Sesquiterpenes and Flavonoids from Serratula Strangulata

Phytochemistry investigation of the whole plants of Serratula strangulata has led to the isolation of two sesquiterpenes, six flavonoids, and two isoflavonoids. Among these, a sesquiterpene and two flavonoids are new compounds. The structures of these new compounds were elucidated by spectroscopic methods and 2D NMR techniques.     

Sesquiterpene Lactones from Daucus glaber

Six new sesquiterpene lactone esters, daucoguaianolactones A–F ( 1 – 6 ), and one new sesquiterpene lactone, daucoeudesmanolactone A ( 7 ) were isolated from the leaves and stems of Daucus glaber (Forssk .) Thell ., along with the known sesquiterpene lactones talasins A and B and badkhysin. The structures of 1 – 6 were established on the basis of extensive 1D‐ and 2D‐NMR spectroscopic studies and that of 7 by X‐ray crystallography. Compounds 4, 7 , and talasins A and B showed moderate cytotoxicity against P‐388 leukemia cells.     

New Sesquiterpenoids from Artemisia anomala

One new guaianolide, anomalactone A ( 1 ), and one new norcadinane sesquiterpene, anomallenodiol ( 2 ), along with two germacranolides, anomalactones B and C ( 3 and 4 , resp.), were isolated from the aerial part of Artemisia anomala S. Moore . Their structures were determined on the basis of extensive spectroscopic analyses.     

Guapsidial A and Guadials B and C: Three New Meroterpenoids with Unusual Skeletons from the Leaves of Psidium guajava

A novel sesquiterpene‐based Psidium meroterpenoid, possessing an unusual coupling pattern, and two new monoterpene‐based meroterpenoids with unprecedented skeletons were isolated from the leaves of Psidium guajava. Their structures and absolute configurations were elucidated by spectroscopic, X‐ray diffraction, and computational methods. The plausible biosynthetic pathway of these meroterpenoids as well as their cytotoxicities toward HepG2 and HepG2/ADM cells were also discussed.     

Phytoquinoids and Secoprezizaane‐Type Sesquiterpenes from Illicium arborescens

A phytochemical investigation of the MeOH extract of Illicium arborescens yielded the two new phytoquinoid epimers, 2,3‐didehydro‐5‐O‐methyl‐11‐epiillifunone E ( 1 ) and 2,3‐didehydro‐5‐O‐methylillifunone E ( 2 ), as well as five new sesquiterpene lactones (8,9‐secoprezizaane‐type sesquiterpenes). Two of them, i.e., 3 and 4 , were minwanensin‐type sesquiterpenes, the other two, i.e., 5 and 6 , had the anisatin‐type (or floridanolide type) skeleton, and the fifth, i.e., 7 , was a dunnianin‐type sesquiterpene. Their structures were established by analyses of 1D‐ and 2D‐NMR, HR‐MS, and chemical evidence. The in vitro cytotoxic activity of compounds 1 – 7 was tested against four human tumor cell lines, including HeLa (cervical epitheloid), WiDr (colon), Daoy (medulloblastoma), and Hep2 (liver carcinoma) human‐tumor cells.     

Three New Bisabolocurcumin Ethers from the Rhizomes of Curcuma longa L.

Three new bisabolocurcumin ethers, named demethoxybisabolocurcumin ether ( 1 ), bisabolocurcumin ether ( 2 ), and didemethoxybisabolocurcumin ether ( 3 ), along with two known compounds, 4 and 5 , were isolated from the AcOEt extract of the rhizomes of Curcuma longa L. Their structures were established by the analysis of NMR and MS data. The new compounds 1 – 3 , which possess a new 1,7‐diarylheptanoid skeleton linked with a bisabolone‐type sesquiterpene substructure by a C? O bond, were found for the first time in a natural source.     

Struktur und stereochemie eines sesquiterpen-esters und dreier sesquiterpen-alkaloide von Celastrus paniculatus Willd

A new sesquiterpene ester (Malkangunin) and three sesquiterpene alkaloids (Celapanin, Celapanigin, Celapagin) were isolated from Celastrus paniculatus Willd. The complete structure and stereochemistry of Malkangunin, a sesquiterpene tetra-ol of the β-dihydroagarofurane type two of whose hydroxyls being esterified with acetic and benzoic acids, is discussed. The alkaloids described here are derived from a new sesquiterpene tetra-ol (Celapanol) which is alternately esterified with acetic, benzoic, nicotinic and β-furoic acids.     

New Sesquiterpenes from a Taiwanese Marine Sponge of the Genus Parahigginsia

An undescribed Taiwanese marine sponge of the genus Parahigginsia yielded two new sesquiterpene hydrocarbons-parahigginine ( 1 ) and parahigginone ( 2 ). The structures of the new compounds were established on the basis of NMR spectroscopic and mass spectrometric data. Compounds 1 and 2 exhibited moderate cytotoxicity against murine P-388 and human KB-16, A-549, and HT-29 tumor cells.     

A new sesquiterpene from the gorgonian coral Menella sp.

A new sesquiterpene named menecubebane B (1) and a known analogue (2) were isolated from the gorgonian coral Menella sp. Their structures were elucidated by the extensive analyses of spectroscopic data and by the comparison with related literature. Cytotoxic effect against both Eca9706 and HeLa cell lines was evaluated, revealing 1 exhibited moderate cytotoxicity against the two cell lines involved with IC₅₀ values being 20.8 and 30.6 μM, respectively.     

Furanocoumarins and Sesquiterpene Ketone from Clausena Lansium Skeels

Three known furanocoumarins, imperatorin (1), wampetin (dehydroindicolactone) (2) and 8-geranoxypsoralen (3) and a new sesquiterpene ketone, (+)-oplopanone (4), were isolated from Clausena lansium Skeels. The stereochemistry of the last two coumarins was determined by NOESY experiments. The idendity of (+)-oplopanone was established by comparison of its physical constants and spectroscopic data with those reported for its enantiomer as well as a comparison of its' TLC behavior with that of an authentic sample.     

Chemical Constituents of the Endophytic Fungus Phomopsis sp. A240 Isolated from Taxus chinensis var. mairei

A new sesquiterpene, eremophil‐9‐ene‐11,12,13‐triol ( 1 ), a new oxazole, 4‐(2‐hydroxyethyl)‐5‐methyloxazole ( 2 ), and the two known lactones, 5′‐hydroxyalternariol ( 3 ) and alternariol ( 4 ), were isolated from the extract of Phomopsis sp. A240, an endophytic fungus isolated from the bark of Taxus chinensis var. mairei. The structures of the isolated compounds were determined by analyses of their spectroscopic data, as well as by comparison with literature reports. The isolated compounds were evaluated for their cytotoxic and antioxidant activities.     

A new sesquiterpene from the South China Sea gorgonian coral Subergorgia suberosa

A new sesquiterpene, namely suberosoid (1), was isolated from the South China Sea gorgonian coral Subergorgia suberosa. The chemical structure of 1 was established as an unusual sesquiterpene containing 4-methylenecyclohex-2-enone system, by extensive analyses of NMR spectroscopy and high-resolution mass spectrometry. Suberosoid (1) exhibited cytotoxic effect against HeLa cell lines with IC₅₀ value being 10.6 μM.     

Sesquiterpene and Aristolochic Acid Derivatives from Thottea hainanensis

One new sesquiterpene named thotteodiol ( 1 ) with a novel skeleton and one new derivative of aristolochic acid named 7‐hydroxyaristolochic acid III methyl ester ( 2 ), together with 20 known compounds, were isolated from the stems and roots of Thottea hainanensis. Their structures were determined by spectroscopic methods.     

Cadinane and Eudesmane Sesquiterpenoids from Chloranthus henryi

Chemical investigation of the leaves and stems of Chloranthus henryi resulted in the isolation and characterization of the three new cadinane‐type sesquiterpenes 1 – 3 and of the new eudesmane‐type sesquiterpene 4 , together with three known compounds. Among the new compounds, the two cadinane‐type sesquiterpenes 1 and 2 possess an unusual aromatic ring B in their molecule. These structures were established on the basis of spectroscopic evidence. In addition, antitumor activities of the isolates were also evaluated.     

Terpenoids-LXXIV: The sesquiterpenes from the soft coral sinularia mayi

Eleven sesquiterpene hydrocarbons, one [sinularene 11] with a new non-famesolic skeleton, and two new sesquiterpene diols from S. mayi were identified or structurally elucidated. Four 4,7-aromadendranediols were synthesized for reference purposes from spathulenol 23 and the stereochemistry assigned by ¹³C spectroscopy.     

A new sesquiterpene glycoside from the aerial parts of Saussurea triangulata

Column chromatographic separation of a MeOH extract of the aerial parts of Saussurea triangulata led to the isolation of a new sesquiterpene glycoside 6, together with three quinic acid derivatives, two phenolics, two sesquiterpene glycosides and two flavonoids. The new compound 6 was identified as amarantholidol A glycoside by spectroscopic and chemical methods.     

Three Unusual New Sesquiterpenes from Alpinia oxyphylla

Two new norcadinene sesquiterpenes oxyphyllones C and D ( 1 and 2 , resp.), and one new 1,10‐secoguaiane sesquiterpene, (+)‐mandassidion ( 3 ), together with two known compounds, oxyphyllenodiol B ( 4 ) and (1R,2R)‐p‐menth‐3‐ene‐1,2‐diol ( 5 ), were isolated from the fruits of Alpinia oxyphylla. Their structures were determined on the basis of spectroscopic analysis, including 2D‐NMR spectroscopic techniques. Compounds 1, 2 , and 3 exhibited no cytotoxicity against three cancer cell lines.     

Phytochemical constituents of the pericarps of Illicium difengpi and their anti-inflammatory activity

Abstract

Phytochemical investigation on the pericarps of Illicium difengpi lead to the isolation and structure elucidation of a new sesquiterpene, sesquicaranoic acid C (1), a new neolignan, difengpiol C (2), and 10 known compounds. The structures and absolute configurations of two new compounds were determined by a combination of NMR and CD spectroscopic analyses. All isolates were evaluated for their inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells.     

Two New Sesquiterpenes from the Marine Fungus Eutypella scoparia FS26 from the South China Sea

A new monocyclofarnesane‐type sesquiterpene, 3,7,10‐trihydroxy‐6,11‐cyclofarnes‐1‐ene ( 1 ), and a new acorane‐type sesquiterpene, 8‐(hydroxymethyl)‐1‐(2‐hydroxy‐1‐methylethyl)‐4‐methylspiro[4.5]dec‐8‐en‐7‐ol ( 2 ), were isolated from the culture of Eutypella scoparia FS26 from the South China Sea, along with three known terpenes, 3 – 5 . The structures of these compounds were determined by extensive analysis of their spectroscopic data as well as by comparison with literature reports. The isolated compounds 1 – 5 were evaluated for their cytotoxic activities against the SF‐268, MCF‐7, and NCI‐H460 tumor cell lines.     

Bisabocurcumin, a new skeleton curcuminoid from the rhizomes of Curcuma longa L.

A new skeleton bisabolane-type sesquiterpene curcuminoid,bisabocurcumin(1),along with 5 known compounds,curcumin(2), demethoxycurcumin(3),bidemethoxycurcumin(4),(1E,4E)-1,5-bis(4-hydroxy-3-methoxyphenyl)-penta-1,4-dien-3-one(5),and (1E,4E)-1-(4-hydroxy-3-methoxyphenyl)-5-(4-hydroxy phenyl-)-penta-1,4-dien-3-one(6)were isolated from the rhizomes of Curcuma longa L.Their structures were determined on the basis of spectroscopic analysis.Bisabocurcumin(1) is firstly obtained from nature with a new skeleton combined by a bisabolane-type sesquiterpene and a 1,7-diphenylheptanoid through a C-C bond.