Biochemical Systematics and Ecology 28: 887-902 (2000)
Anthocyanins in flowers of genus R., sections Cinnamomeae (=R.), Chinenses, Gallicanae and some modern garden roses
Mikanagi, Saito, Yokoi, Tatsuzawa

Table 4 Anthocyanin distribution in flowers of genus Rosa

  Anthocyanins (as %)a
Pigment No. 5 5 9 7 2 10   6 x 8 3 11   4 1 UK1 UK2
Rt. (mm) 33.1 35.0 39.6 37.4 49.2 56.0 37.8 41.2 44.6 43.5 54.0 60.9 35.4 41.8 55.0 58.5
Species, varieties and cultivars 3,5-diglu 3-sop 3-rut 3-glu 3,5-diglu-ρC
   cis  |  trans
3,5-diglu 3-sop 3-rut 3-glu 3,5-diglu-ρC
   cis  |  trans
3,5-diglu 3-glu ? ?
Section Cinnamomeae ( = section Rosa) Cy   Pn   Pg UK1 UK2
R. acicularis (R01) 26 0 1 0 + 1   44 + 9 0 1 5   0 0 2 8
R. arkansana (R02) 61 + 0 0 + 1 32 + 0 0 1 3 0 0 0 0
R. bella (R03) 80 + 3 1 + 1 8 0 + 0 + + 0 0 3 1
R. cinnamomea (R04) 33 + 0 0 + + 62 + 0 0 1 2 0 0 0 0
R. forrestiana (R05) 97 + + + + 1 0 + + + 0 0 0 0 0 0
R. marretii (R06) 98 + 0 + 0 0 0 0 0 0 + 1 0 0 0 0
R. moyesii (R07) 50 17 + 28 + 2 0 + 0 0 0 0 0 0 0 0
R. moyesii cv. Arthur Hillier (R08) 38 4 1 7 + 2 23 + 2 4 + 2 0 0 3 8
R. moyesii cv. Eddie's Crimson (R09) 57 + 0 + + 2 34 0 + + 1 4 0 0 0 0
R. moyesii cv. Fargesii (R10) 23 16 + 13 + + 34 1 + 4 + 2 0 0 0 0
R. moyesii cv. Geranium (R11) 45 6 + 35 + + 0 + 0 0 0 0 0 0 0 0
R. moyesii cv. Highdownensis (R12) 41 2 0 1 + 1 49 0 + 1 1 4 0 0 0 0
R. moyesii cv. Hillieri (R13) 74 6 + 9 1 4 0 + + + 0 0 0 0 0 0
R. nipponensis (R14) 94 + + 1 + + 1 1 + 0 0 0 0 0 0 0
R. nutkana (R15) 30 + 1 0 + + 24 0 6 + + 1 0 0 4 30
R. pendulina var. oxyodon (R16) 95 + + + + 2 + 0 + + 0 0 0 0 0 0
R. rugosa (R17) 32 1 + 1 + + 63 + + + + + 0 0 0 0
R. rugosa var. plena (R18) 35 2 0 1 + + 60 + + 1 + 1 0 0 0 0
R. rugosa cv. Maikwai (R19) 39 + 0 1 + + 53 0 + + + 3 0 0 0 0
R. rugosa cv. Roseraie de l'Hay (R20) 16 0 + 0 + + 76 + + 1 + 2 0 0 0 0
R. rugosa cv. Salmon Pink (R21) + 8 2 24 0 0 0 + 1 61 0 0 0 0 0 0
R. rugosa cv. ScabR. (R22) 26 + 0 0 + + 70 0 + + + 0 0 0 0 0
R. rugosa cv. Scarlet (R23) 79 + 0 0 + 1 17 0 + + + + 0 0 0 0
R. sweginzowii (R24) 74 + 0 0 1 6 14 0 0 0 + 2 0 0 0 0
R. willmottiae (R25) 47 + 0 0 + 2 39 0 + 1 1 6 0 0 0 0
R. x iwara (R26) 52 + 0 + + + 46 0 0 + + 1 0 0 0 0
Section Chinenses Cy   Pn   Pg UK1 UK2
R. chinensis Jacq. 85 0 + 13 + 1   0 0 + + 0 0   0 0 0 0
R. chinensis var. minima 87 0 + 11 + + 0 0 + + 0 0 0 0 0 0
R. chinensis var. spontanea 28 0 2 56 1 1 0 0 1 0 0 0 0 0 0 0
R. chinensis cv. Fabvier 82 0 + 10 + 5 2 0 + + 0 0 0 0 0 0
R. chinensis cv. Miss Lowe 43 + 1 53 + + 0 0 + + 0 0 0 0 0 0
R. chinensis cv. Mutabilis 23 0 + 73 0 0 0 0 + 2 0 + 0 0 0 0
R. chinensis cv. Pompon de Paris 71 0 0 27 + + + 0 + + 0 0 0 0 0 0
R. chinensis cv. Slater's Crim China 58 0 + 33 + 4 0 + + 1 + + 0 0 0 0
Section Gallicanae Cy   Pn   Pg UK1 UK2
R. gallica 92 0 0 6 + 1   0 0 + + 0 0   0 0 0 0
R. gallica cv. Cardinal de Richelieu 97 + 0 1 + 1 + 0 0 + 0 0 0 0 0 0
R. gallica cv. R. Mundi 98 + 0 + 0 + 0 0 0 0 0 0 0 0 0 0
R. gallica cv. Shigyoku 98 + 0 + + 1 + 0 + + 0 0 0 0 0 0
R. gallica cv. Violacea 96 + 0 + + 2 + 0 + + 0 0 0 0 0 0
R. x centifolia cv. Bullata 98 1 0 + 0 0 0 0 0 + 0 0 0 0 0 0
R. x centifolia cv. Muscosa 96 1 0 1 + 2 + 0 + + 0 0 0 0 0 0
R. x damascena 97 1 0 1 + 1 0 0 + + 0 0 0 0 0 0
R. x damascena cv. Bifera 97 + 0 1 + + 0 0 + + 0 0 0 0 0 0
R. x damascena cv. Gloire de Guilan 97 1 0 1 + 1 0 0 + + 0 0 0 0 0 0
Modern garden roses Cy   Pn   Pg UK1 UK2
R. cv. La France 98 0 0 + 0 0   0 0 0 0 0 0   1 0 0 0
R. cv. Ole 69 0 + 3 + + + 0 + + 0 0 22 2 0 0
R. cv. Papa Meilland 94 0 0 1 + + 1 0 + + 0 0 1 0 0 0
R. cv. Seika 96 0 0 3 0 + 0 0 + 0 0 0 0 0 0 0
R. cv. Frensham 85 0 + + + 8 3 0 + + 0 + 0 + + +
R. cv. Orange Bunny 37 0 0 + 0 + 0 0 + 0 0 0 58 3 0 0
R. cv. Red Meillandina 73 0 + 1 1 5 13 0 + + + 2 2 + + +
R. cv. The Fairy 95 0 0 + + 3 0 0 + 0 0 0 1 0 0 0

aPercent of total absorbance of all detected anthocyanins at 530 nm by HPLC analysis. value < 0.1 = 0, 0.1 < value < 0.5 = +, 0.5 < value < 1.5 = 1.
Rts of '+' pigments are identical to each pigments, but chemical structures are not yet confirmed.

3-sop = 3-sophoroside; 3-rut = 3-rutinoside; 3-glu = 3-glucoside
3,5-diglu-ρC = 3-ρ-coumaroylglucoside-5-glucoside


3. Results and discussion

In the survey of anthocyanins in Rosa flowers of 52 taxa by HPLC analysis, 11 major anthocyanin peaks were observed as shown in Fig. 1, and Tables 2 and 4 (pigments 1-11). Among them, the 3-glucosides and 3,5-diglucosides of Cy, Pn and Pg (1, 2, 3, 4, 5 and 6) were confirmed with authentic samples and confirmed the former studies (Arisumi, 1963, 1967; Yokoi, 1974, 1975; Yokoi et al., 1979; Saito et al., 1982 and Mikanagi et al., 1994). In most taxa, Cy 3,5-diglucoside (5) was detected as the major constituent. However, some taxa in section Cinnamomeae contained larger amounts of Pn 3,5-diglucoside (6) than 5, and some taxa in section Chinenses contained larger amounts of Cy 3-glucoside (2) than 5.

The detailed structure of Cy 3-ρ-coumaroylglucoside-5-glucoside (10) which was reported as ρ-coumaroylcyanin by Arisumi (1967) was determined unambiguously in this study. Furthermore, the occurrence of four anthocyanins, Cy 3-rutinoside (7), Pn 3-rutinoside (8), Cy 3-sophoroside (9) and Pn 3-ρ-coumaroylglucoside-5-glucoside (11), are recorded for the first time in genus R. (Fig. 1). Contents of 7, 8, 10 and 11 were small, but 9 accumulated in large amounts in some taxa in section Cinnamomeae. The distribution of anthocyanins in each section is described in detail.

Fig. 1. R. anthocyanins.

1 pelargonidin 3-glucoside, R1,2,3,4 = H
2 cyanidin 3-glucoside, R2,3,4 = H, R1 = OH
3 peonidin 3-glucoside, R2,3,4 = H, R1 = OCH3
4 pelargonidin 3,5-diglucoside, R1,3,4 = H, R2 = glucosyl
5 cyanidin 3,5-diglucoside, R3,4 = H, R1 = OH, R2 = glucosyl
6 peonidin 3,5-diglucoside, R3,4 = H, R1 = OCH3, R2 = glucosyl
(Additional R. anthocyanins)
7 cyanidin 3-rutinoside, R2,4 = H, R1 = OH, R3 = rhamnosyl
8 peonidin 3-rutinoside, R2,4 = H, R1 = OCH3, R3 = rhamnosyl
9 cyanidin 3-sophoroside, R2,3 = H, R1 = OH, 4= glucosyl
10 cyanidin 3-ρ-coumarylglucoside-5-glucoside, R4 = H, R1 = OH, R2 = glucosyl, R3 = ρ-coumaryl
11 peonidin 3-ρ-coumarylglucoside-5-glucoside, R4 = H, R1 = OCH3, R2 = glucosyl, R3 = ρ-coumaryl