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‐FCC‐62 | 74 |
epi ‐25 | OH | CH3 | [h] | epi | Ma‐FCC‐69 | 76 |
epi ‐26 | OH | CH3 | [i] | epi | Ma‐FCC‐61 | 28b |
epi ‐27 | OH | CH3 | [j] | epi | Ma‐FCC‐63 | 76 |
epi ‐28 | OH | CH3 | [k] | epi | Ma‐FCC‐64 | 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 | AtMES‐FCC | 67 |
34 | OH | H | H | n | At‐DFCC‐33 | 26c |
35 | OH | CH3 | H | n | 27 | |
40 | H | CH3 | H | n | AtMES‐2HM‐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 epi‐pFCC. [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.