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12 pages, 3388 KiB

Open AccessCommunication

Briavioids E–G, Newly Isolated Briarane-Diterpenoids from a Cultured Octocoral Briareum violaceum

by Thanh Hao Huynh, Chia-Jung Liu, Yi-Hung Liu, Su-Ying Chien, Zhi-Hong Wen, Lee-Shing Fang, Jih-Jung Chen, Yang-Chang Wu, Jui-Hsin Su and Ping-Jyun Sung

Mar. Drugs 2023, 21(2), 124; https://doi.org/10.3390/md21020124 - 14 Feb 2023

Cited by 3 | Viewed by 2602

Abstract

The chemical screening of a cultured soft coral, Briareum violaceum, led to the isolation of eight natural, briarane-related diterpenoids, including three unreported metabolites, briavioids E–G (1–3), and five known briaranes, briacavatolides B (4) and C ( [...] Read more.

The chemical screening of a cultured soft coral, Briareum violaceum, led to the isolation of eight natural, briarane-related diterpenoids, including three unreported metabolites, briavioids E–G (1–3), and five known briaranes, briacavatolides B (4) and C (5), briaexcavatin L (6), briaexcavatolide U (7) and briarenol K (8). The structures of briaranes 1–8 were established using spectroscopic methods. The absolute configuration of briavioid A (9), obtained in a previous study, was reported for the first time in this study by a single-crystal X-ray diffraction analysis using a copper radiation source. The anti-inflammatory activity of briaranes 1 and 2 and briaranes 4–8 was evaluated by screening their inhibitory ability against the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins in lipopolysaccharide (LPS)-induced RAW 264.7 macrophage cells. Full article

(This article belongs to the Special Issue Challenges on Structural Determination of Marine Natural Products)

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36 pages, 5236 KiB

Open AccessReview

Towards Sustainable Medicinal Resources through Marine Soft Coral Aquaculture: Insights into the Chemical Diversity and the Biological Potential

by Ngoc Bao An Nguyen, Lo-Yun Chen, Mohamed El-Shazly, Bo-Rong Peng, Jui-Hsin Su, Ho-Cheng Wu, I-Ta Lee and Kuei-Hung Lai

Mar. Drugs 2022, 20(10), 640; https://doi.org/10.3390/md20100640 - 14 Oct 2022

Cited by 14 | Viewed by 3776

Abstract

In recent decades, aquaculture techniques for soft corals have made remarkable progress in terms of conditions and productivity. Researchers have been able to obtain larger quantities of soft corals, thus larger quantities of biologically active metabolites, allowing them to study their biological activity [...] Read more.

In recent decades, aquaculture techniques for soft corals have made remarkable progress in terms of conditions and productivity. Researchers have been able to obtain larger quantities of soft corals, thus larger quantities of biologically active metabolites, allowing them to study their biological activity in many pharmacological assays and even produce sufficient quantities for clinical trials. In this review, we summarize 201 secondary metabolites that have been identified from cultured soft corals in the era from 2002 to September 2022. Various types of diterpenes (eunicellins, cembranes, spatanes, norcembranes, briaranes, and aquarianes), as well as biscembranes, sterols, and quinones were discovered and subjected to bioactivity investigations in 53 different studies. We also introduce a more in-depth discussion of the potential biological effects (anti-cancer, anti-inflammatory, and anti-microbial) and the mechanisms of action of the identified secondary metabolites. We hope this review will shed light on the untapped potential applications of aquaculture to produce valuable secondary metabolites to tackle current and emerging health conditions. Full article

(This article belongs to the Special Issue Soft Corals (Octocorallia) Are Marine Bio-Resources towards Biotechnology and Medical Applications)

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10 pages, 3277 KiB

Open AccessArticle

Briarane-Related Diterpenoids from Octocoral Briareum stechei

by Thanh-Hao Huynh, Choo-Aun Neoh, Yu-Chi Tsai, Zhi-Kang Yao, Li-Guo Zheng, Pin-Chang Huang, Zhi-Hong Wen, Jih-Jung Chen, Yu-Jen Wu and Ping-Jyun Sung

Molecules 2021, 26(22), 6861; https://doi.org/10.3390/molecules26226861 - 13 Nov 2021

Cited by 4 | Viewed by 2252

Abstract

A known polyoxygenated briarane, briaexcavatolide P (1), was isolated from a Formosan octocoral Briareum stechei. Moreover, the same species B. stechei, collected from Okinawan waters, yielded three chlorine-containing briaranes, including two new compounds, briastecholides B (2) and [...] Read more.

A known polyoxygenated briarane, briaexcavatolide P (1), was isolated from a Formosan octocoral Briareum stechei. Moreover, the same species B. stechei, collected from Okinawan waters, yielded three chlorine-containing briaranes, including two new compounds, briastecholides B (2) and C (3) as well as a known analogue, briarenol R (4). The structures of 1–4 were established using spectroscopic methods. In addition, briarane 1 demonstrated anti-inflammatory activity in lipo-polysaccharide-induced RAW 264.7 mouse macrophage cells by suppressing the expression of inducible nitric oxide synthase (iNOS) protein. Full article

(This article belongs to the Section Natural Products Chemistry)

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8 pages, 2386 KiB

Open AccessArticle

8-Hydroxybriaranes from Octocoral Briareum stechei (Briareidae) (Kükenthal, 1908)

by Thanh-Hao Huynh, Su-Ying Chien, Junichi Tanaka, Zhi-Hong Wen, Yang-Chang Wu, Tung-Ying Wu and Ping-Jyun Sung

Mar. Drugs 2021, 19(3), 136; https://doi.org/10.3390/md19030136 - 28 Feb 2021

Cited by 7 | Viewed by 2427

Abstract

Chemical investigation of the octocoral Briareum stechei, collected in the Ie Island, Okinawa, Japan, resulted in the isolation of a new briarane-type diterpenoid, briastecholide A (1), as well as the previously reported metabolites, solenolide C (2) and briarenolide [...] Read more.

Chemical investigation of the octocoral Briareum stechei, collected in the Ie Island, Okinawa, Japan, resulted in the isolation of a new briarane-type diterpenoid, briastecholide A (1), as well as the previously reported metabolites, solenolide C (2) and briarenolide S (3). The structures of briaranes 1–3 were characterized through spectroscopic analysis, and the absolute configuration of 2 was corroborated by a single-crystal X-ray diffraction analysis. Briarane 3 exhibited bioactivity against the protein expression of inducible nitric oxide synthase (iNOS). Full article

(This article belongs to the Special Issue Reef Cnidaria and Porifera as Sources of Bioactive Secondary Metabolites—Honoring the 70th Birthday of Professor Yang-Chang Wu)

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14 pages, 3477 KiB

Open AccessArticle

Briarenols W–Z: Chlorine-Containing Polyoxygenated Briaranes from Octocoral Briareum stechei (Kükenthal, 1908)

by You-Ying Chen, Yi-Lin Zhang, Gene-Hsiang Lee, Lun Kelvin Tsou, Mingzi M. Zhang, Hsing-Pang Hsieh, Jih-Jung Chen, Chou-Yuan Ko, Zhi-Hong Wen and Ping-Jyun Sung

Mar. Drugs 2021, 19(2), 77; https://doi.org/10.3390/md19020077 - 31 Jan 2021

Cited by 6 | Viewed by 2861

Abstract

Briareum stechei is proven to be a rich source of 3,8-cyclized cembranoids (briarane) with a bicyclo[8.4.0] carbon core. In the present study, four previously unreported briaranes, briarenols W–Z (1–4), along with solenolide A (5), briarenolide M ( [...] Read more.

Briareum stechei is proven to be a rich source of 3,8-cyclized cembranoids (briarane) with a bicyclo[8.4.0] carbon core. In the present study, four previously unreported briaranes, briarenols W–Z (1–4), along with solenolide A (5), briarenolide M (6), briaexcavatolide F (7), and brianolide (8), were isolated and characterized through spectroscopic analysis, and the absolute configuration of 8 was corroborated by a single-crystal x-ray diffraction analysis. Briaranes 2 and 5 were found to induce significant inflammatory activity in lipopolysaccharide (LPS)-induced RAW 264.7 mouse macrophage cells by enhancing the expression of the inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins. Full article

(This article belongs to the Special Issue Reef Cnidaria and Porifera as Sources of Bioactive Secondary Metabolites—Honoring the 70th Birthday of Professor Yang-Chang Wu)

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10 pages, 3422 KiB

Open AccessArticle

Briarenols Q–T: Briaranes from A Cultured Octocoral Briareum stechei (Kükenthal, 1908)

by Yi-Lin Zhang, Chih-Chao Chiang, Yi-Ting Lee, Zhi-Hong Wen, Yang-Chang Wu, Yu-Jen Wu, Tsong-Long Hwang, Tung-Ying Wu, Chia-Yuan Chang and Ping-Jyun Sung

Mar. Drugs 2020, 18(8), 383; https://doi.org/10.3390/md18080383 - 24 Jul 2020

Cited by 6 | Viewed by 2696

Abstract

Our continuous chemical study of a cultured octocoral Briareum stechei led to the isolation of four new briarane diterpenoids, briarenols Q–T (1–4). The structures of new metabolites 1–4 were established by spectroscopic methods, and compounds 3 and [...] Read more.

Our continuous chemical study of a cultured octocoral Briareum stechei led to the isolation of four new briarane diterpenoids, briarenols Q–T (1–4). The structures of new metabolites 1–4 were established by spectroscopic methods, and compounds 3 and 4 were found to inhibit the generation of inducible nitric oxide synthase (iNOS) from RAW 264.7 stimulated by lipopolysaccharides (LPS). Full article

(This article belongs to the Special Issue Marine Compounds and Inflammation II)

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10 pages, 5185 KiB

Open AccessArticle

11β,20β-Epoxybriaranes from the Gorgonian Coral Junceella fragilis (Ellisellidae)

by Tung-Pin Su, Tsu-Jen Kuo, San-Nan Yang, Gene-Hsiang Lee, Yen-Tung Lee, Yi-Chen Wang, Jih-Jung Chen, Zhi-Hong Wen, Tsong-Long Hwang and Ping-Jyun Sung

Mar. Drugs 2020, 18(4), 183; https://doi.org/10.3390/md18040183 - 31 Mar 2020

Cited by 3 | Viewed by 2942

Abstract

Two 11,20-epoxybriaranes, including a known compound, juncenolide K (1), as well as a new metabolite, fragilide X (2), have been isolated from gorgonian Junceella fragilis collected off the waters of Taiwan. The absolute configuration of juncenolide K (1 [...] Read more.

Two 11,20-epoxybriaranes, including a known compound, juncenolide K (1), as well as a new metabolite, fragilide X (2), have been isolated from gorgonian Junceella fragilis collected off the waters of Taiwan. The absolute configuration of juncenolide K (1) was determined by single-crystal X-ray diffraction analysis for the first time in this study and the structure, including the absolute configuration of briarane 2 was established on the basis of spectroscopic analysis and compared with that of model compound 1. One aspect of the stereochemistry of the known compound 1 was revised. Briarane 2 was found to enhance the generation of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) release from RAW 264.7 cells. Full article

(This article belongs to the Special Issue Bioactive Compounds from Coral Reef Organisms 2021)

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9 pages, 3783 KiB

Open AccessArticle

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

by Thanh-Hao Huynh, Lee-Shing Fang, Yu-Hsin Chen, Bo-Rong Peng, You-Ying Chen, Li-Guo Zheng, Yu-Jen Wu, Zhi-Hong Wen, Jih-Jung Chen, Tzu-Chi Lin and Ping-Jyun Sung

Molecules 2020, 25(6), 1405; https://doi.org/10.3390/molecules25061405 - 19 Mar 2020

Cited by 8 | Viewed by 2783

Abstract

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 [...] Read more.

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. Full article

(This article belongs to the Special Issue Food and Drug Analysis)

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16 pages, 2294 KiB

Open AccessArticle

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

by Sandra L. Molina, Abel M. Forero, Farja I. Ayala, Mónica Puyana, Sven Zea, Leonardo Castellanos, Diego Muñoz, Gonzalo Arboleda, Adrián G. Sandoval-Hernández and Freddy A. Ramos

Mar. Drugs 2020, 18(1), 4; https://doi.org/10.3390/md18010004 - 18 Dec 2019

Cited by 10 | Viewed by 4057

Abstract

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 [...] Read more.

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. Full article

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9 pages, 3056 KiB

Open AccessArticle

Fragilides U–W: New 11,20-Epoxybriaranes from the Sea Whip Gorgonian Coral Junceella fragilis

by Tung-Pin Su, Chien-Han Yuan, Yi-Ming Jhu, Bo-Rong Peng, Zhi-Hong Wen, Yu-Jen Wu, Tung-Ying Wu, Hong-Wen Liu and Ping-Jyun Sung

Mar. Drugs 2019, 17(12), 706; https://doi.org/10.3390/md17120706 - 15 Dec 2019

Cited by 8 | Viewed by 2920

Abstract

Three new 11,20-epoxybriaranes—fragilides U–W (1–3), as well as two known metabolites, junceellonoid D (4) and junceellin (5), were obtained from the octocoral Junceella fragilis. The structures of briaranes 1–3 were elucidated by [...] Read more.

Three new 11,20-epoxybriaranes—fragilides U–W (1–3), as well as two known metabolites, junceellonoid D (4) and junceellin (5), were obtained from the octocoral Junceella fragilis. The structures of briaranes 1–3 were elucidated by spectroscopic methods and briaranes 3 and 5 displayed inhibition effects on inducible nitric oxide synthase (iNOS) release from RAW264.7. Full article

(This article belongs to the Special Issue Bioactive Compounds from Coral Reef Organisms)

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9 pages, 5178 KiB

Open AccessArticle

New 8-Hydroxybriaranes from the Gorgonian Coral Junceella fragilis (Ellisellidae)

by You-Ying Chen, Lee-Shing Fang, Yu-Hsin Chen, Bo-Rong Peng, Tung-Pin Su, Thanh-Hao Huynh, Feng-Yu Lin, Chiung-Chin Hu, Nai-Cheng Lin, Zhi-Hong Wen, Jih-Jung Chen, Chieh-Yu Lee, Jin-Wei Wang and Ping-Jyun Sung

Mar. Drugs 2019, 17(9), 534; https://doi.org/10.3390/md17090534 - 14 Sep 2019

Cited by 8 | Viewed by 3904

Abstract

Three new 8-hydroxybriaranes—fragilides R–T (1–3) were obtained from a sea whip gorgonian coral Junceella fragilis. The structures of briaranes 1–3 were elucidated by using spectroscopic methods, including 1D (¹H and ¹³C NMR), 2D [...] Read more.

Three new 8-hydroxybriaranes—fragilides R–T (1–3) were obtained from a sea whip gorgonian coral Junceella fragilis. The structures of briaranes 1–3 were elucidated by using spectroscopic methods, including 1D (¹H and ¹³C NMR), 2D (COSY, HSQC, HMBC, and NOESY experiments) NMR studies, and (+)-HRESIMS. Fragilides S and T (2 and 3) are the only briaranes known to possess 8α-hydroxy and 17β-methyl groups, respectively. Briarane 2 exerted an inhibition effect on iNOS release from RAW264.7; a macrophage cell line that originated from a mouse monocyte macrophage, stimulated with lipopolysaccharides. Full article

(This article belongs to the Special Issue Terpenoids from Marine Organisms II)

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13 pages, 2693 KiB

Open AccessArticle

Bathyptilones: Terpenoids from an Antarctic Sea Pen, Anthoptilum grandiflorum (Verrill, 1879)

by Santana A.L. Thomas, Anthony Sanchez, Younghoon Kee, Nerida G. Wilson and Bill J. Baker

Mar. Drugs 2019, 17(9), 513; https://doi.org/10.3390/md17090513 - 1 Sep 2019

Cited by 13 | Viewed by 5651

Abstract

An Antarctic coral belonging to the order Pennatulacea, collected during the 2013 austral autumn by trawl from 662 to 944 m depth, has yielded three new briarane diterpenes, bathyptilone A-C (1–3) along with a trinorditerpene, enbepeanone A (4 [...] Read more.

An Antarctic coral belonging to the order Pennatulacea, collected during the 2013 austral autumn by trawl from 662 to 944 m depth, has yielded three new briarane diterpenes, bathyptilone A-C (1–3) along with a trinorditerpene, enbepeanone A (4), which bears a new carbon skeleton. Structure elucidation was facilitated by one- and two-dimensional NMR spectroscopy, mass spectrometry and confirmed by X-ray crystallography. The three compounds were screened in four cancer cell lines. Bathyptilone A displayed selective nanomolar cytotoxicity against the neurogenic mammalian cell line Ntera-2. Full article

(This article belongs to the Special Issue New Challenges in Structure Elucidation of Marine Natural Products: NMR Analyses and Other Advanced Methods)

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8 pages, 2287 KiB

Open AccessCommunication

New 11,20-Epoxybriaranes from the Gorgonian Coral Junceella fragilis (Ellisellidae)

by Chia-Cheng Lin, Jui-Hsin Su, Wu-Fu Chen, Zhi-Hong Wen, Bo-Rong Peng, Lin-Cyuan Huang, Tsong-Long Hwang and Ping-Jyun Sung

Molecules 2019, 24(13), 2487; https://doi.org/10.3390/molecules24132487 - 7 Jul 2019

Cited by 11 | Viewed by 2636

Abstract

Two new 11,20-epoxybriaranes, fragilides P (1) and Q (2), as well as two known analogues, robustolide F (3) and juncin Z (4), were obtained from the gorgonian coral Junceella fragilis. The structures, including the [...] Read more.

Two new 11,20-epoxybriaranes, fragilides P (1) and Q (2), as well as two known analogues, robustolide F (3) and juncin Z (4), were obtained from the gorgonian coral Junceella fragilis. The structures, including the absolute configurations of briaranes 1 and 2, were elucidated by using spectroscopic methods and comparing the spectroscopic and rotation data with those of known related analogues. Briarane 4 decreased the generation of superoxide anions by human neutrophils. The propionate group in 1 is rarely found. Full article

(This article belongs to the Special Issue Terpenes and Terpene Derivatives)

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10 pages, 1952 KiB

Open AccessReview

Natural Product Chemistry of Gorgonian Corals of Genus Junceella–Part III

by Hsu-Ming Chung, Yi-Chen Wang, Chung-Chih Tseng, Nan-Fu Chen, Zhi-Hong Wen, Lee-Shing Fang, Tsong-Long Hwang, Yang-Chang Wu and Ping-Jyun Sung

Mar. Drugs 2018, 16(9), 339; https://doi.org/10.3390/md16090339 - 17 Sep 2018

Cited by 20 | Viewed by 4307

Abstract

The structures, names, bioactivities, and references of 82 natural products, including 48 new metabolites, purified from the gorgonian corals belonging to the genus Junceella are described in this review. All compounds mentioned in this review were obtained from Junceella fragilis, Junceella gemmacea [...] Read more.

The structures, names, bioactivities, and references of 82 natural products, including 48 new metabolites, purified from the gorgonian corals belonging to the genus Junceella are described in this review. All compounds mentioned in this review were obtained from Junceella fragilis, Junceella gemmacea, Junceella juncea, and Junceella sp., collected from tropical Indo-Pacific Ocean. Some of these compounds exhibited potential biomedical activities. Full article

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10 pages, 1386 KiB

Open AccessCommunication

Fragilides K and L, New Briaranes from the Gorgonian Coral Junceella fragilis

by Li-Guo Zheng, Yu-Chia Chang, Chiung-Chih Hu, Zhi-Hong Wen, Yang-Chang Wu and Ping-Jyun Sung

Molecules 2018, 23(7), 1510; https://doi.org/10.3390/molecules23071510 - 22 Jun 2018

Cited by 10 | Viewed by 3062

Abstract

Two new briarane metabolites—fragilides K (1) and L (2)—along with five known analogues—gemmacolide X, praelolide, juncins P and ZI, and gemmacolide V (3–7)—were extracted and purified from Junceella fragilis, a gorgonian coral. Based on [...] Read more.

Two new briarane metabolites—fragilides K (1) and L (2)—along with five known analogues—gemmacolide X, praelolide, juncins P and ZI, and gemmacolide V (3–7)—were extracted and purified from Junceella fragilis, a gorgonian coral. Based on data obtained via spectroscopic techniques, the structures of new briaranes 1 and 2 were determined and the cyclohexane rings in 1 and 2 were found to exist in chair and twist boat conformation, respectively. Additionally, anti-inflammatory analysis showed that briaranes 2, 3, and 6 inhibited pro-inflammatory inducible nitric oxide synthase protein expression and briaranes 3 and 7 suppressed the cyclooxygenase-2 level, in LPS-stimulated murine macrophage-like RAW264.7 cells. Full article

(This article belongs to the Section Natural Products Chemistry)

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