Recent advances and new insights in biosynthesis of dendrobine and sesquiterpenes

Gong, Daoyong; Chen, Xingyue; Guo, Shunxing; Wang, Bochu; Li, Biao

doi:10.1007/s00253-021-11534-1

Cited by 25 publications

(29 citation statements)

References 55 publications

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“…Compound 1, pale yellow oil, with the yield of 0.2% (10.5 mg) from B5a fraction (4.37 g), was elucidated by interpreting peaks of the IR spectrum (Fig. S1) which appeared at 3364 (hydroxyl group), 2955 (C-H sp 3 unsaturation consisting of 2 double bonds and bicyclic skeleton, each consisting of six carbons. This compound showed the presence of an isopropyl group at C-7 and a methyl group at C-10 which was a characteristic of eudesmane-type sesquiterpene compounds [1] and was supported by previous report [19].…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The FPP has a long chain structure and three double bonds, so it can form various cyclic formations with more flexibility such as monocyclic, tricyclic and tetracyclic [2]. Sesquiterpenoids have a C-15 framework and diverse structures due to the presence of functional groups and substituents [3]. In addition, sesquiterpenoids have also various biological activities such as anti-inflammatory, antibacterial, antioxidant, antitumor, and antimalarial [4].…”

Section: ■ Introductionmentioning

confidence: 99%

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Sesquiterpenoids from the Stem Bark of <i>Lansium domesticum</i> Corr. Cv. Kokossan and Their Cytotoxic Activity against MCF-7 Breast Cancer Cell Lines

et al. 2022

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The n-hexane fraction from the stem bark of Lansium domesticum Corr. Cv. Kokosan afforded 3 sesquiterpenoids, namely eudesm-4(15),7-dien-1β-ol (1), eudesm-4(15)-ene-1β,6α-diol (2), and octahydro-4-hydroxy-3a-methyl-7-methylene-a-(1-methylethyl)-1H-indene-1-methanol (3). These three compounds were discovered in the Lansium genus for the first time. Their chemical structures were determined based on data generated from various spectroscopic methods, including one- and two-dimensional NMR, as well as mass spectroscopy. Sesquiterpenoid compounds (1-3) have also been evaluated on MCF-7 breast cancer cell lines and the compound 1 showed the strongest activity with an IC50 value of 17.97 µg/mL while compounds 2 and 3 showed moderate and weak activity with IC50 values of 121.65 and 201.57 µg/mL, respectively. The implication of the findings of these compounds is as an illustration that one of these sesquiterpenoids has potential as an anticancer with the presence of double bond which played important role in the cytotoxic activity that can be studied for new drug discovery.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Sesquiterpenoids from the Stem Bark of <i>Lansium domesticum</i> Corr. Cv. Kokossan and Their Cytotoxic Activity against MCF-7 Breast Cancer Cell Lines

et al. 2022

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“…28 Bioassay-guided isolation provided two aduncin analogues from D. huoshanense, viz. aduncin C (6) and 4-deoxyaduncin (7). 29 The only difference between aduncin C (6) and aduncin was the position of the hydroxyl group, and its structure was elucidated by modern spectroscopic analyses (MS, IR, 1D and 2D NMR).…”

Section: Distribution and Classification Of Picrotoxane Sesquiterpenoidsmentioning

confidence: 99%

“…In this process, cyclase, cytochrome oxidase, methyltransferase, and aminotransferase were considered to be the key enzymes, but this requires further empirical evidence. 7,192…”

Section: Biosyntheses Of Picrotoxane Sesquiterpenoidsmentioning

confidence: 99%

“…A book series titled “Progress in the Chemistry of Organic Natural Products” has summarized some picrotoxanes that were reported before 2010. 3 In recent years, several mini reviews have focused on the syntheses of (−)-picrotoxinin ( 1 ) 4 and (−)-dendrobine ( 94 ), 5 on the biosynthesis and biological activities of dendrobine alkaloids 6,7 and on the chemistry and pharmacological activities of Dendrobium . 8–10 They provided some significant information on picrotoxane sesquiterpenoids, but the information was only partial.…”

Section: Introductionmentioning

confidence: 99%

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