Halogenated organic molecules of Rhodomelaceae origin: chemisty and biology

1引言 2。评论 3。分类 4，结构和发生 4.1。卤化单萜 4.2。卤化倍半萜 4.2.1。Bisabolane倍半萜 4.2.2。Brasilane倍半萜 4.2.3。Chamigrane倍半萜 4.2.4。Cuparane倍半萜 4.2.5。桉和6,8 - Cycloeudesmane倍半萜 4.2.6。Laurane和Cyclolaurane倍半萜 4.2.7。Snyderane倍半萜 4.2.8。倍半萜与新碳骨架 4.2.9。杂倍半萜 4.2.10。卤化倍半萜的发生概要 4.3。卤代烷二萜 4.3.1。Irieane二萜 4.3.2。Labdane二萜 4.3.3。Parguerane，Isoparguerane，Neoparguerane和Pimarane二萜 4.3.4。其他二萜与新的或少见报道骷髅 4.4。卤化三萜类/聚醚 4.4.1。三萜类持有2,7 - 二氧杂双环[4.4.0]癸烷骨架 4.4.2。三萜类持有一个2,8 - 二氧杂双环[5.4.0]十一烷骨架 4.4.3。三萜类持有对称元素（S） 4.5。卤化Nonterpenoid C15-内酯（ACGS） 4.5.1。线性ACGS 4.5.2。五元环醚类（四氢呋喃ACGS，THF ACGS）的ACGS 4.5.3。国际清算银行 - 四氢呋喃类（双四氢呋喃ACGS）的ACGS 4.5.4。的2,6 - 二氧杂双环[3.3.0]辛烷类的ACGS 4.5.5。六元环醚类（四氢吡喃ACGS，THP ACGS）的ACGS 4.5.6。的2,7 - 二氧杂双环[4.3.0]壬烷类ACGS 4.5.7。七元环醚类ACGS 4.5.8。八元环醚类ACGS 4.5.9。九和十元环醚类的ACGS 4.5.10。十二元环醚类ACGS 4.5.11。该Maneonene和Isomaneonene类的ACGS 4.5.12。支ACGS 4.5.13。杂项ACGS 4.6。卤代吲哚 4.7。卤化酚类/芳烃 4.8。其他卤化有机分子 4.9。摘要以卤化有机分子的发生 5，化学分类学意义 6。合成 6.1。倍半萜的合成 6.1.1。Chamigrane倍半萜的合成 6.1.2。Laurane和Snyderane倍半萜的合成 6.1.3。倍半萜的合成与新型碳骨架 6.2。二萜的合成 6.3。三萜类化合物的合成 6.3.1。Thyrsiferol及其衍生物的合成 6.3.2。（+） - Intricatetraol的合成 6.4。C15-内酯的合成（ACGS） 6.4.1。ACGS含四氢呋喃结构单元的合成 6.4.2。七元环ACGS的合成 6.4.3。ACGS含有八元环的环状醚的芯体的合成 6.4.4。ACGS含九元环的环状醚的芯体的合成 6.4.5。Maneonene和Isomaneonene ACGS的合成 6.5。Bromoindoles的合成 6.6。溴苯酚的合成 7，生物合成 7.1。倍半萜的生物合成 7.2。C15-内酯的生物合成 8，生物活性和功能 8.1。生物活性 8.1.1。细胞毒活性 8.1.2。抗菌活性 8.1.3。抗真菌活性 8.1.4。抗病毒活性 8.1.5。酶抑制活性 8.1.6。自由基清除活性 8.2。生物功能 8.2.1。拒食作用 8.2.2。杀虫活性 8.2.3。防污活动 8.2.4。化感活性 8.3。杂项活动 8.4。生物活性和功能的概要 9。为未来的发现与展望结语 </ul

Two halosesquiterpenes from Laurencia composita

Two new chamigrane sesquiterpenes, yicterpenes A (1) and B (2) each with an unprecedented halogenation at C-9 and a hemiketal unit at C-10, were isolated from the marine red algaLaurencia composita. The structures and absolute configurations of them were identified by NMR, ECD, and mass spectrometric methods as well as quantum chemical calculations. Compound&nbsp;1&nbsp;with a chlorination at C-9 was more active against some tested marine-derived organisms than&nbsp;2&nbsp;with a bromination at C-9. &nbsp;Two new chamigrane sesquiterpenes, yicterpenes A (1) and B (2) each with an unprecedented halogenation at C-9 and a hemiketal unit at C-10, were isolated from the marine red alga Laurencia composita. The structures and absolute configurations of them were identified by NMR, ECD, and mass spectrometric methods as well as quantum chemical calculations. Compound 1 with a chlorination at C-9 was more active against some tested marine-derived organisms than 2 with a bromination at C-9

Sesquiterpenes from the marine red alga Laurencia composita.

Four new chamigrane derivatives, laurecomin A (1). laurecomin B (2), laurecomin C (3), and laurecomin D (4), one new naturally occurring sesquiterpene, 2,10-dibromo-3-chloro-7-chamigren-9-ol acetate (5), and three known halogenated structures, deoxyprepacifenol (6), 1-bromoselin-4(14),11-diene (7), and 9-bromoselin-4(14).11-diene (8), were isolated from the marine red alga Laurencia cornposita collected from Pingtan Island, China. The structures of these compounds were unambiguously established by 1D, 2D NMR and mass spectroscopic techniques. The bioassay results showed that 2 was active against both brine shrimp and fungus Colletotrichum lagenarium. (C) 2012 Elsevier B.V. All rights reserved.Four new chamigrane derivatives, laurecomin A (1). laurecomin B (2), laurecomin C (3), and laurecomin D (4), one new naturally occurring sesquiterpene, 2,10-dibromo-3-chloro-7-chamigren-9-ol acetate (5), and three known halogenated structures, deoxyprepacifenol (6), 1-bromoselin-4(14),11-diene (7), and 9-bromoselin-4(14).11-diene (8), were isolated from the marine red alga Laurencia cornposita collected from Pingtan Island, China. The structures of these compounds were unambiguously established by 1D, 2D NMR and mass spectroscopic techniques. The bioassay results showed that 2 was active against both brine shrimp and fungus Colletotrichum lagenarium. (C) 2012 Elsevier B.V. All rights reserved

Terretonin, ophiobolin, and drimane terpenes with absolute configurations from an algicolous Aspergillus ustus

One new meroterpene, 1,2-dihydroterretonin F (2), five new sesterterpenes, (6a)-21-deoxyophiobolin G(3), (6a)-16,17-dihydro-21-deoxyophiobolin G (4), phiobolin U (5), ophiobolin V (6), and ophiobolin W (7),two new sesquiterpenes, (6-strobilactone-B) esters of (E,E)-6,7-epoxy-2,4-octadienoic acids (13 and 14),and twelve known terpenes (1, 8&ndash;12, and 15&ndash;20) were isolated from Aspergillus ustus, a fungus from the fresh tissue of marine green alga Codium fragile. Their structures and absolute configurations were identified by NMR and mass spectroscopic methods as well as quantum chemical calculations. Some of the isolates exhibited antibacterial activity and brine shrimp toxicity.One new meroterpene, 1,2-dihydroterretonin F (2), five new sesterterpenes, (6 alpha)-21-deoxyophiobolin G (3), (6 alpha)-16,17-dihydro-21-deoxyophiobolin G (4), ophiobolin U (5), ophiobolin V (6), and ophiobolin W(7), two new sesquiterpenes, (6-strobilactone-B) esters of (E,E)-6,7-epoxy-2,4-octadienoic acids (13 and 14), and twelve known terpenes (1, 8-12, and 15-20) were isolated from Aspergillus ustus, a fungus from the fresh tissue of marine green alga Codium fragile. Their structures and absolute configurations were identified by NMR and mass spectroscopic methods as well as quantum chemical calculations. Some of the isolates exhibited antibacterial activity and brine shrimp toxicity

Three new xanthone derivatives from an algicolous isolate of Aspergillus wentii

Three new xanthone derivatives, yicathin A (1), yicathin B (2), and yicathin C (3), and three known anthraquinone derivatives, alatinone (4), 1,5-dihydroxy-3-methoxy-7-methylanthraquinone (5), and 5-hydroxy-1,3-dimethoxy-7-methylanthraquinone (6), were isolated from the cultures of&nbsp;Aspergillus wentii&nbsp;pt-1, an endophytic fungus isolated from the marine red alga&nbsp;Gymnogongrus flabelliformis. Their structures were unambiguously elucidated by NMR and mass spectroscopic methods as well as quantum chemical calculations. Compound 2 was active against&nbsp;Escherichia coli, and 3 could inhibit&nbsp;E. coli,&nbsp;Staphylococcus aureus, and&nbsp;Colletotrichum lagenarium.Three new xanthone derivatives, yicathin A (1), yicathin B (2), and yicathin C (3), and three known anthraquinone derivatives, alatinone (4), 1,5-dihydroxy-3-methoxy-7-methylanthraquinone (5), and 5-hydroxy-1,3-dimethoxy-7-methylanthraquinone (6), were isolated from the cultures of Aspergillus wentii pt-1, an endophytic fungus isolated from the marine red alga Gymnogongrus flabelliformis. Their structures were unambiguously elucidated by NMR and mass spectroscopic methods as well as quantum chemical calculations. Compound 2 was active against Escherichia coli, and 3 could inhibit E. coli, Staphylococcus aureus, and Colletotrichum lagenarium. Copyright (C) 2012 John Wiley & Sons, Ltd

Brominated Selinane Sesquiterpenes from the Marine Brown Alga Dictyopteris divaricata

Two new brominated selinane sesquiterpenes, 1-bromoselin-4(14),11-diene (1) and 9-bromoselin-4(14),11-diene (2), one known cadinane sesquiterpene, cadalene (3), and four known selinane sesquiterpenes, α-selinene (4), β-selinene (5), β-dictyopterol (6), and cyperusol C (7), were isolated from a sample of marine brown alga Dictyopteris divaricata collected off the coast of Yantai (China). Their structures were established by detailed MS and NMR spectroscopic analysis, as well as comparison with literature data

A New Epoxy-cadinane Sesquiterpene from the Marine Brown Alga Dictyopteris divaricata

A new epoxy-cadinane sesquiterpene, 4β,5β-epoxycadinan-1β-ol (1), and six known cadinane sesquiterpenes: cadinan-1,4,5-triol (2), 4α,5β-dihydroxycubenol (3), cubenol (4), cadinan-3-ene-1,5-diol (5), cubenol-3-one (6), and torreyol (7), were isolated from a sample of marine brown alga Dictyopteris divaricata collected off the coast of Yantai (China). Their structures were established by detailed MS and NMR spectroscopic analysis, as well as comparison with literature data

Secondary Metabolites from an Algicolous Aspergillus versicolor Strain

Two new compounds, asperversin A (1) and 9ξ-O-2(2,3-dimethylbut-3-enyl)brevianamide Q (2), and nine known compounds, brevianamide K (3), brevianamide M (4), aversin (5), 6,8-di-O-methylnidurufin (6), 6,8-di-O-methylaverufin (7), 6-O-methylaverufin (8), 5α,8α-epidioxyergosta-6,22-dien-3β-ol (9), ergosta-7,22-diene-3β,5α,6β-triol (10), and 6β-methoxyergosta-7,22-diene-3β,5α-diol (11), were obtained from the culture of Aspergillus versicolor, an endophytic fungus isolated from the marine brown alga Sargassum thunbergii. The structures of these compounds were established by spectroscopic techniques. Compounds 4, 7 and 8 exhibited antibacterial activities against Escherichia coli and Staphyloccocus aureus, and 7 also showed lethality against brine shrimp (Artemia salina) with an LC50 value of 0.5 μg/mL