Skip to main content
Top
Published in: Journal of Natural Medicines 3/2023

12-05-2023 | Alkaloids | Note

Cryptadine C, a new C27N3-type Lycopodium alkaloid from Lycopodium cryptomerinum

Authors: Yusuke Hirasawa, Rina Hattori, Manami Ohtani, Hiroshi Morita

Published in: Journal of Natural Medicines | Issue 3/2023

Login to get access

Abstract

A new C27N3-type Lycopodium alkaloid consisting of two decahydroquinolines and a piperidine, cryptadine C (1) was isolated from Lycopodium cryptomerinum. The structure and relative configuration of 1, which is related to those of cryptadines A and B, lycoperine A, and hupercumine A, was elucidated on the basis of spectroscopic data. Cryptadine C showed moderate inhibitory activity against acetylcholinesterase.

Graphical abstract

Appendix
Available only for authorised users
Literature
1.
go back to reference Hirasawa Y, Kobayashi J, Morita H (2009) the Lycopodium alkaloids. Heterocycles 77:679–729CrossRef Hirasawa Y, Kobayashi J, Morita H (2009) the Lycopodium alkaloids. Heterocycles 77:679–729CrossRef
2.
go back to reference Kobayashi J, Morita H (2004) The Lycopodium alkaloids. Alkaloids 61:1–57 Kobayashi J, Morita H (2004) The Lycopodium alkaloids. Alkaloids 61:1–57
3.
go back to reference Ayer WA, Trifonov LS (1994) Lycopodium alkaloids. Alkaloids 45:233–266 Ayer WA, Trifonov LS (1994) Lycopodium alkaloids. Alkaloids 45:233–266
5.
go back to reference MacLean DB (1985) Lycopodium alkaloids. Alkaloids 26:241–298 MacLean DB (1985) Lycopodium alkaloids. Alkaloids 26:241–298
6.
go back to reference MacLean DB (1973) The Lycopodium alkaloids. Alkaloids 14:347–405 MacLean DB (1973) The Lycopodium alkaloids. Alkaloids 14:347–405
7.
go back to reference MacLean DB (1968) The Lycopodium alkaloids. Alkaloids 10:305–382 MacLean DB (1968) The Lycopodium alkaloids. Alkaloids 10:305–382
8.
go back to reference Liu JS, Zhu YL, Yu CM, Zhou YZ, Han YY, Wu FW, Qi BF (1986) The structures of huperzine A and B, two new alkaloids exhibiting marked anticholinesterase activity. Can J Chem 64:837–839CrossRef Liu JS, Zhu YL, Yu CM, Zhou YZ, Han YY, Wu FW, Qi BF (1986) The structures of huperzine A and B, two new alkaloids exhibiting marked anticholinesterase activity. Can J Chem 64:837–839CrossRef
9.
go back to reference Hirasawa Y, Mitsui C, Uchiyama N, Hakamatsuka T, Morita H (2018) Hupercumines A and B, Lycopodium alkaloids from Huperzia cunninghamioides, inhibiting acetylcholinesterase. Org Lett 20:1384–1387CrossRefPubMed Hirasawa Y, Mitsui C, Uchiyama N, Hakamatsuka T, Morita H (2018) Hupercumines A and B, Lycopodium alkaloids from Huperzia cunninghamioides, inhibiting acetylcholinesterase. Org Lett 20:1384–1387CrossRefPubMed
10.
go back to reference Hirasawa Y, Kato Y, Wong CP, Uchiyama N, Goda Y, Hadi AHA, Morita H (2013) Huperminone A, a novel C16N-type Lycopodium alklaoid from Huperzia phlegmaria. Tetrahedron Lett 54:1593–1595CrossRef Hirasawa Y, Kato Y, Wong CP, Uchiyama N, Goda Y, Hadi AHA, Morita H (2013) Huperminone A, a novel C16N-type Lycopodium alklaoid from Huperzia phlegmaria. Tetrahedron Lett 54:1593–1595CrossRef
11.
go back to reference Hirasawa Y, Matsuya R, Shaari K, Lajis NH, Uchiyama N, Goda Y, Morita H (2012) Lycobelines A-C, novel C16N2-type Lycopodium alkaloids from Huperzia goebelii. Tetrahedron Lett 53:3971–3973CrossRef Hirasawa Y, Matsuya R, Shaari K, Lajis NH, Uchiyama N, Goda Y, Morita H (2012) Lycobelines A-C, novel C16N2-type Lycopodium alkaloids from Huperzia goebelii. Tetrahedron Lett 53:3971–3973CrossRef
12.
go back to reference Hirasawa Y, Agawa-Kakimoto M, Zaima K, Uchiyama N, Goda Y, Morita H (2021) Complanadine F, a Novel Dimeric Alkaloid from Lycopodium complanatum. J Nat Med 75:403–407CrossRefPubMed Hirasawa Y, Agawa-Kakimoto M, Zaima K, Uchiyama N, Goda Y, Morita H (2021) Complanadine F, a Novel Dimeric Alkaloid from Lycopodium complanatum. J Nat Med 75:403–407CrossRefPubMed
13.
go back to reference Nugroho AE, Ono Y, Jin E, Hirasawa Y, Kaneda T, Rahman A, Kusumawati I, Tougan T, Horii T, Zaini NC, Morita H (2021) Bisindole Alkaloids from Voacanga grandifolia Leaves. J Nat Med 75:408–414CrossRefPubMed Nugroho AE, Ono Y, Jin E, Hirasawa Y, Kaneda T, Rahman A, Kusumawati I, Tougan T, Horii T, Zaini NC, Morita H (2021) Bisindole Alkaloids from Voacanga grandifolia Leaves. J Nat Med 75:408–414CrossRefPubMed
14.
go back to reference Amelia P, Nugroho AE, Hirasawa Y, Kaneda T, Tougan T, Horii T, Morita H (2021) Two New Bisindole Alkaloids from Tabernaemontana macrocarpa Jack. J Nat Med 75:633–642CrossRefPubMedPubMedCentral Amelia P, Nugroho AE, Hirasawa Y, Kaneda T, Tougan T, Horii T, Morita H (2021) Two New Bisindole Alkaloids from Tabernaemontana macrocarpa Jack. J Nat Med 75:633–642CrossRefPubMedPubMedCentral
15.
go back to reference Nugroho AE, Hirasawa Y, Kaneda T, Shirota O, Matsuno M, Mizukami H, Morita H (2021) Triterpenoids from Walsura trichostemon. J Nat Med 75:415–422CrossRefPubMed Nugroho AE, Hirasawa Y, Kaneda T, Shirota O, Matsuno M, Mizukami H, Morita H (2021) Triterpenoids from Walsura trichostemon. J Nat Med 75:415–422CrossRefPubMed
16.
go back to reference Nugroho AE, Nakajima S, Wong CP, Hirasawa Y, Kaneda T, Shirota O, Tougan T, Horii T, Hadi AHA, Morita H (2022) Walsogynes H-O from Walsura chrysogyne. J Nat Med 76:94–101CrossRefPubMed Nugroho AE, Nakajima S, Wong CP, Hirasawa Y, Kaneda T, Shirota O, Tougan T, Horii T, Hadi AHA, Morita H (2022) Walsogynes H-O from Walsura chrysogyne. J Nat Med 76:94–101CrossRefPubMed
17.
go back to reference Nugroho AE, Tange M, Kusakabe Y, Hirasawa Y, Shirota O, Matsuno M, Mizukami H, Tougan T, Horii T, Morita H (2021) Chukranoids A – I, isopimarane diterpenoids from Chukrasia velutina. J Nat Med 76:756–764CrossRef Nugroho AE, Tange M, Kusakabe Y, Hirasawa Y, Shirota O, Matsuno M, Mizukami H, Tougan T, Horii T, Morita H (2021) Chukranoids A – I, isopimarane diterpenoids from Chukrasia velutina. J Nat Med 76:756–764CrossRef
18.
go back to reference Hirasawa Y, Tanaka T, Hirasawa S, Wong CP, Uchiyama N, Kaneda T, Goda Y, Morita H (2022) Cliniatines A-C, new Amaryllidaceae Alkaloids from Clivia miniata, inhibiting Acetylcholinesterase. J Nat Med 76:171–177CrossRefPubMed Hirasawa Y, Tanaka T, Hirasawa S, Wong CP, Uchiyama N, Kaneda T, Goda Y, Morita H (2022) Cliniatines A-C, new Amaryllidaceae Alkaloids from Clivia miniata, inhibiting Acetylcholinesterase. J Nat Med 76:171–177CrossRefPubMed
19.
go back to reference Ogasawara A, Noguchi R, Shigi T, Nugroho AE, Hirasawa Y, Kaneda T, Tougan T, Horii T, Hadi AHA, Morita H (2022) Caloforines A-G, cumarines from the bark of Calophyllum scriblitifolium. J Nat Med 76:645–653CrossRefPubMedPubMedCentral Ogasawara A, Noguchi R, Shigi T, Nugroho AE, Hirasawa Y, Kaneda T, Tougan T, Horii T, Hadi AHA, Morita H (2022) Caloforines A-G, cumarines from the bark of Calophyllum scriblitifolium. J Nat Med 76:645–653CrossRefPubMedPubMedCentral
20.
go back to reference Koyama K, Hirasawa Y, Kobayashi J, Morita H (2007) Cryptadines A and B, Novel C27N3-Type Pentacyclic Alkaloids from Lycopodium cryptomerinum. Bioorg Med Chem 15:7803–7808CrossRefPubMed Koyama K, Hirasawa Y, Kobayashi J, Morita H (2007) Cryptadines A and B, Novel C27N3-Type Pentacyclic Alkaloids from Lycopodium cryptomerinum. Bioorg Med Chem 15:7803–7808CrossRefPubMed
21.
go back to reference Hirasawa Y, Kobayashi J, Morita H (2006) Lycoperine A, A Novel C27N3-Type Pentacyclic Alkaloid from Lycopodium hamiltonii, Inhibiting Acetylcholinesterase. Org Lett 8:123–126CrossRefPubMed Hirasawa Y, Kobayashi J, Morita H (2006) Lycoperine A, A Novel C27N3-Type Pentacyclic Alkaloid from Lycopodium hamiltonii, Inhibiting Acetylcholinesterase. Org Lett 8:123–126CrossRefPubMed
22.
go back to reference Mill S, Hootele C (1996) A revised structure for the piperidine alkaloid andrachamine. Can J Chem 74:2434–2443CrossRef Mill S, Hootele C (1996) A revised structure for the piperidine alkaloid andrachamine. Can J Chem 74:2434–2443CrossRef
23.
go back to reference Ellman GL, Courtney KD, Andres V Jr, Feather-Stone RM (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 7:88–95CrossRefPubMed Ellman GL, Courtney KD, Andres V Jr, Feather-Stone RM (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 7:88–95CrossRefPubMed
Metadata
Title
Cryptadine C, a new C27N3-type Lycopodium alkaloid from Lycopodium cryptomerinum
Authors
Yusuke Hirasawa
Rina Hattori
Manami Ohtani
Hiroshi Morita
Publication date
12-05-2023
Publisher
Springer Nature Singapore
Published in
Journal of Natural Medicines / Issue 3/2023
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-023-01707-9

Other articles of this Issue 3/2023

Journal of Natural Medicines 3/2023 Go to the issue