Lathyranoic acid A: first secolathyrane diterpenoid in nature from Euphorbia lathyris

[structures: see text] Lathyranoic acid A (1), the first secolathyrane diterpenoid with an unprecedented skeleton, and a new diterpenoid Euphorbia factor L11 (2) were isolated from the seeds of Euphorbia lathyris. Their structures were elucidated by spectroscopic analysis and chemical methods. A biogenetic route involving an enzymatic Baeyer-Villiger oxidation as the key step was postulated for the transformation of 2 to 1 and mimicked by an unusual chemical Baeyer-Villiger oxidation.     

A new guaiane diterpenoid from Euphorbia wallichii

A new guaiane-type diterpenoid, (1alpha,5beta,7alpha)-3,10(18),11-dictytriene-19-acid, was obtained from the roots of Euphorbia wallichii. This is the first isolation of guaiane diterpene from this genus of Euphorbia. The structure was elucidated by spectral methods. And the compound was tested for the cytotoxicities on the cancer cell line P-388 and A-549 in vitro.     

Kansuinine J,a new macrocyclic diterpenoid from the roots of Euphorbia kansui

<正>A new macrocyclic diterpenoid,named kansuinine J(1),was isolated from the roots of Euphorbia kansui.Its structure was characterized on the basis of spectroscopic analysis.     

Secoeuphoractin,a minor diterpenoid with a new skeleton from Euphorbia micractina

A minor diterpenoid with a novel carbon skeleton,secoeuphoractin(1),was isolated from an ethanol extract of the roots of Euphorbia micractina.Its structure including the absolute configuration was determined by extensive spectroscopic studies,especially by 2D NMR and CD data analysis,in combination with a plausible biosynthetic pathway associated with co-occurring diverse diterpenoids.This compound showed activity against HIV-1 replication with an IC_(50) value of 1.76 ± 0.61 μmol/L.     

A new ent-norabietant diterpenoid from roots of Euphorbia lathyris L.

A new highly oxidized ent-norabietane diterpenoid named lathyrisol A (1) was isolated from roots of Euphorbia lathyris L. The structure and absolute configuration of 1 were elucidated on the basis of data obtained by HRESIMS, NMR, and the Cu-Kα radiation X-ray diffraction analysis. This compound is the first example of naturally occurring norabietane diterpenoid with an exocyclic olefin at the C-4 position.     

Skeleton-rearranged pentacyclic diterpenoids possessing a cyclobutane ring from Euphorbia wallichii

[structure: see text] Two novel rearranged trachylobane diterpenoids, designated as wallichanol A (2) and wallichanol B (3), consisting of an unprecedented pentacyclic skeleton named wallichane with a cyclobutane ring, and a new ent-trachylobane diterpenoid, 3-oxo-ent-trachyloban-17-oic acid (1), were isolated from the roots of Euphorbia wallichii. Their structures were elucidated by comprehensive analysis of 2D-NMR spectroscopic data, with the stereochemistry of 1 confirmed by X-ray crystallographic study. All of these compounds potently block osteoclastogenesis in vitro, suggesting a potential therapeutic application in prevention of osteoporosis.     

Chemical studies on the constituents of the chinese medicinal herb Euphorbia helioscopia L

Euphoheliosnoid D (1), a new jatrophone-type diterpenoid, was isolated together with 22 known metabolites from the Chinese medicinal herb Euphorbia helioscopia L. The structure and relative stereochemistry of 1 was elucidated on the basis of spectroscopic methods. Compounds 14-23 were obtained from the species for the first time while compound 14, 2alpha-hydroxy helioscopinolide B, was isolated as a new natural product.     

Diastereoselective Total Synthesis of the Euphorbia Diterpenoid Pepluanol A: A Reductive Annulation Approach

A new titanium(III)-catalyzed reductive annulation constructed a series of diversely functionalized 1,5-diols in good to excellent yields with respect to a wide scope of vinyl epoxide-aldehyde substrates. Taken together with a Diels–Alder reaction and a substrate-controlled diastereoselective cyclopropanation as additional key steps, the synthetic utility of this novel method has been preliminarily explored by the first and concise total synthesis of the Euphorbia diterpenoid (±)-pepluanol A.     

A new diterpenoid from Euphorbia helioscopia

<正>A new jatrophane-type diterpenoid,7β,14β,15β-triacetoxy-3β-benzoyloxy-9-oxojatropha-5E,11E-diene,named euphornin N was isolated from Euphorbia helioscopia L.The structure and relative stereochemistry of the new compound was elucidated by spectroscopic methods.     

Diastereoselective Total Synthesis of the Euphorbia Diterpenoid Pepluanol A: A Reductive Annulation Approach

A new titanium(III)‐catalyzed reductive annulation constructed a series of diversely functionalized 1,5‐diols in good to excellent yields with respect to a wide scope of vinyl epoxide‐aldehyde substrates. Taken together with a Diels–Alder reaction and a substrate‐controlled diastereoselective cyclopropanation as additional key steps, the synthetic utility of this novel method has been preliminarily explored by the first and concise total synthesis of the Euphorbia diterpenoid (±)‐pepluanol A.     

Langduin C, a novel dimeric diterpenoid from the roots of Euphorbia fischeriana

Langduin C, a novel dimeric diterpenoid, was isolated from the roots of Euphorbia fischeriana and its structure was established by spectral data and single-crystal X-ray diffraction analysis.     

A new casbane diterpene from Euphorbia pekinensis

A new casbane diterpenoid, referred to as pekinenin G, together with one cembrane diterpene and four known casbane diterpenoids were isolated from the roots of Euphorbia pekinensis. Their structures were elucidated on the basis of spectroscopic studies and comparison with related known compounds. The six compounds showed different cytotoxic activities against four human cancer cell lines.     

Briarane derivatives from the gorgonian coral Junceella fragilis

A new trihydroxyl briarane-type diterpenoid, junceellolide H (1), along with two known compounds, praelolide (2) and junceellin (3), have been isolated from the gorgonian coral Junceella fragilis. The structure, including the relative configuration of the new diterpenoid 1, was elucidated by extensive spectroscopic methods.     

Octacyclic and decacyclic ent‑abietane dimers with cytotoxic activity from Euphorbia fischeriana steud.

A novel Diels-Alder adduct possesses a 6/6/6/5/6/6/6/6 octacyclic skeleton featured with bicyclo[2.2.2]octane moiety, biseupyiheoid A (1), along with another decacyclic 6/6/6/3/5/6/5/6/6/6 fused diterpenoid dimer, bisfischoid C (2), were isolated from Euphorbia fischeriana. Their structures were determined by spectroscopic, X-ray crystallographic approaches, and quantum mechanical calculations. The structural features of 1 and 2 were hypothesized to involve intramolecular Diels-Alder reactions with different coupling patterns. Dimer 1 showed antiproliferative activity through apoptosis activation in LoVo cells.     

Synthetic study on 13-oxyingenol: construction of the full carbon framework

13-Oxyingenol is a diterpenoid isolated from Euphorbia kansui, and its derivatives have strong anti-HIV activity. We achieved the construction of inside-outside framework of 13-oxyingenol by using ring-closing olefin metathesis.     

A New Abietane Diterpenoid from the Barks of Taxus yunnanensis

Along with the major constituents taxoids, some non-taxane diterpenoids have also been isolated1. During the course of our phytochemical investigation on the bark of Taxus yunnanensis. Cheng et L. K. Fu, a new abietane diterpenoid, taxayunnin (1), and the known taxamairin C (2)2, were isolated. The structure elucidation of taxayunnin 1 was established by spectral analysis.Taxayunnin 1, pale yellow needles, mp 215oC, showed a molecular ion peak at m/z 346 [M+] in its EI mass spectrum, which…     

Structure Revision of Caesalpinistas A and B and Isolation of a New Furanoditerpenoid from the Cotyledons of Caesalpinia decapetala var. japonica

A known cassane‐type furanoditerpenoid, caesalpinista B ( 1 ), and a new diterpenoid, deoxycaesaljaponin A ( 2 ), were isolated from the cotyledons of Caesalpinia decapetala var. japonica. The previously reported configurational assignments of 1 and the related diterpenoid caesalpinista A ( 3 ) were revised on the basis of X‐ray crystallography and chemical conversion. The structure of 2 was elucidated by spectroscopic data and chemical conversion into 3 .     

藏药蓝翠雀花中的新二萜生物碱

蓝翠雀花(Delphinium caeruleum Jacq.ex Camb.)~[1]在甘肃西南部、西藏、青海等地分布较广,藏民常用其治疗牙痛、跌打损伤.其化学成分迄今未见报道.我们将其全草用乙醇浸泡,石油醚脱脂,乙醚除去色素,酸碱常法处理,氯仿萃取得总生物碱.用氧化铝、硅胶进行多次柱层析及硅胶薄层制备层析,分得碱(1)～(4).     

A New Diterpenoid and a New Diterpenoid Alkaloid from Aconitum coreanum

A new diterpenoid, guan fu diterpenoid A ( 1 ), and a new diterpenoid alkaloid, guan fu base S ( 2 ), were isolated from the Chinese medicinal herb Aconitum coreanum (Lèvl. ) Rapaics , together with five known diterpenoid alkaloids guan fu base P, guan fu base R, guan fu base G, guan fu base F, and guan fu base Z. The structures of the two new compounds were elucidated as ent‐kaurane‐16,20‐diol ( 1 ) and (11β,13S)‐2,3,15,16‐tetradehydro‐16,17‐dihydrohetisan‐11,13,14‐triol 11,13‐diacetate ( 2 ) on the basis of HR‐MS and 2D‐NMR analyses. This is the first report of an ent‐kaurane diterpenoid in Aconitum coreanum.     

Polyoxygenated Klysimplexane- and Eunicellin-Based Diterpenoids from the Gorgonian Briareum violaceum

Three new polyoxygenated diterpenoids with a rare 4-isopropyl-1,5,8a-trimethylperhydrophenanthrane structure of the klysimplexane skeleton, briarols A‒C (1‒3), and one eunicellin-based diterpenoid, briarol D (4), were isolated from Briareum violaceum, a gorgonian inhabiting Taiwanese waters. The chemical structures of these compounds were determined by employing extensive analyses of NMR and high-resolution electrospray ionization mass spectrometry (HRESIMS) data. Metabolites 1‒3 were found to possess the rarely found skeleton of the diterpenoid klysimplexin T. All isolated compounds showed very weak cytotoxic activity against the growth of three cancer cell lines. A plausible biosynthetic pathway for briarols A‒C from the coexisting eunicellin diterpenoid briarol D (4) was postulated.