Two Brominated-sesquiteroene from Alga Laurencia Majuscula

Two brominated-sesquiterpenes were isolated from the Alga Laurencia majuscula collected from the Xisha Islands in the South China Sea. Compound 1 was first reported, and determined, on spectral evidence, to be 8-bromo-l-en-chamigrene.     

Tricyclic Sesquiterpene from Laurencia Majuscula

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略大凹顶藻中的新碘代内酯化合物

凹顶藻属于红藻，国际上有关凹顶藻化学成分的研究十分活跃[1~3]，凹顶藻的代谢物大多是萜类化合物，尤其是倍半萜．我们首次研究了采自南中国海西沙群岛海域的略大凹顶藻．生物活性测定结果表明该藻体的乙酸乙酯抽提物具有植物激素作用，且对油菜菌核有中等杀菌作用．从总抽提物中首次分离到一种新的碘代内酯（1，结构见下式）以及胆甾醇和正-二十酸．氯代或溴代化合物在海洋生物的次生代谢物中较常见，但是碘代化合物是较少有的．1结果与讨论碘代内酯（1）为带有特殊香气的白色固体．EIMS高质量区出现m／z550[M+]及423[M-I]+的峰，表明…     

New anti-bacterial halogenated tricyclic sesquiterpenes from Bornean Laurencia majuscula (Harvey) Lucas

Three new halogenated tricyclic sesquiterpenes, omphalaurediol (1), rhodolaurenones B (2) and C (3) were isolated together with nine known haloganated sesquiterpenes such as rhodolaurenone A (4), rhodolaureol (5), isorhodolaureol (6), (?)-laurencenone D (7), elatol (8), (+)-deschloroelatol (9), cartilagineol (10), (+)-laurencenone B (11) and 2-chloro-3-hydroxy-α-chamigren-9-one (12) from a population of Bornean red algae Laurencia majuscula. The structures of three new metabolites were determined based on their spectroscopic data (IR, 1D and 2D NMR, and MS). These compounds showed antibacterial activity against three human pathogenic bacteria (Escherichia coli, Salmonella typhi and Vibrio cholera).     

Sesquiterpenes from Red Alga Laurencia tristicha

Three naturally new sesquiterpenes named 10-hydroxyepiaplysin, 10-hydroxyaplysin and 10-hydroxybromoepiaplysin have been isolated from Laurencia tristicha. On the basis of the spectroscopic techniques their structures were elucidated as （3S, 3αR, 8βS）-（-）-2, 3, 3α, 8β3-tetra- hydro-7-bromo-3-hydroxy-3, 3α, 6,8β-tetramethyl-lH-cyclopenta[b]benzofuran, （3R, 3αR, 8βS）- （-）-2,3,3α, 8β-tetrahydro-7-bromo-3-hydroxy-3, 3α,6,8β-tetramethyl-lH-cyclopenta[b]benzofuran and （3S, 3αR, 8βS）-（-）-2, 3,3R, 8β-tetrahydro-3-hydroxy-3,3α,6,8β-tetramethyl-lH-cyclopenta[b]- benzofuran, respectively.     

Sesquiterpenes from the Marine Red Alga Laurencia saitoi

Together with five known sesquiterpenes, EtOH extraction of Laurencia saitoi yielded four new compounds, including three sesquiterpenes and one norsesquiterpene derivative. Their structures and relative configurations were elucidated by spectroscopic methods, including 1D‐ and 2D‐NMR (¹H,¹H‐COSY, HMQC, HMBC, and NOESY), as well as low‐ and high‐resolution mass‐spectrometric analyses.     

Two new brominated diterpenes from Laurencia decumbens

Two new brominated diterpenes,namely,laurendecumtriol and 11-deacetylpinnaterpene C,were isolated and identified from the marine red alga Laurencia decumbens.Their structures were established on the basis of various NMR spectroscopic techniques and HR-ESI-MS analyses.     

Halogenated Sesquiterpenes from the Marine Red Alga Laurencia saitoi (Rhodomelaceae)

Four new halogenated sesquiterpenes, 10‐bromo‐3‐chloro‐2,7‐epoxychamigr‐9‐en‐8α‐ol ( 1 ), 2,10β‐dibromochamigra‐2,7‐dien‐9α‐ol ( 2 ), (9S)‐2‐bromo‐3‐chloro‐6,9‐epoxybisabola‐7(14),10‐diene ( 3 ), and (9R)‐2‐bromo‐3‐chloro‐6,9‐epoxybisabola‐7(14),10‐diene ( 4 ), were characterized from the marine red alga Laurencia saitoi. In addition, two known halosesquiterpenes, 2,10‐dibromo‐3‐chlorochamigr‐7‐en‐9α‐ol ( 5 ) and isolaurenisol ( 6 ), were also isolated and identified. Their structures were established on the basis of extensive analysis of spectroscopic data.     

Squalene‐Derived Triterpene Polyethers from the Red Alga Laurencia omaezakiana

In our continuing search on halogenated metabolites from species of the red algal genus Laurencia, a novel squalene‐derived triterpene polyether, named omaezakianol ( 2 ), was isolated from Laurencia omaezakiana Masuda along with 15,16‐anhydrothyrsiferol ( 3 ). Their structures were determined by spectral and chemical methods.     

Two new aristolane sesquiterpenes from Laurencia similis

Two new aristolane sesquiterpenes, namely, aristolan-10-ol-9-one and aristolan-8-en-1-one, were isolated from the red alga Laurencia similis. Their structures were established on the basis of various NMR spectroscopic analyses, including 2D NMR techniques (1H-1H COSY, HMQC, HMBC, and NOESY) and HR-FAB-MS.     

A New Cytotoxic Dihydroxy Sterol from Laurencia Majuscula

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Sesquiterpenes and Other Metabolites from the Marine Red Alga Laurencia composita (Rhodomelaceae)

Two new halogenated sesquiterpenes, (8β)‐10‐bromo‐3‐chloro‐2,7‐epoxychamigr‐9‐en‐8‐ol ( 1 ) and 2‐bromo‐3‐chlorobisabola‐7(14),11‐diene‐6,10‐diol ( 3 ), and one new phytol‐derived diterpene, 2,3‐epoxyphytyl acetate ( 4 ), along with cis‐ and trans‐1‐methylcyclohexane‐1,4‐diol ( 5 and 6 ) which were isolated from a natural source for the first time but have been previously synthesized, were isolated from the marine red alga Laurencia composita and characterized. In addition, a known sesquiterpene, pacifenediol ( 2 ), and the known furanone derivative 7 were also identified. Their structures were established by NMR and mass spectroscopic methods.     

Aristolane Sesquiterpenes and Highly Brominated Indoles from the Marine Red Alga Laurencia similis (Rhodomelaceae)

Three new polybrominated 1H‐indoles, compounds 1 – 3 , and three new aristolane sesquiterpenes, compounds 4 – 6 , were isolated from the marine red alga Laurencia similis, together with seven known natural products. Their structures were elucidated on the basis of detailed spectroscopic and mass‐spectrometric analyses, as well as by comparison with literature data.     

Two new bromoindoles from red alga Laurencia similis

Two new bromoindole alkaloids have been isolated from the ethanolic extract of the red alga Laurencia similis.On the basis of chemical and spectroscopic methods(including 1D and 2D NMR technique),their structures have been elucidated as 2,2′,5,5′,6,6′-sixibromo -3,3′-bi-1H-indole and 3,5-dibromo-1-methylindole,respectively.     

Terpenes and Polybromoindoles from the Marine Red Alga Laurencia decumbens (Rhodomelaceae)

Two new brominated diterpenes, namely, laurendecumtriol ( 1 ) and 11‐O‐deacetylpinnaterpene C ( 2 ), one new polybromoindole, 2,3,4,6‐tetrabromo‐1‐methyl‐1H‐indole ( 7 ), and six known natural products were isolated and identified from the marine red alga Laurencia decumbens. Their structures were elucidated on the basis of detailed spectroscopic and mass‐spectrometric analysis as well as by comparison with literature data. Based on 2D‐NMR experiments, the previously reported NMR data for pinnaterpene C ( 3 ) were reassigned.     

New C15 Acetogenins from Two Species of Laurencia from the Aegean Sea

The chemical diversity of the approximately 1,200 natural products isolated from red algae of the genus Laurencia, in combination with the wide range of their biological activities, have placed species of Laurencia in the spotlight of marine chemists’ attention for over 60 years. The chemical investigation of the organic (CH₂Cl₂/MeOH) extracts of Laurencia microcladia and Laurencia obtusa, both collected off the coasts of Tinos island in the Aegean Sea, resulted in the isolation of 32 secondary metabolites, including 23 C₁₅ acetogenins (1–23), 7 sesquiterpenes (24–30) and 2 diterpenes (31 and 32). Among them, six new C₁₅ acetogenins, namely 10-acetyl-sagonenyne (2), cis-sagonenyne (3), trans-thuwalenyne C (4), tinosallene A (11), tinosallene B (12) and obtusallene XI (17), were identified and their structures were elucidated by extensive analysis of their spectroscopic data. Compounds 1–3, 5–11, 13 and 15–32 were evaluated for their antibacterial activity against Staphylococcus aureus and Escherichia coli.     

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.     

New Cytotoxic Laurene‐, Cuparene‐, and Laurokamurene‐Type Sesquiterpenes from the Red Alga Laurencia obtusa

Three new sesquiterpene alcohols, laur‐2‐ene‐3,12‐diol ( 1 ), cuparene‐3,12‐diol ( 2 ), and 8,11‐dihydro‐1‐methoxylaurokamuren‐12‐ol ( 3 ), along with one known diterpene, kahukuen‐10‐ol ( 4 ) have been isolated from the organic extract of the red alga Laurencia obtusa. The chemical structures were elucidated on the basis of spectroscopic analysis. The cytotoxicity of the isolated compounds were evaluated against three cancer cell lines, i.e., KB, HepG2, and MCF‐7. Compound 4 exhibited a wide range of cytotoxic activity against KB, HepG2, and MCF‐7 cell lines with IC₅₀ of 0.100, 0.057, and 0.054 μm, respectively. In addition, 1 showed moderate activities towards KB and MCF‐7 cell lines with IC₅₀ values of 0.171 and 0.184 μM , respectively and 2 exhibited a moderate activity against KB cell line at a concentration of 0.213 μg/ml. On the other hand, compound 3 exhibited no cytotoxic activity against any of the three cell lines.     

A new rearranged chamigrane sesquiterpene from Laurencia okamurai

A new rearranged chamigrane sesquiterpene,named laurenokamurin,was isolated from the marine red alga Laurencia okamurai.Its structure was determined on the basis of spectroscopic methods.     

Two new brominated C15-acetogenins from the red alga Laurencia japonensis

Abstract

We report on the chemical characteristics of the red alga Laurencia japonensis, collected off the coast of Yoshio, Katsuura, Boso Peninsula, Japan. We isolated two new brominated C₁₅-acetogenins in this species, which we name katsuurenyne A (1) and katsuurenyne B (2), along with two already known halogenated terpenes [2,10-dibromo-3-chloro-α-chamigrene (7) and aplysiadiol (8)]. We extensively analysed spectral data (from IR, ESI-MS, 1D-NMR and 2D-NMR) to confirm the structure of these compounds.