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Journal articles on the topic 'Guaiane Sesquiterpenes'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 September 2023

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1

Luo, Xiangchao, Rongcui Wu, Xiao Han, et al. "Guaiane sesquiterpenes from the gorgonian Echinogorgia flora collected in the South China Sea." RSC Advances 12, no. 5 (2022): 2662–67. http://dx.doi.org/10.1039/d1ra08631f.

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Echinoflorine (1), a new dimethylamino-substituted guaipyridine alkaloid with a novel γ-lactone-cyclohepta[c]pyridine fused skeleton, and three new guaiane sesquiterpene lactones, echinofloranolides A–C (2–4), together with eight known guaiane sesquiterpenes were isolated from the gorgonian Echinogorgia flora collected in the South China Sea.

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2

Xu, Houchao, and Jeroen S. Dickschat. "Germacrene B – a central intermediate in sesquiterpene biosynthesis." Beilstein Journal of Organic Chemistry 19 (February 20, 2023): 186–203. http://dx.doi.org/10.3762/bjoc.19.18.

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Germacranes are important intermediates in the biosynthesis of eudesmane and guaiane sesquiterpenes. After their initial formation from farnesyl diphosphate, these neutral intermediates can become reprotonated for a second cyclisation to reach the bicyclic eudesmane and guaiane skeletons. This review summarises the accumulated knowledge on eudesmane and guaiane sesquiterpene hydrocarbons and alcohols that potentially arise from the achiral sesquiterpene hydrocarbon germacrene B. Not only compounds isolated from natural sources, but also synthetic compounds are dicussed, with the aim to give a

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3

Kuroyanagi, Masanori, Osamu Shirota, Setsuko Sekita, and Takahisa Nakane. "Transannular Cyclization of (4S,5S)-Germacrone-4,5-epoxide into Guaiane and Secoguaiane-type Sesquiterpenes." Natural Product Communications 7, no. 4 (2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700406.

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Germacrone (1) and ( 4S,5S)-germacrone-4,5-epoxide (2) were isolated, along with guaiane and secoguaiane-type sesquiterpenes, from Curcuma aromatica plants. Compound 2 was derived from 1 and cyclized through transannular (T-A) reactions into various guaiane and secoguaiane-type sesquiterpenes in C. aromatica. The cyclization reaction of 2 was initiated by protonation at an epoxide oxygen atom, followed by cleavage of the epoxide ring and the formation of a C-C bond between C-1 and C-5 to give guaiane-type derivatives. Acidic and thermal treatments of 2 produced twelve sesquiterpenes having gua

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4

Ishihara, Masakazu, Tomoyuki Tsuneya, and Kenji Uneyama. "Guaiane sesquiterpenes from agarwood." Phytochemistry 30, no. 10 (1991): 3343–47. http://dx.doi.org/10.1016/0031-9422(91)83206-z.

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5

Werner, Ingrid, Pavel Mucaji, Armin Presser, and Sabine Glasl. "Sesquiterpenes and Phenolic Compounds from Achillea clypeolata Sesquiterpenes and Phenolic Compounds from Achillea clypeolata." Zeitschrift für Naturforschung B 62, no. 2 (2007): 267–71. http://dx.doi.org/10.1515/znb-2007-0219.

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The investigation of a dichloromethane extract of flower heads of Achillea clypeolata collected in Bulgaria led to the isolation of one guaiane (4,10,11-trihydroxy-guaiane, 1), four eudesmanes (4(15)-eudesmene-1β ,11-diol, 2, clypeotriol, 3, 3-epi-clypeotriol, 4, cryptomeridiol, 5), one diterpene (sugeroside, 6) and two phenolic compounds (centaureidin, 7 and scopoletin, 8). Their structures were elucidated by UV/vis, EI- and CI-MS as well as by one- and two-dimensional NMR experiments. 4,10,11-Trihydroxy-guaiane (1) and 3-epi-clypeotriol (4) are reported here for the first time.

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6

Miski, Mahmut, Doris H. de Luengo, and Tom J. Mabry. "Guaiane sesquiterpenes from Decachaeta scabrella." Phytochemistry 26, no. 1 (1986): 199–200. http://dx.doi.org/10.1016/s0031-9422(00)81511-3.

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7

Chowdhury, Rasheduzzaman, Choudhury M. Hasan, and Mohammad A. Rashid. "Guaiane sesquiterpenes from Amoora rohituka." Phytochemistry 62, no. 8 (2003): 1213–16. http://dx.doi.org/10.1016/s0031-9422(02)00698-2.

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8

Bruno, Maurizio, Maria C. de la Torre, Benjamín Rodríguez, and Abdallah A. Omar. "Guaiane sesquiterpenes from Teucrium leucocladum." Phytochemistry 34, no. 1 (1993): 245–47. http://dx.doi.org/10.1016/s0031-9422(00)90812-4.

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9

Aati, Hanan Y., Shagufta Perveen, Raha Orfali, et al. "Phytochemical Analysis of Anvillea garcinii Leaves: Identification of Garcinamines F–H and Their Antiproliferative Activities." Plants 10, no. 6 (2021): 1130. http://dx.doi.org/10.3390/plants10061130.

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Anvillea garcinii is a medicinal plant used in the Arab region for intestinal diseases, lung and liver diseases, digestive problems, and as an antidiabetic agent. Repeated chromatographic purifications of A. garcinii leaves led to the isolation of three undescribed guaiane sesquiterpene derivatives, named garcinamines F–H, characterized by the presence of an amino acid unit, along with five known sesquiterpene lactones (garcinamines B–E and 9β-hydroxyparthenolide). The structures of the new compounds were established using spectroscopic (1D and 2D NMR) and spectrometric methods (ESIMS). Garcin

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10

Li, Yahui, Jingwen Liu, Yingchun Wu, Yiming Li, and Fujiang Guo. "Guaiane-type sesquiterpenes from Curcuma wenyujin." Phytochemistry 198 (June 2022): 113164. http://dx.doi.org/10.1016/j.phytochem.2022.113164.

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11

Olennikov, D. N. "Guaiane-Type Sesquiterpenes from Rhaponticum uniflorum." Chemistry of Natural Compounds 55, no. 1 (2019): 157–59. http://dx.doi.org/10.1007/s10600-019-02642-6.

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12

Xie, Yang-Guo, Yi-Gong Guo, Guo-Jing Wu, et al. "Xylopsides A–D, four rare guaiane dimers with two unique bridged pentacyclic skeletons from Xylopia vielana." Organic & Biomolecular Chemistry 16, no. 37 (2018): 8408–12. http://dx.doi.org/10.1039/c8ob01689e.

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13

Wu, Tao, Xin-Jian Yan, Tian-Rong Yang, et al. "Structure-Based Molecular Networking for the Discovery of Anti-HBV Compounds from Saussurea lappa (Decne.) C.B Clarke." Molecules 27, no. 6 (2022): 2023. http://dx.doi.org/10.3390/molecules27062023.

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It is a crucial to find target compounds in natural product research. This study presents a concept of structure-guided isolation to find candidate active molecules from herbs. We establish a process of anti-viral sesquiterpene networking. An analysis of the networking suggested that new anti-HBV sesquiterpene may be attributable to eudesmane-, guaiane-, cadinane-, germacane- and bisabolane-type sesquiterpenes. In order to evaluate the efficiency of the structure-based molecular networking, ethanol extract of Saussurea lappa (Decne.) C.B Clarke was investigated, which led to the isolation of t

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14

Wu, Shi-Biao, Yun Zhao, Hui Fan, et al. "New Guaiane Sesquiterpenes and Furanocoumarins fromNotopterygium incisum." Planta Medica 74, no. 15 (2008): 1812–17. http://dx.doi.org/10.1055/s-0028-1088326.

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15

Mossa, Jaber S., Ilias Muhammad, Farouk S. El-Feraly, Charles D. Huffor, Donald R. McPhail, and Andrew T. McPhail. "Bisabolene and guaiane sesquiterpenes from Pulicaria glutinosa." Phytochemistry 31, no. 2 (1992): 575–78. http://dx.doi.org/10.1016/0031-9422(92)90041-n.

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16

Fukuyama, Yoshiyasu, Hiroyuki Minami, Rina Ichikawa, Kumiko Takeuchi, and Mitsuaki Kodama. "Hydroperoxylated guaiane-type sesquiterpenes from Viburnum awabuki." Phytochemistry 42, no. 3 (1996): 741–46. http://dx.doi.org/10.1016/0031-9422(96)00042-8.

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17

Yang, Li, Jin-Ling Yang, Wen-Hua Dong, et al. "The Characteristic Fragrant Sesquiterpenes and 2-(2-Phenylethyl)chromones in Wild and Cultivated “Qi-Nan” Agarwood." Molecules 26, no. 2 (2021): 436. http://dx.doi.org/10.3390/molecules26020436.

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Recently, cultivated “Qi-Nan” (CQN) agarwood has emerged as a new high-quality agarwood in the agarwood market owing to its similar characteristics, such as high content of resin and richness in two 2-(2-phenylethyl)chromone derivatives, 2-(2-phenylethyl)chromone (59) and 2-[2-(4-methoxyphenyl)ethyl]chromone (60), to the wild harvested “Qi-Nan” (WQN) agarwood. In this study, we compared the chemical constituents and fragrant components of two types of WQN agarwood from A. agallocha Roxb. and A. sinensis, respectively, with CQN agarwood and ordinary agarwood varieties. Additionally, we analyzed

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18

Leiva de Faria, Mary, Ruy de A. Magalhães, Fernando C. Silva, et al. "Enantiodivergent syntheses of cycloheptenone intermediates for guaiane sesquiterpenes." Tetrahedron: Asymmetry 11, no. 20 (2000): 4093–103. http://dx.doi.org/10.1016/s0957-4166(00)00387-6.

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19

Amand, Séverine, Aude Langenfeld, Alain Blond, Joëlle Dupont, Bastien Nay, and Soizic Prado. "Guaiane Sesquiterpenes from Biscogniauxia nummularia Featuring Potent Antigerminative Activity." Journal of Natural Products 75, no. 4 (2012): 798–801. http://dx.doi.org/10.1021/np2009913.

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20

Brocksom, Timothy John, Elisabete T. C. Pesquero, and Fernando T. Lopes. "The Synthesis of Chiral Cycloheptane Precursors of Guaiane Sesquiterpenes." Synthetic Communications 20, no. 8 (1990): 1181–91. http://dx.doi.org/10.1080/00397919008052826.

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21

Ma, Gang-Hua, Kai-Xian Chen, Liu-Qiang Zhang, and Yi-Ming Li. "Advance in biological activities of natural guaiane-type sesquiterpenes." Medicinal Chemistry Research 28, no. 9 (2019): 1339–58. http://dx.doi.org/10.1007/s00044-019-02385-7.

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22

Lee, In-Kyoung, Jeong-Hyung Lee, Eui Il Hwang, and Bong-Sik Yun. "New Guaiane Sesquiterpenes from the Fruits of Torilis japonica." CHEMICAL & PHARMACEUTICAL BULLETIN 56, no. 10 (2008): 1483–85. http://dx.doi.org/10.1248/cpb.56.1483.

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23

Serba, Christelle, Roman Lagoutte, and Nicolas Winssinger. "Rapid and Scalable Synthesis ofcis-Fused Guaiane-Type Sesquiterpenes." European Journal of Organic Chemistry 2016, no. 4 (2016): 644–46. http://dx.doi.org/10.1002/ejoc.201501277.

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24

Lu, Yongping, Weipeng Qi, Guodong Weng, and Xingxian Zhang. "Progresses in Total Synthesis of Guaiane Sesquiterpenes and Their Analogues." Chinese Journal of Organic Chemistry 35, no. 7 (2015): 1407. http://dx.doi.org/10.6023/cjoc201412044.

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25

Fu, Hong-wei, Lin Zhang, Tao Yi, Yu-lin Feng, and Jing-kui Tian. "Guaiane type sesquiterpenes and other constituents from Daucus carota L." Biochemical Systematics and Ecology 38, no. 3 (2010): 309–12. http://dx.doi.org/10.1016/j.bse.2009.12.017.

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26

Yi, Tao, Lin Zhang, Hong-Wei Fu, Shi-Lin Yang, and Jing-Kui Tian. "Two New Guaiane Sesquiterpenes from the Fruits of Daucus carota." Helvetica Chimica Acta 92, no. 12 (2009): 2769–73. http://dx.doi.org/10.1002/hlca.200900106.

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27

Mato, Raquel, Rubén Manzano, Efraím Reyes, et al. "Kinetic Resolution in Transannular Morita-Baylis-Hillman Reaction: An Approximation to the Synthesis of Sesquiterpenes from Guaiane Family." Catalysts 12, no. 1 (2022): 67. http://dx.doi.org/10.3390/catal12010067.

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An approximation to the synthesis of several sesquiterpenes from the Guaiane family is described in which the core structure was obtained through a transannular Morita-Baylis-Hillman reaction performed under kinetic resolution. Several manipulations of the obtained MBH adduct have been carried out directed towards the total synthesis of γ-Gurjunene, to the formal synthesis of Clavukerin A, to the synthesis of a non-natural isomer of isoguaiane and to the synthesis of an advanced intermediate in the total synthesis of Palustrol.

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28

Lee, Ji, Mi-Ran Cha, Mi Kim, Kwangho Lee, Sang-Un Choi, and Shi Ryu. "Two Novel Guaiane Sesquiterpenes from the Whole Plant of Youngia japonica." Planta Medica Letters 2, no. 01 (2015): e31-e34. http://dx.doi.org/10.1055/s-0035-1557794.

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29

ITOKAWA, HIDEJI, HIROSHI MORITA, KENJI OSAWA, KINZO WATANABE, and YOICHI IITAKA. "Novel guaiane- and secoguaiane-type sesquiterpenes from Alpinia japonica (THUNB.) MIQ." CHEMICAL & PHARMACEUTICAL BULLETIN 35, no. 7 (1987): 2849–59. http://dx.doi.org/10.1248/cpb.35.2849.

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30

Gallardo, Amalia B., Mercedes Cueto, Ana R. Díaz-Marrero, Pedro Cuadra, Victor Fajardo, and José Darias. "The recurvatianes: A suite of oxygenated guaiane sesquiterpenes from Perezia recurvata." Phytochemistry 72, no. 2-3 (2011): 284–89. http://dx.doi.org/10.1016/j.phytochem.2010.11.021.

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31

Mendes, Sofia A. C., Tayyab A. Mansoor, Ana Rodrigues, Jácome Bruges Armas, and Maria-José U. Ferreira. "Anti-inflammatory guaiane-type sesquiterpenes from the fruits of Pittosporum undulatum." Phytochemistry 95 (November 2013): 308–14. http://dx.doi.org/10.1016/j.phytochem.2013.06.019.

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32

Wu, Shao-Hua, Jian He, Xiao-Nian Li, et al. "Guaiane sesquiterpenes and isopimarane diterpenes from an endophytic fungus Xylaria sp." Phytochemistry 105 (September 2014): 197–204. http://dx.doi.org/10.1016/j.phytochem.2014.04.016.

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33

El-Desoky, Ahmed H. H., Keisuke Eguchi, Hikaru Kato, et al. "Chamaejasmins, cytotoxic guaiane sesquiterpenes from the root of Stellera chamaejasme L." Fitoterapia 146 (October 2020): 104714. http://dx.doi.org/10.1016/j.fitote.2020.104714.

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34

Chakraborty, Kajal, A. P. Lipton, R. Paulraj, and Rekha D. Chakraborty. "Guaiane sesquiterpenes from seaweed Ulva fasciata Delile and their antibacterial properties." European Journal of Medicinal Chemistry 45, no. 6 (2010): 2237–44. http://dx.doi.org/10.1016/j.ejmech.2010.01.065.

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35

Nakashima, Ken-ichi, Masayoshi Oyama, Tetsuro Ito, et al. "Novel Zierane- and Guaiane-Type Sesquiterpenes from the Root ofMelicope denhamii." Chemistry & Biodiversity 9, no. 10 (2012): 2195–202. http://dx.doi.org/10.1002/cbdv.201100345.

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36

Do, Thanh-Hung, Thammarat Aree, Huu-Hung Nguyen, et al. "Two new guaiane-sesquiterpenes from the cultured lichen mycobiont of Diorygma pruinosum." Phytochemistry Letters 52 (December 2022): 59–62. http://dx.doi.org/10.1016/j.phytol.2022.09.005.

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37

Lou, Yan, Feng Zhao, Hao He, et al. "Guaiane-type sesquiterpenes fromCurcuma wenyujinand their inhibitory effects on nitric oxide production." Journal of Asian Natural Products Research 11, no. 8 (2009): 737–47. http://dx.doi.org/10.1080/10286020903042358.

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38

Mai, Nguyen Thi, Nguyen Thi Cuc, Hoang Le Tuan Anh, et al. "Two new guaiane sesquiterpenes from Datura metel L. with anti-inflammatory activity." Phytochemistry Letters 19 (March 2017): 231–36. http://dx.doi.org/10.1016/j.phytol.2017.01.011.

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39

Huang, Rong, Xiao-Song Xie, Xiao-Wei Fang, Kai-Xia Ma, and Shao-Hua Wu. "Five New Guaiane Sesquiterpenes from the Endophytic FungusXylariasp. YM 311647 ofAzadirachta indica." Chemistry & Biodiversity 12, no. 8 (2015): 1281–86. http://dx.doi.org/10.1002/cbdv.201400405.

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40

Chakraborty, Kajal, A. P. Lipton, R. Paulraj, and Rekha D. Chakraborty. "ChemInform Abstract: Guaiane Sesquiterpenes from Seaweed Ulva fasciata Delile and Their Antibacterial Properties." ChemInform 41, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.201039190.

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41

Kato, Mamoru, Yu-Min He, Dya Fta Dibwe, et al. "New Guaian-type Sesquiterpene from Wikstroemia indica." Natural Product Communications 9, no. 1 (2014): 1934578X1400900. http://dx.doi.org/10.1177/1934578x1400900101.

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From a MeOH extract of powdered roots of Wikstroemia indica, we isolated a new guaian-type sesquiterpene (1) and two known guaian-type sesquiterpenes [oleodaphnal (2), 1α,7α,10α H-guaia-4,11-dien-3-one (3)], together with twelve known compounds: (+)-arctigenin, (+)-matairesinol, (+)-trachelogenin, (+)-nortrachelogenin, (+)-hinokinin, (+)-kusunokinin, 7-methoxycoumarin, 7-hydroxycoumarin (umbelliferone), daphnogitin, daphnoretin, salicifoliol, and (-)-pinoresinol. The structure of compound 1 was determined to be 4,10,11-guaiatrien-3-one-14-oic acid, by the analyses of spectral data.

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42

Thuy, Dinh Thi Thu, Tran Thi Tuyen, Tran Thi Thu Thuy, et al. "Isolation Process and Compound Identification of Agarwood Essential Oils from Aquilaria crassna Cultivated at Three Different Locations in Vietnam." Processes 7, no. 7 (2019): 432. http://dx.doi.org/10.3390/pr7070432.

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Agarwood and agarwood essential oils are commodities with great commercial value. In Vietnam, the agarwood industry has been growing, with more than 10,000 ha of forest land reserved for the cultivation of Aquilaria crassna, an agarwood-producing tree. The aim of this study was to present a hydrodistillation process to recover agarwood essential oil and to compare chemical compositions of agarwood samples harvested from various locations in Vietnam. Three agarwood samples representing products from A. crassna trees cultivated in the provinces of Bac Giang and Khanh Hoa, and on the Phu Quoc isl

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43

Suzuki, Minoru, Nobuhiko Kowata, Hirokazu Kobayashi, and Isao Tanaka. "The Structure of a Germacrane-Type Sesquiterpene Alcohol, a Possible Precursor of Guaiane-Type Sesquiterpenes from the Brown AlgaDictyopteris divaricata." Chemistry Letters 19, no. 12 (1990): 2187–90. http://dx.doi.org/10.1246/cl.1990.2187.

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44

Liu, Yue, JiangHao Ma, Qian Zhao, et al. "Guaiane-Type Sesquiterpenes from Curcuma phaeocaulis and Their Inhibitory Effects on Nitric Oxide Production." Journal of Natural Products 76, no. 6 (2013): 1150–56. http://dx.doi.org/10.1021/np400202f.

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45

Minnaard, Adriaan J., Joannes B. P. A. Wijnberg, and Aede de Groot. "About the Chiral Stability of Germacrene B and the Biomimetic Synthesis of Guaiane Sesquiterpenes." Journal of Organic Chemistry 62, no. 21 (1997): 7346–50. http://dx.doi.org/10.1021/jo970902r.

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46

Yang, Delan, Jun Wang, Wei Li, Wenhua Dong, Wenli Mei, and Haofu Dai. "New guaiane and acorane sesquiterpenes in high quality agarwood ⿿Qi-Nan⿿ from Aquilaria sinensis." Phytochemistry Letters 17 (September 2016): 94–99. http://dx.doi.org/10.1016/j.phytol.2016.07.017.

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47

Hou, Jiqin, Huijun Dong, Ming Yan, et al. "New guaiane sesquiterpenes from Artemisia rupestris and their inhibitory effects on nitric oxide production." Bioorganic & Medicinal Chemistry Letters 24, no. 18 (2014): 4435–38. http://dx.doi.org/10.1016/j.bmcl.2014.08.004.

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48

Chen, Lili, Yunyun Liu, Yifei Li, Wu Yin, and Yongxian Cheng. "Anti-Cancer Effect of Sesquiterpene and Triterpenoids from Agarwood of Aquilaria sinensis." Molecules 27, no. 16 (2022): 5350. http://dx.doi.org/10.3390/molecules27165350.

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Two new guaiane sesquiterpenes, aquisinenoids A and B (1 and 2), two new eudesmane-type sesquiterpenoids, aquisinenoids C and D (3 and 4), one new cucurbitacin, aquisinenoid E (5), and five known cucurbitacins (6–10) were isolated from agarwood of Aquilaria sinensis. The structures of these new compounds, including their absolute configurations, were characterized by spectroscopic and computational methods. The biological evaluation showed that compounds 3 and 9 had an anti-cancer effect on most of the cancer cells at 5 μM, especially in human breast cancer cells. Interestingly, the new compou

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49

Anagnostaki, Elissavet E., and Alexandros L. Zografos. "Non-natural Elemane as the “Stepping Stone” for the Synthesis of Germacrane and Guaiane Sesquiterpenes." Organic Letters 15, no. 1 (2012): 152–55. http://dx.doi.org/10.1021/ol3031999.

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50

Barbosa, Layla R., Ygor W. Vieira, Valdemar Lacerda, et al. "Unequivocal structural assignments of three cycloheptenoid intermediates for guaiane sesquiterpenes: an experimental and theoretical approach." Magnetic Resonance in Chemistry 52, no. 6 (2014): 318–28. http://dx.doi.org/10.1002/mrc.4057.

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