New bis-spirolabdane-type diterpenoids from Leonurus heterophyllus Sw

Twelve natural bis-spirolabdane-type diterpenoids, including eight new, named leoheteronones A-E, 15-epileoheteronones B, D, and E, and four known leopersin B, 15-epileopersin B, leopersin C, and 15-epileopersin C, together with hispanone and galeopsin were isolated from the aerial parts of the medicinal plant Leonurus heterophyllus SW. (Lamiaceae) grown in Vietnam. Their structures were determined by spectroscopic analyses. The current study emphasized the accumulation of C-15 oxygenated bis-spirolabdane-type diterpenoids of both 13R and 13S configurations in L. heterophyllus.     

New Labdane‐Type Diterpenoids from Leonurus heterophyllus

Chemical investigation of the aerial part of Leonurus heterophyllus led to the isolation and characterization of the seven labdane‐type diterpenoids 1 – 7 , including six new ones, 1 – 6 . Compounds 4 and 5 were isolated as a C(15) epimer pair. The determination of the structures and relative configurations of the new compounds were mainly based on 1D‐ and 2D‐NMR spectroscopic methods, and comparison of their NMR data with related compounds. The structure of compound 7 was confirmed by X‐ray crystallographic analysis.     

Two Labdane Diterpenes from Leonurus heterophyllus

The whole plant of Leonurus heterophyllus Sweet. (Lamiaceae), (Chinese name: Yi Mu Cao), is used in traditional Chinese medicine for treatment of gynaecological problems, including irregular menstruation, amenorrhea and postpartum heamorrhage1. About 40 l…     

Cytotoxicity of labdane-type diterpenoids from Hedychium forrestii

Two new labdane-type diterpenoids, hedyforrestin D (1) and 15-ethoxy-hedyforrestin D (2), and three known compounds, yunnancoronarin A (4), B (3) and C (5) were isolated from the rhizomes of Hedychium forrestii. The structure of the new diterpenoids was established as 6beta,15xi-dihydroxylabda-8(17),11,13-trien-15,16-olide (1), and 6beta-hydroxy-15xi-ethoxylabda-8(17),11,13-trien-15,16-olide (2) on the basis of spectroscopic analyses. In addition, the isolated compounds were evaluated for their cytotoxicity against the lung adenocarcinoma cells A549 and leukemia cells K562 through 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) assays. Of these, compounds 3 and 4 exhibited the most activity with IC(50) values of 0.92 and 2.20 microM, respectively, whereas 5 was inactive against A549 cells and 1 was inactive against both cell lines up to a concentration of 300.81 microM. This shows that both the hydroxy substitution and orientation of unsaturated lactone group in the five-membered ring of C-13 to C-16 seem to play an important role in the anti-tumor activities of human lung adenocarcinoma and leukemia.     

Three new diterpenoids from Leonurus japonicus

Phytochemical investigation of the aerial parts of Leonurus japonicus led to the isolation of one unusual clerodane diterpenoid,leojaponin A(1),characterized by a C4–C7oxa-bridge,and two new labdane diterpenoids,leojaponins B(2) and C(3).The structures of these new compounds were determined based on extensive 1D and 2D NMR spectroscopic data.To the best of our knowledge,compound 1 is the first clerodane diterpenoid obtained from Leonurus.japonicus.All of them were evaluated for their cytotoxicity.     

Two new labdane-type diterpenoids cinnamate from Croton decalvatus Esser

Two new labdane diterpene derivatives, crotondecalvatin A (1) and crotondecalvatin B (2) were obtained from the leaves and twigs of Croton decalvatus. The structures of compounds were established on the basis of extensive spectroscopic data.     

Three new labdane-type diterpenoids from Callicarpa macrophylla Vahl.

Three new labdane-type diterpenoids, callicapene M3-M5 (1–3) were isolated from the Callicarpa macrophylla Vahl. Their structures were identified by spectroscopic method. The isolated compounds were evaluated for inhibitory activity on NO production in LPS-activated RAW 264.7 macrophage cells by using MTT assays. Compounds 1–3 showed potent inhibitory activity, with IC₅₀ value of 48.15, 46.31 and 38.72?μM respectively.     

A pair of epimeric cassane-type diterpenoids and a new labdane-type derivative from Caesalpinia decapetala

Caesaldecins A and B (1a/1b), a pair of epimeric cassane-type diterpenoids containing an ether linkage between C-6 and C-20 and an α,β-butenolide ring in the northern hemisphere, were isolated from the leaves of the medicinal plant Caesalpinia decapetala (Roth) Alston, along with a new labdane-type diterpenoid, termed as 8(17),11(Z),13(E)-trien-15,18-dioic acid (2). Structures of 1 and 2 were established by extensive spectroscopic analyses, including HRESIMS, 1D and 2D NMR, and electronic circular dichroism (ECD) calculations. The in vitro antibacterial and inhibitory activities against a panel of bacteria and cancer cell lines were evaluated, respectively. Compound 2 displayed moderate antibacterial activity against the methicillin-resistant Staphylococcus aureus subsp. aureus (MRSA) with an MIC₅₀ value of 5.99?μg?mL^?1.     

New diterpenoids from Calceolaria polifolia

Four new and seven known diterpenes have been isolated from the dichloromethane extract of the aerial parts of Calceolaria polifolia. The structures of the new compounds were established by spectroscopic evidence.     

Two new labdane diterpenoids from aerial parts of Leonurus japonicus and their anti-inflammatory activity

Two new labdane diterpenoids, Leojaponin E (1) and F (2), together with three known compounds were isolated from the dried herb of Leonurus japonicus Houtt., Lamiaceae. Their structures were determined based on extensive spectroscopic analyses. The absolute configurations of 1 and 2 were elucidated on the basis of experimental and calculated electronic circular dichroism spectra. In addition, compounds 1 and 2 exerted inhibition of LPS-induced PGE₂ production in a dose-dependent manner at concentrations ranging from 5 to 20 μM.     

New diterpenoids from Isodon excisoides

<正>Two new ent-kaurane diterpenoids,taihangexcisoidesin C(1) and its acetonide,taihangexcisoidesin D(2) were isolated from the leaves of Isodon excisoides.Their structures were determined by 1D and 2D spectroscopic analysis.     

New cis-clerodane diterpenoids from Croton schiedeanus

The acid fraction of extracts from the aerial part of Croton schiedeanus afforded six cis-clerodane type diterpenoids. Two of them (1 and 4) are new natural compounds. Structural elucidation was achieved on the basis of their spectral data.     

冬凌草中的新对映-贝壳杉烷二萜化合物

对河南省济源地区产冬凌草[Isodon rubescens(Hemsl.)Hara]再次进行了深入 的研究，从其叶的乙酸乙酯提取物中分离得到了16个化合物，其中1和2为两个新的 7，20-环氧-对映-贝壳杉烷类二萜化合物，其结构通过波谱分析确定为16（S）-羟 甲基-1α，6β，7β，11β-甲羟基-7α，20-环氧-对映-贝壳杉烷-15-酮（1）和 16（R）-羟甲基-1α，6β，7β，14β-四羟基-7α，20-环氧-对映-贝壳杉烷-15- 酮（2），分别命名为冬凌草已素（1）和庚素（2）；其余的已知化合物分别鉴定 为lasiodonin（3），冬凌草甲素（oridonin，4），乙素（ponicidin），丙素（ rubescensin C），丁素（rubescensin D），牛尾草丙素（rabdoternin C），荛 花香茶菜乙素（wikstroemioidin B），enmenol-1α-O-β-D-glucoside， enmenol，胡麻素（pedalitin），水杨酸，乌索酸，β-谷甾醇和胡萝卜甙。     

Three New diterpenoids from Isodon Gesneroides

InthePreviouspaPed'],werePOrtedthebioactivditerPeedds,namedasgeSnerofdinAC,wereisolatedfromtlhaPlan.theinveedgationOfthisPlanlettoisolationofthreenewditerPenuldswiasgeSnerofdinsD-F(l-3).AspapewhdealwiththednddridationFigUrel.The1H-13Clong-rangeCOSYoflGesneroidinD(l),~lizedfromaeeone,mPl29.5-l3o.5"C,HRMS(5l8.2477,calc.5l8.25l6)SUggestedtheformulaCasH38O9.EIMS(7oeV)wt(rel.int.%)f5l8mp+(lO),458(3O),4l6(35),356(85),296(1oo).DuetotheabsencesofthecharaCteristicallsorptioninUVandIR…     

New ent-kaurane-type diterpenoids from Isodon nervosus

Two new ent-kaurane-type diterpenoids,6β,7β,13α-trihydroxy-1α-acetoxy-7α,20-epoxy-ent-kaur-16-en-15-one（1）and 15β- hydroxy-6,7-seco-6,11β：6,20-diepoxy-1α,7-olide-ent-kaur-16-ene（2）were isolated from the Isodon nervosus,and the structures were elucidated by spectroscopic analysis.     

New labdane diterpenoids from Hyptis fasciculata

Two new labdane diterpenoids, 15beta-methoxyfaciculatin (1) and 15alpha-methoxyfaciculatin B (2), together with the previously known methoxynepetaefolin (3), were isolated from a methanol extract of the dried aerial parts of a Brazilian medicinal plant, Hyptis faciculata. Their structures were elucidated by analysis of spectroscopic data. Plausible biogenetic correlation between faciculatins and nepetaefolin is briefly discussed.     

Antifungal activity against Botrytis cinerea of labdane-type diterpenoids isolated from the resinous exudate of Haplopappus velutinus Remy (Asteraceae)

Two labdane diterpenoids were isolated, from the resinous exudate of Haplopappus velutinus Remy (Asteraceae); the main compound was identified as 7,13-(E)-labdadien-15,18-dioic-acid-18-methyl ester (1) and the minor compound identified as 7-labden-15,18-dioic-acid-18-methyl ester (2). Their structures were obtained using FTIR, MS, HRMS and NMR data: 1D NMR (¹H, ¹³C and DEPT-135), 2D homonuclear NMR (COSY and NOESY) and heteronuclear NMR (HSQC and HMBC). The trans stereochemistry of the decalin moiety of compounds 1 and 2 was established through NOESY experiments of the reduction product of 1; 7-labden-15,18-diol (1a). Diterpenoids 1 and 1a are described for the first time and showed antifungal activity, inhibiting approximately 40% mycelial growth of Botrytis cinerea.     

New phenolic compounds from the leaves of Artocarpus heterophyllus

One new 2-arylbenzofuran derivative, artocarstilbene B(1), one new benzaldehyde derivative,(E)-3,5-dihydroxy-4-(3-methylbut-1-enyl)benzaldehyde(2), as well as 18 known compounds(3–20) were obtained from the leaves of Artocarpus heterophyllus. Their structures were elucidated on the basis of extensive spectroscopic techniques including 2D NMR and HR-ESIMS. Many compounds exhibited moderate to weak inhibitory activity against the proliferation of the PC-3, NCI-H460, and A549 cancer cell lines.     

New bicyclic taxane diterpenoids from Taxus sumatrana

Investigation of an acetone extract of the leaves and twigs of Taxus sumatrana has resulted in the isolation of two new bicyclic taxoids, tasumatrols M (1), and N (2) and a new baccatin III derivative, tasumatrol O (3) together with the previous known 7-deacetylcanadensene (4) and 2alpha,7beta,13alpha-triacetoxy-5alpha,9alpha-dihydroxy-2(3-->20) abeotaxa-4(20),11-dien-10-one. The structures of these taxanes were established on the basis of spectroscopic analyses, especially 1- and 2D NMR, and chemical derivatization.