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Review
. 2011 Dec;9(12):2643-2682.
doi: 10.3390/md9122643. Epub 2011 Dec 15.

Natural products from the Lithistida: a review of the literature since 2000

Priscilla L Winder  1 , Shirley A Pomponi  1 , Amy E Wright  1
Affiliations
Review

Natural products from the Lithistida: a review of the literature since 2000

Priscilla L Winder et al. Mar Drugs. 2011 Dec.

Abstract

Lithistid sponges are known to produce a diverse array of compounds ranging from polyketides, cyclic and linear peptides, alkaloids, pigments, lipids, and sterols. A majority of these structurally complex compounds have very potent and interesting biological activities. It has been a decade since a thorough review has been published that summarizes the literature on the natural products reported from this amazing sponge order. This review provides an update on the current taxonomic classification of the Lithistida, describes structures and biological activities of 131 new natural products, and discusses highlights from the total syntheses of 16 compounds from marine sponges of the Order Lithistida providing a compilation of the literature since the last review published in 2002.

Keywords: Lithistida; Theonella; desmas; lithistid; natural product.

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Figures

Figure 1
Figure 1
Current classification of lithistid sponges [3].
Figure 2
Figure 2
Theopapuamide A (1) was isolated from Theonella swinhoei and theopapuamides B–D (2–4) and celebesides A–C (5–7) were isolated from Siliquariaspongia mirabilis.
Figure 3
Figure 3
Mirabamides A–D (8–11) were isolated from Siliquariaspongia mirabilis while mirabamides E–H (12–15) were isolated from the Astrophorid sponge Stelleta calvosa. Papuamide A (16) is a related compound.
Figure 4
Figure 4
Barangamides A–D (17–20) and theonellapeptolide IIe (21) were isolated from an Indonesian collection of Theonella swinhoei.
Figure 5
Figure 5
Nagahamide A (22) was isolated from a Japanese collection of Theonella swinhoei and microsclerodermins F (23) and H (25) were isolated from Microscleroderma sp.
Figure 6
Figure 6
Microsclerodermin G (24) and I (26) were isolated from a deep-water collection of Microscleroderma sp. Dehydromicrosclerodermins C–D (27–28) were isolated from an Okinawan collection of Theonella cupola.
Figure 7
Figure 7
Scleritodermin A (29) was isolated from Scleritoderma nodosum and isomotuporins A–D (30–33) were isolated from Theonella swinhoei.
Figure 8
Figure 8
Homophymines A–E (34–38) and A1–E1 (39–43) were isolated from a New Caledonian collection of Homophymia sp.
Figure 9
Figure 9
Paltolides A–C (44–46) were isolated from a specimen of Theonella swinhoei collected in deep-water off Palau.
Figure 10
Figure 10
Mutremdamide A (perthamide C, 47) and perthamides D–F (48–50) were isolated from various specimens of Theonella swinhoei.
Figure 11
Figure 11
Koshikamide B (51) was isolated from Theonella sp. and koshikamides F–H (52–54) were isolated from Theonella swinhoei.
Figure 12
Figure 12
A collection of Theonella swinhoei from the Solomon Islands yielded solomonamides A and B (55,56).
Figure 13
Figure 13
Miraziridine A (57) was isolated from a Japanese collection of Theonella aff. mirabilis.
Figure 14
Figure 14
Koshikamide A2 (58) was isolated from a Japanese collection of Theonella sp.
Figure 15
Figure 15
Koshikamides C–E (59–61) were isolated from various specimens of Theonella swinhoei and T. cupola from the reefs of Palau.
Figure 16
Figure 16
The 48-residue linear peptides, polytheonamides A and B (62,63), were isolated from a Japanese collection of Theonella swinhoei.
Figure 17
Figure 17
Hurghadolide A (64) and swinholide I (65) were isolated from an Egyptian collection of Theonella swinhoei.
Figure 18
Figure 18
Swinholide J (66) was isolated from Theonella swinhoei and ankaraholides A and B (67,68) were isolated from the cyanobacteria, Geitlerinema sp.
Figure 19
Figure 19
Swinhoeiamide A (69) was isolated from a Papua New Guinea collection of Theonella swinhoei. Hemicalyculin (70) was isolated from a Japanese collection of Discodermia calyx.
Figure 20
Figure 20
Bitungolides A–F (71–76) were isolated from an Indonesian collection of Theonella cf. swinhoei.
Figure 21
Figure 21
Leiodolides A and B (77,78) were isolated from a deep-water sponge, Leiodermatium sp. collected in Palau.
Figure 22
Figure 22
Leiodermatolide (79) was isolated from a Floridian collection of the deep-water lithistid, Leiodermatium sp.
Figure 23
Figure 23
Five new discodermolide analogues reported from Discodermia sp.: 2-epidiscodermolide (80), 2-desmethyldiscodermolide (81), 5-hydroxymethyl- discodermolide (82), 19-des-aminocarbonyldiscodermolide (83), and 9(13)-cyclodiscodermolide (84).
Figure 24
Figure 24
Neopeltolide (85) was isolated from a deep-water sponge of the Family Neopeltidae. Mirabalin (86), initially published as mirabilin, was isolated from Siliquariaspongia mirabilis.
Figure 25
Figure 25
Dictyostatin-1 (87) was isolated from a deep-water sponge of the Family Neopeltidae. Theopederin F–J (88–92) were isolated from a Japanese collection of Theonella swinhoei. Theopederin K and L (93,94) were isolated from deep-water specimens of Discodermia sp.
Figure 26
Figure 26
Four onnamide A analogs, 21,22-dihydroxyonnamides A1–A4 (95–98), were isolated from an Okinawan collection of Theonella swinhoei.
Figure 27
Figure 27
Lysoplasmanylinositols 1 and 2 (99,100) were isolated from a Japanese collection of Theonella swinhoei.
Figure 28
Figure 28
Calyceramides A–C (101–103) were isolated from a Japanese collection of Discodermia calyx.
Figure 29
Figure 29
Discoside (104) was isolated from a Bahamian collection of Discodermia dissoluta. Azoricasterol (105) was isolated from a deep-water specimen of Macandrewia azorica.
Figure 30
Figure 30
Motualevic acids A–F (106–111) and (4E)-R-antazirine (112) were isolated from a Fijian collection of Siliquariaspongia sp.
Figure 31
Figure 31
Aurantosides G–I (113–115) and aurantoic acid (116) were isolated from Theonella swinhoei.
Figure 32
Figure 32
New conicasterol and theonellasterol derivatives (117–130) isolated from numerous collections of Theonella swinhoei.
Figure 33
Figure 33
Malaitasterol A (131) was isolated from Theonella swinhoei collected in the Solomon Islands.
Figure 34
Figure 34
The discodermindole analog, 6-hydroxydiscodermindole (132), was isolated from Bahamian collections of Discodermia polydiscus.
Figure 35
Figure 35
A multi-gram total synthesis of discodermolide (133) was completed in order for Novartis to begin Phase I clinical trials.
Figure 36
Figure 36
The total syntheses of callipeltoside A (134)and C (135) were completed with the longest linear sequences of 23 and 20 steps, respectively.
Figure 37
Figure 37
The total synthesis of callipeltin B (136) revised its structure from 18S, 21S to 18R, 21R.
Figure 38
Figure 38
The absolute configuration of reidispongiolide A (137) was determined through total synthesis.
Figure 39
Figure 39
The absolute configuration of papuamide B (138) was revised based on the total synthesis.
Figure 40
Figure 40
The total synthesis of superstolide A (139) and microsclerodermin E (140) have recently been achieved.
Figure 41
Figure 41
Cyclotheonamides E2 and E3 (141,142) are potent inhibitors of serine proteases and their total synthesis has been completed.
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References

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