New Diterpenoid Alkaloids from Spiraea japonica var. Ovalifolia

In the investigation of the chemical constituents of Spireae japonica L. f. var. ovalifolia (Rosaceae), a shrub originated in Songming, Yunnan, five new diterpenoid alkaloids, 19-O-deethylspiramine N (1), deacetylspiramine S (2), spiramidine A (3), spiramidine B (4) and deacetylspiramine F (5), were isolated from aerial parts of the plant and structurally elucidated. Compound 1, a white amorphous powder with [(]+17.99 (c, 0.26, MeOH ), was determined to have the molecular formula of C20H…     

Two New Diterpene Alkaloids from the Roots of Spiraea japonica var. Acuta

Spiraea japonica L. (Rosaceae) is widely distributed in Yunnan Provence, P. R. China. Previous chemical investigations on S. japonica and its varieties have led to the report of 7 new atisane-type diterpenoids and 38 new diterpene alkaloids of atisine- and hetisine-type1-11. This paper describes the isolation and structure elucidation of two new diterpene alkaloids named spiratines A and B (1-2). Their structures were elucidated on the basis of 1D and 2D NMR experiments (HMQC, HMBC, 1…     

A Novel Atisane Diterpenoid from Spiraea japonica var. acuta

A novel ent‐atisane lactone, spiramilactone E ( 1 ), was isolated from Spiraea japonica var. acuta Yu . Its structure was elucidated by extensive spectroscopic analyses, and unequivocally confirmed by single‐crystal X‐ray diffraction (Fig. 2). Compound 1 contains a γ‐lactone moiety between the 6‐OH function and C(20), and β‐configuration for the 7‐OH group, in contrast to known related diterpenes previously isolated from the S. japonica complex.     

Spiramide,a New Diterpene Amide from the Roots of Spiraea japonica var.acuta

Previous chemical investigations on SPiraea j'aponica and its varieties have led to thereport of 7 new atisane-type diterpenoids' and 30 new diterpene alkaloids of atisine- andhetisine-ace'. The chemotaxonomy of S. japonica complex was proposed based onthose chemical data3. A hypothetical pathway of the biosynthesis of atisine-typealkaloids was suggested to be formed from diterpene directly tO the correspoedngalkaloids through double Mannich reactions (unpublished data). In order to search f…     

A new abietane diterpenoid glycoside from ajuga ovalifolia var. calantha

A new abietane diterpenoid glycoside, ajugaside B (1), along with three known compounds (2–4), were isolated from the whole plants of Ajuga ovalifolia var. calantha. The structure of the new compound (1) was elucidated by means of spectroscopic analyses (HRESIMS, IR, NMR and ECD). All of the isolated compounds were evaluated for their antitumor activities against MGC803, MCF-7, A549, HT29 and HepG2 cell lines. Compounds 3–4 showed moderate cytotoxicity against all tested cell lines with IC₅₀ values of 1.8–7.3?μM.     

A new neolignan from the thorns of Gleditsia japonica var. delavayi

A new neolignan, 5-(3″-acetoxypropyl)-2-(4′-hydroxy-3′-methoxyphenyl)-7-methoxy-3-methylbenzofuran (1) along with nine analogues were isolated from the thorns of Gleditsia japonica var. delavayi by solvent extraction and repeated column chromatography. Their structures were elucidated by means of extensive spectroscopic analysis including 1D, 2D-NMR techniques and HR-ESIMS. All the isolates were reported for the first time from this species.     

Ajuforrestin A,an Abietane Diterpenoid from Ajuga ovalifolia var. calanthe,Induces A549 Cell Apoptosis by Targeting SHP2

The Src-homology 2 domain-containing phosphatase 2 (SHP2), which is encoded by PTPN11, participates in many cellular signaling pathways and is closely related to various tumorigenesis. Inhibition of the abnormal activity of SHP2 by small molecules is an important part of cancer treatment. Here, three abietane diterpenoids, named compounds 1–3, were isolated from Ajuga ovalifolia var. calantha. Spectroscopic analysis was used to identify the exact structure of the compounds. The enzymatic kinetic experiment and the cellular thermal shift assay showed compound 2 selectively inhibited SHP2 activity in vitro. Molecular docking indicated compound 2 targeted the SHP2 catalytic domain. The predicted pharmacokinetic properties by SwissADME revealed that compound 2 passed the majority of the parameters of common drug discovery rules. Compound 2 restrained A549 proliferation (IC₅₀ = 8.68 ± 0.96 μM), invasion and caused A549 cell apoptosis by inhibiting the SHP2–ERK/AKT signaling pathway. Finally, compound 2 (Ajuforrestin A) is a potent and efficacious SHP2 inhibitor and may be a promising compound for human lung epithelial cancer treatment.     

New Diterpene Alkaloids from Aconitum sungpanense var. leucanthum

Five new C₁₉ diterpene alkaloids, leucanthumsines A ( 1 ), B ( 2 ), C ( 3 ), D ( 4 ), and E ( 5 ), were isolated from the Chinese medicinal herb Aconitum sungpanense var. leucanthum, together with the known C₁₉ diterpene alkaloids pseudaconine, neoline, 1‐O‐methyldelphisine, crassicaudine, chasmanine, talatisamine, indaconitine, ezochansmanine, and leueantine D. The structures of these new alkaloids were elucidated by HR‐MS and advanced NMR methods, including ¹H‐ and ¹³C‐NMR (DEPT), ¹H,¹H‐COSY, HMQC, and HMBC experiments.     

A New Flavonoid Ketohexofuranoside from Leaves of Crataegus pinnatifida Bge.var. major N.E.Br.

Crataegus pinnatifida Bge.var.major N.E.Br. is widely distributed in the northeast part of China. It is used as a medicinal plant to improve digestion, remove retention of food, promote blood circulation and resolve blood stasis both in traditional and folk medicine 1. Preparations of Crataegus leaves improve the heart function, the coronary blood supply and arrhythmia2. Up to now, fifty flavonoids have been isolated from Crataegus3,4. In our previous paper, some new flavonoid glycosides we…     

Two new diterpenoids from Rabdosia japonica var.glaucocalyx

Two new diterpenoids, named glaucocalyxin F and glaucocalyxin X, respectively, were isolated from the whole plant of Rabdosia japonica （Burm. f.） Hara var. glaucocalyx （Maxim.） Hara. Their structures was established on the basis of spectral analysis.     

A New Cyclohexene Oxide from Uvaria tonkinensis var. subglabra

A new compound, subglain B, was isolated from the stems of Uvaria tonkinensis var.subglabra and its structure was identified as 1S, 2R, 3S, 6R-1-benzoyloxymethylene-1,2-dihydroxy-3-benzoyloxy-6-chlorocyclohex-4-ene (1), by spectral evidences.     

Diterpene Glycosides from the Dry Fronds of Conyza japonica

Phytochemical investigation of the 95% EtOH extract of the dry fronds of Conyza japonica (Thunb .) Less. resulted in the isolation of three new labdane diterpene glycosides, (3β,13S)‐13‐O‐α‐L ‐rhamnopyranosyllabda‐8(17),14‐dien‐3‐yl α‐L ‐rhamnopyranoside ( 1 ), (3β,13S)‐13‐O‐α‐L ‐rhamnopyranosyllabda‐8(17),14‐diene‐3‐yl 2‐O‐acetyl‐α‐L ‐rhamnopyranoside ( 2 ), and (3β,13S)‐13‐O‐α‐L ‐rhamnopyranosylabda‐8(17),14‐dien‐3‐yl 6‐O‐acetyl‐β‐D ‐glucopyranosyl‐(1→2)‐α‐L ‐rhamnopyranoside ( 3 ), together with their aglycone, (13S)‐labda‐8(17),14‐diene‐3,13‐diol ( 4 ). Their structures were characterized by spectroscopic analyses and chemical correlations, including 1D‐ and 2D‐NMR, and HR‐ESI‐MS. Furthermore, compounds 1 – 3 appeared to be promising as active agents against the tested pathogen fungi and oral pathogens as they possessed moderate cytotoxic properties.     

New ent-Isopimarane Diterpene from Mangrove Excoecaria agallocha L.

A new ent-isopimarane diterpenoid,Agallochaone A(1),together with the known 8,13-epoxy-14-labden-3-one(2)and Excoecarin B(3)were isolated from the whole plant of mangrove Excoecaria agallocha L.and identified on the basis of a detailed spectral analysis,including 2D NMR spectrometry and HRESI-MS.     

Caesaljaponins A and B: New Cassane‐Type Furanoditerpenoids from the Seeds of Caesalpinia decapetala var. japonica

Two new cassane‐type furanoditerpenoids, designated caesaljaponin A and caesaljaponin B ( 1 and 2 , resp.), were isolated from seeds of Caesalpinia decapetala var. japonica. The structures were elucidated by spectroscopic data, and the absolute configuration of 1 was determined by X‐ray crystallographic analysis using the anomalous scattering of CuK_α radiation.     

Two New C—glucoside Flavonoids from Leaves of Crataegus pinnatifida Bge. var. major N.E.Br.

Two new C-glucoside flavonoids,namely 8-C-β-D-（2″-O-acetyl) glucofuranosyl apigenin and 3″-O-acetylvitexin, were isolated from beaves of Crataegus pinnatifida Bge. var. major N.E.Br.Their structures were elucidated by the spectroscopic means and chemical evidence.     

Three New Atisane Diterpenoids from Spiraea japonica

Three new atisane diterpenoids, spiratisanins A – C ( 1  –  3 , resp.), featuring a phenylacryloxyl substituted ent‐atisane skeleton, were isolated from Spiraea japonica together with two known atisine diterpene alkaloids, spiramine A ( 4 ) and spiradine F ( 5 ). The structures of these new compounds were elucidated as (5β,7α,8α,9β,10α,12α,16β)‐16‐hydroxyatisan‐7‐yl (2E)‐3‐phenylprop‐2‐enoate ( 1 ), (5β,7α,8α,9β,10α,12α,16α)‐16‐hydroxyatisan‐7‐yl (2E)‐3‐phenylprop‐2‐enoate ( 2 ), and (5β,8α,9β,10α,12α,16β)‐16‐hydroxyatisan‐20‐yl (2E)‐3‐phenylprop‐2‐enoate ( 3 ) on the basis of spectroscopic analysis.     

A New Pregnane Glycoside from Dioscorea collettii var. hypoglauca

Morphologicaldeformationsofthemyceliaorconidiaofmicroorganismssuchascurling,swelling,hyper-divergence,beadformationandinhibitionofgermination,areofteninducedinthepresenceofbioactivesubstances".AnewscreeningbioassaymethodfordetectingthedeformationofmyceliagerminatedfromconidiaofPyriculartaoryzaeP-2bwasfirstdevelopedforthequantitativeapplicationtoscreeningantifungalandantineoplasticagentsbyH.Kobayashi'.Thisbioassayisquick,easytoperform,andhasbeenefficientlyusedinthepreliminaryscreeningofantineo…     

New Diterpenoid Alkaloids from Spiraea fritschiana var. parvifolia

SPiraeafritschianavar.parvdoliadistributedinthenorthofChinaisoneofthethreevarietiesofSfritschiana'.RecentlythreeCZohetisine-typediterpenoidalkaloids,spiradineD(3)',spirafineill(l)andspirafine11(2)wereisolatedfromitsroots.PreliminarypharmaceuticalinvestigationrevealedthatspirdineDhadanti-PAFactivity.CompoundIisobtainedinformofcolorlessneedlecrystals,m.p.192-193"C;[a].'=3--46.07(c2.0,C,H,N).ItsmolecularformulawasdeterminedasC,,H,,NO,byHRMS(341.2279,cafe.:341.2355).ItsiR(KBr)spectrumex…     

Three New Diterpenoids from Rabdosia lophanthoides var. gerardiana

Three new diterpenoids, together with three known ones, were isolated from the air‐dried whole herbs of Rabdosia lophanthoides var. gerardiana. The structures of the new diterpenoids were established as 3,4‐dihydro‐11‐hydroxy‐10‐(1‐hydroxy‐1‐methylethyl)‐2,2,6‐trimethylnaphtho[1,8‐bc]oxocin‐5(2H)‐one ( 1 ), 11,12,15‐trihydroxyabieta‐5,8,11,13‐tetraen‐7‐one ( 2 ), (2R,3S,4S,4aR,8S,9aS,13aS,16aS)‐3,4,4a,8,9,9a,10,11,12,13,14,16a‐dodecahydro‐2‐(hydroxymethyl)‐6,6,10,10‐tetramethyl‐2H‐benzo[4,5]cyclohepta[1,2‐h]pyrano[2,3‐b][1,4]benzodioxepine‐3,4,8,13a,15(6H)‐pentol ( 3 ) by spectroscopic methods, including extensive 1D‐ and 2D‐NMR analyses. The structures of the known compounds were identified by comparison of their physical and spectroscopic data with those reported in the literature.