Penicillosides A and B: new cerebrosides from the marine-derived fungus Penicillium species

New Cerebroside and Nucleoside Derivatives from a Red Sea Strain of the Marine Cyanobacterium Moorea producens

“…Its molecular formula was suggested as C48H93NO8 on the basis of the HRESIMS quasi-molecular ion peak at m/z 812.6982 [M + H] + and 1 H-and 13 C-NMR spectral analyses, requiring three degrees of unsaturation. Its IR spectrum showed characteristic absorption bands at 3435 (hydroxyl), 3320 and 1635 (amide), 3005 and 960 (olefinic), and 1150 (C-O) cm −1 , suggesting the cerebroside nature of 1 [20][21][22][23] (Table 1) which was supported y COSY correlation ( Figure S6). These protons correlated to the carbon signals at δ C 129.9 and 128.8, respectively, in the HSQC spectrum ( Figure S7).…”

“…The aqueous layer was evaporated to dryness and subjected to Sephadex LH-20 using CHCl 3 :MeOH (10:90) to give LCB and sugar. The base was analyzed by EIMS [22].…”

Tricalycoside, a New Cerebroside from Tricalysia coriacea (Rubiaceae)

“…The 13 C‐NMR spectrum ( Table ) of 1 displayed carbon signals at δ (C) 174.3 (C(1′)), 69.4 (C(1)), 50.4 (C(2)), 29.6 – 29.5 (C(7)/C(20) – C(22)/C(4′) – C(15′)), and 14.5 (C(25)/C(18′)), corresponding to the typical signals for sphingolipids. [ ][ ] Moreover, the presence of signals in the 13 C‐NMR spectrum at δ (C) 104.0 (C(1″)), 74.1 (C(2″)), 77.0 (C(3″)), 71.4 (C(4″)), 77.4 (C(5″)), and 61.6 (C(6″)) confirmed the existence of a glycosyl moiety in 1 , as suggested by 1 H‐NMR data. Its nature was identified as d ‐glucose by HPLC analysis after hydrolysis of 1 and conversion of the released sugar to o ‐tolylthiocarbamoyl thiazolidine derivative.…”

“…s )), two terminal methyl groups (each δ (H) 0.85 ( t , J = 6.3)), and an anomeric proton ( δ (H) 4.13 ( d , J = 7.5)), which are the characteristic signals for cerebroside skeleton. [ ][ ] Further signals were observed in the 1 H‐NMR spectrum at δ (H) 5.34 – 5.29 ( m , H–C(10)/H–C(11)/H–C(16)/H–C(17)), 3.10 – 3.06 ( m , H–C(3)), 3.06 – 3.00 ( m , H–C(4)), 3.80 ( q , J = 8.0, 4.0, H–C(5)), and 3.37 – 3.30 ( m , H–C(2′)), suggesting that the two long‐chain moieties of 1 had two olefinic, and four oxymethine groups. Moreover, the 1 H‐NMR spectrum revealed the presence of one glycosyl moiety in 1 , which is characterized by the signals at δ (H) 2.93 ( t , J = 8.0, H–C(2″)), 3.10 – 3.06 ( m , H–C(3″)), 3.85 (br.…”

LAMA-1: A Cerebroside Isolated from the Deep-Sea-Derived Fungus Penicillium chrysogenum

“…Since the late 1990s, hundreds of novel compounds have been isolated and characterized from marine habitats annually [3], in stark contrast to their terrestrial counterparts. The most explored fungal isolates by the natural products chemists are the Penicillium species, which are considered a major source for drug discovery [4][5][6][7][8]. Currently, as reported in many recent reviews [9][10][11][12][13], the Penicillium genus still represents a major producer of diverse biologically active metabolites.…”