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Takuji Sugiyama, Yuji Narukawa, Shunsuke Shibata, Ryo Masui, Fumiyuki Kiuchi
Agarwood (jinkoh in Japanese) is a resinous wood from Aquilaria species of the family Thymelaeaceae and has been used as incense and in traditional medicines. Characteristic chromone derivatives such as agarotetrol have been isolated from agarwood. In previous study, we isolated two new 2-(2-phenylethyl)chromones together with six known compounds from MeOH extract of agarwood. Further chemical investigation of the MeOH extract led to isolation of eighteen 2-(2-phenylethyl)chromones, including three new 5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromones with stereochemistry enantiomeric to agarotetrol-type, viz...
March 10, 2018: Journal of Natural Medicines
Alfinda Novi Kristanti, Mulyadi Tanjung, Nanik Siti Aminah
Background: Aquilaria, a genus belonging to the Thymelaeaceae, produces fragrant resinous agarwood, also known as eaglewood, which has been used as incense since old times. The intense fra-grance is the result of the presence of a wide variety of secondary metabolites. Objective: This genus was reported contained sesquiterpenes, chromones, flavonoids, benzophenones, diterpenoids, triterpenoids, and lignans. Conclusion: Here, we review the different secondary metabolites that have been identified in Aquilaria to show their diversity and to allow comparison with other Thymelaeaceae genera...
February 2018: Mini-reviews in Organic Chemistry
Shuai Wang, Zhangxin Yu, Canhong Wang, Chongming Wu, Peng Guo, Jianhe Wei
Agarwood, a highly precious non-timber fragrant wood of Aquilaria spp. (Thymelaeaceae), has been widely used in traditional medicine, religious rites, and cultural activities. Due to the inflated demanding and depleted natural resources, the yields of agarwood collected from the wild are shrinking, and the price is constantly rising, which restricts agarwood scientific research and wide application. With the sustainable planting and management of agarwood applied, and especially the artificial-inducing methods being used in China and Southeast Asian countries, agarwood yields are increasing, and the price is becoming more reasonable...
February 7, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Sin-Ling Wang, Yun-Chen Tsai, Shu-Ling Fu, Ming-Jen Cheng, Mei-Ing Chung, Jih-Jung Chen
The resinous wood of Aquilaria sinensis, known as agarwood (Chen Xiang in Chinese), is traditionally used for the treatment of abdominal pain, vomiting, circulatory disorders, and dyspnea. Four new 2-(2-phenylethyl)-4H-chromen-4-one derivatives, namely 7-methoxy-2-[2-(4'-hydroxy-phenyl)ethyl]chromone (1), 7-hydroxy-2-[2-(4'-methoxyphenyl)ethyl]chromone (2), 5,6-dihydroxy- 2-[2-(3'-hydroxy-4'-methoxyphenyl)ethyl]chromone (3), and 6-hydroxy-5-methoxy-2-(2-phenyl-ethyl)chromone (4), have been isolated from the resinous wood of A...
January 30, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Hui-Xia Huo, Zhi-Xiang Zhu, Yue-Lin Song, She-Po Shi, Jing Sun, Hui Sun, Yun-Fang Zhao, Jiao Zheng, Daneel Ferreira, Jordan K Zjawiony, Peng-Fei Tu, Jun Li
Sixteen new 2-(2-phenylethyl)chromone dimers, including four pairs of enantiomers (1a/1b, 3a/3b, 6a/6b, and 8a/8b), along with eight optically pure analogues (2, 4, 5, 7, and 9-12) were isolated from the resinous wood of Aquilaria sinensis. Their structures were determined by extensive spectroscopic analysis (1D and 2D NMR, UV, IR, and HRMS) and experimental and computed ECD data. Compounds 1-10 feature an unusual 3,4-dihydro-2H-pyran ring linkage connecting two 2-(2-phenylethyl)chromone monomeric units, while compounds 11 and 12 possess an unprecedented 6,7-dihydro-5H-1,4-dioxepine moiety in their structures...
December 11, 2017: Journal of Natural Products
Yang Yang, Hui-Qin Chen, Fan-Dong Kong, Li-Man Zhou, Wei Li, Wen-Hua Dong, Zhi-Bao Chen, Wen-Li Mei, Hao-Fu Dai
Six previously undescribed uncommon ester-bonded dimeric compounds (aquilacrassnins A-F) containing a sesquiterpenoid and a 5,6,7,8-tetrahydroxy-2-(2-phenylethyl)-5,6,7,8-tetrahydro -4H-chromone units were isolated from the EtOAc extract of agarwood originating from Aquilaria crassna. Their structures were elucidated by spectroscopic (NMR, UV, IR, MS, and ECD) methods. All the compounds were tested for AChE inhibitory activity and cytotoxicity against K562, BEL-7402, SGC-7901, Hela, and A549 tumor cell lines...
January 2018: Phytochemistry
Hong-Xin Liu, Hai-Bo Tan, Yu-Chan Chen, Sai-Ni Li, Hao-Hua Li, Wei-Min Zhang
Two new cyclohexene derivatives colletotricones A and B (1 and 2) and a new thiazole derivative colletotricole A (5), along with six known natural metabolites were isolated from the extract of Colletotrichum gloeosporioides A12, an endophytic fungus derived from Aquilaria sinensis. Among them, the colletotricones A and B possess a cyclohexenone skeleton, whereas the colletotricole A is a thiazole derivative. Their structures were fully assigned with the aid of extensive spectroscopic analysis and data from the literature...
December 4, 2017: Natural Product Research
Ying-Ying Feng, Xian-Juan Dong, Xiao Liu, Ya-Ru Yan, Jin-Ling Wang, She-Po Shi, Xiao-Hui Wang, Peng-Fei Tu
The MYB gene family comprises one of the richest groups of transcription factors in plants. The full length of two MYB genes were isolated through heterologous screening of Aquilaria sinensis calli transcriptome data, and the reverse transcription PCR was performed to obstain the corrected MYB clones, named AsMYB1, AsMYB2. The MYB transmembrane domain and phylogenetic analysis were predicted by different software to analyze the bioinformatics of MYB proteins. The transcript level of AsMYB1, AsMYB2 was performed by real-time quantitative RT-PCR in different tissues and in responds to abiotic stresses including salt, cold, metal and drought stress, and hormone treatments including abscisic acid (ABA), salicylic acid (SA), gibberellins (GA3) and methyl jasmonate (MeJA) treatment...
September 2017: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
Yan-Hong Xu, Yong-Cui Liao, Fei-Fei Lv, Zheng Zhang, Pei-Wen Sun, Zhi-Hui Gao, Ke-Ping Hu, Chun Sui, Yue Jin, Jian-He Wei
No abstract text is available yet for this article.
December 1, 2017: Plant & Cell Physiology
Wei Ye, Xin He, Hongqing Wu, Lei Wang, Weimin Zhang, Yunfei Fan, Haohua Li, Taomei Liu, Xiaoxia Gao
Sesquiterpene synthases are key enzymes for biosynthesis of sesquiterpene compounds and are important for agarwood formation in Aquilaria sinensis.The As-sesTPS gene encoding a novel sesquiterpene synthase was expressed in Escherichia coli strain BL21 (DE3) as an inclusion body and purified by Ni affinity chromatography. The molecular weight of the protein was lower than the theoretical value. Amino acid sequencing results indicated that the 27.2 kDa-recombinant protein was a truncated sesquiterpene synthase from chemically induced A...
November 1, 2017: International Journal of Biological Macromolecules
Chi Thanh Ma, Taeyong Eom, Eunji Cho, Bo Wu, Tae Ryong Kim, Ki Bong Oh, Sang Beom Han, Sung Won Kwon, Jeong Hill Park
Four new and five known sesquiterpenoids were isolated from the agarwood of Aquilaria malaccensis. Aquilanols A and B (1 and 2) have an unprecedented macrocyclic humulene structure with a bicyclic 7/10 ring system. Compound 2 was obtained as a scalemic mixture that was resolved by HPLC analysis using a chiral column. Their structures were deduced based on spectroscopic data analysis, and the absolute configurations were unambiguously determined by X-ray crystallographic data and ECD spectroscopic analysis. A putative biosynthetic pathway of these sesquiterpenoids is proposed...
October 30, 2017: Journal of Natural Products
Yan-Hong Xu, Yong-Cui Liao, Fei-Fei Lv, Zheng Zhang, Pei-Wen Sun, Zhi-Hui Gao, Ke-Ping Hu, Chun Sui, Yue Jin, Jian-He Wei
Sesquiterpenes are one of the most important defensive secondary metabolite components of agarwood. Agarwood, which is a product of the Aquilaria sinensis response to external damage, is a fragrant and resinous wood that is widely used in traditional medicines, incense and perfume. We previously reported that jasmonic acid (JA) plays an important role in promoting agarwood sesquiterpene biosynthesis and induces expression of the sesquiterpene synthase ASS1, which is a key enzyme that is responsible for the biosynthesis of agarwood sesquiterpenes in A...
November 1, 2017: Plant & Cell Physiology
Hong-Ni Wang, Wen-Li Mei, Wen-Hua Dong, Fan-Dong Kong, Wei Li, Jing-Zhe Yuan, Hao-Fu Dai
Two new 2-(2-hydroxy-2-phenylethyl)chromones (1‒2), along with three known 2-(2-phenylethyl)chromones (3‒5), were isolated from the agarwood originating from Aquilaria crassna Pierre ex Lecomte. Their structures were determined by the spectroscopic methods including 1D and 2D NMR analysis and comparison with reported data in the literature. All the compounds were isolated from agarwood of A. crassna for the first time. Compounds 1 and 2 exhibited inhibitory activity against acetylcholinesterase (AChE) with 17...
October 6, 2017: Journal of Asian Natural Products Research
Mao-Xun Yang, Yao-Guang Liang, He-Ru Chen, Yong-Fang Huang, Hai-Guang Gong, Tian-You Zhang, Yoichiro Ito
Four flavonoids including apigenin-7,4'-dimethylether, genkwanin, quercetin, and kaempferol were isolated in a preparative or semi-preparative scale from the leaves of wild Aquilaria sinensis using an improved preparative high-speed counter-current chromatography apparatus. The separations were performed with a two-phase solvent system composed of hexane-ethyl acetate, methanol-water at suitable volume ratios. The obtained fractions were analyzed by HPLC, and the identification of each target compound was carried out by ESI-MS and NMR...
September 5, 2017: Journal of Chromatographic Science
Siti Nazirah Ismail, M Maulidiani, Muhammad Tayyab Akhtar, Faridah Abas, Intan Safinar Ismail, Alfi Khatib, Nor Azah Mohamad Ali, Khozirah Shaari
Gaharu (agarwood, Aquilaria malaccensis Lamk.) is a valuable tropical rainforest product traded internationally for its distinctive fragrance. It is not only popular as incense and in perfumery, but also favored in traditional medicine due to its sedative, carminative, cardioprotective and analgesic effects. The current study addresses the chemical differences and similarities between gaharu samples of different grades, obtained commercially, using ¹H-NMR-based metabolomics. Two classification models: partial least squares-discriminant analysis (PLS-DA) and Random Forests were developed to classify the gaharu samples on the basis of their chemical constituents...
September 25, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Hassan Ga'al, Hatem Fouad, Guofeng Mao, Jiaxin Tian, Mo Jianchu
Mosquitoes pose a threat to humans and animals, causing millions of deaths every year. Vector control by effective eco-friendly pesticides of natural origin is a serious issue that requires urgent attention. The employment of green-reducing extracts for nanoparticles biosynthesis in a rapid and single-step process represents a promising strategy. In this study, silver nanoparticles (AgNPs) were biofabricated using an essential oil of Aquilaria sinensis (AsEO) and Pogostemonis Herba essential oil of Pogostemon cablin (PcEO) in one step and cost-effective manner...
August 31, 2017: Artificial Cells, Nanomedicine, and Biotechnology
Shih-Yao Lin, Asif Hameed, Yi-Han Hsu, You-Cheng Liu, Wei-An Lai, Chiu-Chung Young
A polyphasic approach was used to characterize a Gram-staining negative bacterium (designated strain CC-YHH650T) isolated from agarwood chips. Strain CC-YHH650T was aerobic and rod-shaped, able to grow at 15-37 °C (optimal 30 °С), pH 6.0-8.0 (optimal 7.0) and 0-1 % (w/v) NaCl (optimal 0 %). Phylogenetic analysis based on 16S rRNA genes revealed that strain CC-YHH650T shared highest sequence similarities with Filimonas lacunae (97.5 %), F. zeae (97.4 %), F. endophytica (97.3 %) and F. aurantiibacter (93...
September 2017: International Journal of Systematic and Evolutionary Microbiology
Hyun-Yong Lee, Jin-Seok Lee, Hyeong-Geug Kim, Won-Yong Kim, Seung-Bae Lee, Yung-Hyun Choi, Chang-Gue Son
BACKGROUND: Chronic stress contributes to the development of brain disorders, such as neurodegenerative and psychiatric diseases. Oxidative damage is well known as a causative factor for pathogenic process in brain tissues. The aim of this study is to evaluate the neuroprotective effect of a 30% ethanol extract of Aquilariae Lignum (ALE) in repeated stress-induced hippocampal oxidative injury. METHODS: Fifty BALB/c male mice (12 weeks old) were randomly divided into five groups (n = 10)...
August 10, 2017: BMC Complementary and Alternative Medicine
Hanwen Yuan, Jianping Zhao, Mei Wang, Shabana I Khan, Chunmei Zhai, Qiongming Xu, Jianhua Huang, Caiyun Peng, Guanghua Xiong, Wei Wang, Ikhlas A Khan
Four new benzophenone glycosides named as aquilaside A-D (1-4) along with five known compounds (5-9) were isolated from the methanol extract of the flower buds of Aquilaria sinensis. Their structures were elucidated on the basis of 1D and 2D NMR and mass spectroscopic analyses. All purified compounds were evaluated for their anti-inflammatory and cytotoxic activities. Aquilasides B and C displayed moderate cytotoxicity against SK-MEL cells with IC50 of 17.0 and 12.0μM and weak NF-κB inhibitive activity at 100μM with 30% and 60%, respectively...
September 2017: Fitoterapia
Hemraj Chhipa, Nutan Kaushik
Aquilaria malaccensis Lam, commonly known as Agarwood, is a highly valuable species used in production of agar oil from its infected wood, which is utilized in pharmaceutical and perfumery industry. Agar oil formation in agarwood takes years through the natural process which is induced by natural or artificial injury or microbial infection. The role of soil fungi and bacteria in artificial induction is still an unexplored area. In the present study, we isolated the fungal and bacterial community residing inside the stem of A...
2017: Frontiers in Microbiology
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