Novel secoeunicellins produced by an octocoral Cladiella sp

Zhang, Zhijun; Wang, Yi‐Hsuan; Chen, Shu-Rong; Peng, Bo-Rong; Yang, San‐Nan; Hu, Chiung-Chih; Fang, Lee‐Shing; Hwang, Tsong‐Long; Sung, Ping‐Jyun

doi:10.1016/j.tetlet.2019.151300

Cited by 6 publications

(11 citation statements)

References 6 publications

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“…In conclusion, this study investigated new anti-inflammatory terpenoids derived from soft corals and discovered seven capnellenes sourced from Capnella imbricata, including three previously unknown compounds (1)(2)(3). The study also found that compounds 1 and 2 were the first-ever identified 6-hydroxy capnellenes.…”

Section: Discussionmentioning

confidence: 69%

“…Table 4. 1 H and 13 C NMR data for compound 3 and 1 H NMR data for ∆ 9(12) -Capnellene-2ξ,8β, 10α-triol [9].…”

Section: Resultsmentioning

confidence: 99%

“…In this study, we utilized ChemGPS-NP to establish the chemical relationships between capnellenes discussed in our present research and those mentioned in our previous publications [2] that possess anti-inflammatory activity. We mapped a total of 14 capnellene sesquiterpenes (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) in a chemical space using PC score predictions from the online tool ChemGPS-NPWeb (Figure 5). Additionally, we retrieved previously disclosed inhibitors that target inflammation-related proteins iNOS from the ChEMBL online database and included them in the analysis.…”

Section: Chemgps-np-based Analysis Of the Anti-inflammatory Capnellenesmentioning

confidence: 99%

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Capnellenes from Capnella imbricata: Deciphering Their Anti-Inflammatory-Associated Chemical Features

et al. 2023

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Through our ongoing research on investigating new anti-inflammatory terpenoids derived from soft corals, seven capnellenes sourced from Capnella imbricata were discovered. Among these, three were previously unknown compounds named Δ9(12)-capnellene-6α,8β-diol (1), Δ9(12)-capnellene-6α,8β,10α-triol (2), and Δ9(12)-capnellene-2β,8β,10α-triol (3). The structures of all compounds were determined by spectroscopic analysis (IR, MS, 1D-, and 2D-NMR) and a comparison with the existing literature data. The compounds 1 and 2 were found to be the first-ever identified 6-hydroxy capnellenes. In the inflammation inhibitory assessments, compounds 1–7 were tested for their in vitro activities against inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) protein expressions in LPS-induced RAW264.7 cells. Capnellenes 2 and 5 demonstrated significant reductions in iNOS levels (27.73% and 47.61%) at a concentration of 10 μM. Additionally, capnellenes 1, 5, and 7 (at 10 μM) exhibited statistically significant inhibitions (ranging from 7.64% to 12.57%) against COX-2 protein expressions. Our findings indicated that the oxygen-bearing functionalities at C-8 and C-10 play critical roles in inhibiting iNOS protein induction, which can promote inflammation in LPS-induced RAW264.7 cells. Furthermore, a principal component analysis tool, the chemical global positioning system for natural products (ChemGPS-NP), was applied to confirm these capnellane-based sesquiterpenes as promising candidates for future anti-inflammatory agents targeting iNOS-related targets.

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Section: Discussionmentioning

confidence: 69%

“…Table 4. 1 H and 13 C NMR data for compound 3 and 1 H NMR data for ∆ 9(12) -Capnellene-2ξ,8β, 10α-triol [9].…”

Section: Resultsmentioning

confidence: 99%

Section: Chemgps-np-based Analysis Of the Anti-inflammatory Capnellenesmentioning

confidence: 99%

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Capnellenes from Capnella imbricata: Deciphering Their Anti-Inflammatory-Associated Chemical Features

et al. 2023

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“…Compound 152 exhibited moderate cytotoxicity against the leukemia MOLT‐4 cells with IC 50 value of 18.8 μg/mL. Further examination of the previously investigated specimen yielded two new 6,7‐secoeunicellins, namely cladieunicellins W ( 153 ) and X ( 154 ), and a known eunicellin, klymollin Y ( 155 ) [61] . Secoeunicellin 153 was the first example of secoeunicellin possessing a γ ‐lactone ring and 154 represents the first example of secoeunicellin possessing two tetrahydrofuran moieties.…”

Section: Marine Natural Products From the Genus Of Cladiellamentioning

confidence: 99%

“…Further examination of the previously investigated specimen yielded two new 6,7secoeunicellins, namely cladieunicellins W (153) and X (154), and a known eunicellin, klymollin Y (155). [61] Secoeunicellin 153 was the first example of secoeunicellin possessing a γ-lactone ring and 154 represents the first example of secoeunicellin possessing two tetrahydrofuran moieties. The absolute configuration of 154 was assigned by ECD calculation as 1R,2R,3R,6R,9R,10R,14R.…”

Section: Other Cladiella Spmentioning

confidence: 99%

Cladiella Octocorals: Enormous Sources of Secondary Metabolites with Diverse Structural and Biological Properties

Liang

Guo

2022

Chemistry & Biodiversity

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Marine octocorals belonging to the genus Cladiella, usually encountered on reefs in the Indo-Pacific region, have been proven to be rich sources of diverse secondary metabolites with intriguing structural features and promising bioactivities. In this review, 155 compounds from six unambiguously identified C. krempfi, C. australis, C. pachyclados, C. hirsuta, C. tuberculosa, C. conifera, together with several unidentified Cladiella spp. are summarized covering the literatures from 2006 to August 2022. It is noteworthy that diterpenoids dominated the secondary metabolite profile of this genus counting for 78 %. Structurally, the majority of these diterpenes belonged to eunicellan family characterized by different patterns of ether linkage. The impacts of these chemical compositions on an array of potential pharmacological activities were also reviewed, giving an overview of the potential application of Cladiella secondary metabolites.

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Coniferains A and B, new eunicellin-based diterpenoids from the octocoral Cladiella conifera (Tixier-Durivault, 1943)

Zeng

Tseng

Tsai

et al. 2022

Phytochemistry Letters

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Novel secoeunicellins produced by an octocoral Cladiella sp

Cited by 6 publications

References 6 publications

Capnellenes from Capnella imbricata: Deciphering Their Anti-Inflammatory-Associated Chemical Features

Capnellenes from Capnella imbricata: Deciphering Their Anti-Inflammatory-Associated Chemical Features

Cladiella Octocorals: Enormous Sources of Secondary Metabolites with Diverse Structural and Biological Properties

Coniferains A and B, new eunicellin-based diterpenoids from the octocoral Cladiella conifera (Tixier-Durivault, 1943)

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