Novel Norhumulene and Xeniaphyllane-Derived Terpenoids from a Formosan Soft Coral Sinularia gibberosa

Chen, Shin Pin; Su, Jui Hsin; Yeh, Hsiao Chien; Ahmed, Atallah F.; Dai, Chang‐Feng; Wu, Yang Chang

doi:10.1248/cpb.57.162

Cited by 19 publications

(5 citation statements)

References 5 publications

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“…Compound 1 is a colorless oil, and its molecular formula was determined as C 2) and DEPT data of compound 1 detected 15 carbon signals in total, including two methyls, seven methylenes (one oxygenated and one olefinic), three methines, and three quaternary carbons (one ketonic and one olefinic). Based on these data, compound 1 is a caryophyllane-type sesquiterpenoid similar to gibberosin P, but the hydroxymethyl functionality at C-11 in compound 1 takes the place of a 4-hydroxyvaleryl group in gibberosin P [24]. The planar structure of compound 1 was confirmed with the assistance of 1 H-1 H COSY and HMBC correlations as shown in Figure 2.…”

Section: Structure Elucidation Of Compounds 1-5mentioning

confidence: 74%

Sesquiterpenoids from the Florets of Carthamus tinctorius (Safflower) and Their Anti-Atherosclerotic Activity

Liu

et al. 2022

Nutrients

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(1) Background: The florets of Carthamus tinctorius L. are traditionally used as a blood-activating drug and can be used for the treatment of atherosclerosis, but no compounds with anti-atherosclerotic activity have been reported. (2) Methods: This study investigated the chemical compounds from the florets of C. tinctorius. Comprehensive spectroscopic techniques revealed their structures, and ECD calculations established their absolute configurations. Nile Red staining, Oil Red O staining, and cholesterol assessment were performed on these compounds and their aglycones for the inhibitory activity against the formation of foam cells induced by oxidized low-density lipoprotein (ox-LDL) in RAW264.7 macrophages. In addition, RAW264.7 macrophages were tested for their anti-inflammatory activity by measuring the inhibition of NO production caused by LPS. (3) Results: Five new sesquiterpenoids (1–5) isolated from the florets of C. tinctorius were identified as (–)-(1R,4S,9S,11R)-caryophyll-8(13)-en-14-ol-5-one (1), (+)-(1R,4R,9S,11R)-caryophyll-8(13)-en-14-ol-5-one (2), (–)-(3Z,1R,5S,8S,9S,11R)-5,8-epoxycaryophyll-3-en-14-O-β-D-glucopyranoside (3), (+)-(1S,7R,10S)-guai-4-en-3-one-11-O-β-D-fucopyranoside (4), and (–)-(2R,5R,10R)-vetispir-6-en-8-one-11-O-β-D-fucopyranoside (5). All compounds except for compound 3 reduced the lipid content in ox-LDL-treated RAW264.7 cells. Compounds 3 and 4 and their aglycones were found to reduce the level of total cholesterol (TC) and free cholesterol (FC) in ox-LDL-treated RAW264.7 cells. However, no compounds showed anti-inflammatory activity. (4) Conclusion: Sesquiterpenoids from C. tinctorius help to decrease the content of lipids, TC and FC in RAW264.7 cells, but they cannot inhibit NO production, which implies that their anti-atherogenic effects do not involve the inhibition of inflammation.

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Section: Structure Elucidation Of Compounds 1-5mentioning

confidence: 74%

Sesquiterpenoids from the Florets of Carthamus tinctorius (Safflower) and Their Anti-Atherosclerotic Activity

Liu

et al. 2022

Nutrients

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“…A modified Mosher ester analysis was obtained, and the negative Δδ SR (δ S − δ R ) values of Ha-8, (Δδ H −0.01), Hb-8, (Δδ H −0.05) and CH 3 -13 (Δδ H −0.01), and positive Δδ SR values of H-6 (Δδ H +0.04) Ha-12 (Δδ H +0.01), and Hb-12 (Δδ H +0.04) ( Figure 4 ) revealed the 7 S configuration [ 25 ]. Thus, the structure of 1 was determined as 4-oxohumula-2 E ,5 E ,9 E -trien-7 S ,12-diol, as shown in Figure 1 , and named leptogorgin A ( 1 ).…”

Section: Resultsmentioning

confidence: 99%

“…Interestingly, two new norhumulene were isolated from the soft coral Sinularia hirta [ 24 ]. In addition, one more norhumulene was found in a formazan soft coral Sinularia gibberosa [ 25 ]. Humulanes from the peeled stems of Syringa pinnatifida inhibit NO production in LPS-induced RAW264.7 macrophage cells and decrease the TNF-α and IL-6 levels in RAW264.7 cells [ 26 ].…”

Section: Introductionmentioning

confidence: 99%

Leptogorgins A–C, Humulane Sesquiterpenoids from the Vietnamese Gorgonian Leptogorgia sp.

et al. 2020

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Leptogorgins A–C (1–3), new humulane sesquiterpenoids, and leptogorgoid A (4), a new dihydroxyketosteroid, were isolated from the gorgonian Leptogorgia sp. collected from the South China Sea. The structures were established using MS and NMR data. The absolute configuration of 1 was confirmed by a modification of Mosher’s method. Configurations of double bonds followed from NMR data, including NOE correlations. This is the first report of humulane-type sesquiterpenoids from marine invertebrates. Sesquiterpenoids leptogorgins A (1) and B (2) exhibited a moderate cytotoxicity and some selectivity against human drug-resistant prostate cancer cells 22Rv1.

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“…Moreover, sarcocrassolides P-R (94)(95)(96) showed cytotoxicity against human colon adenocarcinoma (DLD-1), human T-cell acute lymphoblastic leukemia (CCRF-CEM), and human promyelocytic leukemia (HL-60) cell lines with sarcocrassolide R being the most cytotoxic [55]. Lin et al also analyzed the cytotoxicity of crassocolides A (66), B (97), D (98), and E (40), which resulted to be more active than sarcocrassolides P-R except for the compound D.…”

Section: Cytotoxic Compounds From the Genus Sarcophytonmentioning

confidence: 99%

“…Chen et al [98] also extracted a novel skeletal norhumulene (sinugibberoside) and six xeniaphyllane-derived compounds (Gibberosins N-S) from S. gibberosa. Gibberosin O (194) was found to display cytotoxicity toward HepG2 and A-549 cell lines with (IC 50 values of 18.7 and 19.5 mg/mL, respectively, whereas gibberosin Q (195) exhibited cytotoxicity exclusively toward A549 cells with (IC 50 value of 11.0 mg/mL.…”

Section: Cytotoxic Compounds From the Genus Sinulariamentioning

confidence: 99%

Cytotoxic Compounds from Alcyoniidae: An Overview of the Last 30 Years

et al. 2022

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The octocoral family Alcyoniidae represents a rich source of bioactive substances with intriguing and unique structural features. This review aims to provide an updated overview of the compounds isolated from Alcyoniidae and displaying potential cytotoxic activity. In order to allow a better comparison among the bioactive compounds, we focused on molecules evaluated in vitro by using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, by far the most widely used method to analyze cell proliferation and viability. Specifically, we surveyed the last thirty years of research, finding 153 papers reporting on 344 compounds with proven cytotoxicity. The data were organized in tables to provide a ranking of the most active compounds, to be exploited for the selection of the most promising candidates for further screening and pre-clinical evaluation as anti-cancer agents. Specifically, we found that (22S,24S)-24-methyl-22,25-epoxyfurost-5-ene-3β,20β-diol (16), 3β,11-dihydroxy-24-methylene-9,11-secocholestan-5-en-9-one (23), (24S)-ergostane-3β,5α,6β,25 tetraol (146), sinulerectadione (227), sinulerectol C (229), and cladieunicellin I (277) exhibited stronger cytotoxicity than their respective positive control and that their mechanism of action has not yet been further investigated.

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Novel Norhumulene and Xeniaphyllane-Derived Terpenoids from a Formosan Soft Coral Sinularia gibberosa

Cited by 19 publications

References 5 publications

Sesquiterpenoids from the Florets of Carthamus tinctorius (Safflower) and Their Anti-Atherosclerotic Activity

Sesquiterpenoids from the Florets of Carthamus tinctorius (Safflower) and Their Anti-Atherosclerotic Activity

Leptogorgins A–C, Humulane Sesquiterpenoids from the Vietnamese Gorgonian Leptogorgia sp.

Cytotoxic Compounds from Alcyoniidae: An Overview of the Last 30 Years

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