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Isolation of two novel terpenoid skeletons from Croton laui,an aromatic norsesterterpenoid and a highly rearranged neo-clerodane diterpenoid 认领 引用
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作者 Zong-Yi Zhang Xin Wang +4 位作者 Ying Li Yuan Gao Yao-Yue Fan Jian-Min Yue Jin-Xin Zhao 《Chinese Chemical Letters》 SCIE CAS CSCD 2026年第2期284-288,共5页
New-skeleton terpenoids have prompted considerable interest owing to their chemical and biological significance.A chemical study on the bark of Croton laui led to the isolation and identification of a new norsesterter... New-skeleton terpenoids have prompted considerable interest owing to their chemical and biological significance.A chemical study on the bark of Croton laui led to the isolation and identification of a new norsesterterpenoid,crolatinoid A(1),and two new neoclerodane diterpenoids,crolatinoids B and C(2 and 3).Structurally,compound 1 exhibits an unprecedented 12,17-cyclo20-nor phenyllabdane skeleton.Compound 2 features a novel 19(5→4)-abeo-3,5-cycloneoclerodane skeleton,which is hypothetically derived from precursor 3 through an oxa-di-π-methane rearrangement process.Furthermore,compound 1 demonstrated a significant capacity to reverse multidrug resistance in paclitaxel-resistant HCT-15 cells with a reversal fold value of 16.All three compounds displayed adipogenesis inhibition in 3T3-L1 adipocytes. 展开更多
关键词 Croton laui Sesterterpenoid Diterpenoid Multidrug resistance reversal Anti-adipogenesis
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Revision of the absolute configurations of Pallavicinia diterpenoids and further discovery of their Diels-Alder cycloadducts 认领 引用
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作者 Jiao-Zhen Zhang Cheng-Min Zhang +7 位作者 Yong-Jie Wang Pei-Lin Wu Rui-Feng Liu Ye Li Ming-Zhu Zhu Shuang-Zhi Yuan Ze-Jun Xu Hong-Xiang Lou 《Chinese Chemical Letters》 SCIE CAS CSCD 2026年第1期394-398,共5页
Owing to their intricate molecular frameworks and copious chiral centers,the structural identification and configurational assignment of natural products are challenging tasks.Comprehensive spectral data analysis is c... Owing to their intricate molecular frameworks and copious chiral centers,the structural identification and configurational assignment of natural products are challenging tasks.Comprehensive spectral data analysis is crucial for the confirmation of absolute configurations.Ignoring critical parameters will lead to false structure,which may confuse the total synthesis and drug development.Herein,the configurations of seven heterogeneous Pallavicinia diterpenoids(PDs) isolated from Pallavicinia liverworts are revised using a combination of single-crystal X-ray diffraction and electronic circular dichroism(ECD) calculations.Meanwhile,identification of five unprecedented PD heterodimers PD-dimers A-E(18-22) along with eleven previously undescribed PDs(5-9,13-17,23) obtained by the reinvestigation of the Chinese liverwort Pallavicinia subciliata have resulted in corrections and support the revised conclusions. 展开更多
关键词 Revision Absolute configurations Pallavicinia diterpenoids Liverwort Single-crystal X-ray diffraction Electronic circular dichroism calculations
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Haploides A-G:Diterpenoids featuring four new carbon skeletons via non-carbocation-driven skeletal diversification 认领 引用
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作者 Ming-Zhu Zhu Ze-Jun Xu +7 位作者 Jiao-Zhen Zhang Li-Zhi Shi Zong-Xu Gao Yi Li Shuang-Zhi Yuan Yan-Rong Ma Ai-Xia Cheng Hong-Xiang Lou 《Chinese Chemical Letters》 SCIE CAS CSCD 2026年第7期479-483,共5页
A series of highly rearranged labdane diterpenoids featuring previously unreported skeletons,including9,18-cyclolabdanes(1 and 2),1,10-seco-9,18-cyclolabdanes(3-5),7,18-cyclolabdanes(6),and 1,10-seco-1,5-cyclolabdanes... A series of highly rearranged labdane diterpenoids featuring previously unreported skeletons,including9,18-cyclolabdanes(1 and 2),1,10-seco-9,18-cyclolabdanes(3-5),7,18-cyclolabdanes(6),and 1,10-seco-1,5-cyclolabdanes(7),along with seven novel labdanes(8-14),two novel halimane diterpenoids(15 and 16),and three known congeners(17-19),were isolated from Chinese liverwort Haplomitrium mnioides.Their structures were unequivocally determined through comprehensive spectroscopic analysis,single-crystal X-ray diffraction and electronic circular dichroism(ECD)calculations.These diverse diterpenoids were biosynthesized through an aldol-type cascade process,using 19 as the starting material,distinguishing them from compounds generated via conventional carbocation rearrangement.Anti-inflammatory assays revealed that haploide O(15)and haplomitrenolide C(17)significantly inhibited the secretion of proinflammatory cytokines interferon-γ(IFN-γ),tumor necrosis factor-α(TNF-α),and interleukin-6(IL-6)in vitro in concanavalin A(Con A)-induced murine spleen cells. 展开更多
关键词 Labdane diterpenoids New carbon skeletons Haplomitrium mnioides Biosynthesis Single-crystal X-ray diffraction Anti-inflammatory activity
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Structurally diverse rhamnofolane,tigliane,and daphnane diterpenoids from Euphorbia wallichii as anti-liver fibrosis agents 认领 引用
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作者 Fangyu Yuan Xinying Zhu +7 位作者 Shuqi Wu Long Ling Dong Huang Lu Gan Jialuo Huang Yiling Liao Guihua Tang Sheng Yin 《Chinese Journal of Natural Medicines》 SCIE CAS CSCD 2026年第2期247-256,共10页
Twelve new diterpenoids,euphorwallnoids A-L(1-12),comprising five rhamnofolanes(1-5),five tiglianes(6-10),and two daphnanes(11 and 12),along with six known analogues(13-18),were isolated from the whole plants of Eupho... Twelve new diterpenoids,euphorwallnoids A-L(1-12),comprising five rhamnofolanes(1-5),five tiglianes(6-10),and two daphnanes(11 and 12),along with six known analogues(13-18),were isolated from the whole plants of Euphorbia wallichii(E.wallichii).Their structures were determined using spectroscopic analysis,computational methods,chemical derivatization,and single-crystal X-ray diffraction.Euphorwallnoid A(1)features an unusual 5/7/6/5-tetracyclic scaffold,whereas 2-5 represent a rare subclass of 4-deoxygenated rhamnofolanes and 6-8 constitute 13-deoxygenated tiglianes.Notably,compound 1 demonstrated promising anti-liver fibrosis activity by significantly inhibiting the expression of fibronectin(FN),α-smooth muscle actin(α-SMA),and collagen I in transforming growth factorβ1(TGF-β1)-stimulated LX-2 cells at micromolar concentrations. 展开更多
关键词 Euphorbia wallichii Diterpenoids Rhamnofolanes Tiglianes Daphnanes Liver fibrosis
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Mining substrate-promiscuity cytochrome P450s from Euphorbia fischeriana for heterologous bioproduction of diverse labdane-related diterpenoids 认领 引用
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作者 Ke Gao Lin Zhao +4 位作者 Lei Wang Rui Zhang Jianxun Zhu Pengcheng Lin Jiachen Zi 《Chinese Chemical Letters》 SCIE CAS CSCD 2026年第1期389-393,共5页
Many labdane-related diterpenoids(LRDs)exhibit high values in drug development.Their diversity in structure and bioactivity,to a large extent,arise from oxidative modifications which are mainly catalyzed by cytochrome... Many labdane-related diterpenoids(LRDs)exhibit high values in drug development.Their diversity in structure and bioactivity,to a large extent,arise from oxidative modifications which are mainly catalyzed by cytochrome P450s(CYPs).The medicinal plant Euphorbia fischeriana Steud.is rich in LRDs with distinct scaffolds.Herein,we characterized three cytochrome P450s involved in LRD biosynthesis from this plant.Notably,CYP71D450 and CYP701A148 are two substrate-promiscuity CYPs.The former is the first example of CYPs which can oxidize C-3 of ent-atisane skeleton and ent-isopimara-7(8),15-diene,and the latter is the first example of CYPs which can oxidize C-19 of ent-abietane and ent-pimarane skeletons.This study expands the toolkit for bioproduction of diverse LRDs. 展开更多
关键词 Labdane-related diterpenoids Biosynthesis Cytochrome P450 Bioproduction Euphorbia fischeriana
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Penispirolactam and penipyrroloindole,two unusual polycyclic indole diterpenoids with anti-hepatic fibrosis activity from the endophytic fungus Penicillium janthinellum H-6 认领 引用
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作者 Lei Li Xin-Ying Zhu +6 位作者 Jun-Yu Zhu Zhi-Hao Wu Yan-Jiang Zhang Fang-Yu Yuan Dong Huang Sheng Yin Gui-Hua Tang 《Chinese Chemical Letters》 SCIE CAS CSCD 2026年第4期567-572,共6页
Penispirolactam(1)and penipyrroloindole(2),two highly modified paspaline-type indole diterpenoids(IDTs),along with three new(3-5)and two known(6 and 7)paspaline-type IDTs were obtained from the endophytic fungus Penic... Penispirolactam(1)and penipyrroloindole(2),two highly modified paspaline-type indole diterpenoids(IDTs),along with three new(3-5)and two known(6 and 7)paspaline-type IDTs were obtained from the endophytic fungus Penicillium janthinellum H-6 guided by liquid chromatography-mass spectrometry(LCMS)-based molecular network.Architecturally,penispirolactam(1)possesses a unique octacyclic skeleton(6/5/6/6/5/6/6/6)with a spiro core formed by the integration of a C6-C2 unit with the indole moiety,and penipyrroloindole(2)represents a rearranged octacyclic skeleton(6/5/6/5/5/6/6/6)with a pyrrolo[1,2-a]indole core fragment.Their structures,including absolute configurations,were established by detailed spectroscopic analysis,gauge-independent atomic orbital(GIAO)1D nuclear magnetic resonance(NMR)(DP4+)calculation protocol,and electronic circular dichroism(ECD)calculation method.The plausible biosynthetic pathway of compounds 1 and 2 was also speculated.Additionally,the anti-hepatic fibrosis activity of all compounds was explored,and it was found that 1 could exert its effects by inhibiting the transforming growth factor-β(TGF-β)/Smad signaling pathway without cytotoxicity. 展开更多
关键词 Endophytic fungus Penicillium janthinellum H-6 Paspaline-derived indole diterpenoid Penispirolactam Penipyrroloindole Anti-hepatic fibrosis
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Highly oxygenated cembrane diterpenoids from the South China Sea soft coral Sinularia pedunculata and their anti-HBV activities 认领 引用
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作者 Ruonan Sun Chao Huang +4 位作者 Zhen Gao Ligong Yao Yuewei Guo Jieliang Chen Xuwen Li 《Chinese Journal of Natural Medicines》 SCIE CAS CSCD 2026年第7期875-886,共12页
Eleven new highly oxygenated cembrane-type diterpenoids(1−7 and 10−13)and two known analogues(8−9)were isolated from the South China Sea soft coral Sinularia pedunculata.Their structures were determined through extens... Eleven new highly oxygenated cembrane-type diterpenoids(1−7 and 10−13)and two known analogues(8−9)were isolated from the South China Sea soft coral Sinularia pedunculata.Their structures were determined through extensive spectroscopic analysis,quantum mechanical-nuclear magnetic resonance(QM-NMR)approach and X-ray diffraction analysis.Notably,compounds 3 and 4 were rare cembrane diterpenoids featuring a tetrahydropyran moiety with 5,8-ether and 4,8-ether linkages,respectively,while compounds 4 and 9 inhibited HBV DNA replication with IC50 values of 0.87 and 1.15μmol·L−1 in HepAD38 cells,respectively.Mechanism investigation suggested that compound 9 accelerated capsid formation without affecting the levels of HBV cccDNA,total RNA,or pgRNA. 展开更多
关键词 Soft coral Sinularia pedunculata Cembrane diterpenoids Anti-HBV activity
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Lanostane triterpenoids and nor-abietane aromatic diterpenoid from Ganoderma applanatum and their neuroprotective activity 认领 引用
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作者 Han Wu Mengyue Dong +7 位作者 Yifan Guo Zhengbin Zong Mengke Zhang Xin Chen An'an Yang Mingming Cao Jinming Gao Xia Yin 《Food Science and Human Wellness》 SCIE CAS CSCD 2026年第6期2920-2934,共15页
The Ganoderma fungus has been revered for centuries in traditional Chinese medicine and foods with high nutritional value for its purported health benefits.The extracts of Ganoderma applanatum(Pers.)Pat.showed promisi... The Ganoderma fungus has been revered for centuries in traditional Chinese medicine and foods with high nutritional value for its purported health benefits.The extracts of Ganoderma applanatum(Pers.)Pat.showed promising protective activity against neurological damage caused by scopolamine in zebrafish.Eleven highly oxygenated lanostane triterpenoids with one or moreα,β-unsaturated conjugated moiety,including three previously undescribed compounds appterpenactones A-C(1-3),and a nor-abietane diterpenoid,ganorphenol(4),together with related congeners were obtained from the fruiting bodies of G.applanatum.The structures and absolute configurations of the previously undescribed compounds were elucidated by analysis of nuclear magnetic resonance(NMR)spectra,quantum chemical calculations of NMR and electronic circular dichroism spectra,and X-ray crystallographic data.Compound 1 shares an unusual 6/6/5/6/5 ring system scaffold,while compound 4 represents a rearranged aromatic diterpenoid with rare ortho-dimethyl groups.All compounds were evaluated for their neuroprotective activity in glutamate-induced mouse hippocampal neuronal cell line(HT-22 cells).Ganorphenol(4)and applanoic acid C(6)demonstrated significant neuroprotective activity in inhibiting glutamate-induced HT22 cell death.Biochemical assays suggest that applanoic acid C may exert protective effects by activating the Nrf2/HO-1 pathway.Moreover,the further mechanistic study revealed that ganorphenol(4)can exert neuroprotective effects through the PI3K-AKT-mTOR pathway.Collectively,comprehensive experiments and molecular docking studies demonstrated that compounds 4 and 6 are potential neuroprotective agents.These findings provide valuable insights into the actions of trace bioactive components from edible materials and contribute to the broader understanding of neuroprotective compounds. 展开更多
关键词 Ganoderma applanatum Medicinal-edible mushroom Rearranged abeo-lanostane skeleton Aromatic diterpenoid Neuroprotective activity Glutamate-induced HT-22 cell
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Diterpenoids with unexpected 5/6/6-fused ring system and its dimer from Strophioblachia glandulosa 认领 引用 被引量：2
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作者 Xue-Wen Wu Bin-Bao Wang +6 位作者 Yu Qin Yong-Xiang Huang Muhammad Aurang Zeb Bin Cheng Xiao-Li Li Chang-Bo Zheng Wei-Lie Xiao 《Chinese Chemical Letters》 SCIE CAS CSCD 2025年第8期350-354,共5页
Six rearranged nor-diterpenoids with 5/6/6-fused tricyclic system(1–6),and one unprecedented dimer with 5/6/6/6/6/5-fused carbon core(7)were isolated from Strophioblachia glandulosa.Spectroscopic techniques,electroni... Six rearranged nor-diterpenoids with 5/6/6-fused tricyclic system(1–6),and one unprecedented dimer with 5/6/6/6/6/5-fused carbon core(7)were isolated from Strophioblachia glandulosa.Spectroscopic techniques,electronic circular dichroism(ECD),quantum chemical calculations,and single-crystal X-ray diffraction analysis were used to elucidate their structures.A preliminary bioactivity assay revealed compounds 2 and 3 exhibited potent anti-myocardial hypertrophy effect in vitro by significantly inhibiting the expression levels of atrial natriuretic peptide(ANP)and myosin heavy chain 7(MYH7)proteins.Additionally,mitogen-activated protein kinase 14(Mapk14)may be involved in the regulation of compound3 on cardiac hypertrophic disease by network pharmacology prediction and experimental verification. 展开更多
关键词 Strophioblachiag landulosa Diterpenoid Dimer Cardiac hypertrophy Network pharmacology
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Progress in the Total Synthesis of Cephalotane Diterpenoid Natural Products 认领 引用
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作者 Ding Yiming Zhang Tingrong +1 位作者 Zhang Jingwei Deng Jun 《有机化学》 SCIE CAS CSCD 北大核心 2025年第6期2048-2073,共26页
Continuous research on Cephalotaxus plants has ultimately led to the US food and drug administration (FDA) ap-provalof homoharringtonine in 2012 for the treatment of chronic myeloid leukemia. Additionally, another imp... Continuous research on Cephalotaxus plants has ultimately led to the US food and drug administration (FDA) ap-provalof homoharringtonine in 2012 for the treatment of chronic myeloid leukemia. Additionally, another important class of natural products from Cephalotaxus plants is cephalotane diterpenoids. Since the discovery of the first member, harring-tonolide,in 1978, cephalotane diterpenoids have garnered significant attention from the scientific community due to their re-markableanti-cancer activity. The unique structural features of cephalotane diterpenoids, a 7/6/5/6-fused tetracyclic carbon skeleton and a bridged lactone, make them ideal targets for synthetic chemists. Successfully synthesizing these complex diterpenoids is of great importance for the discovery and development of anti-tumor drugs. To date, ten research groups have completed the total synthesis of 24 cephalotane diterpenoids. The latest progress in the total synthesis of cephalotane diterpe-noidsis reviewed, showcasing the importance of these innovative synthetic strategies in the efficient synthesis of complex natural products and their potential significance in advancing the field of drug discovery. 展开更多
关键词 cephalotane diterpenoids total synthesis anti-cancer activity harringtonolide Cephalotaxus
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Profiling the chemical differences of diterpenoid alkaloids in different processed products of Aconiti Lateralis Radix Praeparata by UHPLC-LTQ-Orbitrap mass spectrometry combined with untargeted metabolomics and mass spectrometry imaging 认领 引用
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作者 Yang Yu Changliang Yao +5 位作者 Jianqing Zhang Yong Huang Shuai Yao Hua Qu Tong Zhang Dean Guo 《Chinese Journal of Natural Medicines》 SCIE CAS CSCD 2025年第8期1009-1015,共7页
Aconiti Lateralis Radix Praeparata(Fuzi)represents a significant traditional Chinese medicine(TCM)that exhibits both notable pharmacological effects and toxicity.Various processing methods are implemented to reduce th... Aconiti Lateralis Radix Praeparata(Fuzi)represents a significant traditional Chinese medicine(TCM)that exhibits both notable pharmacological effects and toxicity.Various processing methods are implemented to reduce the toxicity of raw Fuzi by modifying its toxic and effective components,primarily diterpenoid alkaloids.To comprehensively analyze the chemical variations between different Fuzi products,ultra-high performance liquid chromatography-linear ion trap quadrupole Orbitrap mass spectrometry(UHPLC-LTQ-Orbitrap MS)was employed to systematically characterize Shengfuzi,Heishunpian and Baifupian.A total of 249 diterpenoid alkaloids present in Shengfuzi were identified,while only 111 and 61 in Heishunpian and Baifupian were detected respectively,indicating substantial differences among these products.An untargeted metabolomics approach combined with multivariate statistical analysis revealed 42 potential chemical markers.Through subsequent validation using 52 batches of commercial Heishunpian and Baifupian samples,8 robust markers distinguishing these products were identified,including AC1-propanoic acid-3OH,HE-glucoside,HE-hydroxyvaleric acid-2OH,dihydrosphingosine,N-dodecoxycarbonylvaline and three unknown compounds.Additionally,the MS imaging(MSI)technique was utilized to visualize the spatial distribution of chemical constituents in raw Fuzi,revealing how different processing procedures affect the chemical variations between Heishunpian and Baifupian.The distribution patterns of different diterpenoid alkaloid subtypes partially explained the chemical differences among products.This research provides valuable insights into the material basis for future investigations of different Fuzi products. 展开更多
关键词 Aconiti Lateralis Radix Praeparata Diterpenoid alkaloids Processing Untargeted metabolomics Mass spectrometry imaging
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Bioactive oriented discovery of diterpenoids in Coffea arabica basing on 1D NMR and LC-MS/MS molecular network 认领 引用
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作者 Guilin Hu Chenxi Quan +2 位作者 Abdulbaset Al-Romaima Haopeng Dai Minghua Qiu 《Beverage Plant Research》 CAS 2025年第1期353-358,共6页
Coffee diterpenes are a class of characteristic components in coffee,which have potential biological activities including the prevention of cancer,obesity,diabetes,and other diseases.Due to the complex chemical compos... Coffee diterpenes are a class of characteristic components in coffee,which have potential biological activities including the prevention of cancer,obesity,diabetes,and other diseases.Due to the complex chemical composition of roasted coffee beans,analyzing the composition and potential activity of coffee diterpenes has always been a challenge.In the current research,based on activity-oriented research strategies,three novel coffee diterpene esters(1-3)with moderateα-glucosidase inhibitory activity were separated from roasted Arabica coffee beans.The structures of the three new compounds were determined through comprehensive spectral analysis.To explore trace active diterpene esters of the same type in coffee,a molecular network based on LCMS/MS was constructed,and three novel coffee diterpene esters(4-6)were identified. 展开更多
关键词 diterpenoids composition potential activity bioactive compounds Coffea arabica NMR chemical composition coffee diterpene LC MS MS
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Isodons A-H,seco-abietane and abietane-type diterpenoids from Isodon lophanthoides:isolation,structural elucidation,and anti-cholestatic activity 认领 引用 被引量：2
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作者 Huiling Zhou Mingzhu Han +6 位作者 Miaomiao Nan Yingrong Leng Weiming Huang Shengtao Ye Lingyi Kong Wenjun Xu Hao Zhang 《Chinese Journal of Natural Medicines》 SCIE CAS CSCD 2025年第9期1133-1142,共10页
Eight new diterpenoids,Isodons A-H(1-8),comprising seco-abietane and abietane-type structures,together with 13 known analogues(9-21),were isolated from Isodon lophanthoides(Buch.-Ham.ex D.Don)Hara.The compounds(+)-3/(... Eight new diterpenoids,Isodons A-H(1-8),comprising seco-abietane and abietane-type structures,together with 13 known analogues(9-21),were isolated from Isodon lophanthoides(Buch.-Ham.ex D.Don)Hara.The compounds(+)-3/(-)-3,(+)-4/(-)-4,and(+)-5/(-)-5 were identified as three enantiomeric pairs.The planar structures and absolute configurations of 1-8 were determined through high-resolution electrospray ionization mass spectrometry(HR-ESI-MS),1D&2D nuclear magnetic resonance(NMR)spectroscopy,electronic circular dichroism(ECD)calculations,and X-ray diffraction crystallography.A cholesterol 7α-hydroxylase(Cyp7a1)luciferase reporter assay revealed significant anti-cholestatic activities for compounds 1,(+)-4,6,7,12-14,and 16.Additionally,compound 6 demonstrated anti-cholestatic effects through the farnesoid X receptor(FXR)-associated signaling pathways in vitro and in vivo.These findings suggest potential applications for I.Lophanthoides in pharmaceutical development. 展开更多
关键词 Isodon lophanthoides Diterpenoids Anticholestatic effect FXR Cyp7a1
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Diterpenoids and lignans from fossil Chinese medicinal succinum and their activity against renal fibrosis 认领 引用 被引量：1
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作者 Yefei Chen Yunfei Wang +2 位作者 Yunyun Liu Yongming Yan Yongxian Cheng 《Chinese Journal of Natural Medicines》 SCIE CAS CSCD 2025年第7期888-896,共9页
Five previously undescribed diterpenoids,named succipenoids D‒H(1‒5),along with four undescribed lignans,named succignans A‒D(6‒9),were isolated from the dichloromethane extract of Chinese medicinal succinum.Compounds... Five previously undescribed diterpenoids,named succipenoids D‒H(1‒5),along with four undescribed lignans,named succignans A‒D(6‒9),were isolated from the dichloromethane extract of Chinese medicinal succinum.Compounds 1‒5 were characterized as nor-abietane diterpenoids,while compounds 6‒9 were identified as lignans polymerized from two groups of phenylpropanoid units.The structures of these novel compounds,including their absolute configurations,were determined through spectroscopic and computational methods.Biological assessments of renal fibrosis demonstrated that compounds 6 and 7 effectively reduce the expression of proteins associated with renal fibrosis,includingα-smooth muscle actin(α-SMA),collagen I,and fibronectin in transforming growth factor-β1(TGF-β1)induced normal rat kidney proximal tubular epithelial cells(NRK-52e). 展开更多
关键词 Succinum Lignan Diterpenoid Renal fibrosis
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Highly anticipated natural diterpenoids as an important source of new drugs in 2013-2023 认领 引用
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作者 Yingjie Wang Peng Tang +15 位作者 Wenchao Tu Qi Gao Cuizhu Wang Luying Tan Lixin Zhao Hongye Han Liefeng Ma Kouharu Otsuki Weilie Xiao Wenli Wang Jinping Liu Yong Li Zhajun Zhan Wei Li Xianli Zhou Ning Li 《Chinese Chemical Letters》 SCIE CAS CSCD 2025年第1期119-136,共18页
This review covers the structures of diterpenoids,including chain(72),monocyclic(9),labdane-type(67),clerodane-type(127)abietane-type(716),ent-kaurane-type(89),grayanane-type(331),ingenanetype(55),tigliane-type(154),d... This review covers the structures of diterpenoids,including chain(72),monocyclic(9),labdane-type(67),clerodane-type(127)abietane-type(716),ent-kaurane-type(89),grayanane-type(331),ingenanetype(55),tigliane-type(154),daphnane-type(237),and aconitine-type diterpene alkaloids(265)with rich biological activities reported in 2013-2023.And the drugs in clinical use or under clinical investigation of diterpenoids and leading compounds were summarized. 展开更多
关键词 Natural diterpenoids Structures Bioactivities Druggability Leading compounds New drugs
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Ent-pimarane and ent-kaurane diterpenoids from Siegesbeckia pubescens and their anti-endothelial damage effect in diabetic retinopathy 认领 引用
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作者 Mengjia Liu Tingting Luo +4 位作者 Rongxian Li Wenying Yin Fengying Yang Di Ge Na Liu 《Chinese Journal of Natural Medicines》 SCIE CAS CSCD 2025年第2期234-244,共11页
Diabetic retinopathy,a prevalent and vision-threatening microvascular complication of diabetes mellitus,is the leading cause of blindness among middle-aged and elderly individuals.Natural diterpenoids isolated from Si... Diabetic retinopathy,a prevalent and vision-threatening microvascular complication of diabetes mellitus,is the leading cause of blindness among middle-aged and elderly individuals.Natural diterpenoids isolated from Siegesbeckia pubescens demonstrate potent anti-inflammatory properties.This study aimed to identify novel bioactive diterpenoids from S.pubescens and investigate their effects on oxidative stress and inflammatory responses in diabetic retinopathy,both in vitro and in vivo.Three new ent-pimarane-type diterpenoids(1–3)and six known compounds(4–9)were isolated from the aerial parts of S.pubescens.Their structures were elucidated through spectroscopic data interpretation,and absolute configurations were determined by comparing calculated and experimental electronic circular dichroism(ECD)spectra.Among these compounds,14β,16-epoxy-ent-3β,15α,19-trihydroxypimar-7-ene(5)exhibited the most potent protective effect against high glucose and interleukin-1β(IL-1β)-stimulated human retinal endothelial cells.Mechanistically,compound 5 promoted endothelial cell survival while ameliorating oxidative stress and inflammatory response in diabetic retinopathy,both in vivo and in vitro.These findings not only suggest that diterpenoids such as compound 5 are important anti-inflammatory constituents in S.pubescens,but also indicate that compound 5 may serve as a lead compound for preventing or treating vascular complications associated with diabetic retinopathy. 展开更多
关键词 Siegesbeckia pubescens Natural diterpenoid Diabetic retinopathy Oxidative stress Inflammatory response
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Highly fused tetracyclic diterpenoid natural products:Diverse biosynthesis and total synthesis 认领 引用
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作者 Yun-Hong Yu Yu Peng Wei-Dong Z.Li 《Chinese Chemical Letters》 SCIE CAS CSCD 2025年第10期109-124,共16页
A category of highly fused diterpenoid natural products possessing a characteristic perhydropyrene-like or rearranged tetracyclic skeleton structure are distributed in different life forms.Compared to traditional poly... A category of highly fused diterpenoid natural products possessing a characteristic perhydropyrene-like or rearranged tetracyclic skeleton structure are distributed in different life forms.Compared to traditional polycyclic diterpenoids,their biosynthetic pathways are quite unique and diverse.Chemists have pinpointed a range of this type of unusual diterpenoids:cycloamphilectanes and isocycloamphilectanes,kempenes and rippertanes,hydropyrene and hydropyrenol,along with recently disclosed cephalotanes.This review describes developments in this field and discusses the challenges associated with synthesizing this class of highly complex compounds. 展开更多
关键词 Tetracyclic diterpenoid Perhydropyrene skeleton Natural products Biosynthesis Total synthesis Cephalotanes
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Napelline-type C20-diterpenoid alkaloid iminiums from an aqueous extract of ‘‘fu zi'': Solvent-/base-/acid-dependent transformation and equilibration between alcohol iminium and aza acetal forms 认领 引用 被引量：15
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作者 Xian-Hua Meng Zhi-Bo Jiang +3 位作者 Cheng-Gen Zhu Qing-Lan Guo Cheng-Bo Xu Jian-Gong Shi 《Chinese Chemical Letters》 SCIE CAS CSCD 2016年第7期993-1003,共11页
Three new napelline-type C20-diterpenoid alkaloids,named aconicarmichinium A and B trifluoroacetates（1 and 2） and aconicarmichinium C chloride（3）,were isolated from an aqueous extract of ＂fu zi＂,the lateral root... Three new napelline-type C20-diterpenoid alkaloids,named aconicarmichinium A and B trifluoroacetates（1 and 2） and aconicarmichinium C chloride（3）,were isolated from an aqueous extract of ＂fu zi＂,the lateral roots of Aconitum carmichaelii.Their structures were elucidated by extensive spectroscopic data analysis.Compounds 1-3 represent the first examples of napelline-type C20 diterpenoid alkaloid alcohol iminiums,of which the structures were fully characterized.In addition,transformation and equilibration between the alcohol iminiums（1-3） and the aza acetals la-3a were investigated by measurements of the NMR spectra in protic and aprotic deuterium solvents including alkali pyridine-d5,along with evaporation under reduced pressure and gradual additions of TFA,AcOH,and HC1.The results demonstrated that the transformation and equilibration were solvent-,base-,and acid-dependent.Especially,in aqueous biological fluid,these C20-diterpenoid alkaloids would more likely exist as the alcohol iminiums accompanied by anion counterparts in biosystems to increase their solubility, bioavailability, transportations, and functions.The absolute configurations of 1-3 were confirmed by X-ray crystallographic analysis of 2a. 展开更多
关键词 Aconitum carmichaelii Ranunculaceae Napelline-type C20-diterpenoid alkaloid Aconicarmichiniums A–C Alcohol iminium and aza acetal forms of the diterpenoid alkaloid Transformation and equilibration
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Effects of radix curcumae-derived diterpenoid C on Helicobacter pylori-induced inflammation and nuclear factor kappa B signal pathways 认领 引用 被引量：14
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作者 Xuan Huang Bin Lv +3 位作者 Shuo Zhang Qun Dai Bing-Bing Chen Li-Na Meng 《World Journal of Gastroenterology》 SCIE CAS 2013年第31期5085-5093,共9页
AIM:To study effect of diterpenoid C extracted from radix curcumae on Helicobacter pylori(H.pylori)-infected inflammation,intestinal metaplasia,and nuclear factor kappa B(NF-κB)signaling pathway in vitro.METHODS:We u... AIM:To study effect of diterpenoid C extracted from radix curcumae on Helicobacter pylori(H.pylori)-infected inflammation,intestinal metaplasia,and nuclear factor kappa B(NF-κB)signaling pathway in vitro.METHODS:We used I-type H.pylori to infect human gastric epithelial gastric epithelium cell line(GES-1)cell lines,and then H.pylori-infected GES-1 cells were treated with radix curcumae(RC)-derived diterpenoid C of different concentrations(5,10,20μg/mL)and amoxicillin.The expression of p65,IκB kinase(IKK)αand IKKγproteins was detected with Western blotting,and the expression of interleukin(IL)-8,IL-6 and IL-4 was determined with enzyme-linked immunosorbent assay method.Data were analyzed using SPSS software ver18.0.For comparisons between groups of more than two unpaired values,one-way analysis of variance(ANOVA)was used.If an ANOVA F value was significant,post hoc comparisons were performed between groups.If results were not normally distributed,the Mann-Whitney U test was used to compare two groups of unpaired values,whereas for comparisons between groups of more than two unpaired values,the Kruskal-Wallis H test was used.Statistical significance was established at P<0.05.RESULTS:The MTT assay results revealed the inhibited rate of GES-1,and indicated that the IC5 of RCderived diterpenoid C and amoxicillin all were 5μg/mL for gastric GES-1 cells.The expression of IL-8 was significantly increased,especially at 12 h time point;and the expression of IL-4 was decreased in H.pyloriinfected GES-1 cells.After H.pylori-infected GES-1 cells were treated with RC-derived diterpenoid C of different concentrations and amoxicillin,the expression of IL-8was decreased at 12,24,48,72 h points(P<0.01),especially in high-concentration diterpenoid C(20μg/mL)group;and the expression of IL-4 was increased,especially in moderate and high-concentration diterpenoid C(10 and 20μg/mL)groups.RC-derived diterpenoid C had the inhibitory effects on H.pylori-induced p65 translocation from cytoplasm into cell nucleus,H.pylori-stimulant IkBαdegradation,the phosphorylation of p65 and IkBα,and the expression of IKKαand IKKβproteins.CONCLUSION:RC-derived diterpenoid C can block NF-κB signal pathway,effectively reducing the secretion of H.pylori-induced proinflammatory cytokine and increasing the secretion of anti-inflammatory cytokine. 展开更多
关键词 Radix curcumae-derived diterpenoid C Helicobacter pylori Nuclear factor-κB Inflammatory cytokine
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3, 4-seco-Labdane diterpenoids from the leaves of Callicarpa nudiflora with anti-inflammatory effects 认领 引用 被引量：11
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作者 WANG Hong-Gang LUO Fu-Kang +6 位作者 LEI Xiang YAO Yun-Da LIAO Guo-Chao LIU Zhong-Qiu JIANG Zhi-Hong ZHOU Hua WU Peng 《Chinese Journal of Natural Medicines》 SCIE CAS CSCD 2019年第9期707-712,共6页
Four new 3,4-seco-labdane diterpenoids,nudiflopenes J-M,were isolated from the leaves of Callicarpa nudiflora along with six known compounds.The structures of these diterpenoids were determined by comprehensive spectr... Four new 3,4-seco-labdane diterpenoids,nudiflopenes J-M,were isolated from the leaves of Callicarpa nudiflora along with six known compounds.The structures of these diterpenoids were determined by comprehensive spectroscopic analysis.All the isolated compounds were evaluated for their inhibitory effects on NO production in LPS-stimulated RPMs and RAW264.7 cells.The results suggest that nudiflopenes J-M and other four known compounds showed significant inhibitory effects against NO production comparable to the positive control dexamethasone. 展开更多
关键词 Callicarpa nudiflora Verbenaceae 3,4-seco-Labdane diterpenoid Anti-inflammatory RPMs RAW264.7
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