Dataset Information

Unusual Inner-Salt Guaiazulene Alkaloids and bis-Sesquiterpene from the South China Sea Gorgonian Muriceides collaris.

ABSTRACT: Three new guaiazulene alkaloids muriceidines A-C (1-3) and one new bis-sesquiterpene muriceidone A (4), were isolated from the South China Sea gorgonian Muriceides collaris. Muriceidines are the first examples structurally architected by guaiazulene coupling with an inner-salt ? ¹-pipecolic acid via a unique sp² methine-bridged linkage, and the bis-sesquiterpene was comprised by a guaiazulene and a indene units linked through a unprecedented carbon-carbon ?-bond between the high steric bridgehead carbon C-10 of guaiazulene moiety and C-2' of indene moiety. The chiral compounds 2-4 were obtained initially as racemates and further separated by chiral HPLC methods. The inner-salt structures of 1-3 and absolute configurations of 2-4 were fully elucidated by calculated ¹³C NMR, ECD and OR with quantum chemical calculation methods. Compound 1 showed cytotoxicity against K562 cell lines with IC₅₀ value of 8.4??M and antifouling activity against the larvae of the barnacle Balanus albicostatus with EC₅₀ value of 11.9 ?g/mL and potent therapeutic index (LC₅₀/EC₅₀?=?3.66). Also the racemic (±)-3 showed cytotoxicities against both HL-60 and K562 cell lines with IC₅₀ values of 2.2 and 3.7??M, respectively. A semisynthetic trial was performed to validate the proposed biosynthetic hypotheses.

SUBMITTER: Li P

PROVIDER: S-EPMC5550455 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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Unusual Inner-Salt Guaiazulene Alkaloids and bis-Sesquiterpene from the South China Sea Gorgonian Muriceides collaris.

Li Pinglin P Liu Xiaoling X Zhu Hongyan H Tang Xuli X Shi Xuefeng X Liu Yonghong Y Li Guoqiang G

Scientific reports 20170809 1

Three new guaiazulene alkaloids muriceidines A-C (1-3) and one new bis-sesquiterpene muriceidone A (4), were isolated from the South China Sea gorgonian Muriceides collaris. Muriceidines are the first examples structurally architected by guaiazulene coupling with an inner-salt Δ <sup>1</sup>-pipecolic acid via a unique sp<sup>2</sup> methine-bridged linkage, and the bis-sesquiterpene was comprised by a guaiazulene and a indene units linked through a unprecedented carbon-carbon σ-bond between the ...[more]

PMID: 28794492

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Project description:The yellow octocoral Eunicella cavolini is one of the most common gorgonians thriving in Mediterranean hard-bottom communities. However, information regarding its distribution and ecology in several parts of the Mediterranean is lacking, while population trends and conservation status remain largely unknown. We investigated 19 populations of E. cavolini over three representative geographic regions: the NW Mediterranean, CE Adriatic, and N Aegean. Focusing on the upper bathymetric range of the species (<40 m), data were collected on the populations' upper depth limit, density, colony height, and extent of injury. A three-level hierarchical sampling design was applied to assess the existence of spatial patterns, using: a) regions (located thousands of km apart), b) localities within regions (tens to hundreds of km apart), and c) sites within localities (hundreds of m to a few km apart). In the NW Mediterranean and CE Adriatic, the upper distribution limit was at depths ≤15 m, whereas in the N Aegean most populations were found deeper than 30 m. Population density ranged between 4.46-62 colonies per m2, while mean colony height was 15.6±8.9 SD cm with a maximum of 62 cm. The NW Mediterranean sites were characterized by dense populations dominated by small colonies (<20 cm), periodic recruitment, and low proportion of large gorgonians (>30 cm). The CE Adriatic displayed intermediate densities, with well-structured populations, and continuous recruitment. In the N Aegean, most populations presented low densities, high proportion of large colonies, but low number of small colonies, signifying limited recruitment. Disturbance levels, as a function of extent and type of injury, are discussed in relation to past or present human-induced threats. This work represents geographically the most wide ranging demographic study of a Mediterranean octocoral to date. The quantitative information obtained provides a basis for future monitoring at a Mediterranean scale.

Dataset Information

Unusual Inner-Salt Guaiazulene Alkaloids and bis-Sesquiterpene from the South China Sea Gorgonian Muriceides collaris.

Publications

Unusual Inner-Salt Guaiazulene Alkaloids and bis-Sesquiterpene from the South China Sea Gorgonian Muriceides collaris.

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