TY - JOUR
T1 - Determination of the absolute configuration of the novel anti-trypanosomal iridoid molucidin isolated from Morinda lucida by X-ray analysis
AU - Karasawa, Satoru
AU - Yoza, Kenji
AU - Tung, Nguyen Huu
AU - Uto, Takuhiro
AU - Morinaga, Osamu
AU - Suzuki, Mitsuko
AU - Kwofie, Kofi D.
AU - Amoa-Bosompem, Michael
AU - Boakye, Daniel A.
AU - Ayi, Irene
AU - Adegle, Richard
AU - Sakyiamah, Maxwell
AU - Ayertey, Frederick
AU - Aboagye, Frederic
AU - Appiah, Alfred A.
AU - Owusu, Kofi B.A.
AU - Tuffour, Isaac
AU - Atchoglo, Philip
AU - Frempong, Kwadwo K.
AU - Anyan, William K.
AU - Appiah-Opong, Regina
AU - Nyarko, Alexander K.
AU - Yamashita, Taizo
AU - Yamaguchi, Yasuchika
AU - Edoh, Dominic
AU - Koram, Kwadwo
AU - Yamaoka, Shoji
AU - Ohta, Nobuo
AU - Shoyama, Yukihiro
N1 - Publisher Copyright:
© 2015 Elsevier Ltd.
PY - 2015/12/30
Y1 - 2015/12/30
N2 - The strong anti-trypanosomal active compound, molucidin, contains a spirolactone tetracyclic iridoid skeleton and is isolated from Morinda lucida as an enantiomer of oruwacin, which is isolated from the same plant. To confirm the absolute configuration of molucidin, we prepared single crystals of molucidin for X-ray analysis. The absolute configuration of the afforded single crystal was determined by X-ray crystallography using a Cu radiation source. X-ray diffraction data were collected at 93 K in the 2θ range 7.468-134.99° and analyzed using the SHELXL-2014 program. The corresponding chiral quaternary carbon atoms in molucidin were unambiguously determined as 1R, 5S, 8S, 9S, and 10S. Notably, both enantiomers of a single molecule, molucidin and oruwacin, with a rigid structure have been isolated from the same plant species. The biosynthetic pathway for the formation of molucidin is also discussed on the basis of the absolute configuration. Our results for the first time support for structural elucidation of tetracyclic iridoids using X-ray analysis.
AB - The strong anti-trypanosomal active compound, molucidin, contains a spirolactone tetracyclic iridoid skeleton and is isolated from Morinda lucida as an enantiomer of oruwacin, which is isolated from the same plant. To confirm the absolute configuration of molucidin, we prepared single crystals of molucidin for X-ray analysis. The absolute configuration of the afforded single crystal was determined by X-ray crystallography using a Cu radiation source. X-ray diffraction data were collected at 93 K in the 2θ range 7.468-134.99° and analyzed using the SHELXL-2014 program. The corresponding chiral quaternary carbon atoms in molucidin were unambiguously determined as 1R, 5S, 8S, 9S, and 10S. Notably, both enantiomers of a single molecule, molucidin and oruwacin, with a rigid structure have been isolated from the same plant species. The biosynthetic pathway for the formation of molucidin is also discussed on the basis of the absolute configuration. Our results for the first time support for structural elucidation of tetracyclic iridoids using X-ray analysis.
KW - Absolute configuration
KW - Anti-trypanosomal activity
KW - Molucidin
KW - Morinda lucida
KW - Rubiaceae
KW - X-ray analysis
UR - http://www.scopus.com/inward/record.url?scp=84949098102&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2015.11.031
DO - 10.1016/j.tetlet.2015.11.031
M3 - Article
AN - SCOPUS:84949098102
SN - 0040-4039
VL - 56
SP - 7158
EP - 7160
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 52
ER -