Marine-Derived Macrolides 1990–2020: An Overview of Chemical and Biological Diversity
Abstract
:1. Introduction
2. Chemical and Biological Diversity of Marine-Derived Macrolides
2.1. Macrolides Extracted from Marine Organisms
2.1.1. Sponges
2.1.2. Microorganisms and Zooplankton
Fungi
Bacteria
Cyanobacteria
Dinoflagellates
2.1.3. Red algae
2.1.4. Cnidarians
2.1.5. Bryozoans
2.1.6. Mollusks
2.1.7. Tunicates
2.2. Bioactivities of Marine-Derived Macrolides
Drug Class | Compounds | Pharmacology | Activities | Ref. |
---|---|---|---|---|
Cytotoxic a | swinholides A–C (1–3) | KB cells | IC50: 0.041, 0,052, 1.1 μg/mL | [16] |
miyakolide (13) | P388 cells | IC50: 17.5 μg/mL | [21] | |
spongiastatin 1 (18) | HL-60, NCI-116, DMS 114 et al. | GI50: 2.5–3.5 × 10−11 M | [26] | |
dictyostatin 1 (33) | P388 cells | undetermined | [32] | |
superstolide B (37) | KB, P388, NSCLC-N6-L16 cells | IC50: 0.005, 0.003, 0.039 μg/mL | [38] | |
lasonolide A (38) | A-549, P388 cells | IC50: 40, 2 ng/mL | [40] | |
latrunculin S (44), neolaulimalide (45) | P388, A549, HT29, MEL28 cells | IC50: 0.5–1.2 μg/mL, IC50: 0.01–0.05 μg/mL | [46] | |
leucascandrolide A (48) | KB, P388 cells | undetermined | [48] | |
altohyrtins B–C (51–52) 5-desacetylaltohytrin A (53) | KB cell;L1210 cells | IC50: 0.02, 0.4; 0.3 ng/mL; IC50: 0.03, 1.3, 2.3 ng/mL | [53] | |
swinholide H (54) | P388 cells | undetermined | [13] | |
neonorhalichondrin B (55), neohomohalichondrin B (56), 55-methoxyisohomohalichon-drin (57), 53-methoxyneoisohomohalichondrin B (58a) | P388 cells | IC50: 0.4, 0.8, 10, 0.1 ng/mL | [55] | |
salicylihalamides A (59), B (60) | NCI 60 cells | GI50: 7 ± 2 nM; 60 ± 25 nM | [56] | |
callipeltoside B (61), C (62) | NSCLC-N6 cells | IC50: 15.1, 30.0 μg/mL | [60] | |
arenolide (67) | HCT-116, A2780 cells | IC50: 21, 9.8 mM | [62] | |
30-hydroxymycalolide A (68), 32-hydroxymycalolide A (69), 38-hydroxymycalolide B (70) | L1210 cells | IC50: 0.019, 0.013, 0.015 μg/mL | [63] | |
NA (76), NB (77), NC (78), ND (79) and NE (80) | P388, P388dox, KB tumor cells | undetermined | [66] | |
spongidepsin (87) | J774.A1, HEK-392, WEHI-164 cells | IC50: 0.56, 0.66, 0.42 μg/mL | [71] | |
dactylolide (88) | L1210,SK-OV-3 cells | IC50: 3.2 μg/mL | [72] | |
neohalichondramide (101), (19Z)-halichondramide (102) | K562 cells | LC50: 4.9 μg/mL | [81] | |
lasonolides C–E (106–108) | A-549,PANE-1 cells | IC50: 0.13, 4.5, 0.31 μM; 0.38. 4.89, 0.57, 15.6 μM | [83] | |
leiodolides A (112) and B (113) | HCT-116 cells | IC50: 1.4, 3.8 μg/mL | [86,87] | |
tedanolide C (114) | HCT-116 cells | IC50: 0.057 μg/mL | [88] | |
kabiramide F–I (115–118) | NCI cells | undetermined | [89] | |
swinholide I (120), hurghadolide A (121) | HCT-116 cells | IC50: 5.6, 365 nM | [91] | |
oxalatrunculin B (122) | HepG2, HCT-116,1301 cells | undetermined | [92] | |
neopeltolide (123) | A-549, NCI-ADR-RES, P388 cell lines | IC50: 1.2, 5.1, 0.56 μg/mL | [93] | |
phorbaside C (134) | HCT-116 cells | IC50: 2 μM | [97] | |
tausalarin C (147) | K562 cells | IC50: 1 μg/mL | [102] | |
enigmazole A (153) | IC-2 | IC50: 0.37 μg/mL | [105] | |
callyspongiolide (168) | Jurkat J16 T, Ramos B lymphocytes | IC50: 70, 60 nM | [111] | |
phormidolides B (169), C (170) | A-549, HT-29, MDA-MB-231 cells | undetermined | [112] | |
poecillastrins E (171), F (172), G (173) | 3Y1 cells | IC50: 6.7, 1.2, 5.0 ng/mL | [113] | |
macrosphelide M (180) | HL-60 cell | IC50: 33.2 μM | [120] | |
12,13-deoxyroridin E (191) | HL-60, L1210 cells | IC50: 25, 15 μg/mL | [126] | |
myrothecines H, I (270–271) | HepG-2 cells | IC50: 8, 0.4 μM | [156] | |
marinomycins A–D (283–286) | 60 cell line panel | LC50: 0.005–50 μM | [165] | |
arenicolide A (287) | KB cells | IC50: 30 μg/mL | [166] | |
halichoblelide B (293) | P388 cell line | ED50 0.63 | [169] | |
juvenimicin C (303) | Hepa 1c1c7 cells | undetermined | [173] | |
astolides A (311), B (312) | K-562, Pgp-positive MDR subline K-562/4 | IC50: 1.2–1.4 μM | [179] | |
biselyngbyolide A (330), | HeLa S3, HL60 cells | IC50: 0.22, 0.027 μM | [190] | |
biselyngbyolide B (331) | IC50: 3.5, 0.82 μM | [191] | ||
amphidinolide E (339) | L1210, L5178Y cells | undetermined | [194] | |
amphidinolide G,H (341–342) | L1210, KB cells | IC50: 0.0054, 0.00048 μg/mL; 0.0059, 0.00052 μg/mL | [197] | |
amphidinolides O (351), P (352) | L1210, KB cells | IC50: 1.7, 1.6 μg/mL; IC50: 3.6, 5.8 μg/mL. | [208] | |
amphidinolide Q (353) | L1210 cells | IC50: 6.4 μg/mL | [210] | |
amphidinolides R (354), S (355) | L1210, KB cells | IC50: 1.4, 4.0 μg/mL; IC50: 0.67, 6.5 μg/mL | [213] | |
amphidinolide C3 (357) | P388, L1210, KB cells | undetermined | [215] | |
amphidinolide X (371) | L1210, KB cells | IC50: 0.6, 7.5 μg/mL | [226] | |
amphidinolides B6 (374), B7 (375) | DG-75 cells | IC50: 0.02, 0.4 μg/mL | [227] | |
amphidinolide C2 (376) | L1210, KB cells | IC50: 0.8, 3 μg/mL | [228] | |
caribenolide I (377) | HCT-116, HCT 116/VM 46,P388 | IC50: 1.6 nM, 1.6 nM, 0.03 mg/kg | [229] | |
iriomoteolide-2a (387) | DG-75, cells | IC50: 0.006, 0.03 μg/mL | [238] | |
iriomoteolide-3a (388) | DG-75 cells | IC50: 0.08 μg/mL | [239] | |
iriomoteolide-4a (389), -5a (390) | DG-75 cells | IC50: 0.8, 1.0 μg/mL | [240] | |
iriomoteolide-9a (391), -11a (392) | HeLa cells | IC50: 15, 2 μM | [241] | |
iriomoteolide-10a (393) | HeLa, DG-75, MH134 cells | IC50: 1.5, 1.2, 3.3 μM | [242] | |
iriomoteolide-12a (394) | DG-75 cells | IC50: 50 μM | [242] | |
bromophycolide A (411) | A2780 cells | IC50: 6.7 μM | [258] | |
bromophycolide H (419) | DU4475 cell line | IC50: 3.88 μM | [259] | |
bromophycolides J–Q (421–428) | BT-549, DU4475, MDA-MD-468 et al. | IC50: 2.1–7.2 μM | [260] | |
bromophycolide K (425) | DU4475 cell line | IC50: 1.5 μM | [260] | |
bryostatin 10 (458) | P388 cell line | ED50: 0.33 μg/mL | [277] | |
bryostatins 16 (459), 17 (460), 18 (461) | P388 cell line | ED50: 0.0093, 0.019, 0.033 μg/mL | [282] | |
aplyronines D–H (469–473) | HeLa S3 cells | IC50: 0.075, 0.18, 0.19, 0.12, 9.8 nM | [286] | |
dolabelide A (474), dolabelide B (475) | HeLa S3 cells | IC50: 6.3, 1.3 μg/mL | [287] | |
dolabelides C (476), D (477) | HeLa S3 cells | IC50: 1.9, 1.5 μg/mL | [288,289] | |
iejimalides C (487) and D (488) | KB, L1210 cells | IC50: 4.7, 0.2 μg/mL; 10, 0.58 μg/mL | [298] | |
lobatamides A–F (489–494) | NCT’S 60 cells | mean panel GI50’s 1.6 nM | [301,302] | |
biselides A (496), C (497) | NCI-H460, MDA-MB-231 cells | IC50: 3.53, 3.72 μM; IC50: 18.0, 25.5 μM | [303] | |
palmerolide A (501) | HCC-2998, RXF 393 | LC50: 18, 6.5, 6.5 μM | [305] | |
Antibacteria a | curvulone A (221) | B. subtilis, Microbotryum, violaceum, Septoria tritici, Chlorella fusca | undetermined | [139] |
thiocladospolides F–J (264–268) | Edwardsiella tarda | MIC: 4 μg/mL | [154] | |
marinomycins A–D (283–286) | MRSA, VREF | MIC: 0.1–0.6 μM | [165] | |
11′,12′-dehydroelaiophylin (305) | MRSA, vancomycin-resistant Enterococci pathogens | MIC: 1–4 μg/mL | [175] | |
anthracimycin (308) | Bacillus anthracis (strain UM23C1–1) | MIC: 0.031 μg/mL | [177] | |
bromophycolides A (411), B (412) | MRSA and VREF | MIC: 5.9, 5.9 μM; 5.9, 3.0 μM | [258] | |
bromophycolides P–Q (427–428) | MRSA and VREF | MIC: 1.4, 13 μM; 1.8, 5.8 μM | [260] | |
Antifugal a | leucascandrolide A (48) | C. albicans | undetermined | [48] |
neohalichondramide (101), (19Z)-halichondramide (102) | C. albicans | 12.5 mm at 25 μg/disk | [81] | |
neopeltolide (123) | C. albicans | MIC: 0.62 μg/mL | [93] | |
BK223-A (181) BK223-B (182), BK223-C (183) | Botrytis cinerea, Phoma lingam, Phoma bataem, Pyrenophora teres, Sclerotinia sclerotiorum, Moilinia fructigena, Ascochyta pisi and Alternaria alternata | undetermined | [121] | |
15G256ɩ (197),15G256w; (198) | Neuropora crassa OS-1 | undetermined | [128] | |
Astolides A (311), B (312) | C. albicans, A. niger 219, C. tropicales | MIC: 4, 8 μg/mL | [179] | |
bromophycolides A (411), B (412) | C. albicans | MIC: 6.7, 27.7 μM | [258] | |
bromophycolides F, I (417, 420) | amphotericin B-resistant C. albicans | undetermined | [259] | |
Antimitotic | halistatin 1, 2 (15–16) | Inhibition of tubulin polymerization | undetermined | [23,24] |
spirastrellolide A (94) | accelerating the entry of cells into mitosis | IC50: 100 ng/mL | [79] | |
Antiviral | bromophycolides A (411) | HIV strains 96USHIPS7 and UG/92/029 inhibition | IC50: 9.1,9.8 μg/mL | [258] |
Antiplasmodial | kabiramide L (119) | Against P. flaciparum K1 | IC50: 2.6 μM | [90] |
Antiparasite | bromophycolides R–U (429–432) | Against Pla. falciparum. | IC50: 0.9–8.4 μM | [261] |
VCAM b inhibition | halichlorine (47) | Inhibition to VCAM-1 | IC50: 7 μg/mL | [47] |
Prevent fertilization | exiguolide (111) | Inhibited fertilization of sea urchin gametes | IC50: 21 μM | [84] |
NFκB inhibition | fijiolides A (309) | Reducing TNF-α-inducing NFκB activation | IC50: 0.57 μM | [178] |
Prevent fertilization | oscillariolide (321) | Inhibited fertilization of echinoderm eggs | IC50: 0.5 μg/mL | [182] |
Molluscicidal activity | cyanolide A (329) | Against the snail vector B. glabrata | LC50: 1.2 μM | [189] |
Vasoconstrict-ors | zooxanthellatoxins A (380), B (381) | undetermined | [232,233] | |
Fast-acting toxin | prorocentrolide B (382) | Rapid toxic response in the mouse bioassay | undetermined | [234] |
symbiodinolide (395) | Voltage-dependent N-type Ca2+ channel-opening activity | IC50: 7 nM | [14] | |
acuminolide A (396) | IC50: 10−6 M | [246] | ||
Prevent fertilizatoin | haterumalide B (495) | Inhibited fertilization of sea urchin eggs | IC50: 0.01 μg/mL | [302] |
3. Conclusions and Outlook
Author Contributions
Funding
Conflicts of Interest
References
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Zhang, H.; Zou, J.; Yan, X.; Chen, J.; Cao, X.; Wu, J.; Liu, Y.; Wang, T. Marine-Derived Macrolides 1990–2020: An Overview of Chemical and Biological Diversity. Mar. Drugs 2021, 19, 180. https://doi.org/10.3390/md19040180
Zhang H, Zou J, Yan X, Chen J, Cao X, Wu J, Liu Y, Wang T. Marine-Derived Macrolides 1990–2020: An Overview of Chemical and Biological Diversity. Marine Drugs. 2021; 19(4):180. https://doi.org/10.3390/md19040180
Chicago/Turabian StyleZhang, Hairong, Jiabin Zou, Xiaoxue Yan, Junlong Chen, Xiujiao Cao, Jialing Wu, Yinghui Liu, and Tingting Wang. 2021. "Marine-Derived Macrolides 1990–2020: An Overview of Chemical and Biological Diversity" Marine Drugs 19, no. 4: 180. https://doi.org/10.3390/md19040180