Briarane Diterpenoids Isolated from Octocorals between 2014 and 2016

Su, Yin Di; Su, Jui Hsin; Hwang, Tsong‐Long; Wen, Zhi Hong; Sheu, Jyh Horng; Wu, Yang Chang; Sung, Ping‐Jyun

doi:10.3390/md15020044

Cited by 29 publications

(25 citation statements)

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“…Octocorals of the genus Briareum (family Briareidae) [1][2][3][4] are proven to be the most important source to produce briarane-type diterpenoids [5]. The compounds of this type are only found in marine invertebrates, particularly in octocorals and demonstrated a wide spectrum of bioactivities, such as anti-inflammatory activity [6] and cytotoxicity [7].…”

Section: Introductionmentioning

confidence: 99%

Briarenols I—K, New Anti-inflammatory 8,17-Epoxybriaranes from the Octocoral Briareum excavatum (Briareidae)

et al. 2020

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Five 8,17-epoxybriaranes, including three new compounds-briarenols I-K (1-3), along with two known analogues, briaexcavatolide P (4) and briaexcavatin P (5), were isolated from the octocoral Briareum excavatum. The structures of briaranes 1-3 were elucidated by spectroscopic methods, including 1D and 2D NMR studies and (+)-HRESIMS. Briarane 4 exerted inhibition effects on inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) release from RAW 264.7.Molecules 2020, 25, 1405 2 of 9 ( Figure 1). In the current study, the comprehensive workflow of isolation, structure determination, and anti-inflammatory activity evaluation, was implemented on briaranes 1-5.Molecules 2020, 25, x FOR PEER REVIEW 2 of 9 briaexcavatin P (5) [9], (Figure 1). In the current study, the comprehensive workflow of isolation, structure determination, and anti-inflammatory activity evaluation, was implemented on briaranes 1-5. 1: R1 = OAc, R2 = R6 = OH, R3 = n-OC(O)Pr, R4 = H, R5 = β-OH 2: R1 = R2 = OH, R3 = OAc, R4 = R6 = H, R5 = β-OH 3: R1 = OAc, R2 = R3 = R6 = H, R4 = OH, R5 = β-OH 4: R1 = OAc, R2 = OH, R3 = n-OC(O)Pr, R4 = R6 = H, R5 = β-OH 5: R1 = R3 = OAc, R2 = OH, R4 = R6 = H, R5 = β-OH 6: R1 = OAc, R2 = n-OC(O)Pr, R3 = R4 = R6 = H, R5 = β-OH 7: R1 = OAc, R2 = R3 = R6 = H, R4 = OH, R5 = α-OH Figure 1. Structures of briarenols I-K (1-3), briaexcavatolide P (4), briaexcavatin P (5), excavatolide B (6), and briareolide B (7).

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Section: Introductionmentioning

confidence: 99%

Briarenols I—K, New Anti-inflammatory 8,17-Epoxybriaranes from the Octocoral Briareum excavatum (Briareidae)

et al. 2020

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“…Briarane-type and the related cembranoid-based diterpenoids are a unique family of coral-derived natural products, whose scaffolds are characterized by the presence of a highly oxidized γ-lactone-bearing bicyclo [8.4.0] ring system. [1][2][3][4][5] These extraordinary secondary metabolites are exclusively derived from gorgonian corals, conducting them to be the chemotaxonomic markers for the orders of Gorgonacea and Alcyonacea. Biogenetically, briarane analogues are suggested to be originated from host corals rather than the endophytic microorganisms, 6,7 while they are supposed to be generated through 3,8-cyclization of cembranoids.…”

Section: Introductionmentioning

confidence: 99%

“…Due to the structural novelty and complex, chemists continue to engage in the discovery of the chemical diversity, with which a profile of more than 600 briarane-based derivatives has been isolated to date, and the numbers of new entities increasingly developed in recent years. 5,6 Ecologically, briarane diterpenoids exhibited antifouling effects against the larval settlement of barnacle, antibiotic, and insecticide activities. 10,11 Based on the chemoecological effects of briaranes such as antifouling activities, it is expected that briaranes may possess antivirus activity.…”

Section: Introductionmentioning

confidence: 99%

Fragilolides A-Q, norditerpenoid and briarane diterpenoids from the gorgonian coral Junceella fragilis

Cheng

et al. 2017

Tetrahedron

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Chemical investigation of the gorgonian coral Junceella fragilis resulted in the isolation of a new norditerpenoid fragilolide A (1), sixteen new briarane diterpenoids fragilolides B-Q (2-17), together with frajunolides H and N, and three known norcembranoids scabrolide D, sinuleptolide and 5-epi-sinuleptolide. The structures of new compounds were determined on the basis of extensive spectroscopic analysis, including the experimental and calculated ECD data and single-crystal X-ray diffraction for the configurational assignments. The structure of fragilolide A featured an unprecedented 4,13-and 7,11-fused tetracyclic norcembranoid, while the biogenetic relationships of the briarane analogues were postulated. Frajunolide H exerted significant inhibition against a panel of tumor cell lines, and six briarane diterpenoids (3, 6, 8, 12, 16, and frajunolide N) exhibited the inhibitory effects against the HBeAg express of hepatitis B virus in HepAD38 cells. In addition, sinuleptolide and 5-epi-sinuleptolide exerted the effects to inhibit NO production in RAW264.7 macrophage cells, in addition to the activation of ARE and the inhibition of NF-B expression.

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“…Briarane-type diterpenoids represent one of the most common natural product families to be isolated from gorgonian octocorals, with over 700 briarane diterpenoids characterized [28]. The biosynthetic origin of this skeleton was proposed as the result of cyclization between C3 and C8 of a cembrane skeleton, another widely distributed diterpene scaffold in marine gorgonian species, followed by further oxidative processing [29].…”

Section: Chemical Characterization Of E Caribaeorum Chemotypesmentioning

confidence: 99%

Metabolic Profiling of the Soft Coral Erythropodium caribaeorum (Alcyonacea: Anthothelidae) from the Colombian Caribbean Reveals Different Chemotypes

et al. 2019

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The Caribbean soft coral Erythropodium caribaeorum is a rich source of erythrolides—chlorinated briarane diterpenoids. These compounds have an ecological role as feeding deterrents, with a wide variation in their composition depending on the location where the sample is collected. In Colombia, this soft coral can be found at different locations in the Caribbean Sea including Santa Marta, Islas del Rosario, and Providencia—three environmentally different coral reef areas in the south and southwest Caribbean Sea. In order to evaluate differences in erythrolide composition, the metabolic profiles of samples from each of these locations were analyzed by HPLC-MS. Principal component analysis showed changes in the diterpene composition according to the sample origin. Diterpenes from samples collected at each location were isolated to describe the three chemotypes. The chemotype from Santa Marta was highly diverse, with the new erythrolides W and X together with eight known erythrolides. The sample from Islas del Rosario showed a low diversity chemotype constituted by high amounts of erythrolide A and B. The chemotype from Providencia showed low chemical diversity with only two main compounds—erythrolide V and R. Evaluation of cytotoxic activity against the human cancer cell lines PC-3, MCF7, and A549 showed erythrolides A and B as the more active compounds with IC50 values in the range from 2.45 to 30 μM.

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Briarane Diterpenoids Isolated from Octocorals between 2014 and 2016

Cited by 29 publications

References 67 publications

Briarenols I—K, New Anti-inflammatory 8,17-Epoxybriaranes from the Octocoral Briareum excavatum (Briareidae)

Briarenols I—K, New Anti-inflammatory 8,17-Epoxybriaranes from the Octocoral Briareum excavatum (Briareidae)

Fragilolides A-Q, norditerpenoid and briarane diterpenoids from the gorgonian coral Junceella fragilis

Metabolic Profiling of the Soft Coral Erythropodium caribaeorum (Alcyonacea: Anthothelidae) from the Colombian Caribbean Reveals Different Chemotypes

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