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Review
. 2017 May 11;22(5):781.
doi: 10.3390/molecules22050781.

Bioactive Natural Products of Marine Sponges from the Genus Hyrtios

Nourhan Hisham Shady  1 , Ebaa M El-Hossary  2 , Mostafa A Fouad  3 , Tobias A M Gulder  4 , Mohamed Salah Kamel  5 , Usama Ramadan Abdelmohsen  6   7
Affiliations
Review

Bioactive Natural Products of Marine Sponges from the Genus Hyrtios

Nourhan Hisham Shady et al. Molecules. .

Abstract

Marine sponges are known as a rich source for novel bioactive compounds with valuable pharmacological potential. One of the most predominant sponge genera is Hyrtios, reported to have various species such as Hyrtios erectus, Hyrtios reticulatus, Hyrtios gumminae, Hyrtios communis, and Hyrtios tubulatus and a number of undescribed species. Members of the genus Hyrtios are a rich source of natural products with diverse and valuable biological activities, represented by different chemical classes including alkaloids, sesterterpenes and sesquiterpenes. This review covers the literature until June 2016, providing a complete survey of all compounds isolated from the genus Hyrtios with their corresponding biological activities whenever applicable.

Keywords: Hyrtios; alkaloids; bioactive; marine natural products; marine sponges.

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Conflict of interest statement

The authors declare no conflict of interest. The founding sponsors had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript, and in the decision to publish the results.

Figures

Figure 1
Figure 1
Chemical structures of 5-hydroxyindole-3-aldehyde (1), hyrtiosin A (2) and hyrtiosin B (3).
Figure 2
Figure 2
Chemical structure of hyrtiomanzamine (4).
Figure 3
Figure 3
Chemical structures of sesterstatin 4 (5) and sesterstatin 5 (6).
Figure 4
Figure 4
Chemical structures of compound 7, compound 8, isodehydroluffariellolide (9), homofascaplysin A (10) and fascaplysin (11).
Figure 5
Figure 5
Chemical structures of the indole alkaloids (12–16) and compound 17.
Figure 6
Figure 6
Chemical structures of salmahyrtisol A (18), 3-acetyl sesterstatin (19), 19-acetyl sesterstatin 3 (20), salmahyrtisol B (21), hyrtiosal (22), scalarolide (23) and salmahyrtisol C (24).
Figure 7
Figure 7
Chemical structures of sesterstatin 7 (25), 16-epi-scalarolbutenolide (26) and 25-dehydroxy-12-epi-deacetylscalarin (27).
Figure 8
Figure 8
Chemical structure of sesterstatin 6 (28).
Figure 9
Figure 9
Chemical structures of hainanerectamine A (29), hainanerectamine B (30), hainanerectamine C (31) and the alkaloids 32–35.
Figure 10
Figure 10
Chemical structures of the diketotriterpenoid 36, hyrtiolide (37), 16-hydroxyscalarolide (38), 12-deacetyl-∆17-hyrtial (39) and 12-deacetylhyrtial (40).
Figure 11
Figure 11
Chemical structure of hyrtiosulawesine (41).
Figure 12
Figure 12
Chemical structures of 20-formylhyrtiosal (42), 16-O-acetyl-20-formylhyrtiosal (43), 12-α-O-acetylhyrtiolide (44), 5,10-dihydroxyfurospinulosine-1 (45) and compounds 46–52.
Figure 13
Figure 13
Chemical structures of hyrtiazepine (53) and compound 54.
Figure 14
Figure 14
Chemical structures of deoxyhyrtiosine A (55), indole-3-carbaldehyde (56), 12-O-deacetyl-12-epi-scalarine (57) and 5α,8α-epidioxy-cholesta-6-en-3β-ol (58).
Figure 15
Figure 15
Chemical structure of hyrtiosal (59).
Figure 16
Figure 16
Chemical structures of 12-acetoxy,16-epi-hyrtiolide (60), 12β-acetoxy,16β-methoxy,20α-hydroxy-17-scalaren-19,20-olide (61) and the sesterterpenes 62–66.
Figure 17
Figure 17
Chemical structures of serotonin (67) and compounds 68–70.
Figure 18
Figure 18
Chemical structure of hyrtiocarboline (71).
Figure 19
Figure 19
Chemical structures of hyrtioreticulin A (72), hyrtioreticulins C-E (73–75) and hyrtioerectine B (76).
Figure 20
Figure 20
Chemical structures of reticulatin A (77), reticulatin B (78) and hyrtioreticulin F (79).
Figure 21
Figure 21
Chemical structures of similan A (80) and compounds 81–89.
Figure 21
Figure 21
Chemical structures of similan A (80) and compounds 81–89.
Figure 22
Figure 22
Chemical structures of the sesterterpenes 90–102.
Figure 23
Figure 23
Chemical structures of arenarol (103), 5-epiilimaquinone (104) and 21-hydroxy-19-methoxyarenarone (105).
Figure 24
Figure 24
Chemical structure of dipuupehedione (106).
Figure 25
Figure 25
Chemical structures of puupehenone (107) and 15α-methoxypuupehenol (108).
Figure 26
Figure 26
Chemical structures of isospongiaquinone (109), hyrtiophenol (110), 5-epihyrtiophenol (111), 18-hydroxy-5-epihyrtiophenol (112) and 18-hydroxyhyrtiophenol (113).
Figure 27
Figure 27
Chemical structures of compounds 114–116.
Figure 28
Figure 28
Chemical structures of hyrtiosenolide A (117), hyrtiosenolide B (118) and hyrtiosterol (119).
Figure 29
Figure 29
Chemical structure of poipuol (120).
Figure 30
Figure 30
Chemical structure of hyrtinadine A (121).
Figure 31
Figure 31
Chemical structure of compound 122.
Figure 32
Figure 32
Chemical structures of puupehanol (123) and chloropuupehenone (124).
Figure 33
Figure 33
Chemical structures of hyrtimomine D (125) and hyrtimomine E (126).
Figure 34
Figure 34
Chemical structures of aureol (127), N,N-dimethyl-5,6-dibromotryptamine (128), 5,6-dibromoabrine (129) and 5,6-dibromo-L-hypaphorine (130).
Figure 35
Figure 35
Chemical structures of hyrtioseragamine A (131) and hyrtioseragamine B (132).
Figure 36
Figure 36
Chemical structures of hyrtimomine A (133), hyrtimomine B (134) and hyrtimomine C (135).
Figure 37
Figure 37
Chemical structures of hyrtimomines F–K (136–141).
Figure 38
Figure 38
Chemical structures of 6-oxofascaplysin (142), secofascaplysic acid (143) and reticulatate (144).
Figure 39
Figure 39
Chemical structures of hyrtinadine C (145) and hyrtinadine D (146).
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