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
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
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
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
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
Agastol (2), a new diterpene, was isolated from the roots of Agastache rugosa together with its isomer, named isoagastol (3) Their structures were established on the basis of spectral methods The structures of aga...Agastol (2), a new diterpene, was isolated from the roots of Agastache rugosa together with its isomer, named isoagastol (3) Their structures were established on the basis of spectral methods The structures of agastol (2) and isoagastol (3) was elucidated as 11,14 dihydroxy 12 methoxy 19(4→3) abeo abieta 4(18),8,11,13 tetraen 7 one and 11,14 dihydroxy 12 methoxy 19(4→3) abeo abieta 3,8,11,13 tetraen 7 one Isoagastol was isolated for the first time from natural sources展开更多
Two new diterpenoids, forskolin G and H were isolated from the chloroform extract of the roots of Coleus forskohlii, and based on spectroscopic data, their structures were identified as 1a-hydroxy-6b,7b-diacetoxy-8,13...Two new diterpenoids, forskolin G and H were isolated from the chloroform extract of the roots of Coleus forskohlii, and based on spectroscopic data, their structures were identified as 1a-hydroxy-6b,7b-diacetoxy-8,13-epoxylabd-14-ene-11-one (1), and 1a,6b-diacetoxy-8,13-epoxy labd-14-ene-11-one (2), respectively.展开更多
Phytochemical investigation of the leaves and twigs of Callicarpa cathayana led to the isolation of six new clerodane diterpenoids,cathayanalactones A-F(1-6),together with seven analogues(7-13).Their structures were e...Phytochemical investigation of the leaves and twigs of Callicarpa cathayana led to the isolation of six new clerodane diterpenoids,cathayanalactones A-F(1-6),together with seven analogues(7-13).Their structures were established by extensive NMR analyses together with experimental and calculated ECD spectra analyses.Compounds 1,2,3,7 and 11 showed inhibitory activities on lipopolysaccharide-induced nitric oxide production in RAW264.7 cells.展开更多
Two new harziane diterpenoids, named（9R,10R）-dihydro-harzianone（1） and harzianelactone（2）, were isolated from the endophytic fungus Trichoderma sp. Xy24 by using various column chromatography techniques. Their s...Two new harziane diterpenoids, named（9R,10R）-dihydro-harzianone（1） and harzianelactone（2）, were isolated from the endophytic fungus Trichoderma sp. Xy24 by using various column chromatography techniques. Their structures were determined on the basis of extensive spectroscopic（HR-ESI-MS, 1D NMR, 2D NMR and CD） analyses. Among them, 1 was the reductive product of harzianone and 2 was the Baeyer–Villiger monooxygenase catalyzed oxidation product of harzianone. Compound 1 exhibited cytotoxic activity against He La and MCF-7 cell lines with IC（50） values of 30.1 μmol/L and 30.7 μmol/L,respectively.展开更多
The perennial herbaceous plant Euphorbia jolkinii(Euphorbiaceae)is a noxious weed widely distributed in the grasslands of northwestern Yunnan and has greatly threatened the local biodiversity.Phytochemical investigati...The perennial herbaceous plant Euphorbia jolkinii(Euphorbiaceae)is a noxious weed widely distributed in the grasslands of northwestern Yunnan and has greatly threatened the local biodiversity.Phytochemical investigation on the fresh roots of E.jolkinii afforded six new diterpenoids 1,2,4–6,and 8,together with fifteen known diterpenoids.Their structures were elucidated on the basis of 1D and 2D NMR and other spectroscopic methods.Casbane,lathyrane,abietane,and ent-kaurane diterpenoids were reported from this plant for the first time.Selected compounds were evaluated for their antifeedant and anti-RSV(respiratory syncytial virus)activities.Compound 2 and ingenol(3)exhibited moderate antifeedant activity against a generalist insect herbivore,Spodoptera exigua,with EC50 values of 17.88 and 17.71 lg/cm2 respectively.Compound 19 showed significant anti-RSV activity,with 50%inhibition(IC50)value of 10.0 lM and selective index of 8.0.Compounds 1 and 2 were less active against RSV virus,both with IC50 value of 25 lM,and with selective indices of 1.0 and 3.2 respectively.These findings provided new evidence for the biological functions and utilization of the diversified diterpenoid metabolites in the roots of this rich but harmful plant.展开更多
Four new ent-kaurane diterpenoids,namely,3α-tigloyloxypterokaurene L_(3)(1),ent-17-hydroxy-kaura-9(11),15-dien-19-oic acid(2),and wedelobatins A(3)and B(4),together with 11 known ent-kaurane diterpenoids(5-15),were i...Four new ent-kaurane diterpenoids,namely,3α-tigloyloxypterokaurene L_(3)(1),ent-17-hydroxy-kaura-9(11),15-dien-19-oic acid(2),and wedelobatins A(3)and B(4),together with 11 known ent-kaurane diterpenoids(5-15),were isolated from the ethanol extract of Wedelia trilobata.All the structures of 1-15 were elucidated on the basis of spectroscopic studies.展开更多
Callica rpabodinieri is a Chinese traditional medicine herb with anti-inflammatory activity in clinic.Herein,we report two new 9,10-seco and etherified abietane diterpenoids bodinieric acids J and K(1 and 2) and one k...Callica rpabodinieri is a Chinese traditional medicine herb with anti-inflammatory activity in clinic.Herein,we report two new 9,10-seco and etherified abietane diterpenoids bodinieric acids J and K(1 and 2) and one known compound(3) isolated from the leaves and twigs of this plant.Their chemical structures were elucidated by detailed spectrometry data analysis and DP4+NMR calculation methods.Hypothetical biosynthetic pathways of 1-3 were preliminarily speculated.Compound 3 inhibited inflammasome activation and exhibited blockage of NLRP3 inflammasome activation at non-cytotoxic concentrations in vitro.展开更多
Euphorbia lathyris （Caper spurge） is a toxic and potent Chinese materia medica （T/PCMM）. This study sought a method for identifying five diterpenoids （Euphorbia factors LI-L3, L7a, and Ls） with the spectra of UV...Euphorbia lathyris （Caper spurge） is a toxic and potent Chinese materia medica （T/PCMM）. This study sought a method for identifying five diterpenoids （Euphorbia factors LI-L3, L7a, and Ls） with the spectra of UV and mass, quantifying three diterpenoids L1, L2, and L8 in crude extracts of unprocessed and processed E. lathyris seeds by liquid chromatography/ electrospray ionization mass spectrometry （LC-ESI-MS）. The analysis was achieved on an Agilent Eclipse XDB-C18 column （4.6 mm× 150mm i.d., 5 μm） with an isocratic elution with a mobile phase consisting of water and acetonitrile at a flow rate of 0.25 mL/min at column temperature of 30 ℃ and UV detection was set at 272 nm. An ESI source was used with a positive ionization mode. The calibration curve was linear in the ranges of 9.9-79 μg/mL for Euphorbia factor Lb 3.8-30.5μg/mL for Euphorbia factor L2, and 1.0-20.6 μg/mL for Euphorbia factor LB. The average recoveries （n=6） of three diterpenoids were 98.39%, 91.10% and 96.94%, respectively, with RSD of 2.5%, 2.4% and 2.1%, respectively. The contents of the three diterpenoids in processed E. lathyris seeds were 3.435, 1.367 and 0.286 mg/g, respectively, which decreased more sharply than those in unprocessed E. lathyris seeds which were 4.915, 1.944 and 0.425 mg/g, respectively. The method is simple, accurate, reliable and reproducible, and it can be applied to control the quality of unprocessed and processed E. lathyris seeds.展开更多
Plant-derived labdane-related diterpenoids(LRDs)represent a large group of terpenoids.LRDs possess either a labdane-type bicyclic core structure or more complex ring systems derived from labdane-type skeletons,such as...Plant-derived labdane-related diterpenoids(LRDs)represent a large group of terpenoids.LRDs possess either a labdane-type bicyclic core structure or more complex ring systems derived from labdane-type skeletons,such as abietane,pimarane,kaurane,etc.Due to their various pharmaceutical activities and unique properties,many of LRDs have been widely used in pharmaceutical,food and perfume industries.Biosynthesis of various LRDs has been extensively studied,leading to characterization of a large number of new biosynthetic enzymes.The biosynthetic pathways of important LRDs and the relevant enzymes(especially diterpene synthases and cytochrome P450 enzymes)were summarized in this review.展开更多
Five ent-6,7-seco-karuene diterpenoids-enmein,epinodosin,sculponeatin A,C,D,were isolated from the dried leaves of Rabdosia sculponeata One of the compounds,named sculponeatin D,was previously unreported.Its structre ...Five ent-6,7-seco-karuene diterpenoids-enmein,epinodosin,sculponeatin A,C,D,were isolated from the dried leaves of Rabdosia sculponeata One of the compounds,named sculponeatin D,was previously unreported.Its structre was elucidated by the spectral data including 2D COSY,~1H-^(13)C correlation,2D NOESY spectroscopy.展开更多
Salvia dugesii is an invasive plant in Yunnan,China.To tentatively explore its utilization,a systematic phytochemical investigation was carried out on this plant,which led to the isolation of five new neo-clerodane di...Salvia dugesii is an invasive plant in Yunnan,China.To tentatively explore its utilization,a systematic phytochemical investigation was carried out on this plant,which led to the isolation of five new neo-clerodane diterpenoids,dugesins C-G(1-5),together with six known ones.Their structures were determined by comprehensive NMR and MS spectroscopic analysis.It was noteworthy that the eleven isolates,composed of five different carbocyclic systems derived from the neo-clerodane diterpenoid skeleton,were reported from the same plant for the first time.The anti-feedantial,cytotoxic,and antiviral activities of the isolates were evaluated.Dugesin F(4)was tested to be a non-toxic antiviral compound against influenza virus FM1.展开更多
Five new ent-kaurane diterpenoids,named mascaroside Ⅲ–Ⅴ(1–3),and 20-nor-cofaryloside Ⅰ–Ⅱ(4–5),together with seven known diterpenoids,were isolated from methanol extracts of the green coffee beans of Yunnan Ara...Five new ent-kaurane diterpenoids,named mascaroside Ⅲ–Ⅴ(1–3),and 20-nor-cofaryloside Ⅰ–Ⅱ(4–5),together with seven known diterpenoids,were isolated from methanol extracts of the green coffee beans of Yunnan Arabica Coffee.Their chemical structures were elucidated by extensive spectroscopic analyses.Meanwhile,cytotoxicity assay against HL-60,A-549,SMMC-7721,MCF-7 and SW480 cell lines showed that they have not evident inhibition of cytotoxicity.展开更多
Two new myrinsol diterpenoids, euphordracunculins A（1） and B（2）, together with three known analogues, euphorprolitherin B（3）, proliferins A（4） and B（5）,were isolated from the petroleum ether extract of the a...Two new myrinsol diterpenoids, euphordracunculins A（1） and B（2）, together with three known analogues, euphorprolitherin B（3）, proliferins A（4） and B（5）,were isolated from the petroleum ether extract of the aerial parts of Euphorbia dracunculoides Lam. Their structures were elucidated by means of extensive spectroscopic analysis（NMR and ESI-MS） and comparison with data reported in the literature.展开更多
Nine new ent-kaurane diterpenoids, named scopariusols L–T(1–9), were isolated from the aerial parts of Isodon scoparius. Their structures were characterized mainly by analyzing the NMR and HR-ESI-MS data, and the ab...Nine new ent-kaurane diterpenoids, named scopariusols L–T(1–9), were isolated from the aerial parts of Isodon scoparius. Their structures were characterized mainly by analyzing the NMR and HR-ESI-MS data, and the absolute configuration of 1 was determined by single-crystal X-ray diffraction. Compound 1 was active against five human tumor cell lines(HL-60, SMMC-7721, A-549, MCF-7, and SW-480), and it also inhibited NO production in LPS-stimulated RAW264.7 cells, with an IC50 value of 0.6 μmol·L-1.展开更多
Two new diterpenoids taibairubescensin A (1) and B (2) have been isolated from Isodon rubescens. The structures of compound 1 and 2 were elucidated as 2 beta,3 beta-diacetoxy-11 beta,13 alpha-dihydroxy-ent-kaur- 16-en...Two new diterpenoids taibairubescensin A (1) and B (2) have been isolated from Isodon rubescens. The structures of compound 1 and 2 were elucidated as 2 beta,3 beta-diacetoxy-11 beta,13 alpha-dihydroxy-ent-kaur- 16-en-15-one (1) and 3 beta,11 beta-diacetoxy-2 beta,6 alpha-dihydroxy-ent-kaur-16-en-15-one (2) on the basis of spectroscopic analysis.展开更多
文摘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.
基金supported by the National Key R&D Program of China(No.2023YFD1601400)Jiangsu Outstanding Youth Fund Project(No.BK20231535)+2 种基金the National Natural Science Foundation of China(Nos.82074068 and 82430118)the Basic Research Project for the Development of Modern Industrial College of Traditional Chinese Medicine and Health at Lishui University,Specialized Research Funds from the State Key Laboratory of Natural Medicines,China Pharmaceutical University(SKLNMZZ2024JS25)the 111 Project(No.B18056)。
文摘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.
基金supported by the National Natural Science Foundation of China (No.82073728)the Natural Science Foundation of Shandong Province (No.ZR2021MH357)。
文摘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.
基金supported financially by the National Natural Science Foundation of China(Nos.82260682,22477108,81960662,82200550)the Project of Yunnan Characteristic Plant Screening and R&D Service CXO Platform(No.2022YKZY001)+9 种基金the Yunnan Provincial Science and Technology Department(Nos.202101AT070154,202301AT0–70270 and 202401AY070001–303)the Scientific Research Fund Project of Yunnan Provincial Department of Education(No.2023Y0–797)the Program Innovative Research Team in Science and Technology in Kunming Medical University(No.CXTD202202)the Program for Changjiang Scholars and Innovative Research Team in University(No.IRT-17R94)the Project of Innovative Research Team of Yunnan Province(No.202005AE160005)the Open Research Foundation of Yunnan Key Laboratory of Bioactive Peptides in Yunnan Province(No.HXDT-2022–1)a grant(No.2023KF007)from YNCUBFirst-Class Discipline Team of Kunming Medical University(No.2024XKTDPY12)Yunnan Revitalization Talent Support Programthe Yun Ling Scholar Project to W.-L.Xiao。
文摘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.
基金supported by Shenzhen Fundamental Research Program(No.JCYJ20200109114003921).
文摘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).
文摘Agastol (2), a new diterpene, was isolated from the roots of Agastache rugosa together with its isomer, named isoagastol (3) Their structures were established on the basis of spectral methods The structures of agastol (2) and isoagastol (3) was elucidated as 11,14 dihydroxy 12 methoxy 19(4→3) abeo abieta 4(18),8,11,13 tetraen 7 one and 11,14 dihydroxy 12 methoxy 19(4→3) abeo abieta 3,8,11,13 tetraen 7 one Isoagastol was isolated for the first time from natural sources
基金The project is supported by the Applied Basic Research Foundation of Yunnan Province (1999C0081M).
文摘Two new diterpenoids, forskolin G and H were isolated from the chloroform extract of the roots of Coleus forskohlii, and based on spectroscopic data, their structures were identified as 1a-hydroxy-6b,7b-diacetoxy-8,13-epoxylabd-14-ene-11-one (1), and 1a,6b-diacetoxy-8,13-epoxy labd-14-ene-11-one (2), respectively.
基金supported by Yunnan Applicative and Basic Research Program(Nos.2018FY001 and 2018FA048)the National Natural Science Foundation of China(Nos.81422046,81860615 and 21762048)+4 种基金the Foundation of Yunnan Educational Committee(No.2018JS002)the Natural Science Foundation of Yunnan University(No.2017YDQN03)the Key Laboratory of Medicinal Chemistry for Natural Resource,Ministry of Education(No.2017KF02)the Program for Changjiang Scholars and Innovative Research Team in University(No.IRT_17R94)Project of Innovative Research Team of Yunnan Province to XIAO Wei-Lie
文摘Phytochemical investigation of the leaves and twigs of Callicarpa cathayana led to the isolation of six new clerodane diterpenoids,cathayanalactones A-F(1-6),together with seven analogues(7-13).Their structures were established by extensive NMR analyses together with experimental and calculated ECD spectra analyses.Compounds 1,2,3,7 and 11 showed inhibitory activities on lipopolysaccharide-induced nitric oxide production in RAW264.7 cells.
基金supported by the Science & Technology Project of Guangdong Province (No. 2011A080403020)
文摘Two new harziane diterpenoids, named（9R,10R）-dihydro-harzianone（1） and harzianelactone（2）, were isolated from the endophytic fungus Trichoderma sp. Xy24 by using various column chromatography techniques. Their structures were determined on the basis of extensive spectroscopic（HR-ESI-MS, 1D NMR, 2D NMR and CD） analyses. Among them, 1 was the reductive product of harzianone and 2 was the Baeyer–Villiger monooxygenase catalyzed oxidation product of harzianone. Compound 1 exhibited cytotoxic activity against He La and MCF-7 cell lines with IC（50） values of 30.1 μmol/L and 30.7 μmol/L,respectively.
基金the National Natural Science Foundation of China(31200263)the Youth Innovation Promotion association of Chinese Academy of Sciences(awarded to Shi-Hong Luo)+1 种基金the“Western Light”Program of Chinese Academy of Sciences(awarded to Shi-Hong Luo)the“Hundred Talents Program”of Chinese Academy of Sciences(awarded to Sheng-Hong Li).
文摘The perennial herbaceous plant Euphorbia jolkinii(Euphorbiaceae)is a noxious weed widely distributed in the grasslands of northwestern Yunnan and has greatly threatened the local biodiversity.Phytochemical investigation on the fresh roots of E.jolkinii afforded six new diterpenoids 1,2,4–6,and 8,together with fifteen known diterpenoids.Their structures were elucidated on the basis of 1D and 2D NMR and other spectroscopic methods.Casbane,lathyrane,abietane,and ent-kaurane diterpenoids were reported from this plant for the first time.Selected compounds were evaluated for their antifeedant and anti-RSV(respiratory syncytial virus)activities.Compound 2 and ingenol(3)exhibited moderate antifeedant activity against a generalist insect herbivore,Spodoptera exigua,with EC50 values of 17.88 and 17.71 lg/cm2 respectively.Compound 19 showed significant anti-RSV activity,with 50%inhibition(IC50)value of 10.0 lM and selective index of 8.0.Compounds 1 and 2 were less active against RSV virus,both with IC50 value of 25 lM,and with selective indices of 1.0 and 3.2 respectively.These findings provided new evidence for the biological functions and utilization of the diversified diterpenoid metabolites in the roots of this rich but harmful plant.
基金The authors acknowledge the National Basic Research Program of China(973 Program,2009CB522300)the“West Light”program of Chinese Academy of Sciences.
文摘Four new ent-kaurane diterpenoids,namely,3α-tigloyloxypterokaurene L_(3)(1),ent-17-hydroxy-kaura-9(11),15-dien-19-oic acid(2),and wedelobatins A(3)and B(4),together with 11 known ent-kaurane diterpenoids(5-15),were isolated from the ethanol extract of Wedelia trilobata.All the structures of 1-15 were elucidated on the basis of spectroscopic studies.
基金financially supported by the National Natural Science Foundation of China(Nos.81422046 and 21762048)the Yunnan Applicative and Basic Research Program(Nos.2015BC002,2018FY001 and 2018FA048)+4 种基金the Program for Changjiang Scholars and Innovative Research Team in University(No.IRT_17R94)the Key Program of Natural Science of Yunnan Province to W.L.Xiaothe Key Laboratory of Medicinal Chemistry for Natural Resource,Ministry of Education(No.2017KF02)the Natural Science Foundation of Yunnan University(No.2017YDQN03)the Foundation of Yunnan Educational Committee(No.2018JS002)。
文摘Callica rpabodinieri is a Chinese traditional medicine herb with anti-inflammatory activity in clinic.Herein,we report two new 9,10-seco and etherified abietane diterpenoids bodinieric acids J and K(1 and 2) and one known compound(3) isolated from the leaves and twigs of this plant.Their chemical structures were elucidated by detailed spectrometry data analysis and DP4+NMR calculation methods.Hypothetical biosynthetic pathways of 1-3 were preliminarily speculated.Compound 3 inhibited inflammasome activation and exhibited blockage of NLRP3 inflammasome activation at non-cytotoxic concentrations in vitro.
基金supported by the Natural Science Foundation of Zhejiang Province,China (Y2080137)
文摘Euphorbia lathyris （Caper spurge） is a toxic and potent Chinese materia medica （T/PCMM）. This study sought a method for identifying five diterpenoids （Euphorbia factors LI-L3, L7a, and Ls） with the spectra of UV and mass, quantifying three diterpenoids L1, L2, and L8 in crude extracts of unprocessed and processed E. lathyris seeds by liquid chromatography/ electrospray ionization mass spectrometry （LC-ESI-MS）. The analysis was achieved on an Agilent Eclipse XDB-C18 column （4.6 mm× 150mm i.d., 5 μm） with an isocratic elution with a mobile phase consisting of water and acetonitrile at a flow rate of 0.25 mL/min at column temperature of 30 ℃ and UV detection was set at 272 nm. An ESI source was used with a positive ionization mode. The calibration curve was linear in the ranges of 9.9-79 μg/mL for Euphorbia factor Lb 3.8-30.5μg/mL for Euphorbia factor L2, and 1.0-20.6 μg/mL for Euphorbia factor LB. The average recoveries （n=6） of three diterpenoids were 98.39%, 91.10% and 96.94%, respectively, with RSD of 2.5%, 2.4% and 2.1%, respectively. The contents of the three diterpenoids in processed E. lathyris seeds were 3.435, 1.367 and 0.286 mg/g, respectively, which decreased more sharply than those in unprocessed E. lathyris seeds which were 4.915, 1.944 and 0.425 mg/g, respectively. The method is simple, accurate, reliable and reproducible, and it can be applied to control the quality of unprocessed and processed E. lathyris seeds.
文摘Plant-derived labdane-related diterpenoids(LRDs)represent a large group of terpenoids.LRDs possess either a labdane-type bicyclic core structure or more complex ring systems derived from labdane-type skeletons,such as abietane,pimarane,kaurane,etc.Due to their various pharmaceutical activities and unique properties,many of LRDs have been widely used in pharmaceutical,food and perfume industries.Biosynthesis of various LRDs has been extensively studied,leading to characterization of a large number of new biosynthetic enzymes.The biosynthetic pathways of important LRDs and the relevant enzymes(especially diterpene synthases and cytochrome P450 enzymes)were summarized in this review.
文摘Five ent-6,7-seco-karuene diterpenoids-enmein,epinodosin,sculponeatin A,C,D,were isolated from the dried leaves of Rabdosia sculponeata One of the compounds,named sculponeatin D,was previously unreported.Its structre was elucidated by the spectral data including 2D COSY,~1H-^(13)C correlation,2D NOESY spectroscopy.
基金This work was supported financially by the National Basic Research Program of China(2009CB522300)the National Natural Science Foundation of China(No.20702054)+2 种基金Shanghai Landscaping Administration Bureau Program(G102404)the foundation from the Chinese Academy of Sciences(2010KIBA10)the Young Academic and Technical Leader Raising Foundation of Yunnan Province(No.2009CI073).
文摘Salvia dugesii is an invasive plant in Yunnan,China.To tentatively explore its utilization,a systematic phytochemical investigation was carried out on this plant,which led to the isolation of five new neo-clerodane diterpenoids,dugesins C-G(1-5),together with six known ones.Their structures were determined by comprehensive NMR and MS spectroscopic analysis.It was noteworthy that the eleven isolates,composed of five different carbocyclic systems derived from the neo-clerodane diterpenoid skeleton,were reported from the same plant for the first time.The anti-feedantial,cytotoxic,and antiviral activities of the isolates were evaluated.Dugesin F(4)was tested to be a non-toxic antiviral compound against influenza virus FM1.
基金This work was supported financially by Programme of Key New Productions of Yunnan Province,Centre of CHINA(No.2015BB002)The STS Programme of Chinese Academy of Sciences(KFJ-SW-STS-143-8)as well as Foundation of State Key Laboratory of Phytochemistry and Plant Resources in West China(P2015-ZZ09).
文摘Five new ent-kaurane diterpenoids,named mascaroside Ⅲ–Ⅴ(1–3),and 20-nor-cofaryloside Ⅰ–Ⅱ(4–5),together with seven known diterpenoids,were isolated from methanol extracts of the green coffee beans of Yunnan Arabica Coffee.Their chemical structures were elucidated by extensive spectroscopic analyses.Meanwhile,cytotoxicity assay against HL-60,A-549,SMMC-7721,MCF-7 and SW480 cell lines showed that they have not evident inhibition of cytotoxicity.
基金financially supported by the National Natural Science Foundation of China(No.21162044)the Mid-aged and Young Academic and Technical Leader Raising Foundation of Yunnan Province(No.2010C1040)
文摘Two new myrinsol diterpenoids, euphordracunculins A（1） and B（2）, together with three known analogues, euphorprolitherin B（3）, proliferins A（4） and B（5）,were isolated from the petroleum ether extract of the aerial parts of Euphorbia dracunculoides Lam. Their structures were elucidated by means of extensive spectroscopic analysis（NMR and ESI-MS） and comparison with data reported in the literature.
基金supported by the National Natural Science Foundation of China(No.21322204)the NSFC-Joint Foundation of Yunnan Province(No.U1302223)
文摘Nine new ent-kaurane diterpenoids, named scopariusols L–T(1–9), were isolated from the aerial parts of Isodon scoparius. Their structures were characterized mainly by analyzing the NMR and HR-ESI-MS data, and the absolute configuration of 1 was determined by single-crystal X-ray diffraction. Compound 1 was active against five human tumor cell lines(HL-60, SMMC-7721, A-549, MCF-7, and SW-480), and it also inhibited NO production in LPS-stimulated RAW264.7 cells, with an IC50 value of 0.6 μmol·L-1.
文摘Two new diterpenoids taibairubescensin A (1) and B (2) have been isolated from Isodon rubescens. The structures of compound 1 and 2 were elucidated as 2 beta,3 beta-diacetoxy-11 beta,13 alpha-dihydroxy-ent-kaur- 16-en-15-one (1) and 3 beta,11 beta-diacetoxy-2 beta,6 alpha-dihydroxy-ent-kaur-16-en-15-one (2) on the basis of spectroscopic analysis.
