New quassinoids from indonesian Picrasma javanica. Structures of javanicins E, F, G and M.

Koike, Kazuo; Mitsunaga, Katsuyoshi; Ohmoto, Taichi

doi:10.1248/cpb.38.2746

Cited by 17 publications

(29 citation statements)

References 1 publication

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“…The CHCl 3 extract (15 g) was chromatographed on silica gel with EtOAc− n -hexane and EtOAC−MeOH solvent systems to give eight fractions. The separation of fractions 7 and 8, using a combination of various chromatographic methods, afforded 13 new picrajavanicins A−M ( 32 − 44 ) [ 22 , 23 ] and 5 known ones including javanicins B ( 45 ) [ 38 ], F ( 46 ) [ 40 ], and I ( 47 ) [ 37 ], picrasin A ( 48 ), and 2′-isopicrasin A ( 49 ) [ 52 ] from the CHCl 3 -soluble extract of P. javanica (Fig. 3 ).…”

Section: Introductionmentioning

confidence: 99%

Naturally occurring Vpr inhibitors from medicinal plants of Myanmar

et al. 2017

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Human immunodeficiency virus type-1 (HIV-1) is a lentiviral family member that encodes the retroviral Gag, Pol, and Env proteins, along with six additional accessory proteins, Tat, Rev, Vpu, Vif, Nef, and Vpr. The currently approved anti-HIV drugs target the Pol and Env encoded proteins. However, these drugs are only effective in reducing viral replication. Furthermore, the drugs’ toxicities and the emergence of drug-resistant strains have become serious worldwide problems. Resistance eventually arises to all of the approved anti-HIV drugs, including the newly approved drugs that target HIV integrase (IN). Drug resistance likely emerges because of spontaneous mutations that occur during viral replication. Therefore, new drugs that effectively block other viral components must be developed to reduce the rate of resistance and suppress viral replication with little or no long-term toxicity. The accessory proteins may expand treatment options. Viral protein R (Vpr) is one of the promising drug targets among the HIV accessory proteins. However, the search for inhibitors continues in anti-HIV drug discovery. In this review, we summarize the naturally occurring compounds discovered from two Myanmar medicinal plants as well as their structure-activity relationships. A total of 49 secondary metabolites were isolated from Kaempferia pulchra rhizomes and Picrasama javanica bark, and the types of compounds were identified as isopimarane diterpenoids and picrasane quassinoids, respectively. Among the isolates, 7 diterpenoids and 15 quassinoids were found to be Vpr inhibitors lacking detectable toxicity, and their potencies varied according to their respective functionalities.

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Section: Introductionmentioning

confidence: 99%

Naturally occurring Vpr inhibitors from medicinal plants of Myanmar

et al. 2017

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“…Compound 2 showed a molecular formula of C 29 H 34 O 10 , as deduced from the sodium adduct ion peak at m/z 565.2034 (calcd for C 29 H 34 O 10 Na, 565.2044) and 13 C NMR data, indicating 13 degrees of unsaturation. On comparing the 1D NMR spectra of 2 with those of 1, the signals of the C-13 acetoxy group were absent, and the chemical shift of C-13 was shifted upfield from δ C 85.5 to 78.7 in 2.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Compound 3 (picrasjavacin C) was isolated as a colorless gum. The HRESIMS and 13 C NMR spectroscopic data suggested that 3 has the molecular formula C 30 H 36 O 9 . The 1D NMR spectra of 3 displayed similar resonances to those of 1, implying that 3 is a picrasane-type quassinoid.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The EtOAc-soluble fraction showed more potent antifungal activity than that of the n-BuOH-and H 2 O-soluble fractions (Supporting Information). Thus, the EtOAc-soluble fraction was selected and was subjected to silica gel, Sephadex LH-20, and semipreparative HPLC to afford 13 new quassinoids, namely, picrasjavacins A−M (1−13), along with six known congeners, including quassin ( 14), 30 12-norquassin (15), 13 12norquassin acetate ( 16), 13 nigakilactone A ( 17), 31 javanicin Z (18), 22 and picrasin B (19). 32 Compound 1 was acquired as colorless prisms.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…32 Compound 1 was acquired as colorless prisms. Its molecular formula, C 31 H 36 O 11 , was concluded based on the HRESIMS (m/z 607.2138 [M + Na] + , calcd for C 31 H 36 O 11 Na, 607.2150) and 13 C NMR data (Table 1), which required 14 degrees of unsaturation. Its IR spectrum showed absorption bands consistent with the presence of hydroxy (3459 cm −1 ), carbonyl (1727 cm −1 ), and aromatic (1490, 1445, and 1369 cm −1 ) functionalities.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Quassinoids with Inhibitory Activities against Plant Fungal Pathogens from Picrasma javanica

Chen

Bai

et al. 2021

J. Nat. Prod.

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A bioactivity-guided study on the leaves of Picrasma javanica led to the isolation of 19 quassinoids, including 13 new compounds. The structures of the new compounds were elucidated by a combination of spectroscopic data analysis, X-ray crystallography studies, and electronic circular dichroism (ECD) data interpretation. Compounds 1−7 are rare examples of quassinoids with a keto carbonyl group at C-12. The biological activities of 11 of the more abundant isolates were evaluated against five phytopathogenic fungi in vitro, and several of them including 6 and 15 showed moderate inhibitory effects that were comparative to those of the positive control, carbendazim. In addition, the preliminary structure−activity relationships (SARs) of these quassinoids were also investigated.

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Bioactive Compounds from Medicinal Plants in Myanmar

Win

Morita

2021

Progress in the Chemistry of Organic Natural Products 114

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New quassinoids from indonesian Picrasma javanica. Structures of javanicins E, F, G and M.

Cited by 17 publications

References 1 publication

Naturally occurring Vpr inhibitors from medicinal plants of Myanmar

Naturally occurring Vpr inhibitors from medicinal plants of Myanmar

Quassinoids with Inhibitory Activities against Plant Fungal Pathogens from Picrasma javanica

Bioactive Compounds from Medicinal Plants in Myanmar

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