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Rui-Han Zhang, Zhi-Ke Liu, Da-Song Yang, Xing-Jie Zhang, Han-Dong Sun, Wei-Lie Xiao
Plants belonging to the genus Leonurus, also named motherwort, are traditionally used for anti-gynecological disorder in East Asia, and for sedative in Europe. Chemical investigation of the genus Leonurus not only enriched the natural products library, but also enlarged the pharmacological application of this traditional herb. In this review, we systematically summarized the structures of 259 compounds isolated from the genus Leonurus, featured with 147 labdane diterpenoids. The reported bioactivity studies up to 2017 are presented in the second part, with the main focus on the isolated compounds and also concerning the extracts...
January 12, 2018: Phytochemistry
Yumi Fujiwara, Miya Kono, Airi Ito, Michiho Ito
High-quality perilla leaves are purple on upper and lower surfaces and have a good aroma. The Japanese Pharmacopoeia specifies the content of essential oils in perilla leaves but not that of anthocyanins. Several reports have described the chemical species of anthocyanins in red perilla, but a complete analysis of anthocyanins in perilla has not been reported. In this study, the anthocyanins in the leaves of cultivated and wild species of perilla and those in commercially available perilla herbs were studied...
January 11, 2018: Phytochemistry
Juan Song, Rongji Dai, Yulin Deng, Fang Lv
Dregea sinensis Hemsl is an important herbal medicine in the Dai nationality of China. Its prominent clinical application has generated interest in the polyoxypregnane glycosides of the plant. This paper describes an extension of previous research on the polyoxypregnane di- and triglycosides of D. sinensis, aiming at identifying related tetraglycosides. On the basis of HPLC-ESI-MSn analysis in positive mode, twenty-five previously undescribed polyoxypregnane tetraglycosides were characterized (regarding molecular masses and fragmentation in MSn) from an ethyl acetate fraction that was not previously investigated...
January 11, 2018: Phytochemistry
Shu-Lin Zhang, Zi-Ni Yang, Cui He, Hai-Bing Liao, Heng-Shan Wang, Zhen-Feng Chen, Dong Liang
Six previously undescribed oleanane-type triterpenoid saponins, fortunosides A-F, together with six known ones, were isolated from the aerial parts of Lysimachia fortunei Maxim. Their structures were established by spectroscopic data analyses (1D, 2D-NMR and HRESIMS) and chemical methods. All isolated triterpenoid saponins were evaluated for their cytotoxicity against four human liver cancer cell lines (SMMC-7721, Hep3B, HuH7, and SK-Hep-1). Three saponins with the aglycone protoprimulagenin A exhibited moderate cytotoxicity against all of the tested human cancer cell lines, with IC50 values ranging from 4...
January 8, 2018: Phytochemistry
Pierluigi Reveglia, Andrea Chini, Alessandro Mandoli, Marco Masi, Alessio Cimmino, Gennaro Pescitelli, Antonio Evidente
Recent analyses on fungal jasmonic acid (JA)-containing metabolites suggest a mode-of-action of these naturally occurring compounds as inactive storage pools of JA. Plants and/or fungi can catabolize JA into the bioactive jasmonyl-isoleucine (JA-Ile) that in turn activates the JA-Ile-pathway in planta. To extend our knowledge on JA-derivates related to natural occurring JA conjugates, N-[(-)-jasmonyl]-S-tyrosin (JA-Tyr) and the ester JA-Sei between JA and seiridin, a fungal disubstituted furanone, were synthesized...
January 5, 2018: Phytochemistry
Hiroshi Ashihara, Claudio Stasolla, Tatsuhito Fujimura, Alan Crozier
Purine bases and nucleosides are produced by turnover of nucleotides and nucleic acids as well as from some cellular metabolic pathways. Adenosine released from the S-adenosyl-L-methionine cycle is linked to many methyltransferase reactions, such as the biosynthesis of caffeine and glycine betaine. Adenine is produced by the methionine cycles, which is related to other biosynthesis pathways, such those for the production of ethylene, nicotianamine and polyamines. These purine compounds are recycled for nucleotide biosynthesis by so-called "salvage pathways"...
January 4, 2018: Phytochemistry
Xin-Yue Gu, Xiao-Fei Shen, Lun Wang, Zhou-Wei Wu, Fu Li, Bin Chen, Guo-Lin Zhang, Ming-Kui Wang
The investigation of the fruits of Solanum nigrum led to the isolation of four previously undescribed steroidal alkaloids, named solanine A, 7α-OH khasianine, 7α-OH solamargine and 7α-OH solasonine, together with six known ones. The structures of the isolated compounds were elucidated unambiguously by spectroscopic data analyses and chemical methods. Solanine A represents an unusual steroidal alkaloid with an unprecedented 6/5/6/5/5/6 hexacyclic ring system, and its structure was confirmed by X-ray single crystal diffraction analysis...
January 4, 2018: Phytochemistry
Astrid Kännaste, Lauri Laanisto, Leila Pazouki, Lucian Copolovici, Marina Suhorutšenko, Muhammad Azeem, Lauri Toom, Anna-Karin Borg-Karlson, Ülo Niinemets
Diterpenoids constitute an important part of oleoresin in conifer needles, but the environmental and genetic controls on diterpenoid composition are poorly known. We studied the presence of diterpenoids in four pine populations spanning an extensive range of nitrogen (N) availability. In most samples, isoabienol was the main diterpenoid. Additionally, low contents of (Z)-biformene, abietadiene isomers, manoyl oxide isomers, labda-7,13,14-triene and labda-7,14-dien-13-ol were quantified in pine needles. According to the occurrence and content of diterpenoids it was possible to distinguish 'non diterpenoid pines', 'high isoabienol pines', 'manoyl oxide - isoabienol pines' and 'other diterpenoid pines'...
January 2, 2018: Phytochemistry
Phanruethai Pailee, Chutima Kuhakarn, Chanyapat Sangsuwan, Sakchai Hongthong, Pawinee Piyachaturawat, Kanoknetr Suksen, Surawat Jariyawat, Radeekorn Akkarawongsapat, Jitra Limthongkul, Chanita Napaswad, Palangpon Kongsaeree, Samran Prabpai, Thaworn Jaipetch, Manat Pohmakotr, Patoomratana Tuchinda, Vichai Reutrakul
Eleven previously undescribed compounds, including four benzophenones (garciosones A-D), four xanthones (garciosones E-H) and three biphenyls (garciosines A-C), along with eighteen known compounds were isolated from the stems, leaves and twigs of Garcinia speciosa Wall. (Clusiaceae). Their structures were established by extensive spectroscopic analysis. For garciosines A-C, the structures were confirmed by single crystal X-ray diffraction analysis. Most of the isolated compounds were evaluated for their cytotoxic activity and anti-HIV-1 activity using the syncytium inhibition assay and HIV-1 reverse transcriptase (RT) assay...
January 2, 2018: Phytochemistry
Feng Liu, Xueyuan Yang, Yue Liang, Bangjian Dong, Guochen Su, Muhetaer Tuerhong, Da-Qing Jin, Jing Xu, Yuanqiang Guo
A phytochemical investigation to search for new nitric oxide (NO) inhibitors resulted in the isolation of seven previously undescribed daphnane diterpenoids, thyrsoidpenes A-G, from the leaves of Trigonostemon thyrsoideus. Their structures including absolute configurations were elucidated on the basis of extensive NMR spectroscopic data analysis and the time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculations. Thyrsoidpenes B-G feature rare polycyclic caged structures of daphnane diterpenoid orthoester...
December 28, 2017: Phytochemistry
Liqing Jin, Qing Cai, Wenlin Huang, Keyvan Dastmalchi, Joan Rigau, Marisa Molinas, Mercè Figueras, Olga Serra, Ruth E Stark
Potato native and wound healing periderms contain an external multilayered phellem tissue (potato skin) consisting of dead cells whose cell walls are impregnated with suberin polymers. The phellem provides physical and chemical barriers to tuber dehydration, heat transfer, and pathogenic infection. Previous RNAi-mediated gene silencing studies in native periderm have demonstrated a role for a feruloyl transferase (FHT) in suberin biosynthesis and revealed how its down-regulation affects both chemical composition and physiology...
December 27, 2017: Phytochemistry
Nailiang Zhu, Zhonghao Sun, Meigeng Hu, Yedan Li, Dawei Zhang, Haifeng Wu, Yu Tian, Pengfei Li, Junshan Yang, Guoxu Ma, Xudong Xu
The tubers of the medicinal plant Hemsleya penxianensis (Cucurbitaceae) yielded 11 cucurbitane-type triterpenes Xuedanencins A-K by silica gel column, ODS column, and pre-HPLC techniques. Their structures were determined by spectroscopic analysis and examined alongside existing data from prior studies. Separated compounds were evaluated for cytotoxic activity against the Hela human cancer cell line and compounds 7 and 8 showed significant cytotoxicity with IC50 values at 1.82 and 2.45 μM, respectively.
December 26, 2017: Phytochemistry
Zhen-Zhu Zhao, Kuan Zhao, He-Ping Chen, Xue Bai, Ling Zhang, Ji-Kai Liu
Molecular identification suggested an edible mushroom, which was previously named as Craterellus odoratus should be revised as Montagnula donacina. A chemical re-investigation of the culture broth of this fungus resulted in the isolation of four rare tetracyclic bergamotane-type sesquiterpenoids, namely donacinolides A and B, donacinoic acids A and B, and three cadinane-type ones, namely donacinols A-C and a meroterpenoid (Z)-4-hydroxy-3-(3-hydroxy-3-methylbut-1-en-1-yl)benzoic acid. Their structures were established via extensive spectroscopic methods, single crystal X-ray diffraction analysis, and computational methods...
December 26, 2017: Phytochemistry
Yun-Seo Kil, Yang Kang So, Min Jung Choi, Ah-Reum Han, Chang Hyun Jin, Eun Kyoung Seo
Three previously undescribed dihydronaphthalenones, 7-hydroxycatalponol, (4S)-3,4-dihydro-4-hydroxy-2-[(2R)-2,3-dihydroxy-3-methylbutylidene]naphthalen-1(2H)-one, and (6S)-5,6-dihydro-6-hydroxy-2,2-dimethyl-2H-benzo[h]chromen-4(3H)-one and one phthalide, (±)-3-(5-hydroxy-5-methyl-2-oxohex-3-en-1-yl)isobenzofuran-1(3H)-one, were isolated from the wood of Catalpa ovata G. Don (Bignoniaceae), together with six known compounds. The structures of the previously undescribed compounds were elucidated by interpretation of 1D and 2D NMR data...
December 21, 2017: Phytochemistry
Aide Sun, Qingcai Xu, Gangjian Wei, Huayu Zhu, Xuefei Chen
As a critical micronutrient, boron (B) plays an important role in plant growth and embryonic development. To further understand the effects of B uptake, transportation and isotopic fractionation, the contents and isotopic compositions of hydro-soluble B in the sap and structural B fixed in the cell within individual plant tissues were investigated. The B isotope ratio was determined by multi-collector inductively coupled plasma mass spectrometry. The δ11B values in hydro-soluble and structural B in the investigated plant samples ranged from -1...
December 20, 2017: Phytochemistry
Qingwen Hu, Ying-Ying Chen, Qi-Yang Jiao, Afsar Khan, Feng Li, De-Feng Han, Gui-Dong Cao, Hong-Xiang Lou
Under the guidance of anti-fungal bioassay, four previously undescribed oleanane-type and one lupane-type triterpenoid saponins, along with twelve known analogues, were isolated from the extract of Sapindus mukorossi pulps. Their structures were determined on the basis of spectroscopic analysis and chemical methods. In vitro biotests, oleanolic acid 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranoside showed inhibitory activity against Trichophyton rubrum with MIC80 value of 8 μg/mL, while oleanolic acid 3-O-α-L-arabinopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranoside exhibited inhibitory activity against both Trichophyton rubrum and Candida albicans with MIC80 values of 8 μg/mL...
December 16, 2017: Phytochemistry
An-Hua Wang, Xiang-Ge Tian, Yong-Lei Cui, Xiao-Kui Huo, Bao-Jing Zhang, Sa Deng, Lei Feng, Xiao-Chi Ma, Jing-Ming Jia, Chao Wang
A chemical investigation of the roots of Euphorbia ebracteolata identified eighteen diterpenoids and glycosides. On the basis of spectroscopic data, they were determined to be ent-kauranes, ent-atisanes, tigliane derivatives, ingenane, and ent-abietanes, among which were eleven previously undescribed diterpenoids. The inhibitory effects of the isolated compounds against human carboxylesterase 2 (hCE-2) were evaluated in vitro, which revealed moderate inhibitory effects with IC50 values < 50 μM. Next, the inhibitory kinetics were evaluated for the putative hCE-2 inhibitor 4β,9α,16,20-tetrahydroxy-14(13 → 12)-abeo-12αH-1,6-tigliadiene-3,13-dione (IC50 3...
December 15, 2017: Phytochemistry
Micheline Grignon-Dubois, Bernadette Rezzonico
The flavonoid content of Zostera noltei leaves was investigated over a broad spatial scale using chromatographic and spectroscopic techniques (HPLC-DAD, LC/MS and NMR). Samples were collected at fifteen localities covering Mediterranean Sea and NE Atlantic coast, and representative of three types of coastal ecosystems: mesotidal bays, coastal lagoons, and open-sea. Three geographically distinct flavonoid chemotypes were identified on the basis of their respective major compound. One is characterized by apigenin 7-sulfate (Eastern part of Gulf of Cadiz), one by diosmetin 7-sulfate (French Atlantic coast and Mediterranean Sea), and the third contained similar quantities of the above two compounds (Mauritania and South Portugal)...
December 14, 2017: Phytochemistry
Margret Chinonso Ezeoke, Premanand Krishnan, Dawn Su-Yin Sim, Siew-Huah Lim, Yun-Yee Low, Kam-Weng Chong, Kuan-Hon Lim
From the leaves of Elaeocarpus tectorius (Lour.) Poir. four previously undescribed phenethylamine-containing alkaloids were isolated, namely, tectoricine, possessing an unprecedented isoquinuclidinone ring system incorporating a phenethylamine moiety, tectoraline, representing a rare alkamide incorporating two phenethylamine moieties, and tectoramidines A and B, representing the first naturally occurring trimeric and dimeric phenethylamine alkaloids incorporating an amidine function. The structures of these alkaloids were established by detailed spectroscopic analysis...
December 13, 2017: Phytochemistry
Suppisak Chaturonrutsamee, Chutima Kuhakarn, Panida Surawatanawong, Samran Prabpai, Palangpon Kongsaeree, Thaworn Jaipetch, Pawinee Piyachaturawat, Surawat Jariyawat, Radeekorn Akkarawongsapat, Kanoknetr Suksen, Jitra Limthongkul, Chanita Napaswad, Narong Nuntasaen, Vichai Reutrakul
Seven previously undescribed compounds, including three polycyclic polyprenylated acylphloroglucinols (garcinuntins A-C), three biphenyl derivatives (garcinuntabiphenyls A-C) and a lanostane triterpene (garcinuntine), along with thirteen known compounds were isolated from the root of Garcinia nuntasaenii Ngerns. & Suddee. Their structures were elucidated on the basis of spectroscopic techniques. For garcinuntins A-C, the absolute configurations were confirmed by the combination of single X-ray crystallography and ECD calculations...
December 13, 2017: Phytochemistry
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