Chaetoglobosin A
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MedKoo CAT#: 412782

CAS#: 50335-03-0

Description: Chaetoglobosin A is a fungal isolate with anticancer activity in vitro. Derivatives of the compound include MBJ-0038, MBJ-0039, and MBJ-0040

Chemical Structure

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Chaetoglobosin A
CAS# 50335-03-0
Instruction

Theoretical Analysis

MedKoo Cat#: 412782
Name: Chaetoglobosin A
CAS#: 50335-03-0
Chemical Formula: C32H36N2O5
Exact Mass: 528.26
Molecular Weight: 528.650
Elemental Analysis: C, 72.70; H, 6.86; N, 5.30; O, 15.13

Price and Availability

Size Price Availability Quantity
1mg USD 310 2 Weeks
5mg USD 950 2 Weeks
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Synonym: Chaetoglobosin A; BRN1097707; BRN-1097707; BRN 1097707

IUPAC/Chemical Name: (1E,4S,5E,7R,9E,11aR,14S,14aR,15S,15aR,16aS,16bR)-14-((1H-indol-3-yl)methyl)-7-hydroxy-4,6,15,15a-tetramethyl-4,7,14,14a,15,15a,16a,16b-octahydro-3H-cyclotrideca[d]oxireno[2,3-f]isoindole-8,11,12(13H)-trione

InChi Key: OUMWCYMRLMEZJH-VOXRAUTJSA-N

InChi Code: InChI=1S/C32H36N2O5/c1-17-8-7-10-22-29-31(4,39-29)19(3)27-24(15-20-16-33-23-11-6-5-9-21(20)23)34-30(38)32(22,27)26(36)13-12-25(35)28(37)18(2)14-17/h5-7,9-14,16-17,19,22,24,27-29,33,37H,8,15H2,1-4H3,(H,34,38)/b10-7+,13-12+,18-14+/t17-,19-,22-,24-,27-,28+,29-,31+,32+/m0/s1

SMILES Code: C[C@H]1C/C=C/[C@H]2[C@@H]3O[C@@]3([C@H]([C@H]4[C@@H](NC([C@@]24C(/C=C/C([C@@H](/C(C)=C/1)O)=O)=O)=O)Cc(c[nH]5)c6c5cccc6)C)C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 528.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Cheng M, Zhao S, Liu H, Liu Y, Lin C, Song J, Thawai C, Charoensettasilp S, Yang Q. Functional analysis of a chaetoglobosin A biosynthetic regulator in Chaetomium globosum. Fungal Biol. 2021 Mar;125(3):201-210. doi: 10.1016/j.funbio.2020.10.010. Epub 2020 Nov 27. PMID: 33622536.


2: Jiang C, Song J, Zhang J, Yang Q. New production process of the antifungal chaetoglobosin A using cornstalks. Braz J Microbiol. 2017 Jul-Sep;48(3):410-418. doi: 10.1016/j.bjm.2016.11.008. Epub 2017 Feb 4. PMID: 28223029; PMCID: PMC5498411.


3: Zhao S, Lin C, Cheng M, Zhang K, Wang Z, Zhao T, Yang Q. New insight into the production improvement and resource generation of chaetoglobosin A in Chaetomium globosum. Microb Biotechnol. 2022 Oct;15(10):2562-2577. doi: 10.1111/1751-7915.14111. Epub 2022 Aug 5. PMID: 35930651; PMCID: PMC9518988.


4: Xiang B, Hao X, Xie Q, Shen G, Liu Y, Zhu X. Deletion of a Rare Fungal PKS CgPKS11 Promotes Chaetoglobosin A Biosynthesis, Yet Defers the Growth and Development of Chaetomium globosum. J Fungi (Basel). 2021 Sep 13;7(9):750. doi: 10.3390/jof7090750. PMID: 34575788; PMCID: PMC8471558.


5: Liang X, Lin Y, Yu W, Yang M, Meng X, Yang W, Guo Y, Zhang R, Sun G. Chaetoglobosin A contributes to the antagonistic action of Chaetomium globosum strain 61239 toward the apple Valsa canker pathogen Cytospora mali. Phytopathology. 2023 Apr 17. doi: 10.1094/PHYTO-01-23-0036-R. Epub ahead of print. PMID: 37069143.


6: Zhu X, Zhou D, Liang F, Wu Z, She Z, Li C. Penochalasin K, a new unusual chaetoglobosin from the mangrove endophytic fungus Penicillium chrysogenum V11 and its effective semi-synthesis. Fitoterapia. 2017 Nov;123:23-28. doi: 10.1016/j.fitote.2017.09.016. Epub 2017 Sep 27. PMID: 28958956.


7: Zheng QC, Kong MZ, Zhao Q, Chen GD, Tian HY, Li XX, Guo LD, Li J, Zheng YZ, Gao H. Chaetoglobosin Y, a new cytochalasan from Chaetomium globosum. Fitoterapia. 2014 Mar;93:126-31. doi: 10.1016/j.fitote.2013.12.022. Epub 2014 Jan 11. PMID: 24418656.


8: Wang Z, Cui J, Gao W, Yang Q, Chen L, Yang L, Sun Q, Zhang H. Effects of rice straw structure on chaetoglobosin A production by Chaetomium globosum CGMCC 6882. Int J Biol Macromol. 2020 May 1;150:1223-1228. doi: 10.1016/j.ijbiomac.2019.10.132. Epub 2019 Nov 16. PMID: 31743701.


9: Hu Y, Hao X, Lou J, Zhang P, Pan J, Zhu X. A PKS gene, pks-1, is involved in chaetoglobosin biosynthesis, pigmentation and sporulation in Chaetomium globosum. Sci China Life Sci. 2012 Dec;55(12):1100-8. doi: 10.1007/s11427-012-4409-5. Epub 2012 Dec 12. PMID: 23233225.


10: Wang Z, Zhao S, Zhang K, Lin C, Ru X, Yang Q. CgVeA, a light signaling responsive regulator, is involved in regulation of chaetoglobosin A biosynthesis and conidia development in Chaetomium globosum. Synth Syst Biotechnol. 2022 Jul 16;7(4):1084-1094. doi: 10.1016/j.synbio.2022.07.002. PMID: 35949485; PMCID: PMC9356241.


11: Knudsen PB, Hanna B, Ohl S, Sellner L, Zenz T, Döhner H, Stilgenbauer S, Larsen TO, Lichter P, Seiffert M. Chaetoglobosin A preferentially induces apoptosis in chronic lymphocytic leukemia cells by targeting the cytoskeleton. Leukemia. 2014 Jun;28(6):1289-98. doi: 10.1038/leu.2013.360. Epub 2013 Nov 27. PMID: 24280868.


12: Ohtsubo K, Saito M, Sekita S, Yoshihira K, Natori S. Acute toxic effects of chaetoglobosin A, a new cytochalasan compound produced by Chaetomium globosum, on mice and rats. Jpn J Exp Med. 1978 Apr;48(2):105-10. PMID: 713122.


13: Hu Y, Hao X, Chen L, Akhberdi O, Yu X, Liu Y, Zhu X. Gα-cAMP/PKA pathway positively regulates pigmentation, chaetoglobosin A biosynthesis and sexual development in Chaetomium globosum. PLoS One. 2018 Apr 13;13(4):e0195553. doi: 10.1371/journal.pone.0195553. PMID: 29652900; PMCID: PMC5898716.


14: Perlatti B, Nichols CB, Lan N, Wiemann P, Harvey CJB, Alspaugh JA, Bills GF. Identification of the Antifungal Metabolite Chaetoglobosin P From Discosia rubi Using a Cryptococcus neoformans Inhibition Assay: Insights Into Mode of Action and Biosynthesis. Front Microbiol. 2020 Jul 28;11:1766. doi: 10.3389/fmicb.2020.01766. PMID: 32849391; PMCID: PMC7399079.


15: Ding G, Song YC, Chen JR, Xu C, Ge HM, Wang XT, Tan RX. Chaetoglobosin U, a cytochalasan alkaloid from endophytic Chaetomium globosum IFB-E019. J Nat Prod. 2006 Feb;69(2):302-4. doi: 10.1021/np050515+. PMID: 16499339.


16: Hu Y, Zhang W, Zhang P, Ruan W, Zhu X. Nematicidal activity of chaetoglobosin A poduced by Chaetomium globosum NK102 against Meloidogyne incognita. J Agric Food Chem. 2013 Jan 9;61(1):41-6. doi: 10.1021/jf304314g. Epub 2012 Dec 24. PMID: 23214998.


17: Ashrafi S, Helaly S, Schroers HJ, Stadler M, Richert-Poeggeler KR, Dababat AA, Maier W. Ijuhya vitellina sp. nov., a novel source for chaetoglobosin A, is a destructive parasite of the cereal cyst nematode Heterodera filipjevi. PLoS One. 2017 Jul 12;12(7):e0180032. doi: 10.1371/journal.pone.0180032. PMID: 28700638; PMCID: PMC5507501.


18: Ishiuchi K, Nakazawa T, Yagishita F, Mino T, Noguchi H, Hotta K, Watanabe K. Combinatorial generation of complexity by redox enzymes in the chaetoglobosin A biosynthesis. J Am Chem Soc. 2013 May 15;135(19):7371-7. doi: 10.1021/ja402828w. Epub 2013 May 7. PMID: 23611317.


19: Hua C, Yang Y, Sun L, Dou H, Tan R, Hou Y. Chaetoglobosin F, a small molecule compound, possesses immunomodulatory properties on bone marrow-derived dendritic cells via TLR9 signaling pathway. Immunobiology. 2013 Mar;218(3):292-302. doi: 10.1016/j.imbio.2012.05.015. Epub 2012 May 23. PMID: 22739238.


20: Yang MH, Gu ML, Han C, Guo XJ, Yin GP, Yu P, Kong LY. Aureochaeglobosins A-C, Three [4 + 2] Adducts of Chaetoglobosin and Aureonitol Derivatives from Chaetomium globosum. Org Lett. 2018 Jun 1;20(11):3345-3348. doi: 10.1021/acs.orglett.8b01243. Epub 2018 May 17. PMID: 29771535.