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Tricyclon A

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Tricyclon A is an antimicrobial peptide isolated from Viola tricolor.

Category

Functional Peptides

Catalog number

BAT-010993

Molecular Formula

C149H211N37O48S6

Molecular Weight

3480.9

Specification
Reference Reading

IUPAC Name

3-[(1R,4S,7R,13S,16S,19S,22S,25R,28S,34S,37R,46S,49S,52S,55S,58R,64S,67S,70R,73S,76S,82S,85R,88S,91S,94S)-19,94-bis(4-aminobutyl)-37-(2-amino-2-oxoethyl)-52,73-dibenzyl-49-[(2S)-butan-2-yl]-64-(2-carboxyethyl)-55-(carboxymethyl)-34,46,82,91-tetrakis[(1R)-1-hydroxyethyl]-4,67-bis(hydroxymethyl)-28,88-bis[(4-hydroxyphenyl)methyl]-16-(1H-indol-3-ylmethyl)-22,76-bis(2-methylpropyl)-2,5,8,11,14,17,20,23,26,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71,74,77,80,83,86,89,92,95,98-tritriacontaoxo-1a,2a,5a,6a,9a,10a-hexathia-3,6,9,12,15,18,21,24,27,30,33,36,39,42,45,48,51,54,57,60,63,66,69,72,75,78,81,84,87,90,93,96,99-tritriacontazatetracyclo[56.41.4.47,70.425,85]hendecahectan-13-yl]propanoic acid

Synonyms

Gly-Gly-Thr-Ile-Phe-Asp-Cys-Gly-Glu-Ser-Cys-Phe-Leu-Gly-Thr-Cys-Tyr-Thr-Lys-Gly-Cys-Ser-Cys-Gly-Glu-Trp-Lys-Leu-Cys-Tyr-Gly-Thr-Asn

Sequence

(cyclo)-GGTIFDC(1)GESC(2)FLGTC(3)YTKGC(1)SC(2)GEWKLC(3)YGTN-(cyclo)

Storage

Store at -20°C

InChI

InChI=1S/C149H211N37O48S6/c1-11-73(6)119-145(230)173-95(49-79-26-16-13-17-27-79)135(220)172-99(54-118(207)208)137(222)177-102-65-235-237-67-104-141(226)176-101(64-188)139(224)178-103-66-236-238-69-106(180-140(225)100(63-187)175-132(217)90(41-43-117(205)206)162-111(198)59-159-128(102)213)143(228)169-94(48-78-24-14-12-15-25-78)134(219)166-91(46-71(2)3)125(210)157-61-114(201)184-121(75(8)190)147(232)181-107(144(229)170-96(51-81-34-38-84(194)39-35-81)138(223)186-123(77(10)192)148(233)165-87(30-20-22-44-150)124(209)156-60-112(199)163-104)70-240-239-68-105(179-133(218)92(47-72(4)5)167-130(215)88(31-21-23-45-151)164-136(221)97(52-82-55-153-86-29-19-18-28-85(82)86)171-131(216)89(40-42-116(203)204)161-110(197)58-160-129(103)214)142(227)168-93(50-80-32-36-83(193)37-33-80)126(211)158-62-115(202)183-120(74(7)189)146(231)174-98(53-108(152)195)127(212)155-56-109(196)154-57-113(200)182-122(76(9)191)149(234)185-119/h12-19,24-29,32-39,55,71-77,87-107,119-123,153,187-194H,11,20-23,30-31,40-54,56-70,150-151H2,1-10H3,(H2,152,195)(H,154,196)(H,155,212)(H,156,209)(H,157,210)(H,158,211)(H,159,213)(H,160,214)(H,161,197)(H,162,198)(H,163,199)(H,164,221)(H,165,233)(H,166,219)(H,167,215)(H,168,227)(H,169,228)(H,170,229)(H,171,216)(H,172,220)(H,173,230)(H,174,231)(H,175,217)(H,176,226)(H,177,222)(H,178,224)(H,179,218)(H,180,225)(H,181,232)(H,182,200)(H,183,202)(H,184,201)(H,185,234)(H,186,223)(H,203,204)(H,205,206)(H,207,208)/t73-,74+,75+,76+,77+,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98+,99-,100-,101-,102-,103-,104-,105-,106-,107-,119-,120-,121-,122-,123-/m0/s1

InChI Key

IXNJUPHEHRRQGX-DWDQKXESSA-N

Canonical SMILES

CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC2CSSCC3C(=O)NC(C(=O)NC4CSSCC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NCC(=O)NCC(=O)NC(C(=O)N1)C(C)O)CC(=O)N)C(C)O)CC5=CC=C(C=C5)O)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC4=O)CCC(=O)O)CC6=CNC7=CC=CC=C76)CCCCN)CC(C)C)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)N3)CCCCN)C(C)O)CC8=CC=C(C=C8)O)C(C)O)CC(C)C)CC9=CC=CC=C9)NC(=O)C(NC(=O)C(NC(=O)CNC2=O)CCC(=O)O)CO)CO)CC(=O)O)CC1=CC=CC=C1

1. Norprzewalsone A, a Rearranged Polycyclic Polyprenylated Acylphloroglucinol with a Spiro[cyclopentane-1,3'-tricyclo[7.4.0.01,6]tridecane] Core from Hypericum przewalskii

Yulin Duan, Yi Guo, Yanfang Deng, Pengfei Bu, Zhengyi Shi, Yunfang Cao, Yeting Zhang, Hong Hu, Weiguang Sun, Changxing Qi, Yonghui Zhang J Org Chem. 2022 May 20;87(10):6824-6831. doi: 10.1021/acs.joc.2c00503. Epub 2022 May 12.

Norprzewalsone A (1), a rearranged polyprenylated polycyclic acylphloroglucinol (PPAP) with a new carbon skeleton, along with a new congener, norprzewalsone B (2), were isolated from Hypericum przewalskii. Compound 1 possessed a new 5/6/5/6/6 pentacyclic ring system based on a spiro[cyclopentane-1,3'-tricyclo[7.4.0.01,6]tridecane] core, which might be derived from the common [3.3.1]-type bicyclic polyprenylated acylphloroglucinol (BPAP) via the key retro-Claisen, intramolecular cyclization, and Diels-Alder cyclization reactions. Their structures and absolute configurations were confirmed by spectroscopic data, calculated 1D NMR data with DP4+ probability analyses, and electronic circular dichroism calculations and comparison. More significantly, compound 1 exhibited a moderate inhibitory effect on NO production in lipopolysaccharide-stimulated RAW264.7 cells.

2. Granatripodins A-B, limonoids featuring a Tricyclo[3.3.1.02,8]nonane motif: Absolute configuration and agonistic effects on human pregnane-X-receptor

Li Shen, Xiao-Peng Zou, Wan-Shan Li, Attila Mándi, Tibor Kurtán, Jun Wu Bioorg Chem. 2021 Jun;111:104888. doi: 10.1016/j.bioorg.2021.104888. Epub 2021 Apr 5.

Two unprecedented limonoids incorporating a sterically encumbered cyclopropane ring, named granatripodins A (1) and B (2), featuring the presence of a tricyclo[3.3.1.02,8]nonane motif, were obtained from seeds of the Thai Xylocarpus granatum. The planar structures and absolute configurations of these limonoids were unambiguously established by NMR investigations, TDDFT-ECD and DFT-NMR calculations, and single-crystal X-ray diffraction analysis (Cu Kα). Most notably, granatripodin A (1) exhibited agonistic effects on human pregnane-X-receptor at the concentration of 100.0 nM. The biosynthetic origins of these limonoids via a radical cascade reaction are proposed. This study exemplifies a universal approach for the stereochemical assignment of polycyclic compounds with a cyclopropane-embedded cage scaffold.

3. Illihenin A: An Antiviral Sesquiterpenoid with a Cage-like Tricyclo[6.2.2.01,5]dodecane Skeleton from Illicium henryi

Jin-Yao Yong, Wen-Rui Li, Xiao-Jing Wang, Guo-Zhu Su, Mi Li, Jian-Pei Zhang, Hong-Li Jia, Yu-Huan Li, Ru-Bing Wang, Maoluo Gan, Shuang-Gang Ma J Org Chem. 2021 Jan 15;86(2):2017-2022. doi: 10.1021/acs.joc.0c02727. Epub 2021 Jan 4.

Illihenin A (1), a novel sesquiterpenoid, was isolated from the roots of Illicium henryi. The structure was determined by spectroscopic analyses, ECD calculation, and single-crystal X-ray diffraction. Compound 1 represents a class of novel 5/7/6 tricyclic sesquiterpenoids featuring a rare cage-like tricyclo[6.2.2.01,5]dodecane core. A plausible biosynthetic pathway of 1 by rearrangement of allo-cedrane is proposed. Additionally, 1 showed potent antiviral activity against coxsackievirus B3 with an IC50 value of 2.87 μM.