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From Phomopsis Amygdali Niigata 2-A, and Their Seed Germination-Stimulating Activity in the Presence of Abscisic Acid

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From Phomopsis Amygdali Niigata 2-A, and Their Seed Germination-Stimulating Activity in the Presence of Abscisic Acid Biosci. Biotechnol. Biochem., 68 (5), 1125–1130, 2004 Novel Fusicoccins R and S, and the Fusicoccin S Aglycon (Phomopsiol) from Phomopsis amygdali Niigata 2-A, and Their Seed Germination-stimulating Activity in the Presence of Abscisic Acid y Naoto TAJIMA,1 Manabu NUKINA,1;2 Nobuo KATO,3 and Takeshi SASSA1;2; 1Course of the Science of Bioresources, The United Graduate School of Agricultural Sciences, Iwate University (Yamagata University), Ueda-cho, Morioka 020-8550, Japan 2Department of Bioresource Engineering, Faculty of Agriculture, Yamagata University, Wakaba-cho, Tsuruoka 997-8555, Japan 3Institute of Scientific and Industrial Research, Osaka University, Mihogaoka-cho, Ibaraki 567-0047, Japan Received January 13, 2004; Accepted February 2, 2004 Our search for new 3-hydroxyfusicoccins structurally Fusicoccin A (FC A, Fig. 1), a unique metabolite from related to cotylenin A from a culture of Phomopsis Phomopsis (Fusicoccum) amygdali,1,2) is a novel 5-8-5- amygdali Niigata 2-A resulted in the isolation of novel 3- membered tricyclic diterpene glucoside3,4) possessing hydroxy fusicoccins, called fusicoccins R and S, and the potent plant-growth stimulating acitivity.5) The mode of fusicoccin S aglycon, called phomopsiol, together with action of FC A on plant 14-3-3 protein and the Hþ- known 3 -hydroxyfusicoccin J. The structure of pho- ATPase are currently attracting much attention.6) We mopsiol was identified as that of O-demethyl-3-epicotyl- have reported in a previous paper the isolation of new enol based on spectroscopic evidence. The structures of polar fusicoccins P and Q, and 3-epifusicoccins H and Q fusicoccins R and S were also determined to be those of from the 30-deacetyl-FC A-producing fungus, Phomop- 30-deacetyl-3 -hydroxyfusicoccin A and 3 -hydroxy-3- sis amygdali Niigata 2-A (an isolate of a peach epifusicoccin H. The lettuce seed germination-stimulat- Fusicoccum canker fungus), together with the presence ing activity of fusicoccins R and S, phomopsiol and 3 - of two fusicoccin-biosynthetic pathways finally giving hydroxyfusicoccin J was examined in the presence of FC A and its 30-deacetyl derivative, as well as 16-O- ABA; fusicoccin R and 3 -hydroxyfusicoccin J were demethyl-3-epi-FC J.7) highly active, while fusicoccin S and phomopsiol were We have recently found that cotylenin A (CN A, inactive. The possible biosynthetic relationships among Fig. 1),8) the sole fusicoccin-congener isolated as a these novel fusicoccins having a 3 -or3 -hydroxy potent plant-growth regulator from Cladosporium sp. group in their diterpene moiety are briefly discussed. 507W,9,10) induced the differentiation of human acute myeloid leukemia cells11) and apoptosis in human lung Key words: fusicoccin R; fusicoccin S; phomopsiol; carcinoma cells in the presence of interferon- .12) These Phomopsis amygdali; seed germination useful biological activities of CN A toward mammalian O OAc O OH 2' 4' 4'' O 3' O HO OH 5'' HO HO OH O O O 1' 5' 6' O OMe 20 1'' OH 15 HO O 19 2'' 3'' HO O HO O 17 14 8 9 OAc 7 10 13 H 6 11 H H 5 12 2 1 3 18 OH 4 OMe OMe OH 16 HO Fusicoccin A Cotylenin A Fusicoccin H (FC A) (CN A) (FC H) Fig. 1. Structures of Fusicoccins A and H, and Cotylenin A. y To whom correspondence should be addressed. Fax: +81-235-28-2862; E-mail: [email protected] 1126 N. TAJIMA et al. cells prompted us to search for new CN-type fusicoccins plate. having the 3-hydroxy group from the Niigata 2-A Substance A was detected together with 16-O-de- fungus. Based on the isolation of 3 -hydroxy-FC J from methyl-3-epi-FC J in fraction 3 (15:1 CHCl3/EtOH). an Italian fungus,13) we tried to generate CN-type Fraction 3 was rechromatographed by a similar method, fusicoccins by the fungus in a stationary culture using using a 19:1 mixture of CHCl3/EtOH and then a 31:1 rice bran and wheat bran, and succeeded in isolating mixture of EtOAc/EtOH, to give fine colorless crystals novel 3-hydroxyfusicoccins, called fusicoccin R (FC R) (18 mg). Substances B and C were detected together 14) and fusicoccin S (FC S), and the FC S aglycon, called with 16-O-demethyl-FC J in fraction 4 (7:1 CHCl3/ phomopsiol. This paper reports the isolation and EtOH). These were separated by a similar method, using structures of FC R, FC S and phomopsiol, together with EtOAc/EtOH mixtures, to give 5 fractions. Fraction 20 that of 3 -hydroxy-FC J from the Niigata 2-A fungus (31:1 EtOAc/EtOH) was crystallized from EtOAc to (Fig. 3). FC R and 3 -hydroxy-FC J having the 16-O- give substance B (3.3 mg) as fine colorless crystals. methyl group showed high germination-stimulating Fraction 40 (15:1 EtOAc/EtOH) was further purified by activity toward lettuce seeds in the presence of ABA; a similar method, using a 10:1 mixture of EtOAc/ FC S and phomopsiol having no 16-O-methyl group in acetone, to give substance C (13.9 mg) as a colorless the 3-epimeric structures were inactive in this assay. The solid. Substance D was detected together with FC Q in isolation of these 3-hydroxyfusicoccins and phomopsiol fraction 9 (3:1 CHCl3/MeOH). Fraction 9 was separated suggested the presence of new fusicoccin-biosynthetic by a similar method, using a 10:1 mixture of EtOAc/ pathways in the fungus; their possible biosynthetic EtOH, and was further purified by preparative silica gel relationships are discussed (Fig. 3). TLC, using a 2:1 mixture of EtOAc/n-BuOH, to give substance D (6.3 mg) as a colorless solid. In this Materials and Methods experiment, fraction 2 (ca. 2.8 g) containing a 1:1 mixture of the major metabolites of 30-deacety-FC A and General procedures. Optical rotation values were FC J was separated. measured with a Horiba SEPA-300 digital polarimeter. Substance A (Phomopsiol): Mp 120–121 C (EtOAc); 1 13 21 H- and C-NMR spectra were recorded with a Jeol ½ D À28 (c 0.12, MeOH). FAB-MS m=z: 359 EX-400 spectrometer. The DIF-NOE spectra of FC S ½M þ Naþ. HR-FABMS m=z ½M þ Naþ: calcd. for 1 and phomopsiol were recorded with a Jeol Lambda-600 C20H32O4Na, 359.2198; found, 359.2201. The H- and spectrometer. FABMS and HR-FABMS spectra were 13C-NMR data are shown in Table 1. recorded with a JMS-700 mass spectrometer. Wako FC- Substance B (3 -Hydroxy-FC J):13) Mp 134–135 C 25 40 silica gel was employed for flash chromatography, (EtOAc); ½ D þ18 (c 0.20, CHCl3). FAB-MS m=z: þ 1 and silica gel TLC plates (Merck F254 Nos. 5554 and 619 ½M þ Na . H-NMR (400 MHz, CDCl3) : 0.81 (d, 5583) were respectively employed for the TLC analysis J ¼ 7:2 Hz, H17), 0.98 (d, 6.8, H20), 1.07 (d, 6.8, H19), and preparative TLC. 1.20 (s, H18), 1.27 (s, H500), 1.28 (s, H400), 2.95 (m, H6), 3.16 (d, 9.6, H16), 3.17 (sep, 6.8, H15), 3.40 (d, 9.6, Extraction and isolation of the new substances. P. H16), 3.41 (O-Me), 3.48 (t, 9.6, H30), 3.52 (dd, 9.6, 4.0, amygdali Niigata 2-A was cultured in the stationary H60), 3.62 (dd, 9.6, 4.0, H20), 3.79 (d, 11.2, H9), 3.83 (t, mode for 21 days at 25 C in 500-ml flasks as a merlstem 8.8, H40), 3.96 (dd, 11.2, 4.0, H8), 4.98 (d, 4.0, H10), culture, each containing rice bran (26 g), wheat bran 5.15 (br.d, 17.6, H300), 5.17 (br.d, 10.8, H300), 5.54 (d, (13 g) and deionized water (40 ml). The mycelia and 2.4, H1), 5.77 (dd, 17.6, 10.8, H200); 13C-NMR media obtained from 80 flasks were homogenized in (100 MHz, CDCl3) : 8.6 (C17), 20.6 (C20), 21.2 acetone. The aq. acetone solution (10 liters) obtained by (C19), 23.7 (C18), 25.3 (C500), 25.9 (C400), 28.0 (C15), filtration was concentrated in vacuo. The residual aq. 31.7 (C4), 35.3 (C13), 35.4 (C5), 41.0 (C6), 41.2 (C7), solution (700 ml) was adjusted to pH 9.0 with 5% aq. 53.5 (C11), 59.3 (O-Me), 64.1 (C60), 69.3 (C40), 71.9 0 0 0 00 Na2CO3 and extracted 3 times with EtOAc (1.4 liters (C5 ), 73.6 (C2 ), 73.8 (C3 ), 76.2 (C1 ), 77.3 (C16), each) after being saturated with NaCl. The EtOAc 77.8 (C8), 78.2 (C9), 81.7 (C12), 82.5 (C3), 101.3 (C10), extract (34.5 g) obtained by evaporating EtOAc was 114.8(C300), 128.2(C1), 134.5(C10), 142.7(C2), 144.1 washed 3 times with n-hexane (200 ml each) and then 3 (C200), 146.0 (C14). 25 times with a 2:1 mixture of n-hexane/ether (200 ml Substance C (FC R): ½ D þ3:7 (c 0.050, CHCl3). each). The obtained residual extract (6.1 g) was sepa- FAB-MS m=z: 677 ½M þ Naþ. HR-FABMS m=z þ rated by silica gel flash chromatography with CHCl3/ ½M þ Na : calcd. for C34H54O12, 677.3514; found, 1 13 EtOH mixtures and then a 3:1 mixture of CHCl3/MeOH 677.3513.
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