Table 2.
The biological activities of cembranoid isolates from genera Sinularia
| Entry | Compound name (number) | Novelty | Sources | Geographical area of collection | Biological activities | References |
|---|---|---|---|---|---|---|
| 1 | Sinulerectol A (170) | New | Sinularia erecta | Off the coast of Dongsha Atoll, north of the South China Sea | Anti-inflammatory activities through inhibition of superoxide generation and elastase release in fMLP/CB-induced human neutrophils with IC50 value of 2.3 ± 0.4 μM | [49] |
| 2 | Sinulerectol B (171) | New | Sinularia erecta | Off the coast of Dongsha Atoll, north of the South China Sea | Anti-inflammatory activities through inhibition of superoxide generation and elastase release in fMLP/CB-induced human neutrophils with IC50 value of 8.5 ± 0.3 μM | [49] |
| 3 | Sinulerectol C (172) | New | Sinularia erecta | Off the coast of Dongsha Atoll, north of the South China Sea | Anti-proliferation activity against K-562 cell line with IC50 value of 9.2 ± 3.3 μM | [49] |
| 4 | Isodecaryiol (173) | New | Sinularia gravis | Inner reef of Mahambo, Tamatave province at the east coast of Madagascar | Compound not tested | [50] |
| 5 | Nanolobol A (174) | New | Sinularia nanolobata | Off the coast of Jihui Fishing Port, Taitung county, Taiwan | Not cytotoxic against P388, K-562, HT-29 | [51] |
| 6 | Nanolobol B (175) | New | Sinularia nanolobata | Off the coast of Jihui Fishing Port, Taitung county, Taiwan | Not cytotoxic against P388, K-562, HT-29 | [51] |
| 7 | Nanolobol C (176) | New | Sinularia nanolobata | Off the coast of Jihui Fishing Port, Taitung county, Taiwan | Not cytotoxic against P388, K-562, HT-29 | [51] |
| 8 | Sinulariol C (177) | Known | Sinularia nanolobata | Off the coast of Jihui Fishing Port, Taitung county, Taiwan | Anti-inflammatory activity through NO reduction on RAW 264.7 cells to 19.6% and 2.3% at concentration of 50 μM and 100 μM with high cell viability | [51] |
| 9 | Sinularia scabra | Off the coast of Xigu Island, Hainan Province, China | Strong inhibitory activity on the proliferation of Con A-induced T lymphocyte cells with IC50 value of 4.5 µM | [52] | ||
| 10 | 5-epi-Sinuleptolide (178) | New | Sinularia compacta | Tongguling National Nature Reserve of Coral Reefs, South China Sea | Anti-proliferation activity against HCT-116 and A-549 with IC50 values of 10.1 and 14.7 μM, respectively | [53] |
| 11 | Sinularia sp. | Yongxing Island of Xisha Islands in the South China Sea | Anti-proliferation activity against HeLa and HCT-116 with IC50 values of 11.6 and 33.3 μM, respectively | [54] | ||
| 12 | Michaolide F (179) | New | Sinularia compacta | Tongguling National Nature Reserve of Coral Reefs, South China Sea | Exhibited lethality against brine shrimp Artemia salina with lethal ratio of 90.5% at concentration of 50 μg/mL | [53] |
| 13 | 20-Acetylsinularolide B (180) | New | Sinularia compacta | Tongguling National Nature Reserve of Coral Reefs, South China Sea | Exhibited lethality against brine shrimp Artemia salina with lethal ratio of 90.0% at concentration of 50 μg/mL | [53] |
| 14 | 7-Acetylsinumaximol B (7-AB) (181) | Known | Sinularia sandensis | Aquaculture | Exerted a concentration-dependent anti-proliferative effect on NCI-N87 cells and apoptosis induction. Anti-proliferation activity was associated with the release of cytochrome c from mitochondria, activation of pro-apoptotic proteins (such as caspase-3/-9, Bax and Bad), and inhibition of anti-apoptotic proteins (Bcl-2, Bcl-xL, and Mcl-1). 7-AB also triggered endoplasmic reticulum (ER) stress, leading to activation of the PERK/elF2α/ATF4/CHOP apoptotic pathway. 7-AB initiated autophagy in NCI-N87 cells and induced the expression of autophagy-related proteins, including Atg3, Atg5, Atg7, Atg12, LC3-I, and LC3-II | [55] |
| 15 | Sinularolide F (182) | New | Sinularia sp. | Mantanani Island, Sabah | Anti-inflammatory activity through inhibition of NO, IL-1β, IL-6 and anti-proliferation activity through apoptosis induction | [56] |
| 16 | Denticulatolide (183) | Known | Sinularia sp. | Mantanani Island, Sabah | Anti-inflammatory activity through inhibition of NO, IL-1β, IL-6 and anti-proliferation activity through apoptosis induction | [56] |
| 17 | Flexibilisin D (184) | New | Sinularia flexibilis | Off the coast of Liuqiu, Taiwan | Not toxic towards P-388, K-562, and HT-29 cancer cell lines (IC50 values > 40 µM) and did not have anti-inflammatory effect through N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF-CB)-induced superoxide anion generation and elastase release assay in human neutrophils at concentration of 10 µM | [57] |
| 18 | Flexibilisin E (185) | New | Sinularia flexibilis | Off the coast of Liuqiu, Taiwan | Not toxic towards P-388, K-562, and HT-29 cancer cell lines (IC50 values > 40 µM) and did not have anti-inflammatory effect through N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF-CB)-induced superoxide anion generation and elastase release assay in human neutrophils at concentration of 10 µM | [57] |
| 19 | Flexibilisolide H (186) | New | Sinularia flexibilis | Off the coast of Liuqiu, Taiwan | Not toxic towards P-388, K-562, and HT-29 cancer cell lines (IC50 values > 40 µM) and did not have anti-inflammatory effect through N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF-CB)-induced superoxide anion generation and elastase release assay in human neutrophils at concentration of 10 µM | [57] |
| 20 | 11-Dehydrosinulariolide (187) | Known | Sinularia flexibilis | Off the coast of Liuqiu, Taiwan | Anti-proliferation activity against P388, K562, HT29 cancer cell line with IC50 values of 9.3, 23.4, and 15.9 μM, respectively | [57] |
| 21 | Off the coast of Yalong Bay, Hainan, China | Broad anti-proliferation activity against A549, HT-29, SNU-398, and Capan-1 human tumor cell lines with IC50 values of 27.4, 22.7, 8.9, and 9.4 µM, respectively | [58] | |||
| 22 | 11-epi-Sinulariolide acetate (188) | Known | Sinularia flexibilis | Off the coast of Liuqiu, Taiwan | Anti-proliferation activity against P388, K562, HT29 cancer cell line with IC50 values of 6.9, 12.2, and 9.6 μM, respectively | [57] |
| 23 | Off the coast of Yalong Bay, Hainan, China | High anti-inflammatory activity through inhibition levels of TNF-α with IC50 value of 2.7 µM. Moderate anti-proliferation activities against HT-29, SNU-398, and Capan-1 with IC50 values ranging from 24.9 to 32.6 µM | [58] | |||
| 24 | (S)-14-Deoxycrassin (189) | Known | Sinularia flexibilis | Off the coast of Liuqiu, Taiwan | Anti-proliferation activity against P388 and K562 cancer cell line with IC50 values of 16.0 and 26.7 μM, respectively. Anti-inflammatory activity through inhibition of superoxide anion generation and elastase release | [57] |
| 25 | Off the coast of Liuqiu, Taiwan | Anti-proliferation activity against K562 and HT29 cancer cell line with IC50 values of 21.7 and 27.1 μM, respectively | [57] | |||
| 26 | Sinulariolide (190) | Known | Sinularia flexibilis | Off the coast of Yalong Bay, Hainan, China | Low anti-inflammatory activity through inhibition levels of TNF-α with IC50 value of 4.7 µM. Moderate anti-proliferation activities against HT-29, SNU-398, and Capan-1 with IC50 values ranging from 24.7 to 33.6 µM | [58] |
| 27 | Sinularia scabra | Off the coast of Xigu Island, Hainan Province, China | Significant inhibitory effects on the proliferation of LPS induced B lymphocyte cells with IC50 value of 9.2 µM | [52] | ||
| 28 | Sandensolide (191) | Known | Sinularia flexibilis | National Museum of Marine Biology & Aquarium, Pingtung, Taiwan | Anti-oral cancer activity by inducing oxidative stress-mediated cell death pathways through suppressing colony formation, inducing apoptosis, cell cycle arrest, induction of reactive oxygen species (ROS) and was observed in in vitro cultured human OSCC models (Ca9.22, SCC9 and HSC-3 cell lines) | [59] |
| 29 | Sinulin C (192) | New | Sinularia sp. | Yongxing Island of Xisha Islands in the South China Sea | Not cytotoxic against HeLa, HCT-116, and A549 tumour cell lines and did not have inhibitory activity against PTP1B | [54] |
| 30 | Sinulin D (193) | New | Sinularia sp. | Yongxing Island of Xisha Islands in the South China Sea | Mild inhibitory activity against PTP1B with IC50 value of 47.5 mM (with sodium orthovanadate as positive control, IC50 881 μM) | [54] |
| 31 | (1R,3S,4S,7E,11E)-3,4-Epoxycembra-7,11,15-triene (194) | Known | Sinularia sp. | Yongxing Island of Xisha Islands in the South China Sea | Mild inhibitory activity against PTP1B with IC50 value of 12.5 mM (with sodium orthovanadate as positive control, IC50 881 μM) | [54] |
| 32 | Xidaosinularide A (195) | New | Sinularia flexibilis | Off the coast of Yalong Bay, Hainan, China | Low anti-inflammatory activity through inhibition levels of TNF-α with IC50 value of 20.7 µM | [58] |
| 33 | Xidaosinularide B (196) | New | Sinularia flexibilis | Off the coast of Yalong Bay, Hainan, China | Low anti-inflammatory activity through inhibition levels of TNF-α with IC50 value of 38.9 µM | [58] |
| 34 | Xidaosinularide C (197) | New | Sinularia flexibilis | Off the coast of Yalong Bay, Hainan, China | Very low anti-inflammatory activity through inhibition levels of TNF-α with IC50 value > 50 µM | [58] |
| 35 | Sinuladiterpene I (198) | Known | Sinularia flexibilis | Off the coast of Yalong Bay, Hainan, China | Moderate anti-inflammatory activity through inhibition levels of TNF-α with IC50 value of 13.3 µM | [58] |
| 36 | Flexilarin B (199) | Known | Sinularia flexibilis | Off the coast of Yalong Bay, Hainan, China | Low anti-inflammatory activity through inhibition levels of TNF-α with IC50 value of 4.2 µM | [58] |
| 37 | 1E,3E,7E,-11-hydroxy-12-methoxy-1-isopropyl-4,8,12-trimethyl-icyclotetradeca-1,3,7-triene (200) | New | Sinularia sp. | Xisha Islands, South China Sea, China | Moderate inhibitory activity against Aß42 aggregation with percent inhibition of 20.6% at 10 µM (showed equal potency than the positive control curcumin (20.5%)) | [60] |
| 38 |
3E,7E-11-hydroxy-12-methoxy-1-isopropenyl-4,8,12-trimethyl-icyclo tetradeca-3,7-diene (201) |
New | Sinularia sp. | Xisha Islands, South China Sea, China | Showed no potent activity against Aß42 aggregation inhibition (2.1%) and no cytotoxicity against human tumor cell lines (SH-SY5Y, MDA-MB-426, A549, Hep3B, and HT-29) with proliferation inhibitory rate < 50% at concentration of 10 and 100 µM, respectively | [60] |
| 39 |
1E,3Z,7E,-11-hydroxy-12- methoxy-1-isopropyl-4,8,12-trimethyl-icyclotetradeca-1,3,7-triene (202) |
New | Sinularia sp. | Xisha Islands, South China Sea, China | Moderate inhibitory activity against Aß42 aggregation with percent inhibition of 37.2% at 10 µM (showed higher potency than the positive control curcumin (20.5%)) | [60] |
| 40 | 1Z,3Z,7E,-11-hydroxy-12-methoxy-1-isopropyl-4,8,12-trimethyl-icyclotetradeca-1,3,7-triene (203) | New | Sinularia sp. | Xisha Islands, South China Sea, China | Showed no potent activity against Aß42 aggregation inhibition (1.5%) and no cytotoxicity against human tumour cell lines (SH-SY5Y, MDA-MB-426, A549, Hep3B, and HT-29) with proliferation inhibitory rate < 50% at concentration of 10 and 100 µM, respectively | [60] |
| 41 | Xiguscabrate A (204) | New | Sinularia scabra | Off the coast of Xigu Island, Hainan Province, China | No inhibitory activity on the proliferation of Con A-induced T lymphocyte cells with IC50 values > 50 µM | [52] |
| 42 | Xiguscabrate B (205) | New | Sinularia scabra | Off the coast of Xigu Island, Hainan Province, China | Strong inhibitory activity on the proliferation of Con A-induced T lymphocyte cells with IC50 value of 8.4 µM | [52] |
| 43 | Xiguscabral A (206) | New | Sinularia scabra | Off the coast of Xigu Island, Hainan Province, China | No inhibitory activity on the proliferation of Con A-induced T lymphocyte cells with IC50 values of 15.8 µM | [52] |
| 44 | Xiguscabrol A (207) | New | Sinularia scabra | Off the coast of Xigu Island, Hainan Province, China | Strong inhibitory activity on the proliferation of Con A-induced T lymphocyte cells with IC50 value of 5.5 µM | [52] |
| 45 | Xiguscabrol B (208) | New | Sinularia scabra | Off the coast of Xigu Island, Hainan Province, China | Strong inhibitory activity on the proliferation of Con A-induced T lymphocyte cells with IC50 value 3.9 µM | [52] |
| 46 | 8-epi-Xiguscabrol B (209) | New | Sinularia scabra | Off the coast of Xigu Island, Hainan Province, China | Strong inhibitory activity on the proliferation of Con A-induced T lymphocyte cells with IC50 value of 2.3 µM | [52] |
| 47 | (2R,11S,12S)-Isosarco phytoxide (210) | Known | Sinularia scabra | Off the coast of Xigu Island, Hainan Province, China | Considerable specific inhibition on B cell proliferation, with IC50 value of 4.4 µM and selectivity index (SI) of 10.9, much better than the positive control CsA (SI = 3.0). It dose-dependently inhibited CD19+ B cells proliferation by LPS induction. 180 also showed modulatory effects on cytokines production, with the manifestation of decreased IL-6 production and slightly increased IL-10 production. 180 could suppress the derivational expression of CD86 on CD19+ B cells upon LPS stimulation. In vitro, LPS addition led to B cells growth and plasma cells formation (from 2.31% to 11.0%) and compound 180 dose-dependently inhibited the percentage of plasma cells | [52] |
| 48 | ( −)-14-Deoxycrassin (211) | Known | Sinularia scabra | Off the coast of Xigu Island, Hainan Province, China | Strong inhibitory activity on the proliferation of Con A-induced T lymphocyte cells with IC50 value of 6.1 µM | [52] |
| 49 | Sinulacrassin A (212) | New | Sinularia crassa | West Island, South China Sea | Compound not tested | [61] |
| 50 | Sinulacrassin B (213) | New | Sinularia crassa | West Island, South China Sea | Inhibitory effect toward α-Glucosidase with IC50 value of 10.65 ± 0.16 μM; not toxic against LO2 cells with IC50 > 100 μM | [61] |
| 51 | Sinulacrassin C (214) | New | Sinularia crassa | West Island, South China Sea | No inhibitory effect toward α-Glucosidase | [61] |
| 52 | ent-Xishaflavalin G (215) | New | Sinularia crasa | West Island, South China Sea | No inhibitory effect toward α-Glucosidase | [61] |
| 53 | S-( +)-Cembrane A (216) | Known | Sinularia crassa | West Island, South China Sea | Inhibitory effect toward α-Glucosidase with IC50 value of 30.31 ± 1.22 μM; not toxic against LO2 cells with IC50 > 100 μM | [61] |
| 54 | Humilisin A (217) | New | Sinularia humilis | Ximao Islands, Hainan, China | No anti-inflammatory effects in LPS-stimulated BV-2 microglial cells | [62] |
| 55 | Humilisin B (218) | New | Sinularia humilis | Ximao Islands, Hainan, China | No anti-inflammatory effects in LPS-stimulated BV-2 microglial cells | [62] |
| 56 | Humilisin C (219) | New | Sinularia humilis | Ximao Islands, Hainan, China | No anti-inflammatory effects in LPS-stimulated BV-2 microglial cells | [62] |
| 57 | Humilisin D (220) | New | Sinularia humilis | Ximao Islands, Hainan, China | No anti-inflammatory effects in LPS-stimulated BV-2 microglial cells | [62] |
| 58 | Humilisin E (221) | New | Sinularia humilis | Ximao Islands, Hainan, China | No anti-inflammatory effects in LPS-stimulated BV-2 microglial cells | [62] |
| 59 | Humilisin F (222) | New | Sinularia humilis | Ximao Islands, Hainan, China | Significant anti-inflammatory effects in LPS-stimulated BV-2 microglial cells with 83.96% ± 2.02% and 65.70% ± 2.76% NO level decrease at 10 and 20 μM, respectively; low toxicity toward BV-2 microglial cells | [62] |