Phyllobilins the Abundant Tetrapyrrolic Catabolites of the Green. Plant Pigment Chlorophyll. Bernhard Kräutler
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1 Electronic Supplementary Material (ESI) for Chemical Society Reviews. This journal is The Royal Society of Chemistry 2014 Phyllobilin-TutRev-ESI-BKräutler S1 Phyllobilins the Abundant Tetrapyrrolic Catabolites of the Green Plant Pigment Chlorophyll Bernhard Kräutler Institute of rganic Chemistry and Centre of Molecular Biosciences, University of Innsbruck, Innrain 80/82, A-6020-Innsbruck, Austria Supporting Information Atom numbering Phyllobilin nomenclature Generalized formulas of NCCs and FCCs Lists of the known NCCs, FCCs and DNCCs References
2 S N N 15 5 N N C phytoporphyrin C171 C131 C182 C181 C17 C C19 N24 C14 N23 C13 C11 C12 C16 C15 C121 C122 C123 C10 C82 C83 C C21 C1 C2 C3 C31 C32 N21 N22 C9 84 C8 C81 C4 82 C6 C85 C5 C7 C C A N N D B N N C E C 2 C 3 pheophorbide a 10 C21 C181 C32 C31 C3 C2 C1 C20 41 C4 N21 C19 N24 C18 C16 C17 C171 C172 C173 C15 C132 C133 C5 51 C71 C6 C7 C8 C81 C82 N22 N23 C14 C13 C C9 C C10 C12 C135 C121 Figure S1. Atom numbering for phyllobilins. Top. Phytoporphyrin formula with adapted atom numbering (left) and deduced atom numbering system used here for phyllobilin skeleton (right). Bottom. Formula of pheophorbide a (Pheo a) with conventional atom numbering (left) and corresponding atom numbering for Chl-catabolites, used in earlier publications (right).
3 S3 Figure S2a. Phyllobilin nomenclature (part a): phyllobilane, two isomeric phyllobilenes-c, and corresponding examples of three natural phyllobilins.
4 S4 Figure S2b. Phyllobilin nomenclature (part b): phyllobilene-b and two phyllobiladienes-b,c, and corresponding examples of three natural phyllobilins.
5 S N N R 1 R 4 N 19 1 N R 1 N N N N R 3 2 C C 2 R 2 R 3 2 C C 2 R 2 FCCs NCCs Figure S3. Generalized formulas for FCCs and NCCs, two type-i phyllobilins (for specifications of R 1 to R 4 in known natural type-i phyllobilins, see Tables S1 and S2).
6 S6 Table S1: Structures of natural non-fluorescent Chl-catabolites (NCCs): labels R 1 to R 4 refer to the generalized formula of NCCs (Figure S3); atom numbering, as shown in Figure S1. R 1 [a] R 2 R 3 R 4 C16 [b] provisional names [c] Ref. C 3 C()C 2 n v-ncc-1 1, 2 C 3 C()C 2 epi So-NCC-2 (Mc-NCC-42) C 3 C=C 2 n Sw-NCC-58 C 3 C=C 2 epi Cj-NCC-1 (So-NCC-4 / Pc-NCC-2 / Md-NCC-2 / Mc-NCC-61) C 3 C=C 2 epi Cj-NCC-2 (So-NCC-5) -Glc C 3 C=C 2 epi Nr-NCC-2 (Zm-NCC-2 / Pc-NCC-1 / Md-NCC-1 / Tc-NCC-2 / Mc-NCC-59 / Ug-NCC-43) -Glc C 3 C()C 2 epi Zm-NCC-1 (Tc-NCC-1 / Ug-NCC-27) -(6 -- Mal)-Glc C 3 C=C 2 epi Nr-NCC-1 C=C 2 n Bn-NCC-4 (At-NCC-5) C=C 2 n Bn-NCC-3 (At-NCC-2) C=C 2 epi So-NCC-3 (Mc-NCC-49) C()C 2 epi So-NCC-1 (Mc-NCC-26) -Mal C=C 2 n Bn-NCC-1 -Glc C=C 2 n Bn-NCC-2 (At-NCC-1) C 3 C 3 [d] [d] C = C 2 epi [e] Mc-NCC-58 C = C 2 epi [f] Mc-NCC , 5, 7-9 4, 8 5, , 15 14, 16 4, 5 4, 5 16, 17 14, [a] abbreviations: Mal = malonyl; Glc = -glucopyranosyl; [b] configuration at C16 from correlation with NCCs derived from pfcc (n = normal ) or from epi-pfcc (epi = epimeric ), the absolute configuration at C16 is still unknown; [c] for specific provisional names see references: v-ncc-1 (from barley, ordeum vulgare) 1, 2, So-NCC s (from spinach, Spinacia oleracea), 3, 4 Cj-NCCs (from Katsura tree, Cercidiphyllum japonicum), 7, 8 Sw-NCC-58 (from Peace Lily, Spathiphyllum wallisii), 6 Pc-NCCs (from Pyrus communis), 9 Md-NCCs (from Malus domestica), 9 At-NCCs (from Arabidopsis thaliana, At-NCC-3 carries a -C 2 -group at C2, see ref. 18 ), 14, 18 Nr-NCCs (from tobacco, Nicotiana rustica), 10 Zm- NCCs (from maize, Zea mays) 11, and Bn-NCCs (from oilseed rape, Brassica napus), Tc- NCCs (from Lime tree, Tilia cordata), 12 ), Ug-NCCs (from Dutch Elm tree, Ulmus glabra 13 ) and Mc-NCCs (from banana peels, Musa acuminata, Cavendish cultivar). 5 [d] R 3 = daucic acid;); [e] R-configuration at C10; [f] S-configuration at C10 (configuration derived from CDspectra 5 ).
7 S7 Table 2. Structures of natural fluorescent Chl-catabolites (FCCs): labels R 1 to R 3 refer to the generalized formula of FCCs (Figure S3); atom numbering, as shown in Figure S1. R 1 R 2 R 3 C16 [a] provisional names [b] Ref. C 3 n Bn-FCC-2 (pfcc) 19 C 3 epi Ca-FCC-2 (epi-pfcc) n At-FCC-2 n At-FCC-1 C 3 epi Mc-FCC-62 C 3 C 3 epi Mc-FCC-71 [d] C 3 5 -daucyl [e] epi Mc-FCC-56 C 3 4 -daucyl [f] epi Mc-FCC-53 -Glc [c] C 3 5 -daucyl [e] epi Mc-FCC-49 -Glc [c] C 3 4 -daucyl [f] epi Mc-FCC C 3 [g] n Sw-FCC-62 6 C 3 [h] epi Ma-FCC C 3 [g] epi Ma-FCC C 3 [i] epi Ma-FCC C 3 [j] epi Ma-FCC [a] relative configuration at C16: n = normal, i.e. derived from pfcc, or epi = epimeric, i.e. derived from epi-pfcc; [b] Bn-FCC-2 (from oilseed rape, Brassica napus); 19 Ca-FCC- 2 (from sweet pepper, Capsicum annuum); 20 At-FCCs (from Arabidopsis thaliana); 14 Mc- FCCs (from banana peels, Musa acuminata, Cavendish cultivar, 5, 6, 21, 22 ); Ma-FCCs (from banana leaves, Musa acuminata, Cavendish cultivar, 23, 24 ); Sw-FCC-62 (from senescent leaves of Spathiphyllum wallisii, 6 ). [c] Glc = -glucopyranosyl; [d] apparently an artefact, from methanolysis of 'persistent' FCC-daucyl-esters, such as Mc-FCC-56 and Mc-FCC-53; [e] daucic acid bound at 5 -; [f] daucic acid bound at 4 -; 5 [g] R 3 = 6 glucopyranosyl-(1-1 )-2-[3,4-dihydroxyphenyl]-ethyl; 6 [h] R 3 = -galactopyranosyl-(1-6)- -galactopyranosyl-(1-1)-glyceryl; 23 [i] R 3 = 6-(1 )-glucopyranosyl; 24 [j] R 3 = 6-(1 )- glucopyranosyl 24.
8 S8 Table 3. Structures of natural dioxobilane-type non-fluorescent Chl-catabolites (DNCCs): labels R 1, R 2 and R 4 refer to the general constitutional formula of DNCCs, shown below; atom numbering, as shown in Figure S1. R 1 R 2 R 4 C16 [a] provisional names [b] Ref. C 3 C()-C 2 n - 25 C 3 C()-C 2 n - C 3 C 2 =C 2 [c] UNCC-Pvir UNCC-Pp C 2 =C 2 n At-DNCC C 3 C()-C 2 epi Ap-DNCC C 2 =C 2 n At-DNCC-33 C 3 C 2 =C 2 n At-DNCC-38 C 3 C 2 =C 2 n At-DNCC , [a] relative configuration at C16: n = normal, if derived for pfcc or epi = epimeric, if derived for epi-pfcc; [b] for specific provisional names see references: e.g. Ap-DNCC (from Acer platanoides 29 ); At-DNCCs (from Arabidopsis thaliana); 28, 30 [c] relative configuration at C16 not determined. R N N R 1 N N 2 C C 2 R 2 DNCCs Generalized constitutional formula of DNCCs (type-ii phyllobilins)
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