Monoterpenoid indole alkaloid adducts and dimers from Melodinus fusiformis

Eight unprecedented monoterpenoid indole alkaloid (MIA) adducts and dimers, melofusinines A-H (1-8), and three undescribed melodinus-type MIA monomers, melofusinines I-K (9-11), together with six putative bioge-netic precursors were isolated from the twigs and leaves of Melodinus fusiformis Champ. ex Benth. Compounds 1 and 2 are unusual hybrid indole alkaloids incorporating an aspidospermatan-type MIA with a monoterpenoid alkaloid unit via C-C coupling. Compounds 3-8 feature the first MIA dimers constructed through an aspidospermatan-type monomer and a rearranged melodinus-type monomer with two different types of cou-plings. Their structures were elucidated by spectroscopic data, single crystal X-ray diffraction, and calculated electric circular dichroism spectra analysis. In addition, dimers 5 and 8 showed significant neuroprotection ef-fects on MPP +-injured primary cortical neurons.

Automated summary

Eight unprecedented monoterpenoid indole alkaloid (MIA) adducts and dimers, melofusinines A-H (1-8), and three undescribed melodinus-type MIA monomers, melofusinines I-K (9-11), were isolated from Melodinus fusiformis. Compounds 1 and 2 are hybrid indole alkaloids incorporating an aspidospermatan-type MIA with a monoterpenoid alkaloid unit. Compounds 3-8 are the first MIA dimers constructed through an aspidospermatan-type monomer and a rearranged melodinus-type monomer.