HETEROCYCLES

An International Journal for Reviews and Communications in Heterocyclic Chemistry
Web Edition ISSN: 1881-0942
Published online by The Japan Institute of Heterocyclic Chemistry

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Search65,753 Compounds

Nomenclature:

The natural products are listed under the name used in the original literature.

The abbreviations:

The following abbreviations have been used:

• act:
• biological activity

• cd:
• circular dichroism

• Cnmr:
• 13C-nuclear magnetic resonance spectrum

• Hnmr:
• 1H-nuclear magnetic resonance spectrum

• ir:
• infrared spectrum

• mass:
• mass spectrum

• syn:
• total synthesis

• uv:
• ultraviolet spectrum

Journal:

This database lists the natural products with heterocyclic ring system whose synthesis has been determined since 1975. The journals which have been covered are as follows:

Angew. Chem. Int. Ed. Engl.
Angew. Chem. Int. Ed.
Bull. Chem. Soc. Japan
Chem. and Ind.
Chem. Ber.
J. Chem. Soc., Chem. Commun.
Chem. Commun.
Chem. Eur. J.
Chemistry Lett.
Chem. Pharm. Bull.
Coll. Czech. Chem. Commun.
Eur. J. Inorg. Chem.
Eur. J. Org. Chem.
Experientia
Helv. Chim. Acta
Heterocycles
J. Am. Chem. Soc.
J. Antibiot.
J. Chem. Soc., Perkin Trans. 1
J. Heterocycl. Chem.
J. Med. Chem.
J. Nat. Prod.
J. Org. Chem.
J. Pharm. Sci.
Liebigs Ann. Chem.
Monatsh. Chem.
Org. Lett.
Phytochemistry
Planta medica
Synlett
Synth. Commun.
Synthesis
Tetrahedron
Tetrahedron Asymmetry
Tetrahedron Lett.
Yakugaku Zasshi

Editor:

Editor:
Kunio Ogasawara

Associate Editors:
Toshio Honda
Yoshiharu Iwabuchi

This journal will list the new natural products with a heterocyclic ring system, collected from current chemical literature, whose structure has been established.

• Search by Group: AllPolyketidesAromaticsTerpenesSteroidsAlkaloidsAntibioticsMiscellaneous
• Search by Journal: Chem. Pharm. Bull.Helv. Chim. ActaHeterocyclesJ. Antibiot.J. Nat. Prod.J. Org. Chem.Org. Biomol. Chem.Org. Lett.Phytochem. Lett.PhytochemistryPlanta medicaTetrahedronTetrahedron Lett.
• Year: 2014201420142014201420142014201420142014201420142014
• Vol: 6297896777791216107107807055
• No: 11111111112143, 4421, 22  1744-4745-48

Alkaloids

Kopsinine, 5β-Hydroxy-

C21H26N2O3 = 354

Tetrahedron 2014, 70, 9099

M. Kitajima, M. Anbe, N. Kogure, S. Wongseripipatana, H. Takayama

DOI: 10.1016/j.tet.2014.10.002

CrossRef

[	NS	]	Kopsia jasminiflora
[	mp	]
[	bp	]
[	α	] D	- 38   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Vobasidine C

C21H26N2O3 = 354

J. Nat. Prod. 2014, 77, 2504

D. S.-Y. Sim, K.-W. Chong, C.-E Nge, Y.-Y. Low, K.-S. Sim, T.-S. Kam

DOI: 10.1021/np500589u

CrossRef

[	NS	]	Tabernaemontana
[	mp	]
[	bp	]
[	α	] D	- 117   [ CHCl3 ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]	cytotoxicity

Alkaloids

Vobasidine D

C21H22N2O4 = 366

J. Nat. Prod. 2014, 77, 2504

D. S.-Y. Sim, K.-W. Chong, C.-E Nge, Y.-Y. Low, K.-S. Sim, T.-S. Kam

DOI: 10.1021/np500589u

CrossRef

[	NS	]	Tabernaemontana
[	mp	]
[	bp	]
[	α	] D	- 70   [ CHCl3 ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Strychnine-chloromethochloride, Deoxy-iso-

C22H24N2OCl = 367.5

Tetrahedron Lett. 2014, 55, 6538

Y.-S. Shi, Y.-B. Liu, S.-G. Ma, L. Li, J. Qu,Y. Li, S.-S. Yu

DOI: 10.1016/j.tetlet.2014.09.127

CrossRef

[	NS	]	Strychnos nux-vomica
[	mp	]
[	bp	]
[	α	] D	+ 45.98   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Kopsinine, 5,6-Seco-

C21H24N2O4 = 368

Tetrahedron 2014, 70, 9099

M. Kitajima, M. Anbe, N. Kogure, S. Wongseripipatana, H. Takayama

DOI: 10.1016/j.tet.2014.10.002

CrossRef

[	NS	]	Kopsia jasminiflora
[	mp	]
[	bp	]
[	α	] D	- 248   [ CHCl3 ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Vobasidine A

C21H24N2O4 = 368

J. Nat. Prod. 2014, 77, 2504

D. S.-Y. Sim, K.-W. Chong, C.-E Nge, Y.-Y. Low, K.-S. Sim, T.-S. Kam

DOI: 10.1021/np500589u

CrossRef

[	NS	]	Tabernaemontana
[	mp	]
[	bp	]
[	α	] D	- 35   [ CHCl3 ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]	cytotoxicity

Alkaloids

Tacamine-N-oxide

C21H26N2O4 = 370

J. Nat. Prod. 2014, 77, 2504

D. S.-Y. Sim, K.-W. Chong, C.-E Nge, Y.-Y. Low, K.-S. Sim, T.-S. Kam

DOI: 10.1021/np500589u

CrossRef

[	NS	]	Tabernaemontana
[	mp	]
[	bp	]
[	α	] D	- 6   [ CHCl3 ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Tubotaiwine, 14S-Hydroxy-19R-methoxy-

C21H26N2O4 = 370

Tetrahedron 2014, 70, 9099

M. Kitajima, M. Anbe, N. Kogure, S. Wongseripipatana, H. Takayama

DOI: 10.1016/j.tet.2014.10.002

CrossRef

[	NS	]	Kopsia jasminiflora
[	mp	]
[	bp	]
[	α	] D	+ 123   [ CHCl3 ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Vinmajine H

C22H19N3O3 = 373

Tetrahedron 2014, 70, 8723

G.-G. Cheng, Y.-L. Zhao, Y. Zhang, P.-K. Lunga, D.-B. Hu, Y. Li, J. Gu, C.-W. Song, W.-B. Sun, Y.-P. Liu, X.-D. Luo

DOI: 10.1016/j.tet.2014.09.026

CrossRef

[	NS	]	Vinca major
[	mp	]
[	bp	]
[	α	] D	+ 51.3   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Stryvomicine A

C23H27N2O3 = 379

Tetrahedron Lett. 2014, 55, 6538

Y.-S. Shi, Y.-B. Liu, S.-G. Ma, L. Li, J. Qu,Y. Li, S.-S. Yu

DOI: 10.1016/j.tetlet.2014.09.127

CrossRef

[	NS	]	Strychnos nux-vomica
[	mp	]
[	bp	]
[	α	] D	– 34.10   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Vinmajine C

C23H28N2O3 = 380

Tetrahedron 2014, 70, 8723

G.-G. Cheng, Y.-L. Zhao, Y. Zhang, P.-K. Lunga, D.-B. Hu, Y. Li, J. Gu, C.-W. Song, W.-B. Sun, Y.-P. Liu, X.-D. Luo

DOI: 10.1016/j.tet.2014.09.026

CrossRef

[	NS	]	Vinca major
[	mp	]
[	bp	]
[	α	] D	- 36.7   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Evollionine B

C20H19N3O5 = 381

Helv. Chim. Acta 2014, 97, 1481

Y.-H. Li, J. He, Y. Li, X.-D. Wu, L.-Y. Peng, R.-N. Du, X. Cheng, Q.-S. Zhao, R.-T. Li

DOI: 10.1002/hlca.201300449

CrossRef

[	NS	]	Evodia rutaecarpa
[	mp	]
[	bp	]
[	α	] D
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Vinmajine B

C22H26N2O4 = 382

Tetrahedron 2014, 70, 8723

G.-G. Cheng, Y.-L. Zhao, Y. Zhang, P.-K. Lunga, D.-B. Hu, Y. Li, J. Gu, C.-W. Song, W.-B. Sun, Y.-P. Liu, X.-D. Luo

DOI: 10.1016/j.tet.2014.09.026

CrossRef

[	NS	]	Vinca major
[	mp	]
[	bp	]
[	α	] D	+ 45.5   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Vinmajine D

C22H26N2O4 = 382

Tetrahedron 2014, 70, 8723

G.-G. Cheng, Y.-L. Zhao, Y. Zhang, P.-K. Lunga, D.-B. Hu, Y. Li, J. Gu, C.-W. Song, W.-B. Sun, Y.-P. Liu, X.-D. Luo

DOI: 10.1016/j.tet.2014.09.026

CrossRef

[	NS	]	Vinca major
[	mp	]
[	bp	]
[	α	] D	- 15.2   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Vinmajine G

C21H24N2O5 = 384

Tetrahedron 2014, 70, 8723

G.-G. Cheng, Y.-L. Zhao, Y. Zhang, P.-K. Lunga, D.-B. Hu, Y. Li, J. Gu, C.-W. Song, W.-B. Sun, Y.-P. Liu, X.-D. Luo

DOI: 10.1016/j.tet.2014.09.026

CrossRef

[	NS	]	Vinca major
[	mp	]
[	bp	]
[	α	] D	- 92.2   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Vinmajine E

C23H26N2O5 = 410

Tetrahedron 2014, 70, 8723

G.-G. Cheng, Y.-L. Zhao, Y. Zhang, P.-K. Lunga, D.-B. Hu, Y. Li, J. Gu, C.-W. Song, W.-B. Sun, Y.-P. Liu, X.-D. Luo

DOI: 10.1016/j.tet.2014.09.026

CrossRef

[	NS	]	Vinca major
[	mp	]
[	bp	]
[	α	] D	+ 41.1   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Colubrine-chloromethochloride, α-

C23H26N2O3Cl = 413.5

Tetrahedron Lett. 2014, 55, 6538

Y.-S. Shi, Y.-B. Liu, S.-G. Ma, L. Li, J. Qu,Y. Li, S.-S. Yu

DOI: 10.1016/j.tetlet.2014.09.127

CrossRef

[	NS	]	Strychnos nux-vomica
[	mp	]
[	bp	]
[	α	] D	– 78.5   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Colubrine-chloromethochloride, β-

C23H26N2O3Cl = 413.5

Tetrahedron Lett. 2014, 55, 6538

Y.-S. Shi, Y.-B. Liu, S.-G. Ma, L. Li, J. Qu,Y. Li, S.-S. Yu

DOI: 10.1016/j.tetlet.2014.09.127

CrossRef

[	NS	]	Strychnos nux-vomica
[	mp	]
[	bp	]
[	α	] D	– 105.0   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Plakinamine N

C29H48N2 = 424

J. Nat. Prod. 2014, 77, 2475

S. N. Sunassee, T. Ransom, C. J. Henrich, J. A. Beutler, D. G. Covell, J. B. McMahon, K. R. Gustafson

DOI: 10.1021/np500556t

CrossRef

[	NS	]	Corticium niger
[	mp	]
[	bp	]
[	α	] D	+ 8.8   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]	growth inhibit activity

Alkaloids

Pyrrolocin B

C26H37NO5 = 443

J. Nat. Prod. 2014, 77, 2537

R. C. Jadulco, M. Koch, T. B. Kakule, E. W. Schmidt, A. Orendt, H. He, J. E. Janso, G. T. Carter, E. C. Larson, C. Pond, T. K. Matainaho, L. R. Barrows

DOI: 10.1021/np500617u

CrossRef

[	NS	]	NRRL 50135
[	mp	]
[	bp	]
[	α	] D	- 150   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]	antimycobacterial activity

Alkaloids

Pyrrolocin C

C26H37NO5 = 443

J. Nat. Prod. 2014, 77, 2537

R. C. Jadulco, M. Koch, T. B. Kakule, E. W. Schmidt, A. Orendt, H. He, J. E. Janso, G. T. Carter, E. C. Larson, C. Pond, T. K. Matainaho, L. R. Barrows

DOI: 10.1021/np500617u

CrossRef

[	NS	]	NRRL 50135
[	mp	]
[	bp	]
[	α	] D	+ 130   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]	antimycobacterial activity

Alkaloids

Taipinisine

C29H32N4O = 452

J. Nat. Prod. 2014, 77, 2504

D. S.-Y. Sim, K.-W. Chong, C.-E Nge, Y.-Y. Low, K.-S. Sim, T.-S. Kam

DOI: 10.1021/np500589u

CrossRef

[	NS	]	Tabernaemontana
[	mp	]
[	bp	]
[	α	] D	- 29   [ CHCl3 ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]	cytotoxicity

Alkaloids

Vinmajine A

C25H31N3O5 = 453

Tetrahedron 2014, 70, 8723

G.-G. Cheng, Y.-L. Zhao, Y. Zhang, P.-K. Lunga, D.-B. Hu, Y. Li, J. Gu, C.-W. Song, W.-B. Sun, Y.-P. Liu, X.-D. Luo

DOI: 10.1016/j.tet.2014.09.026

CrossRef

[	NS	]	Vinca major
[	mp	]
[	bp	]
[	α	] D	- 23.2   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Pyrrolocin A

C27H39NO5 = 457

J. Nat. Prod. 2014, 77, 2537

R. C. Jadulco, M. Koch, T. B. Kakule, E. W. Schmidt, A. Orendt, H. He, J. E. Janso, G. T. Carter, E. C. Larson, C. Pond, T. K. Matainaho, L. R. Barrows

DOI: 10.1021/np500617u

CrossRef

[	NS	]	NRRL 50135
[	mp	]
[	bp	]
[	α	] D	+ 56.1   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]	antimycobacterial activity

Alkaloids

Plakinamine O

C31H50N2O2 = 482

J. Nat. Prod. 2014, 77, 2475

S. N. Sunassee, T. Ransom, C. J. Henrich, J. A. Beutler, D. G. Covell, J. B. McMahon, K. R. Gustafson

DOI: 10.1021/np500556t

CrossRef

[	NS	]	Corticium niger
[	mp	]
[	bp	]
[	α	] D	+ 17.5   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]	growth inhibit activity

Alkaloids

Cephatonine-2-O-β-D-glucopyranoside

C26H35NO10 = 521

Tetrahedron 2014, 70, 8893

Y.-H. Li, H.-M. Li, Y. Li, J. He, X. Deng, L.-Y. Peng, L.-H. Gao, Q.-S. Zhao, R.-T. Li, X.-D. Wu

DOI: 10.1016/j.tet.2014.09.088

CrossRef

[	NS	]	Sinomenium acutum
[	mp	]
[	bp	]
[	α	] D	- 55.3   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Pyrapaxilline

C37H47NO5 = 585

J. Antibiot. 2014, 67, 787

C. Matsui, Y. Ikeda, H. Iinuma, N. Kushida, T. Kunisada, S. Simizu, K. Umezawa

DOI: 10.1038/ja.2014.63

CrossRef

[	NS	]	Eupenicillium shearii
[	mp	]
[	bp	]
[	α	] D	– 11   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]	inhibition of LPS-induced NO production

Alkaloids

Sallisonine C

C37H40N2O7 = 624

Tetrahedron 2014, 70, 8893

Y.-H. Li, H.-M. Li, Y. Li, J. He, X. Deng, L.-Y. Peng, L.-H. Gao, Q.-S. Zhao, R.-T. Li, X.-D. Wu

DOI: 10.1016/j.tet.2014.09.088

CrossRef

[	NS	]	Sinomenium acutum
[	mp	]
[	bp	]
[	α	] D	+ 3.5   [ MeOH ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]

Alkaloids

Sallisonine B

C38H40N2O7 = 636

Tetrahedron 2014, 70, 8893

Y.-H. Li, H.-M. Li, Y. Li, J. He, X. Deng, L.-Y. Peng, L.-H. Gao, Q.-S. Zhao, R.-T. Li, X.-D. Wu

DOI: 10.1016/j.tet.2014.09.088

CrossRef

[	NS	]	Sinomenium acutum
[	mp	]
[	bp	]
[	α	] D	+ 31.3   [ CHCl3 ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]	ability to inhibit NO production of LPS-stimulated RAW264.7 macrophages

Alkaloids

Sallisonine A

C38H42N2O7 = 638

Tetrahedron 2014, 70, 8893

Y.-H. Li, H.-M. Li, Y. Li, J. He, X. Deng, L.-Y. Peng, L.-H. Gao, Q.-S. Zhao, R.-T. Li, X.-D. Wu

DOI: 10.1016/j.tet.2014.09.088

CrossRef

[	NS	]	Sinomenium acutum
[	mp	]
[	bp	]
[	α	] D	+ 69.4   [ CHCl3 ]
[	Ph	]	uv Hnmr Cnmr ir Xray mass cd syn
[	act	]	cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, SW480

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