A new morphinandienone alkaloid from the stems of Fissistigma tungfangense

Abstract

A new morphinandienone alkaloid, fissistigmine A (1), together with three known alkaloids (2-4), were isolated and identified from the stems of Fissistigma tungfangense. Among them, fissistigmine A (1) represents the first example of a novel naturally occurring morphinandienone alkaloid with a unique cleavage of the C-9-N-17 bond. All isolated compounds were evaluated for their anti-rheumatoid arthritis activities via examining their anti-proliferative effects on synoviocytes in vitro. Compound 1 exhibited inhibitory effect on the proliferation of synoviocytes with an IC value of 114.6 ± 2.2 μM.

Fissistigma oldhamii (Hemsl.) Merr.: Ethnomedicinal, Phytochemistry, and Pharmacological Aspects

“…The alkaloid fissistigmine A ( 20 ) has been found in the stem of F. oldhamii [ 14 ] and the related species Fissistigma tungfangense Y.Tsiang & P.T.Li. This compound inhibited the proliferation of synoviocytes in vitro with a potency comparable to the reference product methotrexate (IC 50 = 114.6 and 112.8 µM, respectively), suggesting its potential use for the treatment of rheumatoid arthritis [ 63 ]. Fissistigmine ( 20 ) has been isolated from the stem part of the plant together with the related aporphine alkaloids fissistigamides A-B ( 18 – 19 ) [ 14 ].…”

“…Nevertheless, it is a rarely described compound worthy of further investigation. Another chalcone derivative has been recently described, namely, 4 ,5 -dimethoxy-2 -hydroxy-3 ,6 -quinodihydrochalcone (63), identified in the dried stems of F. oldhamii var. longistipitatum, and has revealed modest antiproliferative action against HepG2 hepatocytes (IC 50 = 10.8 µM) [13].…”

Herbal compounds for rheumatoid arthritis: Literatures review and cheminformatics prediction

“…FLS plays an essential role in the development of synovial inflammation of RA (Li et al, ). Triptolide, celastrol, geniposide, paeoniflorin, clematichinenoside AR, kirenol, tanshinone IIA, bauchampine A, baicalein, 1,7‐dihydroxyl‐3,4‐dimethoxylxanthone, catechin, licochalcone A, luteolin, quercetin, ramosissimin, α‐mangostin, berberine, fissistigmine A, matrine, norisoboldine, sinomenine, tamaractam, caffeic acid, paeonol, chlorogenic acid, and daphnetin have been reported to induce apoptosis of FLS or inhibit its proliferation (Bi, Xin, Gao, Lin, & Qian, ; Chen et al, ; Chen et al, ; Hong et al, ; Hua et al, ; Jie et al, ; Kusunoki et al, ; Li et al, ; Liu et al, ; Liu, Feng, Wang, Zhao, & Li, ; Lou et al, ; Luo et al, ; Pan, Zhu, Lv, & Pei, ; Shu et al, ; Su et al, ; Su, Sun, Ao, & Zhao, ; Sun et al, ; Sun, Ding, & Yao, ; Sung et al, ; Tang, Wei, & Wang, ; Wang et al, ; Wang, Jiang, & Sun, ; Wang, Sun, & Jin, ; Xu et al, ; Yang, Dong, & Li, ; Yao et al, ; Yi et al, ; Zhang et al, ; Zhang et al, ; Zheng, Wei, Zhu, & Liu, ; Zhou et al, ; Zuo, Xia, Li, Ou‐Yang, & Chen, ). Some previous researches have shown that betulinic acid, kaempferol, leonurine, oxymatrine, and piperlongumine can inhibit the migration and invasion of FLS in RA models (Li et al, ; Liang et al, ; Liu, Feng, et al, ; Pan et al, ; Sun, Xu, Du, Zhang, & Zhu, ).…”

“…In addition to inflammatory damage, FLS also plays an essential role in cartilage destruction (Pan et al, ). Therefore, the decrease in FLS activity by some components is also beneficial to the protection of cartilage in RA models, including triptolide, celastrol, geniposide, paeoniflorin, clematichinenoside AR, kirenol, tanshinone IIA, bauchampine A, betulinic acid, baicalein, 1,7‐dihydroxyl‐3,4‐dimethoxylxanthone, catechin, kaempferol, licochalcone A, luteolin, quercetin, ramosissimin, α‐mangostin, berberine, fissistigmine A, matrine, norisoboldine, oxymatrine, piperlongumine, sinomenine, tamaractam, caffeic acid, chlorogenic acid, paeonol, daphnetin, and leonurine (Bi et al, ; Chen et al, ; Chen et al, ; Deng et al, ; Hong et al, ; Hua et al, ; Jie et al, ; Kusunoki et al, ; Li et al, ; Li et al, ; Li et al, ; Liang et al, ; Liu et al, ; Liu, Feng, et al, ; Lou et al, ; Lou et al, ; Luo et al, ; Pan et al, ; Pan et al, ; Shu et al, ; Su et al, ; Su et al, ; Sun et al, ; Sun et al, ; Sun et al, ; Sung et al, ; Tang et al, ; Wang et al, ; Wang, Dai, et al, ; Wang, Sun, & Jin, ; Xu et al, ; Yang, Dong, & Li, ; Yao et al, ; Yi et al, ; Zhang et al, ; Zhang, Chen, et al, ; Zheng et al, ; Zhou et al, ; Zuo et al, ).…”