Monoterpenoid indole alkaloid adducts and dimers from Melodinus fusiformis

Zhi Wen Liu; Min Song; Jun Ya Wang; De Zhi Wang; Biao Sun; Lei Shi; Ren Wang Jiang; Min Ma; Xiao Qi Zhang

doi:10.1016/j.phytochem.2023.113678

Monoterpenoid indole alkaloid adducts and dimers from Melodinus fusiformis

Zhi Wen Liu, Min Song, Jun Ya Wang, De Zhi Wang, Biao Sun, Lei Shi, Ren Wang Jiang, Min Ma, Xiao Qi Zhang

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

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 biogenetic 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 couplings. 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 effects on MPP ⁺-injured primary cortical neurons.

Original language	English (US)
Article number	113678
Journal	Phytochemistry
Volume	211
DOIs	https://doi.org/10.1016/j.phytochem.2023.113678
State	Published - Jul 2023
Externally published	Yes

Keywords

Apocynaceae
Dimeric alkaloids
Melodinus fusiformis Champ. ex benth.
Monoterpenoid indole alkaloids
Neuroprotection effect

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Plant Science
Horticulture

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10.1016/j.phytochem.2023.113678

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title = "Monoterpenoid indole alkaloid adducts and dimers from Melodinus fusiformis",

abstract = "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 biogenetic 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 couplings. 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 effects on MPP +-injured primary cortical neurons.",

keywords = "Apocynaceae, Dimeric alkaloids, Melodinus fusiformis Champ. ex benth., Monoterpenoid indole alkaloids, Neuroprotection effect",

author = "Liu, {Zhi Wen} and Min Song and Wang, {Jun Ya} and Wang, {De Zhi} and Biao Sun and Lei Shi and Jiang, {Ren Wang} and Min Ma and Zhang, {Xiao Qi}",

note = "Publisher Copyright: {\textcopyright} 2023 Elsevier Ltd",

year = "2023",

month = jul,

doi = "10.1016/j.phytochem.2023.113678",

language = "English (US)",

volume = "211",

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T1 - Monoterpenoid indole alkaloid adducts and dimers from Melodinus fusiformis

AU - Liu, Zhi Wen

AU - Song, Min

AU - Wang, Jun Ya

AU - Wang, De Zhi

AU - Sun, Biao

AU - Shi, Lei

AU - Jiang, Ren Wang

AU - Ma, Min

AU - Zhang, Xiao Qi

PY - 2023/7

Y1 - 2023/7

N2 - 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 biogenetic 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 couplings. 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 effects on MPP +-injured primary cortical neurons.

AB - 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 biogenetic 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 couplings. 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 effects on MPP +-injured primary cortical neurons.

KW - Apocynaceae

KW - Dimeric alkaloids

KW - Melodinus fusiformis Champ. ex benth.

KW - Monoterpenoid indole alkaloids

KW - Neuroprotection effect

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JO - Phytochemistry

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Monoterpenoid indole alkaloid adducts and dimers from Melodinus fusiformis

Abstract

Keywords

ASJC Scopus subject areas

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