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1.
Leila Hammoud Francisco León Ignacio Brouard Javier Gonzalez-Platas Samir Benayache Paul Mosset Fadila Benayache 《Tetrahedron letters》2018,59(27):2668-2670
Three new sesquiterpene-humulenes, (?)- asteriscunolides I (1), J (2) and (?)-(2Z,6E,9Z)-8-oxo-1α-acetoxy-2,6,9-humulatrien-12-oic acid (3) were isolated from the leaves-flowers of the Saharan medicinal plant Asteriscus graveolens along with six known compounds. The structures of the compounds were determined on the basis of spectroscopic mono and bidimensional NMR, mass spectrometry and by single-crystal X-ray diffraction. Compounds 1–3 were evaluated for cytotoxic assay, no significant activity was detected. 相似文献
2.
Jittra Kornsakulkarn Siriporn Saepua Rapheephat Suvannakad Sumalee Supothina Nattawut Boonyuen Masahiko Isaka Samran Prabpai Palangpon Kongsaeree Chawanee Thongpanchang 《Tetrahedron》2017,73(25):3505-3512
Twelve new compounds, including nine tropolones, nemanolones A?I (1–9), three 7-isochromenones, nemanecins A?C (10–12), and a new naturally isolated 4-isochromanone (13), along with two known compounds, 7,8-dihydroxy-3-methyl isochroman-4-one (XJP), and chaetoquadrin F, were isolated from culture broth of the fungus Nemania sp. BCC 30850. Structures of these compounds were elucidated by NMR and MS spectroscopic analyses. Nemanolones exhibited cytotoxic activities and two of them, compounds 1 and 2, also showed antibacterial activity against Bacillus cereus and antifungal activity against Candida albicans. 相似文献
3.
Wirongrong Kaweetripob Chulabhorn Mahidol Siriporn Wongbundit Pittaya Tuntiwachwuttikul Somsak Ruchirawat Hunsa Prawat 《Tetrahedron》2018,74(2):316-323
Sesterterpene, erectusolide A (1), six phenolic alkenes, erectuseneols A?F (2–7) and nine known compounds, luffalactone (8), luffariolide E (9), (6E)- and (6Z)-neomanoalide 24,25-diacetates (10 and 11), 6,6-dimethylundecane-2,5,10-trione (12), threo- and erythro-cavernosines (13 and 14), (4E,6E)-dehydromanoalide (15), echinoclerodane A (16), were isolated from the marine sponge Hyrtios erectus. Compound 13 was isolated for the first time from a natural source. The structures of these compounds were elucidated on the basis of spectroscopic analysis. The phenolic alkenes 3 and 7, the sesterterpenes 8–11 and 15, and compounds 12–14 were evaluated for cytotoxic activities against six cancer cell lines, MOLT-3, HepG2, HeLa, HuCCA-1, A549, and MDA-MB-231. 相似文献
4.
Huei-Jyun Shih Yen-Ju Tseng Chiung-Yao Huang Zhi-Hong Wen Chang-Feng Dai Jyh-Horng Sheu 《Tetrahedron》2012,68(1):244-249
Seven new diterpenoids, namely, flexibilisolides C–G (1–5), flexibilisin C (6), and a novel 11,12-secoflexibillin (7), along with seven known compounds, 8–14, were isolated from the Dongsha Atoll soft coral Sinularia flexibilis. The structures of the new metabolites were elucidated by extensive spectroscopic analysis and comparison of the NMR data with those of known analogues. Compounds 1, 8, and 11 were shown to exhibit moderate cytotoxic activity against HeLa and B16 cancer cell lines, and compound 10 was found to exhibit more potent cytotoxic activity against SK-Hep1 and B16 cancer cell lines. Moreover, compounds 1, 2, 8, 9, and 11–14 could significantly inhibit the accumulation of the pro-inflammatory iNOS protein and 1, 8, 11, and 14 could reduce the accumulation of COX-2 protein in LPS-stimulated RAW264.7 macrophage cells. 相似文献
5.
Lei-Lei Gou Kun Hu Qian Yang Xiao-Nian Li Han-Dong Sun Chun-Lei Xiang Pema-Tenzin Puno 《Tetrahedron》2019,75(19):2797-2806
Phytochemical investigation of the aerial parts of Isodon ternifolius from three regions in Yunnan Province afforded 9 new diterpenoids, ternifoliusins A–I (1–9), together with 26 known diterpenoids. Among them, ternifoliusins A–D possess rare 6,7:8,15-diseco-7,20-olide-6,8-cyclo-ent-kaurane diterpenoid scaffold. The structures of all compounds were determined by comprehensive spectroscopic analysis, as well as quantum chemical calculation methods. Moreover, the molecular constitutions and configurations of ternifoliusins A, E, and F (1, 5, 6) were confirmed by single-crystal X-ray diffraction analysis. Ten compounds were assayed for their cytotoxic activity against the HL-60, SMMC-7721, A-549, MCF-7, and SW-480 human tumor cell lines, and compounds 13, 17, 19, 20, 31 and 34 were demonstrated to be active against all of the five human tumor cell lines. 相似文献
6.
Masahiko Isaka Somporn Palasarn Sujinda Sommai Sukitaya Veeranondha Kitlada Srichomthong Palangpon Kongsaeree Samran Prabpai 《Tetrahedron》2017,73(12):1561-1567
Seven new lanostane triterpenoids, astraeusins M–Q (1–5), 26-epi-artabotryol C1 (6), and 26-epi-astrasiaone (7), together with seventeen known compounds (8–24), were isolated from the food mushroom Astraeus asiaticus. The C-26 configuration of artabotriol C1 and astrasiaone, originally reported as 26R (6 and 7, respectively), was revised to be 26S (16 and 17, respectively). Astraeusin M (1) exhibited antimalarial activity against Plasmodium falciparum K1 with an IC50 value of 3.0 μg/mL. 相似文献
7.
Hiroshi Nagai Minami Watanabe Shingo Sato Mioko Kawaguchi Yue-Yun Xiao Kazutaka Hayashi Ryuichi Watanabe Hajime Uchida Masayuki Satake 《Tetrahedron》2019,75(17):2486-2494
The marine cyanobacterium Moorea producens is a rich source of diverse compounds that possess a variety of biological activities. In the present study, eight new aplysiatoxin derivatives, namely 6, 8–13, and 15, along with aplysiatoxin (1), debromoaplysiatoxin (2), 3-methoxyaplysiatoxin (3), anhydroaplysiatoxin (4), anhydrodebromoaplysiatoxin (5), oscillatoxin B2 (7), and 30-methyloscillatoxin D (14) were isolated and identified from the Okinawan M. producens. In cytotoxicity and diatom growth inhibition tests, the fifteen compounds tested (1–15) showed moderate or no activity at a concentration of 10?μg/mL. 相似文献
8.
《Journal of Saudi Chemical Society》2022,26(4):101489
Boerhavia erecta is a tropical plant that is widely used in folk medicine. Roots of this plant are applied as a diuretic, stomachic, anthelminthic, febrifuge, and expectorant. The whole plant has been used for treating gastrointestinal, liver, and infertility problems. More than 40 metabolites have been identified in its leaves, roots, and the aerial parts. Among them, isoflavonoids such as rotenoids and coumaronochromonoids are major components. Some of these compounds exhibited potent cytotoxicity, COX inhibition and opioid and cannabinoid receptor. However, little is known about the inhibition of α-glucosidase enzyme of these compounds. As part of our ongoing search for α-glucosidase inhibitors from Vietnamese medicinal plants, we conducted bioactive-guided isolation of the aerial part of Boerhavia erecta. Twelve known compounds were isolated and elucidated, including boeravinone M (1), boeravinone G (2), boeravinone P (3), boeravinone B (4), boeravinone E (5), boeravinone A (6), boeravinone H (7), 9-O-methyl-4-hydroxyboeravinone B (8), boeravinone T (9), boeravinone J (10), boeravinone C (11), and 10-demethylboeravinone C (12). Isolates 2–5, 7, and 12 showed potent α-glucosidase inhibition, which is stronger than acarbose, a positive control. Among them, compound 5 showed strongest inhibition with IC50 value of 85.1 µM. A kinetic study indicated that 5 was a mixed-type inhibitor. Compound 5 was determined to be a potential inhibitor of the α-glucosidase enzyme based on in silico molecular docking mode. Compounds were tested for cytotoxicity against K562 and antimicrobial activity against antibiotic-resistant, pathogenic bacteria Enterococcus faecium, Staphylococcus aureus, and Acinetobacter baumannii. Only compounds 4 and 12 showed moderate activity against K562 cell line. As regards antimicrobial activity, compounds 6 and 10 showed strong inhibition toward Enterococcus faecium. In silico studies of cytotoxicity and antimicrobial activity were also performed, indicating that in vitro and in silico data were consistent. 相似文献
9.
Li Zhang Jing Shi Cheng Li Liu Lang Xiang Shi Ying Ma Wei Li Rui Hua Jiao Ren Xiang Tan Hui Ming Ge 《Tetrahedron letters》2018,59(51):4517-4520
Three new borrelidin-type macrolactones, designated as borrelidins J?L (4–6), together with borrelidin A (1), borrelidin E (2), and 12-desnitrile-12-carboxyl-borrelidin (3) were isolated from a plant endophytic Streptomyces sp. NA06554. Their structures were determined by extensive spectroscopic analysis including HRESIMS, 1D and 2D NMR data. The antibacterial activities for compounds 1–6 were examined. Borrelidins A (1) and L (6) showed potent and moderate antibacterial activity against Micrococcus luteus, respectively, whereas other derivatives (2–5) are almost inactive, which allows us to propose a plausible structure-activity relationship. 相似文献
10.
Siriporn Saepua Jittra Kornsakulkarn Wiwat Somyong Pattiyaa Laksanacharoen Masahiko Isaka Chawanee Thongpanchang 《Tetrahedron》2018,74(8):859-866
Eleven new compounds, including two quinone derivatives of bioxanthracene, conoideocrellones A (1) and B (2), two bioxanthracenes 3 and 4, four isocoumarins and isocoumarin glycosides 7–10, two phenolic compounds 16 and 17, and a diterpenoid compound, conoideocin A (18), were isolated from culture of the scale-insect pathogenic fungus Conoideocrella tenuis BCC 44534. Seventeen known compounds, compounds 5 and 6, ES-242-2 and its atropisomer, isocoumarins and isocoumarin glycosides 11–15, 3,4,6-trihydroxymellein, cis-4,6-dihydroxymellein, metarhizins A (19) and B (20), BR-050 (21), 5α,8α-epidioxy-24(R)-methylcholesta-6,22-dien-3β-ol, zeorin, and conoideocrellide A, were also isolated from this fungus. Structures of these compounds were elucidated by NMR and MS data analyses. Compound 4 was active against Plasmodium falciparum K1 (IC50 6.6?μg/mL), while it did not show cytotoxicity. Conoideocrellone A (1) and compounds 3 and 7 exhibited cytotoxic activity, while conoideocin A (18) showed broad range of biological activities including antimalarial, antibacterial, and cytotoxic activities. 相似文献
11.
Ken-ichi Nakashima Masayoshi Oyama Tetsuro Ito Yukihiro Akao Joko Ridho Witono Dedy Darnaedi Toshiyuki Tanaka Jin Murata Munekazu Iinuma 《Tetrahedron》2012,68(10):2421-2428
Six novel quinolinone alkaloids bearing a phenylpropanoid or a coumarin moiety, named melicodenines C–H (1–6), two new cinnamyl alcohol derivatives, named melicodins A (7) and B (8), and a new coumarinolignan, named melicodin C (9), were isolated from the leaves of Melicope denhamii (Seem.) T. G. Hartley. Their structures were established by spectroscopic analyses including extensive 2D-NMR experiments. Compounds 1–5 and 9 possess a cyclobutane ring and are hypothetically produced by a [2+2] cycloaddition, whereas compound 6 is presumed to form through a Diels–Alder cycloaddition followed by the elimination of an acetone molecule. Ten quinolinone alkaloids (1–6, 10–13) and a coumarinolignan (9) were tested for anti-proliferative activity against DLD-1 human colon cancer cells. Melicodenine G (5) showed the most potent inhibitory activity, causing the induction of apoptosis with an IC50 value of 9.4±0.3 μM. 相似文献
12.
《Arabian Journal of Chemistry》2022,15(11):104292
Six new compounds (huangjusus A-F), including three caffeic acid glycosides (1–3), one quinic acid derivative (4), one dihydroflavone glycoside (11) and one monoterpene (31), together with thirty-eight known compounds (5–10, 12–30, 32–44), were obtained from “Jinsi Huangju” (Chrysanthemum morifolium Ramat.) flowers. Their structures were elucidated on the basis of the data obtained from different spectroscopic techniques. Among these compounds, five new (1–4 and 11) and ten known (5–9, 12, 13, 17, 40, and 42) compounds demonstrated significant 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging effects with IC50 values of 4.22–19.90 μM. Furthermore, three new compounds (1, 11, and 31) and seven known compounds (13, 19, 21, 29, 30, 39, and 41) exhibited potent hepatoprotective activities against N-acetyl-p-aminophenol (APAP)-induced toxicity in HepG2 cells with the cell survival rates of 61.53 %, 63.55 %, 60.01 %, 63.05 %, 59.75 %, 59.15 %, 61.07 %, 62.72 %, 58.86 %, and 58.76 % (positive control bicyclol, 58.41 %), respectively, at a concentration of 10 μM. These results indicate the potency of the flowers against radicals and in hepatoprotections. 相似文献
13.
Two new aromatic compounds (1, 2), new d-arabinitol ester (3), and two known compounds (4, 5) were isolated from mushroom Hericium erinaceum. The structures of 1–5 were elucidated on the basis of spectral data. Compounds 1, 2, 4, and 5 exhibited α-glucosidasae inhibitory activity. 相似文献
14.
Saranyoo Klaiklay Vatcharin Rukachaisirikul Kwanruthai Tadpetch Yaowapa Sukpondma Souwalak Phongpaichit Jirayu Buatong Jariya Sakayaroj 《Tetrahedron》2012,68(10):2299-2305
Four new diphenyl ethers, pestalotethers A–D (1–4), three new chromones, pestalochromones A–C (5–7), one new xanthone, pestaloxanthone (8), and one new butenolide, pestalolide (9), together with 11 known compounds were isolated from the mangrove-derived fungus Pestalotiopsis sp. PSU-MA69. Their structures were established by spectroscopic techniques. Compounds 1–3 and 5–7 are the rare chlorinated fungal metabolites of diphenyl ethers and chromones, respectively. Pestalolide (9) displayed weak antifungal activity against Candida albicans and Cryptococcus neoformans. 相似文献
15.
Fen Zhao Yun-Bao Liu Shuang-Gang Ma Jing Qu Shi-Shan Yu Zhen-Feng Fang Li Li Yi-Kang Si Jian-Jun Zhang 《Tetrahedron》2012,68(31):6204-6210
Six new trace sesquiterpenes, corialactones A–D (1–4), coriantone (5), corianol (6), together with nine known ones (7–15), were isolated from the roots of Coriaria nepalensis. The structures of 1–6 were elucidated through a combination of extensive NMR spectroscopic analysis, HRESIMS, CD, Rh2(OCOCF3)4-induced CD, Snatzke's method, and X-ray crystallography. Compounds 2–4, and 6 possess characteristic structural units compared with the previously reported sesquiterpenes from this family. In vivo system, compounds 5, 6 and 10 showed anti-convulsant activity by 20%, 60%, and 20% at the dose of 5 mg/kg, respectively. 相似文献
16.
Yin Nian Hai-Yan Wang Jia Su Lin Zhou Gang Feng Yan Li Ming-Hua Qiu 《Tetrahedron》2012,68(32):6521-6527
Phytochemical investigation on the roots of Cimicifuga heracleifolia afforded nine new 9,19-cycloartane triterpenes (1–9), along with seven known constituents (10–16). The new structures were elucidated by spectroscopic and chemical methods. Biological evaluation of the compounds against human HL-60, SMMC-7721, A549, MCF-7, and SW-480 cell lines indicated that eight cimigenol-type compounds (1–3, 5, 10–12, 14) showed different levels of cytotoxic activities, with IC50 values ranging from 0.83 to 23.94 μM. In addition, their structural and bioactive features enriched the structure–activity relationships we proposed before. 相似文献
17.
《Arabian Journal of Chemistry》2022,15(1):103506
The phytochemical investigation on the chemical constituents of dichloromethane-methanol (1:1) stem-bark extract of Cola lateritia K. Schum. (Sterculiaceae) led to the isolation and characterization of five pentacyclic triterpenoids, one fatty acid and two phytosteroids. The compounds were identified as heptadecanoic acid (1), maslinic acid (2), betulinic acid (3), lupenone (4), lupeol (5), friedelin (6), β-stigmasterol (7) and ß-sitosterol-3-O-ß-D-glucoside (8). Their structures were determined by NMR analysis (1H, 13C, DEPT-135, COSY, HMBC and HSQC), high-resolution mass spectrometry (HR-ESI-MS) and comparisons with published data in the literature. This work, to the best of our knowledge, is the first isolation and identification of these compounds in pure forms from Cola lateritia. Also, compounds 1–3 are reported for the first time from Cola genus. In vitro antibacterial activity of the isolated compounds (1–8) and the crude extract were evaluated against Bacillus subtilis, Staphylococcus epidermidis, Enterococcus faecalis, Mycobacterium smegmatis, Staphylococcus aureus, Enterobacter cloacae, Klebsiella oxytoca, Proteus vulgaris, Klebsiella pneumonia, Escherichia coli, Proteus mirabilis and Klebsiella aerogenes with streptomycin, nalidixic acid and ampicillin as standard antibacterial drugs. Compound 2 was active against E. faecalis (MIC = 18.5 µg/mL), and it was 6.9 and 28 times lower and active than that of streptomycin (MIC 128 µg/mL) and nalidixic acid (MIC > 512 µg/mL) respectively. All the isolated compounds and crude extract showed significant activities against the tested bacterial strains. 相似文献
18.
Chang-Shan Niu Yong Li Yun-Bao Liu Shuang-Gang Ma Fei Liu Li Cui Hai-Bo Yu Xiao-Jing Wang Jing Qu Shi-Shan Yu 《Tetrahedron》2018,74(3):375-382
During our continuing study on the roots of Pieris formosa, twelve new grayanane diterpenoids (1–12), together with eight known compounds (13–20), were obtained. Their structures with absolute configurations were characterized by a series of spectroscopic methods and X-ray diffraction. Compounds 1, 2, 4–5, 7–8, 14, and 19 exhibited significant analgesic activity in an acetic acid-induced writhing test. In particular, 7 and 14 were found to be 5 times more potent than morphine in the acetic acid-induced writhing test model. Compounds 1, 4, 9, 13, and 18 showed antifeedant activity against Plutella xylostella at 0.5 mg/mL. Compound 4 exhibited a 38.3% inhibitory effect against the KCNQ2 potassium channel at a concentration of 10 μM. 相似文献
19.
Bin Yang Huaming Tao Xiuping Lin Junfeng Wang Shengrong Liao Junde Dong Xuefeng Zhou Yonghong Liu 《Tetrahedron》2018,74(1):77-82
Four new prenylated indole alkaloids (1–4), and four new chromone derivatives (7–10), together with six known compounds (5, 6, and 11–14), have been isolated from the mangrove sediment derived fungus Penicillium sp. SCSIO041218, cultured in the 1% NaCl PDB substrate. The structures of new compounds were determined by analysis of the NMR and MS spectroscopic data. The absolute configuration of the prenylated indole alkaloids were elucidated based on the comparison of ECDs with known analogues. The absolute configurations of the chromone derivatives were determined by time-dependent density functional theory calculations of the ECD spectra. In all of these isolated compounds, penixanthones A and B (12 and 13) exhibited antiallergic activities in vitro. 相似文献
20.
Abdul-Wahab Salae Apinya Rodjun Chatchanok Karalai Chanita Ponglimanont Suchada Chantrapromma Akkharawit Kanjana-Opas Supinya Tewtrakul Hoong-Kun Fun 《Tetrahedron》2012,68(3):819-829
Eleven new diterpenoids: pimaranes (1,2), rosanes (3) abietanes (4–7), icetexanes (8), and rearranged icetexanes (9–11), together with fifteen known diterpenes (12–26) and two known sesquiterpenes (27,28) have been isolated from the roots and twigs of Premna obtusifolia. The structures of these compounds were elucidated on the basis of spectroscopic analysis and X-ray crystallographic data of 8 and 9 were also determined. The antibacterial and anti-inflammatory activities of the isolates were evaluated. 相似文献