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. 2016 Feb 26;55(16):4882–4907. doi: 10.1002/anie.201508928

Table 2.

Structures of natural fluorescent type‐I phyllobilins (FCCs, top section) and type‐II phyllobilins (DFCCs, iso‐DFCC, bottom section): labels R1, R2, and R4 refer to the generalized formula of FCCs (with atom numbering), shown in Figure 15.

No.[a] R1 R2 R4 C16[b] Provisional names[c] Ref.
22 H H H n At‐FCC‐2 60
6 H CH3 H n Bn‐FCC‐2 (pFCC) 25, 60
epi ‐6 H CH3 H epi Ca‐FCC‐2 (epi‐pFCC) 47
24 OH H H n At‐FCC‐1 60
23 OH CH3 H n 32‐OH‐pFCC 27
epi ‐23 OH CH3 H epi Mc‐FCC‐62 51
23‐Me OH CH3 CH3 epi Mc‐FCC‐71[e] 51
epi ‐41 OH CH3 5′‐daucyl[f] epi Mc‐FCC‐56 28a
epi ‐42 OH CH3 4′‐daucyl[g] epi Mc‐FCC‐53 28a, 85
25 OH CH3 [h] n Sw‐FCC62 74
epi ‐25 OH CH3 [h] epi Ma‐FCC69 76
epi ‐26 OH CH3 [i] epi Ma‐FCC61 28b
epi ‐27 OH CH3 [j] epi Ma‐FCC63 76
epi ‐28 OH CH3 [k] epi Ma‐FCC64 76
epi ‐43 O‐Glc[d] CH3 5′‐daucyl[f] epi Mc‐FCC‐49 85
epi ‐44 O‐Glc[d] CH3 4′‐daucyl[g] epi Mc‐FCC‐46 85
45 O‐Glc[d] CH3 H n AtMESFCC 67
34 OH H H n At‐DFCC‐33 26c
35 OH CH3 H n 27
40 H CH3 H n AtMES2HM‐iso‐DFCC 26a

[a] Compound numbering (see text), R3=vinyl. [b] Relative configuration at C16: n=normal, that is, derived from pFCC, or epi=epimeric, that is, derived from epipFCC. [c] Bn‐FCC‐2 (from oilseed rape, B. napus),25 Ca‐FCC‐2 (from sweet pepper, C. annuum),47 At‐FCCs (from A. thaliana),60 Mc‐FCCs (from banana peels),28a, 51 Ma‐FCCs (from banana leaves, M. acuminata, Cavendish cultivar),28b, 76 and Sw‐FCC‐62 (from senescent leaves of S. wallisii).74 [d] Glc=β‐glucopyranosyl. [e] Apparently an artefact from the methanolysis of persistent FCC daucyl esters. [f] Daucic acid bound at 5′‐OH. [g] Daucic acid bound at 4′‐OH. [h] R4=6‐β‐glucopyranosyl‐(1‐1′)‐2‐[3,4‐dihydroxyphenyl]ethyl. [i] R4=6‐α‐galactopyranosyl‐(1‐6)‐β‐galactopyranosyl‐(1‐1)‐glyceryl. [j] R4=6‐β‐glucopyranosyl. [k] R4=6‐α‐glucopyranosyl.