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Kigamicin B

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Category Antibiotics
Catalog number BBF-01544
CAS
Molecular Weight 779.78
Molecular Formula C40H45NO15

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Product Description

Kigamicin B is produced by the strain of Amycolatopsis sp. ML-630-mFl. It showed activity against gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA) with MIC of 0.025-0.78 μg/mL.

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IUPAC Name 2,6,9,30-tetrahydroxy-8-[5-(5-hydroxy-6-methyloxan-2-yl)oxy-6-methyloxan-2-yl]oxy-23-methyl-11,14,16,24-tetraoxa-27-azaoctacyclo[15.14.1.03,12.05,10.013,32.019,31.021,29.023,27]dotriaconta-1(32),2,5(10),12,19,21(29),30-heptaene-4,28-dione
Canonical SMILES CC1C(CCC(O1)OC2CCC(OC2C)OC3CC(C4=C(C3O)OC5=C6C7=C(C8=C(C9=C(CC1(N(C9=O)CCO1)C)C=C8CC7OCO6)O)C(=C5C4=O)O)O)O
InChI InChI=1S/C40H45NO15/c1-15-19(42)4-6-24(52-15)54-21-5-7-25(53-16(21)2)55-23-12-20(43)28-34(46)31-35(47)30-26-17(10-18-13-40(3)41(8-9-51-40)39(48)27(18)33(26)45)11-22-29(30)37(50-14-49-22)38(31)56-36(28)32(23)44/h10,15-16,19-25,32,42-45,47H,4-9,11-14H2,1-3H3
InChI Key ZDEHLGNKHHJJAC-UHFFFAOYSA-N
Appearance White Powder
Antibiotic Activity Spectrum Gram-positive bacteria
Melting Point 225-227°C
1. Kigamicins, novel antitumor antibiotics. I. Taxonomy, isolation, physico-chemical properties and biological activities
Setsuko Kunimoto, Jie Lu, Hiroyasu Esumi, Yohko Yamazaki, Naoko Kinoshita, Yoshiko Honma, Masa Hamada, Michiyo Ohsono, Masaaki Ishizuka, Tomio Takeuchi J Antibiot (Tokyo). 2003 Dec;56(12):1004-11. doi: 10.7164/antibiotics.56.1004.
Novel antibiotics named kigamicin A, B, C, D, and E were discovered from the culture broth of Amycolatopsis sp. ML630-mF1 by their selective killing activity against PANC-1 cells only under a nutrient starved condition. Under a condition of nutrient starvation, kigamicins A, B, C, and D inhibited PANC-1 cell survival at 100 times lower concentration than in normal culture. Kigamicins showed antimicrobial activity against Gram-positive bacteria including methicillin resistant Staphylococcus aureus (MRSA). Kigamicin D inhibited the growth of various mouse tumor cell lines at IC50 of about 1 microg/ml.
2. Kigamicins, novel antitumor antibiotics. II. Structure determination
Setsuko Kunimoto, Tetsuya Someno, Yohko Yamazaki, Jie Lu, Hiroyasu Esumi, Hiroshi Naganawa J Antibiot (Tokyo). 2003 Dec;56(12):1012-7. doi: 10.7164/antibiotics.56.1012.
Kigamicin A (1), B (2), C (3), D (4) and E (5) are novel antitumor antibiotics. Their structures were determined by spectroscopic analyses including various NMR measurements. Kigamicins have a unique aglycone of fused octacyclic ring system containing seven of six-membered rings and one oxazolidine. The aglycone links a sugar chain composed of one to four deoxysugars. These sugars were found to be amicetose and oleandrose.

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