Chemical Constituents from Streptomyces sp. YG-7 Collected from Yingge Ridge and the α-Glucosidase Inhibitory Activity

doi:10.3969/j.issn.1000-2561.2019.07.026

Abstract

Abstract:

The α-glucosidase activities of secondary metabolites from Streptomyces sp. YG-7 actinomycetes isolated from the soils collected from the virgin tropical rainforest Yingge Ridge were investigated. Nine compounds were isolated and purified by various chromatographic techniques, and the structures were identified as (1) 2-acetamido-5- chlorobenzamide, (2) cyclo (L-Pro-L-Leu), (3) 3,6-dibenzylidene-2,5-piperazinedione, (4) albonoursin, (5) (3Z, 6S)-3-benzylidene-6-isobutylpiperazine-2,5-dione, (6) 3-hydroxy-2-methyl-4-pyrone, (7) isophthalic acid, (8) methyl 3-carbamoylbenzoate, and (9) 2,3-dihydroxypropyl hexadecanoate through a combined analysis of physicochemical properties and spectral data. Among them, compounds 1, 7 and 8 were new natural products, and compounds 1, 3-5, 7-8 exhibited significantly α-glucosidase inhibitory activity.

Key words: actinomycetes, Yingge Ridge, chemical constituent, α-glucosidase

CLC Number:

R915

PAN Jieming,CHEN Huiqin,WANG Hao,MEI Wenli,CAI Caihong,TAN Zhiqiong,DAI Haofu. Chemical Constituents from Streptomyces sp. YG-7 Collected from Yingge Ridge and the α-Glucosidase Inhibitory Activity[J]. Chinese Journal of Tropical Crops, 2019, 40(7): 1428-1433.

Figures/Tables 4

化合物 Compound	抑制率 Inhibition ratio/%
1	15.70±0.35^b
2	—
3	13.45±0.43^bc
4	14.79±0.56^bc
5	17.76±0.42^b
6	—
7	12.67±0.28^bc
8	17.78±0.17^b
9	—
阿卡波糖^A	20.36±0.22^b
DMSO^B	0.0 ± 0.0^c

Fig. 1 The colony and microscopic morphological characters of YG-7 B: Conidiophores and conidia (Light microscope 40×)

Fig. 2 Phylogenetic tree based on 16S rDNA sequences of strain YG-7

Fig. 3 Chemical structures of compounds 1-9

References 18

[1]	Thong W L, Shin-ya K, Nishiyama M , et al. Methylbenzene-containing polyketides from a Streptomyces that spontaneously acquired rifampicin resistance: Structural elucidation and biosynjournal[J]. Journal of Natural Products, 2016,79(4):857-864. DOI URL
[2]	Wu C, Du C, Gubbens J , et al. Metabolomics-driven discovery of a prenylated isatin antibiotic produced by Streptomyces species MBT28[J]. Journal of Natural Products, 2015,78(10):2355-2363. DOI URL
[3]	Kim S H, Shin Y, Lee S H , et al. Salternamides A-D from a halophilic Streptomyces sp. actinobacterium[J]. Journal of Natural Products, 2015,78(4):836-843. DOI URL
[4]	王淑霞, 朱天骄, 卢圳域 , 等. 海洋新放线菌及其次级代谢产物研究进展[J]. 中国抗生素杂志, 2007(9):513-519.
[5]	Errakhi R, Lebrihi A, Barakate M . In vitro and in vivo antagonism of actinomycetes isolated from Moroccan rhizospherical soils against Sclerotium rolfsii: a causal agent of root rot on sugar beet (Beta vulgaris L.)[J]. Journal of Applied Microbiology, 2009,107(2):672-681. DOI URL
[6]	林家怡, 吴世捷, 庄雪影 , 等. 海南鹦歌岭轮叶三棱栎 (Trigonobalanus verticillata) 群落特征与保护对策[J]. 生态学报, 2007,27(6):2230-2238.
[7]	Nilubon J A, Megh R B, Jun K . α-Glucosidase inhibitors from devil tree (Alstonia scholaris)[J]. Food Chemistry, 2007,103(4):1319-1323. DOI URL
[8]	Kelleher J M, Mcauliffe M T, Monihan H A , et al. Studies on the preparation and crystal polymorphism of 2-acetamidobenzamide and related compounds[J]. Arkivoc, 2007,16:209-226.
[9]	Zhao P J, Wang H X, Li G H , et al. Secondary metabolites from endophytic Streptomyces sp. Lz531[J]. Chemistry & Biodiversity, 2010,4(5):899-904.
[10]	Kwak M K, Kim H, Song Y S , et al. Antioxidant activity of diketopiperazines from Bacillus idriensis[J]. Journal of Korean Chemistry Society, 2015,59(6):545-550. DOI URL
[11]	Arnone A, Nasini G, Pava O , et al. Structure elucidation of diatretol-a new diketopiperazine metabolite from the fungus Clitocybe diatreta[J]. European Journal of Organic Chemistry, 2010,1996(11):1875-1877.
[12]	Wang P, Xi L J, Liu P P , et al. Diketopiperazine derivatives from the marine-derived actinomycete Streptomyces sp. FXJ7. 328[J]. Marine Drugs, 2013,11(4):1035-1049. DOI URL
[13]	Tsurumi S, Takagi T, Hashimoto T . A γ-pyronyl-triterpenoid saponin from Pisum sativum[J]. Phytochemistry, 1992,31(7):2435-2438. DOI URL
[14]	Derissen J L . The crystal structure of isophthalic acid[J]. Acta Crystallographica Section B, 1974,30(11):2764-2765. DOI URL
[15]	Keshipour S, Shaabani A . Selective aerobic hydrolysis of nitriles to amides using cobalt (II)/zinc[J]. Research on Chemical Intermediates, 2015,41(8):5071-5078. DOI URL
[16]	Chang H S, Chen Y S, Cheng M J , et al. Chemical constituents of the fungus Mycoleptodiscus sp. 09F0149[J]. Chemistry of Natural Compounds, 2018,54(2):396-398. DOI
[17]	郭秀春, 郑立, 周文辉 , 等. 海洋微生物中二酮哌嗪类化合物的研究进展[J]. 微生物学通报, 2009,36(10):1596-1603.
[18]	Watve M G, Tickoo R, Jog M M , et al. How many antibiotics are produced by the genus Streptomyces[J]. Archives of Microbiology, 2001,176(5):386-390. DOI URL