Four new isomeric macrolides of combretastatin D-2 congeners named isocorniculatolide A (1), 11-O-methylisocorniculatolide A (2), 11-O-methylcorniculatolide A (3), and 12-hydroxy-11-O-methylcorniculatolide A (4), and the known corniculatolide A (5), arjunolic acid, and maslinic acid were isolated from the CHCl(3) extract of the bark of Aegiceras corniculatum. The structures of the new compounds (1-4) were elucidated by a combination of spectroscopic analysis (1-5), chemical modifications, and single-crystal X-ray analysis (1).
Two new resin glycosides, ipomeolides
A (1) and B
(2), both with an unusual nonlinear heteropentasaccharide
core, along with five known compounds were isolated from the n-hexane/CHCl3 (1:1) extract of the aerial parts
of Ipomoea pes-caprae. Ipomeolides A (1) and B (2) are macrolactone analogues of the rare (11R)-jalapinolic acid, and macrolactonization occurred at
C-2 of the second saccharide moiety. Compounds 1 and 2 show structural variation even in the pentasaccharide core.
The structures of 1 and 2 were established
by a combination of spectroscopic techniques as well as chemical modifications
such as acetyl and acetonide derivatives as well as hydrolysis products.
The new glycosidic acid was named ipomeic acid (1c).
Compounds 1, 1b, and 2b were
evaluated for cytotoxicity against human tumor cell lines. Compounds 1b and 2b were not effective on epithelial cells,
but affected survival of K-562, which is of hematopoietic origin.
A sublethal concentration of compound 1 (4 μM)
when used in combination with 1 μM doxorubicin, an anticancer
agent, significantly enhanced cytotoxicity to tumor cells. Such combined
synergistic potency against leukemia cells and the absence of effects
on epithelial cells may be beneficial for chemotherapy with minimal
side effects to treat CML (chronic myeloid leukemia) malignancies.
Excolides A-B (1-4) represent the first examples of a new class of secolabdanoids with an unprecedented framework, which were isolated from the stems of Excoecaria agallocha. Their structures were determined by spectroscopic analysis, chemical modifications, CD, and single-crystal X-ray analysis (1 and 4) as excolide A (1), 11-epi-excolide A (2), 11,13-di-epi-excolide A (3), and excolide B (4). In addition, the structure of rhizophorin A (7), a novel bicyclic secolabdanoid, was revised as excolide A (1).
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