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Progress in the studies on tryptanthrin, an alkaloid of history

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Abstract

Tryptanthrin, an indoloquinazoline alkaloid, was first obtained by sublimation of natural indigo and later isolated from the culture of fungus Candida lipolytica and a variety of other natural sources. Tryptanthrin showed a variety of intriguing biological properties such as antibacterial, antifungal, antiprotozoal, and antiparasitic activities, inhibitory activities against COX-2, 5-LOX, NO synthase and PGE(2) expression, as well as cytotoxic and antitumor activities. Present review covers recent studies on the natural sources, biological activities and mechanisms of their actions, synthesis, structure–activity relationship, and metabolism of tryptanthrin.

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Fig. 1
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Notes

  1. Spectral data for tryptanthrin were collected as follows: IR(KBr) υ 1725, 1688, 1610, 1519, 1550, 1350, 1310, 760 cm−1; UV (EtOH) λmax (ε) 225 (4.46), 251 (4.68), 280–420 (4.04) nm; MS m/z (rel. intensity) 248 (M, 100), 220 (45), 192 (30), 102 (15). 13C NMR (CDCl3, 62.5 MHz) δ 182.6 (C6), 158.1 (C12), 146.6 (C4a), 146.3 (C10a), 144.3 (C5a), 138.3 (C9), 135.1 (C3), 130.7 (C4), 130.2 (C2), 127.5 (C1), 127.2 (C8), 125.4 (C7), 121.9 (C6a), 118.0 (C10).

  2. In which crystal data of tryptanthrin were given: C15H8N2O2, MW = 248.2; monoclinic, a = 7.46 (6), b = 7.66 (6), c = 20.78 (16) Å, β = 109.0 (5)o, V = 1122.7 Å 3; F (000) = 512; Space group P21/c (C 52h , No. 14) from systematic absences; Z = 4, D = 1.47 g cm−3.

  3. Chem Abstr., 134, 128466(2001), Wikipedia encyclopedia has claimed that Isatis indigotica is a wrong expression of Isatis tinctoria: http://www.wikipedia.org.

  4. Where the reactions of nucleophilic nitrene complexes to the carbonyl group of aldehydes and ketones to provide the corresponding amines are well described.

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Acknowledgments

Present work is partially supported by Korean Science Foundation (KRF-2008-521-E00189).

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  1. College of Pharmacy, Yeungnam University, Gyeongsan, 712-749, South Korea

    Yurngdong Jahng

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Jahng, Y. Progress in the studies on tryptanthrin, an alkaloid of history. Arch. Pharm. Res. 36, 517–535 (2013). https://doi.org/10.1007/s12272-013-0091-9

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