Biochemical Systematics and Ecology 28: 887-902 (2000)
Anthocyanins in flowers of genus Rosa, sections Cinnamomeae (=Rosa), 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
  Cy   Pn   Pg    
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)
Rosa acicularis (R01) 26 0 1 0 + 1   44 + 9 0 1 5   0 0 2 8
Rosa arkansana (R02) 61 + 0 0 + 1   32 + 0 0 1 3   0 0 0 0
Rosa bella (R03) 80 + 3 1 + 1   8 0 + 0 + +   0 0 3 1
Rosa cinnamomea (R04) 33 + 0 0 + +   62 + 0 0 1 2   0 0 0 0
Rosa forrestiana (R05) 97 + + + + 1   0 + + + 0 0   0 0 0 0
Rosa marretii (R06) 98 + 0 + 0 0   0 0 0 0 + 1   0 0 0 0
Rosa moyesii (R07) 50 17 + 28 + 2   0 + 0 0 0 0   0 0 0 0
Rosa moyesii cv. Arthur Hillier (R08) 38 4 1 7 + 2   23 + 2 4 + 2   0 0 3 8
Rosa moyesii cv. Eddie's Crimson (R09) 57 + 0 + + 2   34 0 + + 1 4   0 0 0 0
Rosa moyesii cv. Fargesii (R10) 23 16 + 13 + +   34 1 + 4 + 2   0 0 0 0
Rosa moyesii cv. Geranium (R11) 45 6 + 35 + +   0 + 0 0 0 0   0 0 0 0
Rosa moyesii cv. Highdownensis (R12) 41 2 0 1 + 1   49 0 + 1 1 4   0 0 0 0
Rosa moyesii cv. Hillieri (R13) 74 6 + 9 1 4   0 + + + 0 0   0 0 0 0
Rosa nipponensis (R14) 94 + + 1 + +   1 1 + 0 0 0   0 0 0 0
Rosa nutkana (R15) 30 + 1 0 + +   24 0 6 + + 1   0 0 4 30
Rosa pendulina var. oxyodon (R16) 95 + + + + 2   + 0 + + 0 0   0 0 0 0
Rosa rugosa (R17) 32 1 + 1 + +   63 + + + + +   0 0 0 0
Rosa rugosa var. plena (R18) 35 2 0 1 + +   60 + + 1 + 1   0 0 0 0
Rosa rugosa cv. Maikwai (R19) 39 + 0 1 + +   53 0 + + + 3   0 0 0 0
Rosa rugosa cv. Roseraie de l'Hay (R20) 16 0 + 0 + +   76 + + 1 + 2   0 0 0 0
Rosa rugosa cv. Salmon Pink (R21) + 8 2 24 0 0   0 + 1 61 0 0   0 0 0 0
Rosa rugosa cv. Scabrosa (R22) 26 + 0 0 + +   70 0 + + + 0   0 0 0 0
Rosa rugosa cv. Scarlet (R23) 79 + 0 0 + 1   17 0 + + + +   0 0 0 0
Rosa sweginzowii (R24) 74 + 0 0 1 6   14 0 0 0 + 2   0 0 0 0
Rosa willmottiae (R25) 47 + 0 0 + 2   39 0 + 1 1 6   0 0 0 0
Rosa x iwara (R26) 52 + 0 + + +   46 0 0 + + 1   0 0 0 0
Section Chinenses
Rosa chinensis Jacq. 85 0 + 13 + 1   0 0 + + 0 0   0 0 0 0
Rosa chinensis var. minima 87 0 + 11 + +   0 0 + + 0 0   0 0 0 0
Rosa chinensis var. spontanea 28 0 2 56 1 1   0 0 1 0 0 0   0 0 0 0
Rosa chinensis cv. Fabvier 82 0 + 10 + 5   2 0 + + 0 0   0 0 0 0
Rosa chinensis cv. Miss Lowe 43 + 1 53 + +   0 0 + + 0 0   0 0 0 0
Rosa chinensis cv. Mutabilis 23 0 + 73 0 0   0 0 + 2 0 +   0 0 0 0
Rosa chinensis cv. Pompon de Paris 71 0 0 27 + +   + 0 + + 0 0   0 0 0 0
Rosa chinensis cv. Slater's Crim China 58 0 + 33 + 4   0 + + 1 + +   0 0 0 0
Section Gallicanae
Rosa gallica 92 0 0 6 + 1   0 0 + + 0 0   0 0 0 0
Rosa gallica cv. Cardinal de Richelieu 97 + 0 1 + 1   + 0 0 + 0 0   0 0 0 0
Rosa gallica cv. Rosa Mundi 98 + 0 + 0 +   0 0 0 0 0 0   0 0 0 0
Rosa gallica cv. Shigyoku 98 + 0 + + 1   + 0 + + 0 0   0 0 0 0
Rosa gallica cv. Violacea 96 + 0 + + 2   + 0 + + 0 0   0 0 0 0
Rosa x centifolia cv. Bullata 98 1 0 + 0 0   0 0 0 + 0 0   0 0 0 0
Rosa x centifolia cv. Muscosa 96 1 0 1 + 2   + 0 + + 0 0   0 0 0 0
Rosa x damascena 97 1 0 1 + 1   0 0 + + 0 0   0 0 0 0
Rosa x damascena cv. Bifera 97 + 0 1 + +   0 0 + + 0 0   0 0 0 0
Rosa x damascena cv. Gloire de Guilan 97 1 0 1 + 1   0 0 + + 0 0   0 0 0 0
Modern garden roses
Rosa cv. La France 98 0 0 + 0 0   0 0 0 0 0 0   1 0 0 0
Rosa cv. Ole 69 0 + 3 + +   + 0 + + 0 0   22 2 0 0
Rosa cv. Papa Meilland 94 0 0 1 + +   1 0 + + 0 0   1 0 0 0
Rosa cv. Seika 96 0 0 3 0 +   0 0 + 0 0 0   0 0 0 0
Rosa cv. Frensham 85 0 + + + 8   3 0 + + 0 +   0 + + +
Rosa cv. Orange Bunny 37 0 0 + 0 +   0 0 + 0 0 0   58 3 0 0
Rosa cv. Red Meillandina 73 0 + 1 1 5   13 0 + + + 2   2 + + +
Rosa 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 Rosa (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. Rosa 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 Rosa 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