Endogenous gibberellins in immature seeds of Prunus persica L.: identification of GA118, GA119, GA120, GA121, GA122 and GA126
Gibberellin A118, GA119, GA120, GA121, GA122 and GA126 were identified in immature seeds of Prunus persica L. as well as eleven known gibberellins.
Introduction
Gibberellins possessing a 1,2- double bond as well as a 3β-hydroxyl group, such as GA3 (1) and GA7 (2), exhibit high biological activity in many bioassay systems (Reeve and Crozier, 1974). The metabolic conversion of GA5 (14) into GA3 (1) has been shown in many plant systems, e.g. seedlings of Zea mays (Fujioka et al., 1990), cell suspensions cultures of Prunus persica (Koshioka et al., 1988), cell-free systems from seeds of Marah macrocarpus (Albone et al., 1990, MacMillan et al., 1997) and anthers of Oryza sativa (Kobayashi et al., 1991). Thus, GA3 (1) in higher plants is currently thought to be biosynthesized from GA5 (14) by 3β-hydroxylation which is accompanied by a rearrangement of the 2,3-double bond to the 1,2-location (Fujioka et al., 1990). Furthermore it has been shown that GA7 (2) is formed in a similar manner from 2,3-didehydro GA9 (15) in M. macrocarpus (Albone et al., 1990, MacMillan et al., 1997).
While investigating the presence of endogenous gibberellins in immature seeds of Prunus cerasus, we noted the co-occurrence of GA3 (1) and GA95 (1,2-didehydro GA20) (5); however, GA5 (14) could not be detected (Nakayama et al., 1996). This led us to speculate that GA95 (5) could be the direct precursor of GA3 (1) by 3β-hydroxylation without an A-ring double bond rearrangement. Additionally, GA30 (3) and GA87 (4), A-ring analogues of GA3 (1) that possess both a 1,2-double bond and a 3β-hydroxyl group, were identified in immature seeds of P. cerasus (Nakayama et al., 1996). Hence GA30 (3) and GA87 (4) could also be biosynthesized from A-ring analogues of GA95 (5) by 3β-hydroxylation without the double bond rearrangement in this plant tissue.Fig. 1
We analyzed the endogenous gibberellins in immature seeds of P. persica, with special emphasis on identifying potential precursors of GA3 (1). Herein we report the co-occurrence of GA3 (1) and GA95 (5) and their A-ring analogues in immature seeds of P. persica.
Section snippets
Results and discussion
The acidic EtOAc fraction of an extract from immature seeds of P. persica was analyzed by GC–MS. Based on comparisons of mass spectra and Kovats retention indices (KRIs) with methyl ester trimethylsilyl ether derivatives of authentic compounds, GA3 (1), GA9 (20), GA17 (30), GA19 (31), GA30 (3), GA44 (33), GA63 (28), GA68 (29), GA87 (4), GA95 (5) and GA97 (32) were identified as endogenous gibberellins (Table 1). GA95 (5) had been found in immature seeds of P. cerasus (Nakayama et al, 1996). Its
Extraction and isolation
Fruit of Prunus persica cv. Kansuke-hakutou growing at Chiba University, Japan, were collected 40 days after anthesis. After freezing on dry ice, the immature seeds (290 g fr. wt) were harvested and kept frozen at−80°C until extraction and analysis. The immature seeds were extracted once with MeOH, then twice with 80% aq. MeOH. The MeOH extracts were combined and reduced to the aq. phase in vacuo. The aq. residue was adjusted to pH 7.0 with 0.5 M K–Pi buffer (pH 7.3) and partitioned with EtOAc.
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