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Viscotoxin B

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Viscotoxin B is a small protein that is toxic to many cell types. It belongs to the thionin family and is isolated from Viscum album L.

Category

Functional Peptides

Catalog number

BAT-011043

CAS number

11063-16-4

Molecular Formula

C197H322N64O67S6

Molecular Weight

4851

Specification
Reference Reading

IUPAC Name

(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(aS,1R,3aS,6aS,7S,9aS,10S,12aR,13S,16S,17aR,22S,25S,28S,31S,34S,37S,40R,43S,46S,58S,61S,64S,67S,70R,73S,76S,79S,82S,88R,91S,94S,97S)-91-(4-aminobutyl)-10,25,34-tris(2-amino-2-oxoethyl)-28,94,97-tris[(2S)-butan-2-yl]-22,43,61,67-tetrakis(3-carbamimidamidopropyl)-64-(2-carboxyethyl)-17a-[[(2S)-2-[[(2S)-2,6-diaminohexanoyl]amino]-3-hydroxypropanoyl]amino]-9a,13,16,37-tetrakis[(1R)-1-hydroxyethyl]-a,6a,58,76,82-pentakis(hydroxymethyl)-31-[(4-hydroxyphenyl)methyl]-3a,73-dimethyl-46,79-bis(2-methylpropyl)-1a,2,4a,7a,8,10a,11,14,17,18a,20,23,26,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71,74,77,80,83,86,89,92,95,98-heptatriacontaoxo-14a,15a,21a,22a,25a,26a-hexathia-2a,3,5a,8a,9,11a,12,15,18,19a,21,24,27,30,33,36,39,42,45,48,51,54,57,60,63,66,69,72,75,78,81,84,87,90,93,96,99-heptatriacontazatetracyclo[86.31.4.440,70.03,7]heptacosahectane-12a-carbonyl]pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-6-aminohexanoic acid

Synonyms

H-Lys-Ser-Cys(1)-Cys(2)-Pro-Asn-Thr-Thr-Gly-Arg-Asn-Ile-Tyr-Asn-Thr-Cys(3)-Arg-Leu-Gly-Gly-Gly-Ser-Arg-Glu-Arg-Cys(3)-Ala-Ser-Leu-Ser-Gly-Cys(2)-Lys-Ile-Ile-Ser-Ala-Ser-Thr-Cys(1)-Pro-Ser-Asp-Tyr-Pro-Lys-OH

Sequence

H-KSC(1)C(2)PNTTGRNIYNTC(3)RLGGGSRERC(3)ASLSGC(2)KIISASTC(1)PSDYPK-OH

InChI

InChI=1S/C197H322N64O67S6/c1-17-91(8)146-184(318)239-114(65-100-43-47-102(273)48-44-100)165(299)236-116(68-137(203)276)168(302)255-150(97(14)270)187(321)249-130-86-331-330-84-128(247-161(295)109(39-29-59-216-197(211)212)227-162(296)110(51-52-144(283)284)231-159(293)107(37-27-57-214-195(207)208)228-171(305)121(77-263)225-141(280)73-218-139(278)71-217-140(279)72-219-156(290)112(63-89(4)5)233-160(294)108(230-178(130)312)38-28-58-215-196(209)210)176(310)223-95(12)154(288)241-123(79-265)172(306)234-113(64-90(6)7)164(298)244-120(76-262)157(291)220-74-143(282)226-127-83-329-333-87-131(191(325)260-61-31-41-134(260)181(315)238-117(69-138(204)277)169(303)256-152(99(16)272)189(323)258-149(96(13)269)183(317)221-75-142(281)224-105(36-26-56-213-194(205)206)158(292)235-115(67-136(202)275)167(301)253-146)250-179(313)129(248-174(308)124(80-266)243-155(289)104(201)33-20-23-53-198)85-332-334-88-132(251-188(322)151(98(15)271)257-175(309)126(82-268)242-153(287)94(11)222-170(304)122(78-264)246-185(319)147(92(9)18-2)254-186(320)148(93(10)19-3)252-163(297)106(229-177(127)311)34-21-24-54-199)192(326)261-62-32-42-135(261)182(316)245-125(81-267)173(307)237-118(70-145(285)286)166(300)240-119(66-101-45-49-103(274)50-46-101)190(324)259-60-30-40-133(259)180(314)232-111(193(327)328)35-22-25-55-200/h43-50,89-99,104-135,146-152,262-274H,17-42,51-88,198-201H2,1-16H3,(H2,202,275)(H2,203,276)(H2,204,277)(H,217,279)(H,218,278)(H,219,290)(H,220,291)(H,221,317)(H,222,304)(H,223,310)(H,224,281)(H,225,280)(H,226,282)(H,227,296)(H,228,305)(H,229,311)(H,230,312)(H,231,293)(H,232,314)(H,233,294)(H,234,306)(H,235,292)(H,236,299)(H,237,307)(H,238,315)(H,239,318)(H,240,300)(H,241,288)(H,242,287)(H,243,289)(H,244,298)(H,245,316)(H,246,319)(H,247,295)(H,248,308)(H,249,321)(H,250,313)(H,251,322)(H,252,297)(H,253,301)(H,254,320)(H,255,302)(H,256,303)(H,257,309)(H,258,323)(H,283,284)(H,285,286)(H,327,328)(H4,205,206,213)(H4,207,208,214)(H4,209,210,215)(H4,211,212,216)/t91-,92-,93-,94-,95-,96+,97+,98+,99+,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,146-,147-,148-,149-,150-,151-,152-/m0/s1

InChI Key

ZWPXAQXYYQZXSU-ZNZVWFPBSA-N

Canonical SMILES

CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(C(=O)NC2CSSCC(C(=O)NC(C(=O)N1)CCCCN)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C3CSSCC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NCC(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N3)CCCNC(=N)N)CCC(=O)O)CCCNC(=N)N)CO)CC(C)C)CCCNC(=N)N)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C4CCCN4C2=O)CC(=O)N)C(C)O)C(C)O)CCCNC(=N)N)CC(=O)N)C(C)CC)CC5=CC=C(C=C5)O)CC(=O)N)C(C)O)C)CO)CC(C)C)CO)NC(=O)C(CO)NC(=O)C(CCCCN)N)C(=O)N6CCCC6C(=O)NC(CO)C(=O)NC(CC(=O)O)C(=O)NC(CC7=CC=C(C=C7)O)C(=O)N8CCCC8C(=O)NC(CCCCN)C(=O)O)C(C)O)CO)C)CO)C(C)CC

1. Viscotoxin and lectin content in foliage and fruit of Viscum album L. on the main host trees of Hyrcanian forests

Sanaz Yousefvand, Farnoosh Fattahi, Seyed Mohsen Hosseini, Konrad Urech, Gerhard Schaller Sci Rep. 2022 Jun 20;12(1):10383. doi: 10.1038/s41598-022-14504-3.

Mistletoe (Viscum album L.) is a hemiparasitic plant that absorbs water and nutrients from the host tree. Mistletoe contains two groups of cytotoxic, immunomodulatory and antitumor proteins, viscotoxins and lectins. This study evaluated the quantity and quality of viscotoxins and total lectins in the stems with leaves (foliage) and fruit of mistletoe on Parrotia persica and Carpinus betulus in September with immature green berries and in December with mature white berries. Viscum album L. plants were harvested from host species located in the Hyrcanian forests of Iran in 2019. The highest level of viscotoxins was detected in the December foliage of V. album settled on C. betulus (9.25 mg/g dry weight [DW]), and the highest content of lectins was found in the December foliage of V. album settled on P. persica (0.79 mg/g DW) and C. betulus (0.73 mg/g DW) respectively. The immature green berries of V. album from both host species contained much higher concentrations of viscotoxins and lectins than the mature white berries. Four isoforms of viscotoxins, viscotoxin A1, A2, A3 and B could be identified in all samples of both host species. Viscotoxin A3 was the predominant viscotoxin isoform followed by viscotoxin A1.

2. Comparative membrane interaction study of viscotoxins A3, A2 and B from mistletoe (Viscum album) and connections with their structures

Alexandre Coulon, Amor Mosbah, André Lopez, Anne-Marie Sautereau, Gerhard Schaller, Konrad Urech, Pierre Rougé, Hervé Darbon Biochem J. 2003 Aug 15;374(Pt 1):71-8. doi: 10.1042/BJ20030488.

Viscotoxins A2 (VA2) and B (VB) are, together with viscotoxin A3 (VA3), among the most abundant viscotoxin isoforms that occur in mistletoe-derived medicines used in anti-cancer therapy. Although these isoforms have a high degree of amino-acid-sequence similarity, they are strikingly different from each other in their in vitro cytotoxic potency towards tumour cells. First, as VA3 is the only viscotoxin whose three-dimensional (3D) structure has been solved to date, we report the NMR determination of the 3D structures of VA2 and VB. Secondly, to account for the in vitro cytotoxicity discrepancy, we carried out a comparative study of the interaction of the three viscotoxins with model membranes. Although the overall 3D structure is highly conserved among the three isoforms, some discrete structural features and associated surface properties readily account for the different affinity and perturbation of model membranes. VA3 and VA2 interact in a similar way, but the weaker hydrophobic character of VA2 is thought to be mainly responsible for the apparent different affinity towards membranes. VB is much less active than the other two viscotoxins and does not insert into model membranes. This could be related to the occurrence of a single residue (Arg25) protruding outside the hydrophobic plane formed by the two amphipathic alpha-helices, through which viscotoxins are supposed to interact with plasma membranes.