Odookeanynes A and B, Acetylene-Containing Lipopeptides from an Okeania sp. Marine Cyanobacterium

Abstract

Odookeanynes A (1) and B (2), two acetylenecontaining lipopeptides, were isolated from an Okeania sp. marine cyanobacterium collected in Okinawa, Japan. Their structures were elucidated by spectroscopic analysis and Marfey's analysis of acid hydrolysates. Odookeanynes A (1) and B (2) dose-dependently promoted the differentiation of mouse 3T3-L1 preadipocytes in the presence of insulin. ■ RESULTS AND DISCUSSIONThe marine cyanobacterium Okeania sp. (150 g, wet weight) was collected at the shore of Odo, Okinawa, Japan, and extracted with MeOH. The extract was filtered, concentrated,

Marine natural products

“…Notably, the 1amidino-3-(2-aminoethyl)-3-pyrroline amino acid moiety in 239 was shown to enhance activity and selectivity in three human trypsin isoforms over a hundred-fold compared to 240 that contained a 4-amidinobutylamide moiety. Other new cyanobacterial-sourced peptides included the linear peptides amantamide B 241 from Oscillatoria sp., identied via a MS/MSbased molecular networking approach, 97 acetylene-containing odookeanynes A 242 and B 243 from Okeania sp., 98 as well as the cyclic depsipeptides triproamide 244 and pemukainalides A 245 and B 246 isolated from Symploca hydnoides. 99 A novel peptide-polyketide hybrid NP, iezoside 247, was reported from the marine benthic species Leptochromothrix valpauliae.…”

Differentiation-Promoting Effects of Okeaniamides A and B from an Okeania sp. Marine Cyanobacterium on Preadipocytes

“…23 D +1.62 (c 1.00, acetone); IR (neat) 3496, 3389, 3063, 2936, 2835, 1747, 1700, 1598, 1450, 1161, 965, 754, 689 cm −1 ; 1 H NMR (500 MHz, acetone-d 6 ) δ 8.04−8.01 (m, 4H), 7.72−7.67 (m, 2H), 7.60−7.55 (m, 4H), 5.64 (d, J = 16.6, 1H), 5.58 (d, J = 16.6, 1H), 5.57 (d, J = 16.6, 1H), 5.49 (d, J = 16.6, 1H), 4.44 (dd, J = 9.1, 3.7, 1H), 3.49 (s, 3H), 3.12 (dd, J = 16.3, 3.7, 1H), 2.89 (dd, J = 16.3, 9.1 1H); 13 C NMR (125 MHz, acetone-d 6 ) δ 192.87, 192.81, 171.4, 170.2, 135.4, 135.2, 134.8, 134.7, 129.84, 129.80, 128.72, 128.69, 77.4, 67.6, 67.5, 58.8, 38.6; HRESIMS m/z 407.1097 [M + Na] + (calcd for C 21 H 20 O 7 Na, 407.1107). Protocols are the same as reported in a prior study 22. …”