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1.
Rui-Hua Guo Chang-An Geng Xiao-Yan Huang Yun-Bao Ma Quan Zhang Li-Jun Wang Xue-Mei Zhang Rong-Ping Zhang Ji-Jun Chen 《Bioorganic & medicinal chemistry letters》2013,23(5):1201-1205
A series of hemslecin A derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activities, namely, inhibiting the secretion of hepatitis B surface antigen (HBsAg), hepatitis B e antigen (HBeAg), and HBV DNA replication on HepG 2.2.15 cells. Most of the derivatives showed enhanced anti-HBV activities, of which compounds A1–A7, B5, C and E exhibited significant activities inhibiting HBV DNA replication with IC50 values of 2.8–11.6 μM, comparable to that of the positive control, tenofovir. Compounds A1–A3, A5, B5, and C displayed low cytotoxicities, which resulted in high SI values of 89.7, 55.6, 77.8, >83.4, >55.8, and >150.5, respectively. 相似文献
2.
《Bioorganic & medicinal chemistry letters》2014,24(10):2353-2359
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. 相似文献
3.
Bixue Xu Zhengming Huang Changxiao Liu Zegui Cai Weidong Pan Peixue Cao Xiaojiang Hao Guangyi Liang 《Bioorganic & medicinal chemistry》2009,17(8):3118-3125
A series of derivatives of Matijing-Su (MTS, N-(N-benzoyl-l-phenylalanyl)-O-acetyl-l-phenylalanol) was synthesized and evaluated for their anti-hepatitis B virus (HBV) activities in 2.2.15 cells. The IC50 of compounds 9c (1.40 μM), 9g (2.33 μM) and 9n (2.36 μM), etc. and the selective index of 9n (45.93) of the inhibition on the replication of HBV DNA were higher than those of the positive control lamivudine [41.59, (IC50: 82.42 μM)]. Compounds 11d, 12a and 12e also exhibited significant anti-HBV activities. 相似文献
4.
Leplaeric acid E 5, leplazarin 6a and 21-epileplazarin 6b, three new 3,4-seco-lanostane type triterpenes have been isolated from the stem bark of Leplaea mayombensis (Pellegr.) Staner along with fourteen known compounds from the fruits and roots. Leplaeric acid E, leplazarin and 21-epileplazarin, 15-α-hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioic acid, mayomlactones A and B, lanosta-7,24-dien-3-one, leplaeric acid A, B and C were screened in vitro for antiplasmodial activity against chloroquine-sensitive (Pf3D7) and chloroquine-resistant (PfINDO) strains of Plasmodium falciparum and for cytotoxicity against CAL-27, CaCo2, Skov-3, and HepG2 cells line. Three compounds including 15-α-hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioic acid (IC50 5.65–7.09 μM), lanosta-7,24-dien-3-one (IC50 7.18–9.07 μM), and leplaeric acid C (IC50 7.59–8.47 μM) were the most active against both strains of P. falciparum. All the compounds exhibited cytotoxicity against the three-cell lines with IC50 ranging from 12.30 to 181.88 μM. These results confirm the usage of the medicinal plant L. mayombensis for the management of malaria and suggest that further lead optimization studies on potent compounds identified from this study could lead to the identification of potential of lead molecules as scaffold for new antimalarial drug discovery. 相似文献
5.
Lithocarpic acids O–S,five homo-cycloartane derivatives from the cupules of Lithocarpus polystachyus
《Bioorganic & medicinal chemistry letters》2014,24(23):5395-5398
Chemical investigation of the cupules of Lithocarpus polystachyus resulted in the identification of four 3,4-seco-homo-cycloartane and one homo-cycloartane derivatives named lithocarpic acids O–S. Their structures were determined based on extensive 1D/2D NMR, IR, MS spectroscopic analyses and chemical methods. Lithocarpic acid O (1) exhibited inhibitory activities on mouse and human isozymes of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) with IC50 values of 0.49 and 1.1 μM, respectively. 相似文献
6.
Jun Li Ai-Ping Meng Xin-Lan Guan Jian Li Qiang Wu Sheng-Ping Deng Xiao-Jian Su Rui-Yun Yang 《Bioorganic & medicinal chemistry letters》2013,23(7):2238-2244
Four new lignans, strebluslignanol F (1), (7′R,8′S,7″R,8″S)-erythro-strebluslignanol G (2), isomagnaldehyde (3) and isostrebluslignanaldehyde (4), along with 12 known lignans (5–16) were isolated from the ethyl acetate-soluble part of MeOH extract of the root of Streblus asper. Their structures were elucidated through various spectroscopic methods, including 1D NMR (1H NMR, 13C NMR), 2D NMR (HMQC, HMBC and NOESY) and HRMS. The stereochemistry at the chiral centers was determined using CD spectra, as well as analyses of coupling constants and optical rotation data. The isolated lignans were evaluated for their anti-HBV activities in vitro using the HBV transfected HepG2.2.15 cell line. The most active lignans, (7′R,8′S,7″R,8″S)-erythro-strebluslignanol G, magnolol, isomagnolol and isolariciresinol, exhibited significant anti-HBV activities with IC50 values of 1.58, 2.03, 10.34 and 3.67 μM, respectively, for HBsAg with no cytotoxicity, and of 3.24, 3.76, 8.83 and 14.67 μM, respectively, for HBeAg with no cytotoxicity. (7′R,8′S,7″R,8″S)-erythro-Strebluslignanol G and magnolol showed significant anti-HBV activities to inhibit the replication of HBV DNA with the IC50 values of 9.02 and 8.67 μM, respectively. 相似文献
7.
Three new naturally occurring monoterpenoids, japopenoid A (1), japopenoid B (23) japopenoid C (24), and one new caffeoylquinic acid derivative (28), together with thirty-one known compounds (2–22, 25–27, 29–35), were isolated and identified from the flower buds of Lonicera japonica Thunb. Their structures were determined by extensive 1D and 2D NMR spectroscopic methods, high-resolution mass spectrometry, and the absolute configurations of 1, 23, 24 were determined by comparison of their electronic circular dichroism (ECD) spectrum with literature and theoretical calculation. Structurally, compound 1 is a monoterpenoid featured with an unusual tricyclic skeleton. All compounds (1–35) were evaluated for their cytotoxicities against human liver cancer cell lines (HepG 2 and SMMC-7721). Compound 12 exhibited the most potent activity with IC50 values of 26.54 ± 1.95 and 8.72 ± 1.57 μg/ml against HepG 2 and SMMC-7721, and the IC50 values of compound 13 were 26.54 ± 1.95 and 12.35 ± 1.43 μg/ml, respectively. Western blot results further proved that compound 13 induces hepatoma cell apoptosis via the intrinsic apoptosis pathway. In addition, most terpenoids showed inhibitory activity against HBsAg and HBeAg secretion, and HBV DNA replication. In particular, 25 μg/mlof compound 11 inhibits HBsAg and HBeAg secretion, and HBV DNA replication by 39.39 ± 5.25, 15.64 ± 1.25, and 16.13 ± 4.10% compared to the control (p < 0.05). These results indicated that L. japonica flower buds could be served as functional food for anti-hepatoma and anti-HBV activities. 相似文献
8.
Janggyoo Choi Kee Dong Yoon Jinwoong Kim 《Bioorganic & medicinal chemistry letters》2018,28(3):476-481
Three novel butyrolactones (1–3) and butanoates (4–6), namely taraxiroside A–F, were isolated from Taraxacum officinale along with twenty-two known compounds (7–28). Their chemical structures were elucidated by interpretation of spectroscopic data and comparison with those of literatures. All isolates were evaluated for their α-glucosidase inhibitory activities. Novel compounds 1–6 (IC50 145.3–181.3?μM) showed inhibitory activities similar to that of acarbose (IC50 179.9?μM). Compound 7 and 12 were the most potent inhibitor with IC50 values of 61.2 and 39.8?μM respectively. Compounds 2 and 12 showed as mixed-type inhibition, whereas compound 7 and acarbose showed competitive inhibition. 相似文献
9.
Xu-Dong Zhou Chen Zhang Shan He Bin Zheng Ke-Wu Zeng Ming-Bo Zhao Yong Jiang Peng-Fei Tu 《Bioorganic & medicinal chemistry letters》2017,27(24):5441-5445
One new highly oxygenated nortriterpene, named sieverlactone (1), one new sesquiterpene, 1β,10β-epoxy-8α-acetoxyachillin (2), one new natural product, 5-propinyl-thiophene-2-carboxylic acid (3), and one new thiophene, 3-hydroxy-5-propinyl-2-acetyl-thiophene (4), together with 10 other known compounds (5?14), were isolated from the dried aerial parts of Artemisia sieversiana. Their structures were elucidated by a combination of extensive spectroscopic analysis, including 1D, 2D NMR spectroscopic and mass spectrometric data. Meanwhile, the stereochemistry of 1 and 2 was confirmed by single-crystal X-ray diffraction technique using Cu radiation. All the isolates were evaluated for their anti-neuroinflammatory effects on the lipopolysaccharide-induced nitric oxide production in BV-2 murine microglial cells. Compounds 2, 5, and 6 exhibited the significant activities with IC50 values of 6.5?±?0.5, 11.9?±?0.7, and 10.1?±?0.3?μM, respectively, comparable to the positive control, quercetin, with an IC50 value of 16.3?±?0.4?μM. 相似文献
10.
Fei Li Xi-Xi Guo Guang-Zhi Zeng Wei-Wei Qin Bo Zhang Ning-Hua Tan 《Bioorganic & medicinal chemistry letters》2018,28(14):2523-2527
To further investigate on the structure-activity relationships of immunosuppressive Astin C, seventeen analogues 1–17 were designed and synthetized via amino acid substitution strategy by the solid-phase peptide synthesis method for the first time. In comparison with Astin C (IC50?=?12.6?±?3.3?μM), only compounds 2 (IC50?=?38.4?±?16.2?μM), 4 (IC50?=?51.8?±?12.7?μM), 5 (IC50?=?65.2?±?15.6?μM), and 8 (IC50?=?61.8?±?12.4?μM) exhibited immunosuppressive activity in the Lymph node cells of mice. These results showed that the Astin C analogues containing D-amino acid residues, hydrophobic long-chain alkyl substituents, and aryl substituents performed better than those carrying hydrophilic amino acid residues and short-chain alkyl substituents. Moreover compounds 15, 16, and 17 had no immunosuppressive activity, which suggested that cis-3,4-dichlorinated proline played an important role in the immunosuppressive activity of Astin C. 相似文献
11.
Kongara Damodar Jeong Tae Lee Jin-Kyung Kim Jong-Gab Jun 《Bioorganic & medicinal chemistry letters》2018,28(11):2098-2102
Syntheses of natural homoisoflavonoids, (±)-portulacanones A–C (4, 8 and 9), portulacanone D (6), isolated from Portulaca oleracea L. (POL) and their derivatives (3, 5 and 7) have been achieved for the first time along with the synthesis of known derivatives (1 and 2) and their in vitro inhibitory effect against NO production in LPS-induced RAW-264.7 macrophages was evaluated as an indicator of anti-inflammatory activity. All the compounds tested had a concentration-dependent inhibitory effect on NO production by RAW-264.7 macrophages without obvious cytotoxicity. Compounds 3 (97.2% at 10?μM; IC50?=?1.26?µM) followed by 6 (portulacanone D) (92.5% at 10?μM; IC50?=?2.09?µM), 1 (91.4% at 10?μM; IC50?=?1.75?µM) and 7 (83.0% at 10?μM; IC50?=?2.91?µM) were the most potent from the series. This finding was further correlated with the suppressed expression of iNOS induced by LPS. Our promising preliminary results may provide the basis for the assessment of compound 3 as a lead structure for a NO production-targeted anti-inflammatory drug development and also could support the usefulness of POL as a folklore medicinal plant in the treatment of inflammatory diseases. 相似文献
12.
Eight secondary metabolites (1–8) including a new seco-anthraquinone (wentiquinone C, 1) and a new benzamide derivative (methyl 4-(3,4-dihydroxybenzamido)butanoate, 2), as well as three other derivatives (4, 7, and 8) that were isolated from natural source for the first time, were characterized from the EtOAc extracts of the marine alga-derived endophytic fungus Aspergillus wentii EN-48. The structures of the isolated compounds were elucidated on the basis of 1D and 2D NMR experiments. Each of the isolated compounds was evaluated for α,α-diphenyl-picrylhydrazyl (DPPH) radical scavenging activity, and some of them showed potent activities with IC50 values ranging from 5.2 to 99.4 μg/mL, compared to the positive control, butylated hydroxytoluene (BHT), with an IC50 of 36.9 μg/mL. 相似文献
13.
Zong-Ying Liu Yue-Ming Wang Zhuo-Rong Li Jian-Dong Jiang David W. Boykin 《Bioorganic & medicinal chemistry letters》2009,19(19):5661-5664
A series of 3,4-diarylthiazol-2(3H)-ones and three 3,4-diarylthiazol-2(3H)-imines were synthesized and evaluated for their cytotoxicity in a panel of human cancer cell lines. Compounds 21 and 22 showed potential anticancer activity against human CEM cells with IC50 values of 0.12 and 0.24 μM, respectively. 相似文献
14.
《Phytochemistry》2012
Seven compounds, (7′S,8′S)-trans-streblusol A, (7′R,8′S)-erythro-streblusol B, (7′S,8′S)-threo-streblusol B, 8′R-streblusol C, streblusquinone, (8R,8′R)-streblusol D, and streblusol E, along with 15 known compounds (8–22) were isolated from the n-butanol-soluble part of the MeOH extract of stem bark of Streblus asper. Their structures were elucidated through application of extensive spectroscopic methods, including ESI-MS and 2D NMR spectroscopy (HMQC and HMBC). The stereochemistry at the chiral centers was determined using CD spectra, as well as analyses of coupling constants and optical rotation data. The isolated lignans and allylbenzene derivatives were evaluated for their anti-HBV activities in vitro using the HBV transfected Hep G2.2.15 cell line. The most active compounds, magnolol and 9-β-xylopyranosyl-isolariciresinol, exhibited significant anti-HBV activities with IC50 values of 2.03 and 6.58 μM for secretion of HBsAg, with no cytotoxicity, and of 3.76 and 24.86 μM for secretion of HBeAg, with no cytotoxicity. 相似文献
15.
Namki Cho Ana Lisa Valenciano Yongle Du Jason Clement Maria B. Cassera Michael Goetz David G.I. Kingston 《Bioorganic & medicinal chemistry letters》2018,28(20):3368-3371
Bioassay-guided fractionation of an extract of Carpha glomerata (Cyperaceae) led to the isolation of seven compounds. Compounds 1 (carphorin A), 3 (carphorin C), 4 (carphorin D), and 5 (carphabene) are new compounds, and compound 2 (8-(3″-hydroxyisoamyl)-naringenin) was isolated for the first time as a natural product. All structures were elucidated based on analyses of their HR-ESIMS and 1D and 2D NMR data. Compounds 1, 2, and 6, which have prenyl or hydroxyprenyl side chains, exhibited antiplasmodial activities with IC50 values of 5.2?±?0.6, 3.4?±?0.4, and 6.7?±?0.8?µM against the drug-resistant Dd2 strain of Plasmodium falciparum. In addition the prenylated stilbene 5 also showed good activity, with IC50 5.8?±?0.7?µM. 相似文献
16.
Shiyu Li Xiao Lv Kai Cheng Yongbing Tian Xufeng Huang Haiyan Kong Yajun Duan Jihong Han Chenzhong Liao Zhouling Xie 《Bioorganic & medicinal chemistry letters》2019,29(9):1090-1093
Inhibition of MAO-B has been an effective strategy for the treatment of Parkinson’s disease. To find more potent and selective MAO-B inhibitors with novel chemical scaffold, we designed and synthesized a series of new 2,3-dihydro-1H-inden-1-amine derivatives on basis of our previous study. Furthermore, the corresponding structure-activity relationship (SAR) of these compounds is detailedly discussed. Compounds L4 (IC50?=?0.11?μM), L8 (IC50?=?0.18?μM), L16 (IC50?=?0.27?μM) and L17 (IC50?=?0.48?μM) showed similar MAO-B inhibitory activity as Selegiline. Moreover, L4, L16 and L17 also exhibited comparable selectivity with Selegiline, indicating that L4, L16 and L17 could be promising selective MAO-B inhibitors for further study. 相似文献
17.
《Phytochemistry》2013
Bioassay-guided fractionation and chemical investigation of the extract of Rhus verniciflua bark resulted in the identification of six polyphenols, rhusopolyphenols A–F (1–6), together with four known compounds including (2R,3S,10S)-7,8,9,13-tetrahydroxy-2-(3,4-dihydroxyphenyl)-2,3-trans-3,4-cis-2,3,10-trihydrobenzopyrano[3,4-c]-2-benzopyran-1-one (7), peapolyphenol C (8), cilicione-b (9) and (αR)-α,3,4,2′,4′-pentahydroxydihydrochalcone (10). The structures of these polyphenols were elucidated by spectroscopic analysis, including 1D and 2D NMR, and HR-ESIMS, and their absolute configurations were further confirmed by a combination of chemical methods and CD data analysis. All isolates were evaluated for their antiproliferative activities against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15), and compounds 4–6, 9 and 10 showed antiproliferative activity against the tested cells, with IC50 values of 3.31–18.51 μM. On the basis of the expanded understanding that inflammation is a crucial cause of tumor progression, the anti-inflammatory activities of these compounds were determined by measuring nitric oxide (NO) levels in the medium of murine microglia BV-2 cells. Compounds 5 and 10 significantly inhibited NO production in lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cells with IC50 values of 28.90 and 12.70 μM, respectively. 相似文献
18.
《Phytochemistry》2012
Six previously unreported and 11 known terpenoids were isolated from Abies holophylla. The structures of the six compounds were established as two unusual bisabolane sesquiterpenoids, three nortriterpenoids, and one 3,4-seco-triterpenoid based on the detailed analysis of their 1D and 2D NMR spectroscopic data. In addition, electronic circular dichroism (ECD) calculations and molecular orbital (MO) analysis were used to assign the absolute configuration of one bisabolane sesquiterpenoid, abiesesquine A. Abiesesquine A showed the strongest inhibitory effects against LPS-induced nitric oxide (NO) production in RAW264.7 macrophages with an IC50 value of 113.1 μM. Lanosta-7,9(11),24-trien-26-oic acid showed potent cytotoxic activity against COLO-205, LOVO, and QGY-7703 tumor cells with IC50 values of 0.9, 4.2, and 2.0 μM, respectively. (23R,25R)-3,4-seco-9βH-Lanosta-4(28),7-dien-26,23-olid-3-oic acid, exhibited a significant antiproliferation effect against A549 cells (IC50 = 14.7 μM). 相似文献
19.
Two new lignans, named (+)-(7′S, 7″S, 8′R, 8″R)-4, 4′, 4″-trihydroxy-3, 5′, 3″-trimethoxy-7-oxo-8-ene [8-3′, 7′-O-9″, 8′-8″, 9′-O-7″] lignoid (1) and (1S)-4-Hydroxy-3-[2-(4-hydroxy-3-methoxy-phenyl)-1-hydroxymethyl-2-oxo-ethyl]-5-methoxy-benzaldehyde (2), along with five known (3–7) ones, have been isolated from the 95% ethanol extract of the seeds of Herpetospermum caudigerum Wall. The structures of the new compounds, including the absolute configurations, were elucidated by spectroscopic and CD analysis. Compounds 1, 2, and 7 displayed inhibitory activities on HBsAg secretion with IC50 values of 20.5, 0.34, and 4.89 μM, while 1, 2, and 7 displayed inhibitory activities on HBeAg secretion with IC50 values of 3.54, 4.83 × 10−4, and 8.02 μM, and cytotoxicity on HepG 2.2.15 cells with CC50 values of 12.7, 2.96 × 105, and 11.4 μM, respectively. 相似文献
20.
Jinrun Dong Xingrong Peng Lei Li Shuangyang Lu Lin Zhou Minghua Qiu 《Bioorganic & medicinal chemistry letters》2018,28(9):1520-1524
Eight new C21 steroidal glycosides, namely cynanotins A–H (1–8), together with fifteen known analogues, were isolated from the roots of Cynanchum otophyllum. Their structures were elucidated by spectroscopic analysis and chemical methods. In this study, all of isolates were tested for their vitro inhibitory activities against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480). Compounds 3–15 showed moderate cytotoxic activities against HL-60 cell lines with IC50 values ranging from 11.4 to 37.9?µM. Compounds 5, 9, and 10 showed marked or moderate cytotoxic activities against five human tumor cell lines with IC50 values ranging from 11.4 to 36.7?µM. Compound 11 displayed moderate cytotoxic activities against HL-60, SMMC-7721, MCF-7 and SW480 cell lines with IC50 values of 12.2–30.8?µM. Compared to the positive control (IC50: 35.0?µM), compounds 5, 9–11 exhibited more potential inhibitory activity against MCF-7 cells (IC50: 16.1–25.6?µM). 相似文献