Annotinolide F and lycoannotines A–I, further Lycopodium alkaloids from Lycopodium annotinum. (November 2017)

• Record Type: Journal Article
• Authors: Tang, Yu; Xiong, Juan; Zou, Yike; Wang, Wei; Huang, Chao; Zhang, Hai-Yan; Hu, Jin-Feng
• Is Part Of: Phytochemistry. Volume 143(2017)
• Page Start: 1
• Page End: 11
• Publication Date: 2017-11
• Subjects: Lycopodium annotinum -- Lycopodiaceae -- Lycopodium alkaloids -- Annotinolide F -- Lycoannotines; UBEQCGRXMNPQRL-KPHDYIETSA-N -- NZKKGFGHXZLPOJ-DSZLRUIBSA-N -- BCZFSDNVXODRAJ-JTTNIQEDSA-N -- NIMQJFLRNIVHJU-OCMPLTTASA-N -- AAZRLGLWPJJDGC-YZCJFMELSA-N -- SRCDVLQWMPMBLH-FSPSUXSGSA-N -- SRCDVLQWMPMBLH-OHHDELOUSA-N -- RQBRFYQTEDRMAQ-FCTVGVJYSA-N -- QSIDDXUOVFNDJJ-VVHMCBODSA-N -- NZKBZKCUTLIPCD-FGLHLUCPSA-N -- BINMAMVAPBWXFT-XKVFNRALSA-N -- RVCOIDFCWQXKHH-FPHDVWFLSA-N -- XZMYQBCMWCZCML-TWJWRFFLSA-N -- NTHHPTLNNFPRMV-DPAVQSFQSA-N -- JJPMUZRSJKMFRK-OQMKEHIESA-N -- YHPKLMGYAYSJRU-DNNBLBMLSA-N -- MMJZHDCFAKVBEV-OYBMDUGZSA-N -- QHZWEOCNEIHLNV-AZKPJATDSA-N -- YALIEYKTCHEXBJ-XKVFNRALSA-N -- MVITYUVPZPGMRM-RLFDSYHXSA-N -- GVBRFBGOACODDW-JOONLNEMSA-N -- JSUSMWBWHPSTEL-HSGISMCXSA-N -- XZMYQBCMWCZCML-FAXLKDOZSA-N -- AVMVHEHORMCQQO-VVHMCBODSA-N -- QGKKHEMGNWFUNZ-HBRAZQMNSA-N -- ANHVSCXCALAIQN-IATRGZMQSA-N; Lyconnotine (PubChem CID: 442487) -- Lycophlegmine (PubChem CID: 158260) -- Anhydrolycodoline (PubChem CID: 102442792) -- Lycopodatine C (PubChem CID: 11708569) -- Lycopodine (PubChem CID: 5462445) -- Obscurumine B (PubChem CID: 12188648) -- Lycodine (PubChem CID: 5462443) -- Fawcettidine (PubChem CID: 442473); Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2017.07.003
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Seven lycopodine-type (annotinolide F and lycoannotines A–F), two lycodine-type (lycoannotines G and H), and one fawcettimine-type (lycoannotine I) previously undescribed naturally occurring Lycopodium alkaloids together with thirteen known ones were isolated from the whole plant of Lycopodium annotinum . Their structures and absolute configurations were determined by extensive spectroscopic methods, single-crystal X-ray diffraction, chemical transformation, and electronic circular dichroism (ECD) calculations. Among the isolates, annotinolide F, lycoannotines A and B are unusual 7, 8- seco -lycopodane derivatives, and annotinolide F even further possesses a rare 8, 5-lactone framework through a lactonization after the C-7/C-8 bond cleavage. Lycoannotine C is an uncommon 8, 15- seco lycopodine-type alkaloid, whereas lycoannotine I represents the first example of a naturally occurring C-9/ N bond cleavage product of fawcettimine-type alkaloid. Among them, only lycoannotine I was found to show considerable anti-butyrylcholinesterase (anti-BuChE) activity. Graphical abstract: Ten previously undescribed Lycopodium alkaloids together with thirteen known ones were isolated from the whole plant of Lycopodium annotinum . Among them, lycoannotine I showed anti-BuChE activity. Highlights: Ten hitherto unknown Lycopodium alkaloids were isolated from Lycopodium annotinum. Their absolute configurations were determined by extensive methods. Annotinolide F has an unusual 7, 8- seco -lycopodane-derived 8, 5-lactone skeleton. Lycoannotine C is an uncommon 8, 15- seco lycopodine-type alkaloid. Lycoannotine I is the first fawcettimine alkaloid with a cleavage of the C-9/ N bond.