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1.
Juan Hua Shi‐Hong Luo Yan Liu Yan‐Chun Liu Yan‐Yun Tan Ling Feng Chao‐Jiang Xiao Ke‐Qin Zhang Sheng‐Hong Li Xue‐Mei Niu 《化学与生物多样性》2017,14(10)
Three new macrocyclic diterpenoids, euphoscopoids A – C ( 1 – 3 ), including two new jatrophanes and a new lathyrane, were isolated from the whole plant of Euphorbia helioscopia. Their structures were elucidated by spectroscopic methods. Antifeedant and cytotoxic activities of these isolates were evaluated. All compounds showed significant antifeedant activity against a generalist plant‐feeding insect, Helicoverpa armigera, with EC50 values ranging from 2.05 to 4.34 μg/cm2. In addition, compound 2 showed moderate cytotoxicity against tumor cell lines NCI‐H1975, HepG2, and MCF‐2, while compounds 1 and 3 were not active at 80 μm . The results suggested not only the defensive function of macrocyclic diterpenoids in E. helioscopia against insect herbivores, but also their potential applications as new natural insect antifeedants. 相似文献
2.
Chemical investigation of the Xisha soft coral Sarcophyton sp. has led to the isolation of eight cembrane-type diterpenoids, including three new compounds, namely sarcophynoids A-C ( 1 – 3 ), and five known analog compounds ( 4 – 8 ). Their structures were clarified based on spectroscopic analysis, and computer-assisted methods including TDDFT-ECD calculation and the quantum mechanical-nuclear magnetic resonance (QM-NMR) method. All the above compounds were tested for their antibacterial activities. Among them, compounds 4 – 7 and 8 exhibited antibacterial activities against S. aureus, B. subtilis, and P. aeruginosa, with MIC of 4–64 μg/mL. 相似文献
3.
Jun Cao Yunshao Xu Ruohan Lou Wei Shi Jiali Chen Lishe Gan Jinjian Lu Ligen Lin 《化学与生物多样性》2021,18(9):e2100309
Ten new cassane-type diterpenoids were isolated from the seeds of Caesalpinia bonduc (L.) Roxb., including 6α-hydroxycaesalpinin P ( 1 ), 14-epi-caesalpinin E1 ( 2 ), 6-deacetylcaesalmin Z ( 3 ), 14-epi-caesalmin Z ( 4 ), caesalpinolides I ( 5 ), K ( 6 ), L ( 7 ), M ( 9 ) and N ( 10 ), and 14-epi-neocaesalpin L ( 8 ). Their planar structures and absolute configurations were fully determined by comprehensive spectroscopic methods, including 2D NMR and electronic circular dichroism spectra. Compounds 1 – 4 are tetracyclic cassane diterpenoids possessing a furan ring, and compounds 5 – 10 are tetracyclic cassane diterpenoids possessing a fused butenolide moiety. The anti-inflammatory and cytotoxic activities of the isolates were evaluated, while none of them showed obvious effects. The current study identified ten new cassane-type diterpenoids from the seeds of C. bonduc (L.) Roxb., which enriched the chemical diversity of the titled herbal medicine. 相似文献
4.
Majekodunmi O. Fatope Gouri B. Varma Nasser M. Alzri Ruchi G. Marwah Rani S. Nair 《化学与生物多样性》2010,7(7):1862-1870
The twigs and leaves of Blepharispermum hirtum Oliver (Asteraceae) were investigated for their larvicidal and antimicrobial activity. Fractionation of the extracts of the twigs, directed by brine shrimp test and antibacterial activities, led to the isolation of compounds 1 – 4 ; two of which are new ent‐kaurene diterpenoids, blepharispins A and B ( 1 and 2 , resp.). The structures of compounds 1 and 2 were established from spectral data. The absolute configuration at C(15) in 1 was inferred from Mosher ester analysis and relative configurations were suggested by a NOESY experiment. Compound 4 was significantly larvicidal to newly hatched naupleii of Artemia salina L. (BST LC50=1.3 (3.7–0.0) μg/ml), but the blepharispins were not (BST LC50>500 μg/ml). Nevertheless, compound 1 inhibited the growth of Staphylococcus aureus and Bacillus subtilis at a MIC value of 62.5 μg/ml. The significance of the bioactivity results and the presence of ent‐kaurene diterpenoids in B. hirtum are discussed from biosynthetic and local utilization viewpoints. 相似文献
5.
6.
Four new diterpenoids named cuceolatins A–D, including three labdane‐type ( 1 – 3 ) and one abietane‐type ( 4 ) as well as three known labdane analogs ( 5 – 7 ), were reported from the leaves of Cunninghamia lanceolata. Structural assignments for these compounds were conducted by analyses of spectroscopic data, and their absolute configurations were determined by time‐dependent density functional theory (TD‐DFT) based electronic circular dichroism (ECD) calculations. Among them, the abietane‐type diterpenoid (11‐hydroxy‐12‐methoxyabieta‐8,11,13‐trien‐3‐one ( 4 )) showed significant cytotoxicity against human MDA‐MB‐231, MCF‐7, and HeLa tumor cell lines with IC50 measurements of 4.3, 2.8 and 4.5 μm , respectively, while the labdane‐type diterpenoids with a 4α‐carboxy group ( 1 – 3 and 5 ) exhibited moderate antibacterial activity towards Bacillus subtilis and Staphylococcus aureus with IC50 values all below 25 μm . 相似文献
7.
Three new 4,5‐seco‐20(10→5)‐abeo‐abietane diterpenoids, 16‐hydroxysalvilenone ( 1 ), 15‐hydroxysalprionin ( 2 ), and 11β,15‐dihydroxysalprionin‐12‐one ( 3 ), and nine known abietane diterpenoids, 4 – 12 , along with one known sempervirane diterpenoid, hispidanol A ( 13 ), were isolated from the aerial parts of Isodon lophanthoides var. graciliflorus. The structures of compounds 1 – 3 were determined on the basis of spectroscopic methods including extensive analysis of NMR and mass spectroscopic data. All diterpenoids were tested for their TNF‐α inhibitory effects on LPS‐induced RAW264.7 cells. Compound 9 (16‐acetoxyhorminone) was the most potent with an IC50 value of 3.97±0.70 μm . 相似文献
8.
Six new 6,7‐seco‐ent‐kaurane diterpenoids, sculponeatins N–S ( 1 – 6 , resp.), together with eleven known analogues, 7 – 17 , were isolated from the aerial parts of Isodon sculponeatus. The structures of compounds 1 – 6 were elucidated by spectroscopic methods including extensive 1D‐ and 2D‐NMR experiments, as well as HR‐ESI‐MS analysis. All diterpenoids obtained were assayed for their cytotoxic activity against K562 and HepG2 human tumor cell lines. Among them, compound 1 showed the most significant cytotoxicity with the IC50 values of 0.21 and 0.29 μM , respectively. The structure–activity relationships are discussed. 相似文献
9.
Three new isopimarane diterpenoids ( 1 – 3 ) and one new abietane diterpenoid ( 4 ) were isolated and identified from the roots of Euphorbia pekinensis, together with four known diterpenoids. Their structures were elucidated on the basis of extensive spectroscopic methods (IR, MS, NMR, and CD), and their cytotoxicities and anticomplement activities were evaluated. 相似文献
10.
Patrícia Rijo M. Fátima Simões A. Paula Francisco Rosario Rojas Robert H. Gilman Abraham J. Vaisberg Benjamín Rodríguez Cristina Moiteiro 《化学与生物多样性》2010,7(4):922-932
The antimycobacterial activities of eight diterpenes, 1 – 8 , isolated previously from Plectranthus and eleven esters, 9 – 19 , of 7α‐acetoxy‐6β,12‐dihydroxyabieta‐8,12‐diene‐11,14‐dione ( 5 ) were evaluated against the MTB strains H37Rv and MDR. Only diterpenoids with a quinone framework revealed anti‐MTB activity. Abietane 5 and its 6,12‐dibenzoyl, 12‐methoxybenzoyl, 12‐chlorobenzoyl, and 12‐nitrobenzoyl esters, 9, 11, 12 , and 13 , respectively, showed potent activities against the MDR strain with MIC values between 3.12 and 0.39 μg/ml. Cytotoxic activities towards 3T3 and Vero cells were also evaluated. Compound 11 , with the best selectivity index, may be a suitable lead for further chemical modifications. The complete structural elucidation of the new esters, 9 – 14, 16, 18 , and 19 , as well as the NMR data of known derivatives 15 and 17 are reported. 相似文献
11.
Yu-Ting Song Dan-Dan Yu Ming Zhi Su Hui Luo Jian-Guo Cao Li-Gong Yao Lin-Fu Liang Yue-Wei Guo Fan Yang 《化学与生物多样性》2023,20(4):e202300217
Two new highly functionalized cembrane diterpenoids named ximaolobophytolides A ( 1 ) and B ( 2 ) as minor components, together with seven related known compounds ( 3 – 9 ), have been isolated and identified from the Ximao soft coral Lobophytum sp. They were characterized by the presence of an α-methylene-γ-lactone moiety. Based on the comprehensive analyses of 1D and 2D NMR spectroscopic data, the absolute configurations of these two new compounds were elucidated by the combination of quantum mechanical (QM)-NMR and time-dependent density functional theory/electronic circular dichroism (TDDFT-ECD) calculation approaches. In the anti-tumor bioassays, compounds 3 – 9 showed moderate to significant inhibitory effects (IC50 values ranging from 29.66 to 0.39 μM) against the proliferations of five tumor cells HEL, A549, H1975, MDA-MB-231, and H1299. It might be worthy to point out that compounds 4 , 7 , and 8 exhibited better anti-tumor activities than that of the positive control Doxorubicin. 相似文献
12.
Three new labdane-type diterpenoids, calcaratarin E, villosumtriol, and 12-epi-villosumtriol ( 1 – 3 ) were isolated from the fruits of Amomum villosum, along with seven known diterpenoids ( 4 – 10 ). Through comprehensive analysis of chemical evidence and spectral data including UV, 1D and 2D NMR, HR-ESI-MS, IR, and X-ray crystallography, the structures of these novel compounds were successfully determined. Additionally, the inhibitory effects of compounds 2 – 10 on NO production in lipopolysaccharide (LPS)-induced RAW264.7 cells were evaluated. Notably, compound 6 exhibited the most significant inhibitory effect with an IC50 value of 1.74±0.69 μM. 相似文献
13.
Xin‐Hua Ma Zhi‐Biao Wang Lei Zhang Wei Li Cui‐Min Deng Tian‐Hua Zhong Guang‐Yu Li Wei‐Ming Zheng Yong‐Hong Zhang 《化学与生物多样性》2017,14(5)
One new ent‐kaurane diterpenoid, 11β,16α‐dihydroxy‐ent‐kauran‐19‐oic acid ( 1 ), together with eight known analogues 2 – 9 were isolated from the aerial parts of Wedelia prostrata. One of the acidic diterpenoids, kaurenoic acid ( 3 ), was converted to seven derivatives, 10 – 16 . All compounds were evaluated for their cytotoxic activity in vitro against human leukemia (K562), liver (HepG‐2), and stomach (SGC‐7901) cancer cell lines. Only four kaurenoic acid derivatives, 13 – 16 , with 15‐keto and substitutions at C(19) position, exhibited notable cytotoxic activities on these tumor cell lines with IC50 value ranging from 0.05 to 3.71 μm . Compounds 10 – 12 , with oxime on C(15) showed moderate inhibitory effects and compounds 1 – 9 showed no cytotoxicities on them. Structure–activity relationships were also discussed based on the experimental data obtained. The known derivative, 15‐oxokaurenoic acid 4‐piperdin‐1‐ylbutyl ester ( 17 ), induced typical apoptotic cell death in colon SW480 cells upon evaluation of the apoptosis‐inducing activity by flow‐cytometric analysis. 相似文献
14.
New Derivatives of Nonactic and Homononactic Acids from Bacillus pumilus Derived from Breynia fruticosa
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Li Han Peiyuan Huo Huahong Chen Songtao Li Yi Jiang Liya Li Lihua Xu Chenglin Jiang Xueshi Huang 《化学与生物多样性》2014,11(7):1088-1098
Six new nonactic and homononactic acid derivatives, ethyl homononactate ( 1 ), ethyl nonactate ( 2 ), homononactyl homononactate ( 6 ), ethyl homononactyl nonactate ( 7 ), ethyl homononactyl homononactate ( 8 ), and ethyl nonactyl nonactate ( 9 ), as well as four known compounds, homononactic acid ( 3 ), nonactic acid ( 4 ), homononactyl nonactate ( 5 ), and bishomononactic acid ( 10 ), were isolated from culture broth of Bacillus pumilus derived from Breynia fruticosa. The structures of new compounds were elucidated by spectroscopic analysis and chemical methods. The optical purities of 1 – 6 were determined by HPLC/MS after treatment with L ‐phenylalanine methyl ester. The dimeric compounds 5 – 9 showed weak cytotoxic activities against five human cancer cell lines (IC50 19–100 μg/ml). 相似文献
15.
Zha‐Jun Zhan Yan‐Tao Wen Feng‐Yun Ren Gui‐Wei Rao Wei‐Guang Shan Cheng‐Ping Li 《化学与生物多样性》2012,9(12):2754-2760
Two new labdane diterpenoids, namely hedycoronals A and B ( 1 and 2 , resp.), were isolated from the rhizomes of Hedychium coronarium, together with eight known diterpenoids, 4 – 11 , and a known diarylheptanoid, 3 . The structures of 1 and 2 were established by detailed interpretation of their 1D‐ and 2D‐NMR spectra and HR‐ESI‐MS data. Inhibitory activities against human umbilical vein endothelial cells (HUMECs) proliferation and cytotoxic activities against four cancer cell lines were assessed for all the isolates. Most of these metabolites showed moderate or potent cytotoxic activities against four cancer cell lines. Moreover, compounds 3 and 8 exhibited promising inhibitory activities against HUMECs with the IC50 values of 6.4 to 3.3 μM . 相似文献
16.
Chun Hong Yang Paul J. De Barro Fang Hao Wan 《Entomologia Experimentalis et Applicata》2013,147(3):282-292
The differences in the ability of the invading whitefly, Bemisia tabaci (Gennadius) (commonly known as biotype B and hereafter as B) and Trialeurodes vaporariorum (Westwood) (both Hemiptera: Aleyrodidae) to utilize salivary phenol‐oxidizing enzymes – polyphenol oxidase (PPO) and peroxidase (POD) to detoxify plant defensive phenolic compounds were explored. Polyphenol oxidase and POD were found in the saliva of both B and T. vaporariorum. For tomato colonies, the PPO and POD activities in the watery saliva of B were 2.27‐ and 1.34‐fold higher than those of T. vaporariorum. The PPO activities against specific phenolic compounds commonly found in plants were compared. The activities of those from B were significantly greater than those from T. vaporariorum. We also measured PPO activity in both species after they had fed on plants that were undamaged or had been previously damaged with either a plant pathogen [Phytophthora infestans (Mont.) de Bary (Peronosporales)] infection, mechanical damage, B infestation, or exogenous salicylic acid. For B, PPO activities in watery saliva increased 229, 184, 152, and 139% in response to the four treatments, whereas those of T. vaporariorum only increased 133, 119, 113, and 103%, respectively. Biotype B infestation significantly increased the total phenolic content of tomato leaves. Meanwhile, feeding on tomato infestation with B had no significant effect on the survival rate of B, but decreased the survival rate of T. vaporariorum significantly. These results suggest that B has stronger ability utilizing PPO to detoxify high concentrations of phenolics than T. vaporariorum, and this contributes to a significant advantage for B to hold high fitness on plants with induced resistance. Possible roles of salivary PPO in the competition between B and T. vaporariorum are discussed. 相似文献
17.
An‐Ran Wang Hong‐Chuan Song Hong‐Mei An Qian Huang Xie Luo Jin‐Yan Dong 《化学与生物多样性》2015,12(4):451-473
Chloranthus, a genus of the family Chloranthaceae, which is mainly distributed in eastern and southern Asia, has been used in Chinese folk medicine due to its antitumor, antifungal, and anti‐inflammatory activities. This review compiles the research on isolation, structure elucidation, structural diversity, and bioactivities of Chloranthus secondary metabolites reported between 2007 and 2013. The metabolites listed encompass 82 sesquiterpenoids, 50 dimeric sesquiterpenoids, 15 diterpenoids, one coumarin, and five other compounds. Among them, dimeric sesquiterpenoids, the characteristic components of plants from the genus Chloranthus, have attracted considerable attention due to their complex structures and significant biological features, e.g., antitumor, antibacterial, antifungal, anti‐inflammatory, and hepatoprotective activities, and potent and selective inhibition of the delayed rectifier (IK) K+ current and tyrosinase. 相似文献
18.
Fen Liu Mei-Hong Chen Yan-Xia Hu Qiong Zhan Jin-Yan Zhang Zi-Yue Zhang Si-Si Wang Wen-Cai Ye Lei Wang 《化学与生物多样性》2023,20(4):e202300234
Six new phloroglucinol derivatives, xanchryones I−N ( 1 – 6 ), were isolated from the leaves of Xanthostemon chrysanthus. Compounds 1 – 6 are unusual phloroglucinol-amino acid hybrids constructed through C2−N and O−C1′ bonds forming a peculiar oxazole ring. The structures and absolute configurations of compounds 1 – 6 were determined by MS, NMR, and single-crystal X-ray diffraction. Moreover, the anti-inflammatory and antibacterial activities of these compounds were evaluated. 相似文献
19.
Motohiko Ukiya Shingo Sawada Takashi Kikuchi Yasunori Kushi Makoto Fukatsu Toshihiro Akihisa 《化学与生物多样性》2013,10(2):177-188
Seventeen steviol derivatives, i.e., 2 – 18 , and 19 isosteviol derivatives, i.e., 19 – 37 , were prepared from a diterpenoid glycoside, stevioside ( 1 ). Upon evaluation of the cytotoxic activities of these compounds against leukemia (HL60), lung (A549), stomach (AZ521), and breast (SK‐BR‐3) cancer cell lines, nine steviol derivatives, i.e., 5 – 9 and 11 – 14 , and five isosteviol derivatives, i.e., 28 – 32 , exhibited activities with single‐digit micromolar IC50 values against one or more cell lines. All of these active compounds possess C(19)‐O‐acyl group, and among which, ent‐kaur‐16‐ene‐13,19‐diol 19‐O‐4′,4′,4′‐trifluorocrotonate ( 14 ) exhibited potent cytotoxicities against four cell lines with IC50 values in the range of 1.2–4.1 μM . Compound 14 induced typical apoptotic cell death in HL60 cells upon evaluation of the apoptosis‐inducing activity by flow‐cytometric analysis. These results suggested that acylation of the 19‐OH group of kaurane‐ and beyerane‐type diterpenoids might be useful for enhancement of their cytotoxicities with apoptosis‐inducing activity. 相似文献
20.
Host plant nitrogen enrichment has both positive and negative effects on the larval growth of a specialist butterfly
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Christophe Lebigre Caroline Vanderbeken Camille Turlure Nicolas Schtickzelle 《Ecological Entomology》2018,43(4):494-505
1. The nitrogen limitation hypothesis posits that phytophagous insects benefit from nitrogen enrichment of their host plants through a reduction of the concentration of toxic compounds and an increase of free amino acids and proteins. However, species' response to nitrogen enrichment varies substantially and high nitrogen levels are associated with population decline, suggesting there are major costs to feeding on nitrogen‐rich host plants. 2. To test the hypothesis that larval growth performance is maximal at intermediate nitrogen enrichment, nitrogen levels were measured in 18 populations of the host plant of Lycaena helle, a specialist butterfly inhabiting nutrient‐poor wet meadows. The nitrogen content of host plants was then modified to mirror average natural nitrogen levels (C), highest field‐recorded levels (T1), and levels higher than those observed across our study populations (T2). 3. Caterpillars fed with T1 leaves had a greater maximum body mass than caterpillars of the C group because of their improved food assimilation during the early stages of their development. Caterpillars of C and T2 groups had similar growth patterns but high nitrogen content had detrimental effects, as caterpillars fed with T2 leaves had a slower ingestion rate than C and T1 groups. 4. Quantifying the fitness consequences of these changes in growth performance is necessary to fully understand the implications of nitrogen enrichment for L. helle (rapid growth may result in fitness costs). However, conservation plans for this emblematic glacial relict species should also consider the preservation of its host plant quality to ensure its persistence. 相似文献