Menverins H–L,New Highly Oxygenated Guaiane Lactones from the Gorgonian Coral Menella kanisa

By further chemical investigation of South China Sea gorgonian Menella kanisa, five new highly oxygenated guaiane lactones, menverins H–L ( 1 – 5 , resp.), were obtained. Their structures were established by employing spectroscopic methods, computer modeling, and comparison of their data with those of related metabolites.     

Further Highly Oxygenated Guaiane Lactones from the South China Sea Gorgonian Menella sp.

Four new highly oxygenated guaiane lactones, 1‐epimenverin B ( 1 ), menverin F ( 2 ), 1‐deoxymenverin F ( 3 ), and menverin G ( 4 ), together with the two known related analogues menverins B ( 5 ) and C ( 6 ), were isolated from the South China Sea gorgonian Menella sp. Their structures and relative configuration were elucidated by analysis of spectroscopic data and by comparison with those of known related compounds.     

Three New Polyoxygenated Steroids from Two Species of the South China Sea Gorgonian Muricella flexuosa and Menella verrucosa Brundin

Three new polyoxygenated steroids, muricesteroid ( 1 ), and menellsteroids A ( 2 ) and B ( 3 ), were isolated from two species of the South China Sea gorgonian Muricella flexuosa and Menella verrucosa Brundin , respectively. The structures of these new compounds were elucidated on the basis of extensive spectroscopic analysis, chemical methods and comparison with known related compounds.     

Suberoretisteroids A–E,Five New Uncommon Polyoxygenated Steroid 24‐Ketals from the Hainan Gorgonian Suberogorgia reticulata

Five new uncommon polyoxygenated steroids, namely suberoretisteroids A–E ( 1 – 5 ), were isolated from the gorgonian Suberogorgia reticulata, never studied so far. The structures and relative configurations of these new compounds were elucidated on the basis of extensive spectral analysis. This work led to the structural revision of some steroids previously found in the Indian gorgonian Gorgonella umbraculum.     

Sarcophytonolides A–D,Four New Cembranolides from the Hainan Soft Coral Sarcophyton sp.

Four new cembranolide diterpenes, sarcophytonolides A–D ( 1 – 4 ), were isolated from a Hainan soft coral Sarcophyton sp. Their structures were elucidated on the basis of detailed spectroscopic analysis and by comparison with related model compounds.     

Pintoxolanes A–C,Highly Functionalized 3,14‐Oxa‐bridged Cembranoids from the Caribbean Gorgonian Coral Eunicea pinta

Three new cembrane‐based diterpenes possessing the rare 3,14‐oxa‐bridged moiety were isolated from the hexane extract of a southwestern Caribbean gorgonian octocoral, Eunicea pinta, together with seven known cembranoid diterpenes. The structures of pintoxolanes A–C ( 1 – 3 , resp.), including their relative configurations, were deduced from spectroscopic data and chemical‐correlation experiments. Experimental evidence hinting to a plausible biogenesis of the 3,14‐oxalane moiety is provided. Preliminary cytotoxicity data for compounds 1 – 3 toward human cancer cell lines are also provided.     

Cephalotanins A–D,Four Norditerpenoids Represent Three Highly Rigid Carbon Skeletons from Cephalotaxus sinensis

Four polycyclic norditerpenoids, cephalotanins A–D ( 1 – 4 ) representing three unprecedented carbon skeletons with highly rigid ring systems, were isolated from Cephalotaxus sinensis and structurally characterized by a combination of various methods. Compounds 1 and 2 are new skeletal norditerpenoid trilactones, while 3 and 4 are two norditerpenoids featuring different new carbon skeletons. Biosynthetic pathways for 1 – 4 were proposed by involving diverse and very fascinating chemical events with the coexisting cephalotane troponoids as the precursors. Compound 1 exhibited good NF‐κB inhibition with an IC₅₀ value of 4.12±0.61 μΜ.     

Japonicumins A–D: Four New Compounds from Lycopodium japonicum

Three new serratane‐type triterpenoids, japonicumins A–C ( 1 – 3 ), as well as a unique, new C₁₃ terpenoid, japonicumin D ( 4 ), were isolated from the dried whole plants of Lycopodium japonicum, together with the known compound lycoclavanol ( 5 ). Their structures were identified by extensive mass‐spectrometric and spectroscopic (especially 2D‐NMR) experiments. Compounds 1 – 5 exhibited no activity against human‐tumor A 549 cells.     

Oliveridepsidones A–D,antioxidant depsidones from Garcinia oliveri

Four new prenylated depsidones, oliveridepsidones A–D, were isolated from the bark of Garcinia oliveri collected in Vietnam. Their structures were elucidated using mainly NMR techniques (¹H and ¹³C NMR, HMQC, HMBC and NOE experiments). Copyright © 2012 John Wiley & Sons, Ltd.     

Suberosanones A – C,New Metabolites Possessing Cyclopentenone System from the South China Sea Gorgonian Coral Subergorgia suberosa

Two unusual novel bicyclic lactones, suberosanones A and B ( 1 and 2 , resp.), characterized by the co‐occurrence of cyclopentenone and butanolide rings within the same molecule, along with one tricyclic cyclopentenone derivative, suberosanone C ( 3 ), were isolated from the South China Sea gorgonian coral Subergorgia suberosa. Their structures were unambiguously established by detailed spectroscopic analyses (NMR, IR, and HR‐MS). The absolute configurations of 1 and 2 were determined by quantum‐chemical calculations using the time‐dependent density‐functional theory (TDDFT) method. All compounds showed neither antifouling activity against Balanus amphitrite larvae settlement nor antibacterial activity against a panel of bacterial strains at concentrations up to 25 μg/ml.     

Eupatozansins A – C,Sesquiterpene Lactones from Eupatorium chinense var. tozanense

Phytochemical investigation of Eupatorium chinense var. tozanense has resulted in the isolation of three new germacranolides, designated as eupatozansins A–C ( 1 – 3 ), along with five known compounds, (5S,6R,7R,8R)‐8‐angeloyloxy‐2‐oxoguaia‐1(10),3,11(13)‐trien‐12,6‐olide ( 4 ), costunolide ( 5 ), leptocarpin ( 6 ), 2α‐hydroxyeupatolide 8‐O‐angelate ( 7 ), and quercetin ( 8 ). The structures of the new compounds were identified by 1D and 2D NMR experiments, as well as high‐resolution mass spectrometry. The in vitro cytotoxic activities of compounds 1 – 8 were evaluated.     

Longistylumphyllines A–C,Three New Alkaloids from Daphniphyllum longistylum

Three new alkaloids, longistylumphyllines A–C (1–3), together with the six known alkaloids deoxycalyciphylline B, deoxyisocalyciphylline B, methyl homosecodaphniphyllate, daphnicyclidin A, daphnicyclidin B, and daphnicyclidin F, were isolated from the stems and leaves of Daphniphyllum longistylum. Their structures and relative configuration were elucidated on the basis of spectroscopic data, especially 1D and 2D NMR techniques.     

Highly Oxygenated Triterpenoids from the Marine Red Alga Laurencia mariannensis (Rhodomelaceae)

Two new and one known squalenoid‐derived triterpenoids, namely, laurenmariannol ( 1 ) and (21α)‐21‐hydroxythyrsiferol ( 2 ), and the known thyrsiferol ( 3 ) were isolated and identified from the marine red alga Laurencia mariannensis, which was collected off the coast of Hainan and Weizhou Islands of China. The structures of these compounds were established by means of spectroscopic analyses, as well as by comparison with literature data. Compounds 1 and 2 displayed significant cytotoxic activity against P‐388 tumor cells with IC₅₀ values of 0.6 and 6.6 μg/ml, respectively.     

Design of donor–acceptor–donor (D–A–D) type small molecule donor materials with efficient photovoltaic parameters

Four Donor–Acceptor–Donor (D–A–D) type of donor molecules (M1‐M4) with triphenylamine (TPA) as donor moiety, thiophene as bridge, and thiazolothiazole as acceptor unit were designed and its photovoltaic parameters were equated with reference molecule “R.” DFT functional CAM‐B3LYP/6‐31G (d,p) was found best for geometry optimization and TD‐CAM‐B3LYP/6‐31G (d,p) was found suitable for excited state calculations. Among designed donor molecules, M4 manifests suitable lowest band gap of 4.73 eV, frontier molecular orbital energy levels as well as distinctive broad absorption of 455.3 nm due to the stronger electron withdrawing group. The electron‐withdrawing substituents contribute to red shifts of absorption spectra and better stabilities for designed molecules. The theoretically determined reorganization energies of designed donor molecules suggested excellent charge mobility property. The lower λ_e values in comparison with λ_h illustrated that these four donor materials would be ideal for electron transfer and M4 would be best amongst the investigated molecules with lowest λ_e of 0.0177. Furthermore, the calculated Voc of M4 is 2.04 V with respect to PC₆₀BM (phenyl‐C61‐butyric acid methyl ester). This study revealed that the designed donor materials are suitable and recommended for high performance organic solar cell devices.     

Micromelosides A–D,four new coumarins from the stem bark of Micromelum falcatum

Four new coumarins, micromelosides A–D, together with four known coumarins were isolated from the stem bark of Micromelum falcatum. The complete assignments of the ¹H and ¹³C NMR chemical shifts for these new compounds were achieved by means of 1D and 2D NMR techniques, including ¹H‐¹H COSY, HSQC, HMBC and NOE difference. Copyright © 2009 John Wiley & Sons, Ltd.     

Eremosides A – C,New Iridoid Glucosides from Eremostachys loasifolia

Eremosides A–C ( 1 – 3 ), three new iridoid glucosides, were isolated from the AcOEt‐soluble fraction of the EtOH extract of the whole plant of Eremostachys loasifolia, along with buddlejoside B ( 4 ), 10‐O‐benzoylcatalpol ( 5 ), and pakiside A ( 6 ) reported for the first time from this species. The structures of these compounds were elucidated by spectroscopic data including 2D‐NMR, FAB‐MS, ESI‐MS, as well as by acid and basic hydrolyses.     

Itosides A – I,New Phenolic Glycosides from Itoa orientalis

Eight new benzoylated gentisyl alcohol (=2‐(hydroxymethyl)benzene‐1,4‐diol) glucosides, itosides A–H ( 1 – 8 ), together with the new pyrocatechol (=benzene‐1,2‐diol) glycoside itoside I ( 9 ) were isolated from the bark and twigs of Itoa orientalis (Flacourtiaceae). In itosides B–D ( 2 – 4 ), the gentisyl alcohol moiety was esterified by 1‐hydroxy‐6‐oxocyclohex‐2‐ene‐1‐carboxylic acid, while itosides E–H ( 5 – 8 ) contained instead an additional 2‐hydroxybenzoic acid moiety. The compounds were accompanied by the known derivatives 4‐hydroxytremulacin ( 10 ), poliothyrsoside ( 11 ), poliothyrsin ( 12 ), homaloside D ( 13 ), tremulacin, and pyrocatechol β‐D ‐glucopyranoside. The structures of the new compounds were elucidated by spectral and chemical methods.     

Dimorphamides A – C,New Polyphenolic Amides from Atriplex dimorphostagia

Dimorphamides A–C ( 1 – 3 , resp.), three new polyphenolic amides, have been isolated from the BuOH‐soluble fraction of the whole plant of Atriplex dimorphostagia, along with two known compounds, thymidine and N‐[(E)‐feruloyl]tyramine. Their structures have been determined on the basis of spectral studies.     

Chlojaponilactones B – E,Four New Lindenane Sesquiterpenoid Lactones from Chloranthus japonicus

Reinvestigation of the AcOEt‐soluble part of the EtOH extract of whole plants of Chloranthus japonicus afforded four new lindenane‐type sesquiterpenoid lactones, chlojaponilactones B–E ( 1 – 4 , resp.), together with nine known sesquiterpenoids. Their structures and relative configurations were established on the basis of extensive spectroscopic data and by comparison with the relevant literature.     

Evollionines A–C,Three New Alkaloids Isolated from the Fruits of Evodia rutaecarpa

A phytochemical study of the CHCl₃ extract of the dried unripe fruits of Evodia rutaecarpa (Juss. ) Benth. (Rutaceae) resulted in the isolation of three new alkaloids, evollionines A–C ( 1 – 3 , resp.), together with two known compounds, evodianinine and wuzhuyumide I. The structures of the new compounds were elucidated on the basis of detailed spectroscopic evidence and confirmed in the case of compound 1 by single‐crystal X‐ray analysis.