Amomaxins A and B, Two Unprecedented Rearranged Labdane Norditerpenoids with a Nine-Membered Ring from Amomum maximum

Yin, Hong; Luo, Jian‐Guang; Shan, Si‐Ming; Wang, Xiao-Bing; Luo, Jun; Yang, Ming‐Hua; Kong, Ling–Yi

doi:10.1021/ol400348a

Cited by 33 publications

(29 citation statements)

References 19 publications

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“…An investigation has shown that the extract of A. maximum acts as anthelmintic against the cestode, Raillietina echinobothrida (Chetia et al 2014). Phytochemical studies revealed the characterisation of labdane triterpenoids, diterpenes (Luo et al 2014), amomaxins A and B as well as isocoronarin (Yin et al 2013) from the plant. No record of the composition of its essential oil could be found in the literature.…”

Section: Introductionmentioning

confidence: 99%

Volatile constituents ofAmomum maximumRoxb andAmomum microcarpumC. F. Liang & D. Fang: two Zingiberaceae grown in Vietnam

Hương

Đài

Thăng

et al. 2015

Natural Product Research

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The chemical composition of essential oils obtained from the hydrodistillation of different parts of Amomum maximum Roxb and Amomum muricarpum C. F. Liang & D. Fang (Zingiberaceae) grown in Vietnam are reported. The analysis was performed by means of gas chromatography-flame ionisation detectoorand gas chromatography coupled with mass spectrometry. The major compounds identified in the oils of A. maximum were β-pinene (20.4-40.8%), α-pinene (6.8-15.0%), β-elemene (2.5-12.8%) and β-caryophyllene (2.3-10.3%). Moreover, β-phellandrene (11.6%) was present in the root oil. The main compound identified in all the oil samples of A. muricarpum was α-pinene (24.1-54.7%) and β-pinene (9.2-25.9%). In addition, limonene (7.4%) and δ-3-carene (9.4%) were present in the leaves and stem oils, respectively. However, while β-phellandrene (8.3%) could be seen prominent in the root oil, the fruits contained significant amount of zingiberene (6.3%). The largest amount of τ-muurolol (13.0%) was found in the flower oil.

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Section: Introductionmentioning

confidence: 99%

Volatile constituents ofAmomum maximumRoxb andAmomum microcarpumC. F. Liang & D. Fang: two Zingiberaceae grown in Vietnam

Hương

Đài

Thăng

et al. 2015

Natural Product Research

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“…As shown in Fig. 8 , the pathways of 1 – 8 originating from cadalenequinone, which was considered as the biosynthetic monomeric precursor of involucratustones A–C 4 , were presumed, in which nucleophilic addition 9 26 , S N 2 nucleophilic displacement 27 , [3 + 3] benzannulation 28 , oxidative cleavage 29 , decarboxylation 30 31 , oxidative phenol coupling 32 were included.…”

Section: Resultsmentioning

confidence: 99%

“…In the Fig. 8 , it is revealed that the formation of nor-cadinane-dimer 4 is attributed to the decarboxylation reaction, which is the most common biogenetic pathway to form norterpenoids 2 9 33 34 35 . However, interesting, different from the most norterpeniods, the carbon skeletons of dinor-cadinane-dimers 5 and 6 , dodecanor-cadinane-dimer 7 , and tetradecanor-cadinane-dimer 8 were speculated to be produced by the key oxidative cleavage reaction.…”

Section: Resultsmentioning

confidence: 99%

“…The occurrence of nor-cadinane-dimer is also surprisingly low, with the only two, aquatidial 2 and parviflorene I 3 . Recently, we have reported three unprecedented cadinane dimers, involucratustones A–C 4 , from Stahlianthus involucratus , a folklore medicine to treat inflammation, pain, and fever 5 , as part of a continued program searching for novel terpenoids from Zingiberaceae plants 6 7 8 9 . These prompt us to perform a further phytochemical investigation on S. involucratus .…”

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Involucratusins A–H: Unusual Cadinane Dimers from Stahlianthus involucratus with Multidrug Resistance Reversal Activity

Luo

Wang

et al. 2016

Sci Rep

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Three novel cadinane dimers, involucratusins A–C (1–3), five unique nor-cadinane-dimers, involucratusins D–H (4–8), together with a known compound (9) were isolated from the rhizomes of Stahlianthus involucratus. Their challenging structures and absolute configurations were determined by spectroscopic data, CD experimentation, chemical conversions and single-crystal X-ray diffraction. Compounds 1–3 are unusual cadinane dimers with new connection and novel cores. Compound 4 is a unique nor-cadinane-dimer, and 5 and 6 are two pairs of hemiketal racemates with novel dinor-cadinane-dimer backbone. Compounds 7 and 8 represent unusual dodecanor-cadinane-dimer and tetradecanor-cadinane-dimer carbon skeletons, respectively. The possible biogenetic pathways of 1–8 were proposed, involving nucleophilic addition, SN2 nucleophilic displacement, [3 + 3] benzannulation, oxidative cleavage, decarboxylation, and oxidative phenol coupling reactions. Multidrug resistance (MDR) reversal activity assay of the isolates were evaluated in doxorubicin-resistant human breast cancer cells (MCF-7/DOX). The combined use of these novel cadinane dimers at a concentration of 10 μM increased the cytotoxicity of doxorubicin by 2.2–5.8-fold. It is the first report about the MDR reversal activity of cadinane dimers.

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“…AMS-19 to AMS-21 were combined and subjected to prep-HPLC with MeOH-H 2 O (45 : 55, v/v, 10 mL/ min) to give 1 (6 mg Nitric Oxide (NO) Production Bioassay The protocol for NO production bioassays was provided in previously published papers. 30) N-Monomethyl-L-arginine was used as the positive control. All experiments were performed in three replicates.…”

Section: Experimental General Experimental Procedures Optical Rotationsmentioning

confidence: 99%

Teucvisins A–E, Five New neo-Clerodane Diterpenes from Teucrium viscidum

Luo

Zhu

et al. 2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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Two new neo-clerodane diterpenoids, teucvisins A and B (1, 2), and three new 19-nor-neoclerodane diterpenoids, teucvisins C-E (3-5), together with ten known constituents (6-15) were isolated from the whole plants of Teucrium viscidum. All the isolates were evaluated for their inhibitory activities of lipopolysaccharide (LPS)-induced nitric oxide production in RAW264.7 macrophages. The results indicated that compounds 11 and 15 showed moderate inhibition with an IC 50 value of 21.9 and 22.4 µM, respectively. Key words clerodane diterpene; Teucrium viscidum; anti-inflammatoryThe genus Teucrium (Lamiaceae) includes approximately 300 species which are mainly distributed in the Mediterranean area. In China, there are eighteen species and ten varieties, mostly distributed in southern part of China. Teucrium species are generally aromatic and ornamental plants, meanwhile, a large number of species are used in folk medicine and pharmacy for their diverse bioactivities, such as anti-inflammatory, 1) antiacetylcholinesterase, 2) antidiabetic, 3-5) antifeedancy 6,7) and antimicrobial effects. 8) Teucrium viscidum, a folk medicine in China, is used to treat hematemesis, pulmonary abscesses, traumatic injuries, and bites from rabid dogs or venomous snakes.9) Previous phytochemical studies of this plant have afforded diterpenes, 10-13) triterpenoids, sterols and lignans.14) Our further investigation on this plant led to the isolation of five new neo-clerodane diterpenes, teucvisins A-E (1-5) (Fig. 1), together with ten known diterpenes (6-15). Herein, we described the isolation and structure elucidation of 1-5 and the anti-inflammatory activities of all the isolates. C-NMR spectrum (Table 1) revealed the presence of 20 carbons, which could in combination with the heteronuclear single quantum coherence (HSQC) and be assigned to two lactone carbonyls (δ C 178.1, 177.8), four olefinic carbons (δ C 144.4, 139.7, 125.2, 108.2), four oxygenated carbons (δ C 78.4, 72.4, 70.1, 69.6) and ten aliphatic resonances (δ C 51.8, 48.4, 42.7, 40.0, 34.2, 33.7, 32.7, 23.5, 21.4, 16.6). The fulfilled analysis of NMR data including HSQC, heteronuclear multiple bond connectivity (HMBC) and rotating frame Overhauser enhancement spectroscopy (ROESY) experiments, allowed for an unambiguous assignment of all proton and carbon signals. The above total data showed that 1 was a neo-clerodane diterpene, whose NMR data were similar to teucrin H2, previously isolated from the genus Teucrium. Results and Discussion

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Amomaxins A and B, Two Unprecedented Rearranged Labdane Norditerpenoids with a Nine-Membered Ring from Amomum maximum

Cited by 33 publications

References 19 publications

Volatile constituents ofAmomum maximumRoxb andAmomum microcarpumC. F. Liang & D. Fang: two Zingiberaceae grown in Vietnam

Volatile constituents ofAmomum maximumRoxb andAmomum microcarpumC. F. Liang & D. Fang: two Zingiberaceae grown in Vietnam

Involucratusins A–H: Unusual Cadinane Dimers from Stahlianthus involucratus with Multidrug Resistance Reversal Activity

Teucvisins A–E, Five New <i>neo</i>-Clerodane Diterpenes from <i>Teucrium viscidum</i>

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