DNA replication. The six of nine phenols 26-29, 31 and 32 exhibited activities inhibiting HBsAg and HBeAg secretion with IC50 values from 0.23 to 5.18mM, and HBV DNA replication with IC50 value from<0.06 to 2.62mM. Moreover, isooriention (45) displayed significant anti-HBV activities against the secretions of HBsAg and HBeAg with IC50 value of 0.79 and 1.12mM, as well as HBV DNA replication with IC50 value of 0.02mM. Copyright © 2015. Published by Elsevier B.V.
    Fitoterapia 02/2015; 102. DOI:10.1016/j.fitote.2015.01.020 · 2.22 Impact Factor
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    ABSTRACT: Four new compounds swertiachiralatone A (1), swertiachoside A (2), swertiachirdiol A (3) and swertiachoside B (4), together with twenty-six known ones were isolated from the ethanol extract of Swertia chirayita. Their structures were elucidated by extensive spectroscopic analyses (1D- and 2D-NMR, HRESIMS, UV, IR and [α]D). All compounds were evaluated for anti-hepatitis B virus (anti-HBV) activities on HepG 2.2.15 cells line in vitro, of which compounds 14 and 19 showed inhibitory activity on hepatitis B surface antigen (HBsAg) secretion with IC50 values of 0.31±0.045 and 1.49±0.033mM; compounds 14 and 28 exhibited activity against hepatitis B e antigen (HBeAg) secretion with IC50 values of 0.77±0.076 and 5.92±1.02mM; and eight compounds (8,9,13,14,24-26,29) possessed activity against HBV DNA replication with IC50 values of 0.07-0.33mM. In particular (+)-cycloolivil-4'-O-β-d-glucopyranoside (14) exhibited inhibition not only on the secretions of HBsAg and HBeAg with IC50 values of 0.31±0.045mM (SI=4.29) and 0.77±0.076mM (SI=1.75), respectively, but also on HBV DNA replication with an IC50 value of 0.29±0.034mM (SI=4.66). Copyright © 2014 Elsevier B.V. All rights reserved.
    Fitoterapia 11/2014; 100C:27-34. DOI:10.1016/j.fitote.2014.11.011 · 2.22 Impact Factor
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    ABSTRACT: Hepatitis B induced by HBV is a serious health problem. Artemisia capillaris (Yin-Chen) has long been used to treat hepatitis in traditional Chinese medicine. Coumarins, flavonoids and organic acids were revealed as its hepatoprotective and choleretic components, but its anti-HBV active components remain unknown. This current study focused on its anti-HBV active constituents by various chromatographic methods.
    Journal of Ethnopharmacology 09/2014; 156. DOI:10.1016/j.jep.2014.08.043 · 2.94 Impact Factor
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    ABSTRACT: Thirty-nine caudatin analogs were designed and synthesized. Their anti-hepatitis B virus (HBV) activities were evaluated in vitro. Among them, twenty-three compounds showed much better anti-HBV activity than caudatin, and eleven compounds significantly inhibited the HBV DNA replication with IC50 values < 10 μΜ. Interestingly, three compounds (22, 28, 29) exhibited excellent activity against the secretion of HBsAg (IC50 = 63.02 μΜ, 52.81 μΜ, 56.08 μΜ), HBeAg (IC50 = 204.80 μΜ, 173.51 μΜ, 70.39 μΜ), along with HBV DNA replication (IC50 = 24.55 μΜ, 5.69 μΜ, 8.23 μΜ) with lower cytotoxicity. The structure-activity relationships (SARs) of these caudatin analogs were also discussed.
    Medicinal Chemistry 09/2014; 11(2). DOI:10.2174/1573406410666140902111326 · 1.39 Impact Factor
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    ABSTRACT: Two new sesquiterpenoid glycosides, nicotabalactonecoside (1) and nicotabadiolcoside (2), along with four known terpenoids (3-6) were isolated from the leaves of Nicotiana tabacum. The structures of compounds 1 and 2 were determined as dihydrodeacetylphytuberin-2-one 11-O-β-d-glucopyranoside and 1,2-dehydro-4-epieremophil-9-ene-11,12-diol 12-O-β-d-glucopyranoside by extensive spectroscopic analyses (HR-ESI-MS, UV, IR, 1D, and 2D NMR) and chemical method. Compound 1 is an unusual phytuberin-type sesquiterpenoid with a 6/5/5 tricyclic system.
    Journal of Asian Natural Products Research 06/2014; 16(6):1-6. DOI:10.1080/10286020.2014.922553 · 0.97 Impact Factor
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    ABSTRACT: 28 Derivatives of panaxadiol (PD) and panaxatriol were synthesized and evaluated for their anti-HBV activity on HepG 2.2.15 cells, of which 17 derivatives inhibited HBV DNA replication. Compounds 4, 9, 10, 14, and 15 showed moderate activity against HBV DNA replication with IC50 values ranged from 7.27 to 28.21 μM compared with PD. In particular, 3-O-2'-thenoyl panaxadiol (4) inhibited not only HBV DNA replication (IC50 = 16.5 μM, SI > 115.7) but also HBsAg (IC50 = 30.8 μM, SI > 62.0) and HBeAg (IC50 = 18.2 μM, SI > 105.14) secretions. Their structure-activity relationships were discussed for guiding future research toward the discovery of new anti-HBV agents.
    06/2014; 4(3):163-174. DOI:10.1007/s13659-014-0018-2
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    ABSTRACT: Three new polyacetylenes, 8 - (Z) - decene - 4, 6-diyne - 1, 3, 10-triol (1), 1, 3S, 8S - trihydroxydec - 9 - en - 4, 6 - yne (2), 3S, 8S - dihydroxydec - 9 - en - 4, 6 - yne 1 - O - β - D - glucopyranoside (3), and one new glucosyl caffeoate, 1 - O - ethyl - 6 - O - caffeoyl - β - D - glucopyranose (4), together with 34 known compounds were isolated from Artemisia capillaris. The structures of the new compounds were determined by extensive spectroscopic analyses including 1D and 2D NMR, HRESIMS, [α]D and CD experiments. Among them, 19 compounds showed activity inhibiting HBsAg secretion; 20 compounds showed activity inhibiting HBeAg secretion; and 25 compounds possessed inhibitory activity against HBV DNA replication according to our anti-HBV assay on HepG 2.2.15 cell line in vitro. The most active compound 12 could inhibit not only the secretions of HBsAg and HBeAg, but also HBV DNA replication with IC50 values of 15.02μM (SI=111.3), 9.00μM (SI=185.9) and 12.01μM (SI=139.2).
    Fitoterapia 06/2014; 95. DOI:10.1016/j.fitote.2014.03.017 · 2.22 Impact Factor
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    ABSTRACT: Dehydroandrographolide and andrographolide, two natural diterpenoids isolated from Andrographis paniculata possessed activity against HBV DNA replication with IC50 values of 22.58 and 54.07 μM and low SI values of 8.7 and 3.7 in our random assay. Consequently, 48 derivatives of dehydroandrographolide and andrographolide were synthesized and evaluated for their anti-HBV properties to yield a series of active derivatives with lower cytotoxicity, including 14 derivatives against HBsAg secretion, 19 derivatives against HBeAg secretion and 38 derivatives against HBV DNA replication. Interestingly, compound 4e could inhibit not only HBsAg and HBeAg secretions but also HBV DNA replication with SI values of 20.3, 125.0 and 104.9. Furthermore, the most active compound 2c with SI value higher than 165.1 inhibiting HBV DNA replication was revealed with the optimal log P value of 1.78 and log D values. Structure–activity relationships (SARs) of the derivatives were disclosed for guiding the future research toward the discovery of new anti-HBV drugs.
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    ABSTRACT: The ethyl acetate extract of the flower of Albizia julibrissin was isolated and purified by silica gel, Sephadex LH-20 and MCI GEL CHP-20P column chromatography to yield 29 compounds. Their structures were elucidated as 8-hydroxy-2, 6-dimethyl-2E, 6Z-octadienoic acid (1), 8-O-formyl-2, 6-dimethyl-2E, 6Z-octadienoic acid (la), 8-hydroxy-2, 6-dimethyl-2E, 6E-octadienoic acid (2), 8-O-formyl-2, 6-dimethyl-2E, 6E-octadienoic acid (2a), (2E, 6S)-2, 6-dimethyl-6-O-beta-D-xylpyranosyloxy-2, 7-menthia-folic acid (3), clovan-2beta, 9alpha-diol (4), 2beta-O-formyl-clovan-9alpha-ol (4a), 2beta, 9alpha-O-diformyl-clovan (4b), vomifoliol (5), (6S, 9R)-roseoside (6), vanillin (7), 4-O-ethylgallic acid (8), 3-ethoxy4-hydroxy-benzoic acid (9), p-hydroxybenzaldehyde (10), gallic acid (11), protocatechoic acid (12), stearic acid (13), palmitic acid (14), 2, 3-dihydroxypropyl hexadecanoate (15), linoleic acid (16), scopoletin (17), indole-3-carboxaldehyde (18), 2-furoic acid (19), 5-(hydroxymethyl)-2-furaldehyde (20), (22E, 24R)-5alpha, 8alpha-epidioxy-ergosta-6, 22-dien-3beta-ol (21), (22E, 24R)-5alpha, 8alpha-epidioxy-ergosta-6, 9, 22-trien-3beta-ol (22), (+)-lariciresinol 9'-stearate (23), formononetin (24) and uridine (25). Compounds 1a, 2a, 4a and 4b were new artifacts from the separation process, and others were obtained from A. julibrissin for the first time.
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    ABSTRACT: Six new 14 - noreudesmane sesquiterpenoids, nicotabacosides A-F (1-6), along with five known sesquiterpenoids (7-11), were isolated from the leaves of Nicotiana tabacum. The structures of compounds 1-6 were elucidated as isorishitin 3 - O - β - D - glucopyranoside (1), rishitin 3 - O - β - D - glucopyranoside (2), rishitin 2 - O - β - D - glucopyranosde (3), 1, 6 - dehydro - rishitin 3 - O - β - D - glucopyranoside (4), 2 - hydroxyl - ligudentatol 3 - O - β - D - glucopyranoside (5) and oxyglutinsone 3 - O - β - D - glucopyranoside (6) based on extensive spectroscopic analyses (HRESIMS, UV, IR, 1D and 2D NMR). Their absolute configurations were determined by the X-ray single-crystal diffraction and comparison of their electronic circular dichroism (ECD) spectra.
    Fitoterapia 04/2014; DOI:10.1016/j.fitote.2014.04.010 · 2.22 Impact Factor
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    ABSTRACT: Dehydroandrographolide and andrographolide, two natural diterpenoids isolated from Andrographis paniculata possessed activity against HBV DNA replication with IC50 values of 22.58 and 54.07μM and low SI values of 8.7 and 3.7 in our random assay. Consequently, 48 derivatives of dehydroandrographolide and andrographolide were synthesized and evaluated for their anti-HBV properties to yield a series of active derivatives with lower cytotoxicity, including 14 derivatives against HBsAg secretion, 19 derivatives against HBeAg secretion and 38 derivatives against HBV DNA replication. Interestingly, compound 4e could inhibit not only HBsAg and HBeAg secretions but also HBV DNA replication with SI values of 20.3, 125.0 and 104.9. Furthermore, the most active compound 2c with SI value higher than 165.1 inhibiting HBV DNA replication was revealed with the optimal logP value of 1.78 and logD values. Structure-activity relationships (SARs) of the derivatives were disclosed for guiding the future research toward the discovery of new anti-HBV drugs.
    Bioorganic & medicinal chemistry letters 03/2014; DOI:10.1016/j.bmcl.2014.03.060 · 2.33 Impact Factor
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    ABSTRACT: (+)-Paeoveitol and (-)-paeoveitol, a pair of new norditerpene enantiomers, were isolated from the root of Paeonia veitchii. Their structures and absolute configurations were determined on the basis of extensive analysis of 1D and 2D NMR spectra, crystal X-ray diffraction, and electronic circular dichroism (ECD). A possible biogenesis involving two molecules of paeoniflorin was postulated.
    Organic Letters 12/2013; 16(2). DOI:10.1021/ol403315d · 6.32 Impact Factor
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    ABSTRACT: (±)-Sweriledugenin A, a pair of novel enantiomeric lactones, were isolated from Swertia leducii under the guidance of LC-MS investigation. The enantiomeric separation was achieved by HPLC on a chiral column. Their structures were determined by extensive NMR spectra, X-ray, and quantum calculations. (+)-Sweriledugenin A and (-)-sweriledugenin A showed activities inhibiting HBV DNA replication with the IC50 values of 36.86 and 26.55 μM on the HepG 2.2.15 cell line in vitro.
    Organic Letters 12/2013; 16(2). DOI:10.1021/ol403198d · 6.32 Impact Factor

Publication Stats

424 Citations
155.33 Total Impact Points

Institutions

  • 2008–2015
    • Kunming University of Science and Technology
      Yün-nan, Yunnan, China
  • 2009–2014
    • Chinese Academy of Sciences
      Peping, Beijing, China