Hamigerans R and S: Nitrogenous Diterpenoids from the New Zealand Marine Sponge Hamigera tarangaensis

Abstract

Seven new members of the hamigeran family of diterpenoids have been isolated from the New Zealand marine sponge Hamigera tarangaensis. Among the new additions are hamigeran R (1), considered to be the first benzonitrile-based marine natural product, and hamigeran S (2), the first dimeric structure in the series. The formation of 1 and 2 is thought to occur via the reaction of hamigeran G with a nitrogen source, where the nitrile carbon of 1 is derived from the terpenoid skeleton.

Bioactive natural products from marine sponges belonging to family Hymedesmiidae

“…However, the other hamigerans exhibited moderate cytotoxic activity against HL-60 cell line with IC 50 values ranging from 11.6-43 mM. 41,44,45 Hamigeran L showed the lowest cytotoxic activity in the same assay. Regarding to (P-388) cell line, the most potent cytotoxic compound was hamigeran D with IC 50 value of 8 mM, while hamigeran B, C and 4-bromohamigeran B showed less cytotoxic activity with IC 50 values of 13.5, 16 and 13.9 mM, respectively.…”

“… 43 Debromohamigeran A (78) 43 and 4-bromohamigeran A (79) 44 are derivatives of hamigeran A and were also isolated from the same sponge. Hamigeran B derivatives are also represented as, 4-bromohamigeran B (80) 43 and debromohamigeran B (81) 44 ( Fig. 13 ).…”

“… 41 While the other hamigeran derivatives were identified as debromohamigeran I (94), debromohamigeran J 44 (95), and 4-bromohamigeran K (96) 41 Hamigeran L derivatives were also identified as, hamigeran L 11- O -methyl ester (97) 41 and hamigeran L 12- O -methyl ester (98). 44 Finally isomeric derivatives of hamigerans 45 were later isolated as 10-epihamigeran K (99) ( Fig. 14 ), 18-epihamigeran N (100), 18-epihamigeran P (101) and 19-epihamigeran Q (102).…”

Exploring Chemical Diversity of <em>Phorbas</em> Sponges as a Source of Novel Lead Compounds in Drug Discovery

“…The genus Phorbas belongs to the class Demospongiae, order Poecilosclerida, family Hymedesmiidae [14], being the biggest representative of the family that contains 10 accepted genera, including beyond Phorbas, Hamigera, Acanthancora, Hemimycale [15][16][17][18]. The genus Phorbas stands out in the number of isolated MNPs, but also in relation to a large number of bioactive compounds, mainly displaying cytotoxic activity [19].…”

Hamigeran G Does Not Affect Golgi Structure or Function in HEK293 Cells

“…The hamigerans are structurally related diterpenoid secondary metabolites that were first isolated from the New Zealand marine sponge, Hamigera tarangaensis (Bergquist and Fromont, 1988). Currently, 34 naturally occurring hamigerans have been reported [3][4][5][6][7]. These compounds show a range of biological activity that includes anticancer, antibacterial, antifungal, and antiviral activity.…”