Lobophorin A
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| Category | Others |
| Catalog number | BBF-05094 |
| CAS | 247171-46-6 |
| Molecular Weight | 1157.39 |
| Molecular Formula | C61H92N2O19 |
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Description
Lobophorins A is an anti-inflammatory macrolide produced by tropical marine bacteria.
Specification
| Synonyms | (1S,3S,4S,4aS,6aS,7E,10S,11E,12aS,15R,16aS,20aS,20bR)-10-[[3-Amino-2,3,4,6-tetradeoxy-4-[(methoxycarbonyl)amino]-3-C-methyl-β-D-xylo-hexopyranosyl]oxy]-4-[(O-2,6-dideoxy-4-O-methyl-β-L-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-α-L-ribo-hexopyranosyl-(1→3)-2,6-dideoxy-α-L-ribo-hexopyranosyl)oxy]-2,3,4,4a,6a,9,10,12a,15,16,20a,20b-dodecahydro-21-hydroxy-14-(hydroxymethyl)-1,3,7,11,15,20a-hexamethyl-18H-16a,19-metheno-16aH-benzo[b]naphth[2,1-j]oxacyclotetradecin-18,20(1H)-dione |
| IUPAC Name | methyl N-[(2R,3R,4S,6R)-4-amino-6-[[(1S,3R,6S,7Z,9S,11Z,13S,16S,17S,18S,20S,21R,22S)-23-hydroxy-17-[(2R,4R,5S,6S)-5-hydroxy-4-[(2S,4R,5R,6S)-4-hydroxy-5-[(2R,4R,5R,6S)-4-hydroxy-5-methoxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4-(hydroxymethyl)-3,8,12,18,20,22-hexamethyl-25,27-dioxo-26-oxapentacyclo[22.2.1.01,6.013,22.016,21]heptacosa-4,7,11,14,23-pentaen-9-yl]oxy]-2,4-dimethyloxan-3-yl]carbamate |
| Canonical SMILES | CC1CC(C(C2C1C3(C(C=C2)C(=CCC(C(=CC4C=C(C(CC45C(=O)C(=C3O)C(=O)O5)C)CO)C)OC6CC(C(C(O6)C)NC(=O)OC)(C)N)C)C)OC7CC(C(C(O7)C)O)OC8CC(C(C(O8)C)OC9CC(C(C(O9)C)OC)O)O)C |
| InChI | InChI=1S/C61H92N2O19/c1-27-14-17-42(78-47-25-59(10,62)54(35(9)77-47)63-58(71)73-13)28(2)19-37-20-36(26-64)31(5)24-61(37)56(69)48(57(70)82-61)55(68)60(11)39(27)16-15-38-49(60)29(3)18-30(4)51(38)80-46-23-43(50(67)32(6)74-46)79-44-22-41(66)53(34(8)76-44)81-45-21-40(65)52(72-12)33(7)75-45/h14-16,19-20,29-35,37-47,49-54,64-68H,17-18,21-26,62H2,1-13H3,(H,63,71)/b27-14-,28-19-,55-48?/t29-,30-,31+,32-,33-,34-,35+,37+,38-,39-,40+,41+,42-,43+,44-,45+,46-,47-,49+,50-,51-,52-,53-,54-,59-,60+,61-/m0/s1 |
| InChI Key | BFIFMYVVBKSDFE-KNMPCJSWSA-N |
Properties
| Density | 1.31±0.1 g/cm3 (Predicted) |
Reference Reading
1. Heterologous Expression Leads to Discovery of Diversified Lobophorin Analogues and a Flexible Glycosyltransferase
Bin Tan, Siqiang Chen, Qingbo Zhang, Yuchan Chen, Yiguang Zhu, Imran Khan, Weimin Zhang, Changsheng Zhang Org Lett. 2020 Feb 7;22(3):1062-1066. doi: 10.1021/acs.orglett.9b04597. Epub 2020 Jan 23.
The heterologous expression of the lobophorin biosynthetic gene cluster from marine-derived Streptomyces pactum SCSIO 02999 has led to the discovery of new analogues that carry d-kijanose (or its variants with a 3-amino or hydroxyl group) at C-9. The identification of intermediates resulting from the inactivation of lobG1 (encoding C-17 kijanosyltransferase) and lobG3 (encoding C-9 digitoxosyltransferase) demonstrates the substrate flexibility of LobG3 to also accept d-kijanose and its variants. Notably, two lobophorins with d-kijanose at C-9 show improved bioactivities.
2. Lobophorin Producing Endophytic Streptomyces olivaceus JB1 Associated With Maesa japonica (Thunb.) Moritzi & Zoll
Soohyun Um, Jaeyoun Lee, Seung Hyun Kim Front Microbiol. 2022 Apr 29;13:881253. doi: 10.3389/fmicb.2022.881253. eCollection 2022.
In this study, we focused on endophytes of Maesa japonica (Thunb.) Moritzi & Zoll. and the plant-microbe interaction at metabolite levels. We isolated seven endophytes associated with M. japonica (JB1-7), and focused on Streptomyces olivaceus JB1 because of antibacterial activities of its secondary metabolites. We confirmed lobophorin analogs production from the bacterial strain JB1 by using spectroscopic techniques such as NMR, UV, and LC/Q-TOF-MS. In the LC/MS system, thirteen reported lobophorin analogs and twelve unreported analogs were detected. Among metabolites, lobophorin A was clearly detected in the dried foliar residues of M. japonica which implies that JB1 resides in the host and accumulates its secondary metabolites likely interacting with the plant. Antimicrobial activity tests of the secondary metabolites against undesirable contaminants isolated from the external surface of M. japonica supported the host and microbe mutualistic relationship. In the meantime, lobophorin producing Streptomyces spp. were isolated from marine environments such as marine sediments, algae, corals, and sponges. As lobophorin producing Streptomyces is isolated commonly from marine environments, we conducted a saline water stress tolerance test with JB1 showing saline medium does not accelerate the growth of the bacterium.
3. Streptomyces sp. VN1, a producer of diverse metabolites including non-natural furan-type anticancer compound
Hue Thi Nguyen, Anaya Raj Pokhrel, Chung Thanh Nguyen, Van Thuy Thi Pham, Dipesh Dhakal, Haet Nim Lim, Hye Jin Jung, Tae-Su Kim, Tokutaro Yamaguchi, Jae Kyung Sohng Sci Rep. 2020 Feb 4;10(1):1756. doi: 10.1038/s41598-020-58623-1.
Streptomyces sp. VN1 was isolated from the coastal region of Phu Yen Province (central Viet Nam). Morphological, physiological, and whole genome phylogenetic analyses suggested that strain Streptomyces sp. VN1 belonged to genus Streptomyces. Whole genome sequencing analysis showed its genome was 8,341,703 base pairs in length with GC content of 72.5%. Diverse metabolites, including cinnamamide, spirotetronate antibiotic lobophorin A, diketopiperazines cyclo-L-proline-L-tyrosine, and a unique furan-type compound were isolated from Streptomyces sp. VN1. Structures of these compounds were studied by HR-Q-TOF ESI/MS/MS and 2D NMR analyses. Bioassay-guided purification yielded a furan-type compound which exhibited in vitro anticancer activity against AGS, HCT116, A375M, U87MG, and A549 cell lines with IC50 values of 40.5, 123.7, 84.67, 50, and 58.64 µM, respectively. In silico genome analysis of the isolated Streptomyces sp. VN1 contained 34 gene clusters responsible for the biosynthesis of known and/or novel secondary metabolites, including different types of terpene, T1PKS, T2PKS, T3PKS, NRPS, and hybrid PKS-NRPS. Genome mining with HR-Q-TOF ESI/MS/MS analysis of the crude extract confirmed the biosynthesis of lobophorin analogs. This study indicates that Streptomyces sp. VN1 is a promising strain for biosynthesis of novel natural products.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
