Hantupeptins B and C, cytotoxic cyclodepsipeptides from the marine cyanobacterium Lyngbya majuscula

Phytochemistry
Ashootosh TripathiLik Tong Tan

Abstract

Hantupeptins B (2) and C (3) were isolated, along with the previously reported hantupeptin A (1), from the marine cyanobacterium, Lyngbya majuscula, collected from Pulau Hantu Besar, Singapore. Their structures were elucidated by interpretation of extensive 1D and 2D NMR spectroscopic data. Compounds 2 and 3 are cyclic depsipeptides consisting of five alpha-amino/hydroxy acid residues, including phenyllactic acid, proline, N-methyl-valine, valine, N-methyl-isoleucine, and a beta-hydroxy acid unit with different degrees of unsaturation at the terminal end of each molecule. The absolute configurations of the common amino acids and phenyllactic acid were determined by the advanced Marfey's and chiral HPLC analyses, respectively. The complete stereochemistry of 3-hydroxy-2-methyl-7-octynoic acid moiety in hantupeptin A was elucidated by a combination of homonuclear J-resolved 2D NMR experiments and by Mosher's method. Hantupeptins B and C showed moderate in vitro cytotoxicity when tested against MOLT-4 (leukemic) and MCF-7 (breast cancer) cell lines.

References

Nov 28, 2006·Journal of Natural Products·Sutaporn BunyajetpongKunimitsu Kaya
Jun 3, 2008·Phytochemistry·Lik Tong TanTripathi Ashootosh
Dec 20, 2008·Journal of Natural Products·Ashootosh TripathiLik Tong Tan

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Citations

Nov 30, 2011·Journal of Natural Products·Shi-Hui DongJian-Min Yue
Jul 27, 2010·Biofouling·Lik Tong TanSerena Lay Ming Teo
Jul 16, 2010·Marine Drugs·Li Liu, Kathleen S Rein
Jul 23, 2014·Chemistry : a European Journal·Eduardo BustoWolfgang Kroutil
Jul 16, 2014·Pharmaceutical Biology·Maruthanayagam VeerabadhranSundararaman Muthuraman
Mar 19, 2013·Biotechnology Advances·Saradavey Vinothkumar, P S Parameswaran
Dec 24, 2011·Natural Product Reports·John W BluntMichèle R Prinsep
May 24, 2017·Journal of Natural Products·Jehad AlmalitiWilliam H Gerwick
Feb 1, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ye' Zaw PhyoMadalena M M Pinto
Dec 7, 2017·Frontiers in Pharmacology·Shivankar AgrawalSunil K Deshmukh
Sep 13, 2011·Journal of Applied Toxicology : JAT·M NagarajanM Sundararaman
Jun 4, 2019·Marine Drugs·Justine DemayBenjamin Marie
May 1, 2021·International Journal of Molecular Sciences·Jia-Nan ZhangHong-Jie Zhang
Oct 16, 2021·Natural Product Reports·Tanja M VoserAnthony R Carroll
Jan 15, 2022·Journal of Natural Products·Ma Yadanar PhyoLik Tong Tan

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