TY - JOUR
T1 - The chemistry of leaf-movement in Mimosa pudica L.
AU - Ueda, Minoru
AU - Yamamura, Shosuke
N1 - Funding Information:
Isolation ofmimopudine (7). The n-BuOH layer corresponding to 12.2 kg of M. pudica was used for the isolation of 7. The n-BuOH layer was carefully separated by Amberlite XAD-4 column chromatography (q~ 55 x 320 ram, Organo Co.) eluted with MeOH-H20 (8 : 2, 9 : 1 and 10:0 x 1 L each), and the 80% MeOH eluate showed weak leaf-opening activity. Then, the 80% MeOH eluate was carefully separated by Amberlite XAD-7 column chromatography (0 55 × 320 mm) eluted with MeOH-H20 (0 : 10, 1 : 9, 3 : 7, 4 : 6, 5 : 5, and 10:0 × 1 L each), and the 30% MeOH and 40% MeOH eluates showed weak leg-opening activities. The bioactive 30% MeOH aq. fraction was further purified by Toyopearl HW-40 Fine column chromatography (0 30 x 300 mm) with 35% MeOH aq., HPLC using preparative Develosil ODS HG-5 column (~20 × 250 mm) with 40% MeOH aq. (flow rate: 4.0 mL/min, detection: 260 nm) and purification by HPLC using analytical CAPCELL PAK UG80 column (~0 4.6 x 250 mm, Shiseido Co.) with 40% MeOH aq. (flow rate: 1.0 mL/min, detection: 260 nm) to give L-Tryptophan (6.1 mg) as a colorless powder. On the other hand, the other bioactive fraction, 40% MeOH eluate, was purified by Toyopearl HW-40 Fine column chromatography (¢ 30 x 300 mm) with 35% MeOH aq., HPLC using preparative Cosmosil 5C18AR column (~ 20 x 250 mm) with 40% CH3CN aq. (flow rate: 4,0 mL/min, detection: 260 rim), and HPLC using a combination of two analytical columns (Develosil HG-5 and Develosil UG-5) (0 4.6 × 250 mm) with 20% CH3CN aq. (flow rate: 0.5 mL/min, detection: 260 nm) to give mimopudine (7, 0.5 mg) as a yellow powder, mimopudine (7) : 1H NMR (400 MHz, 1920, rt) 6 7.90 (2 H, d, J = 7 Hz, HI), 6.60 (2 H, d, J = 7 Hz, H2), 5.30 (1 H, br.s, H2'), 4.05 (1 H, d, br.s, HI'); 13C NMR (100 MHz, D20, 35 °C) t~ 182.2 (C3), 146.0 (C1), 119.5 (C2), 90.5 (C2'), 65.0 (CI').; ESI MS (positive): m/z 360 \[M+Na\÷], 338 \[M+H\÷], 191 \[M+2Na\2]÷ , 169 \[M+2H\]2+H; R ESI MS (positive): calcd, for \[M+H\+] (C~4H20OsNs) 338.1464, found trgz 338.1434; IR & 1636, 1537, 1400 cmk ACKNOWLEDGMENT We are indebted to the Ministry of Education, Science and Culture (Japan) for Grants-in-Aid for Scientific Research on Special Promotion Research No. 09101001, the Asahi Glass Foundation and Pioneering Research Project in Biotechnology given by the Ministry of Agriculture, Forestry and Fisheries for financial support. We also thank Dr. Yushi Shichi (Nissan Ark Co.) and Prof. Koji Suzuki (Keio University) for the metal ion analyses.
PY - 1999/9/3
Y1 - 1999/9/3
N2 - Two well-known movements are observed in Mimosa pudica L. (Ojigi-so in Japanese): one is the very rapid movement of the leaves when it is stimulated by touch, heating, etc., and the other is the very slow, periodical movement of the leaves called nyctinastic movement which is controlled by a biological clock. We have isolated chemical substances controlling these two leaf- movements. These movements were regulated by the different chemical substances. We have succeeded in the identification of the chemical substances related to the two different kinds of mimosa leaf-movement, which have been discussed for over 80 years.
AB - Two well-known movements are observed in Mimosa pudica L. (Ojigi-so in Japanese): one is the very rapid movement of the leaves when it is stimulated by touch, heating, etc., and the other is the very slow, periodical movement of the leaves called nyctinastic movement which is controlled by a biological clock. We have isolated chemical substances controlling these two leaf- movements. These movements were regulated by the different chemical substances. We have succeeded in the identification of the chemical substances related to the two different kinds of mimosa leaf-movement, which have been discussed for over 80 years.
KW - Biologically active compounds
KW - Natural products
KW - Plants
UR - http://www.scopus.com/inward/record.url?scp=0033520247&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0033520247&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(99)00619-5
DO - 10.1016/S0040-4020(99)00619-5
M3 - Article
AN - SCOPUS:0033520247
VL - 55
SP - 10937
EP - 10948
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 36
ER -