Four stilbenoids from Pleione bulbocodioides

Complete assignments of 1H and 13C NMR data of three new dihydrophenanthrofurans from Pleione yunnanensis

“…[1] P. bulbocodioides has been chemically investigated and many bibenzyls and dihydroxyphenanthrenes were isolated. [2 -9] Our previous chemical research on P. yunnanensis had resulted in the isolation of some bibenzyl derivatives; [10] further investigation on the same source led to the isolation of five dihydrophenanthrenes, including three new 9,10-dihydrophenanthrofurans (1-3), and two known dihydrophenanthrenes (4)(5). The new compounds were named as pleionesins A (1), B (2), and C (3), respectively.…”

New Polyphenols and Triterpene from the Pseudobulbs of Pleione Formosana

“…The EtOAc and n-BuOH-soluble fractions were separatedly subjected to silica gel column chromatography (CC). Fractions rich in polyphenolic compounds were further separated and purified on Sephadex LH-20 column followed by C 18 CC and semipreparative RP-18 HPLC to give a new dihydrophenanthrene, pleioanthrenin (1), two bibenzyls, pleiobibenzynin A (2) and B (3), and a cycloartane triterpenoid, (24R)-cyclomargenyl p-coumarate (4), together with 1-(4-hydroxybenzyl)-4,7-dimethoxy-9,10-dihydrophenanthrene-2-ol (5), 3 bulbocol (6), 4 3¢,5-dihydroxy-2-(4-hydroxylbenzyl)-3-methoxybibenzyl (7), 5 bulbocodin C (8), 6 arundin (9), 7 3,3¢-dihydroxy-2,6-bis(4-hydroxybenzyl)-5-methoxybibenzyl (10), 8 2,6-bis(4-hydroxybenzyl)-3¢,5-dimethoxy-3-hydroxybibenzyl (11), 8 (24R)-cyclomargenol (12).…”

New Bibenzyl Derivatives from the Tubers of Pleione yunnanensis

“…ROLFE and Pleione yunnanensis ROLFE, could be used as Pseudobulbus Cremastrae seu Pleiones (Chinese name: "Shan-Ci-Gu"), a traditional Chinese medicine used for the treatment of tumours, burns and frostbite. 1) Studies on the tubers of Cremastra appendiculata led to the isolation of many phenanthrenes 2) ; chemical researches on the tubers of Pleione bulbocodioides also resulted in the isolation of several bibenzyls [3][4][5][6] and dihydrophenanthrenes. [7][8][9] However, no detailed chemical study on P. yunnanensis has been reported.…”

“…[7][8][9] However, no detailed chemical study on P. yunnanensis has been reported. Our investigation on the tubers of P. yunnanensis resulted in the isolation of four new (1)(2)(3)(4) and five known bibenzyls (5)(6)(7)(8)(9). The new compounds were given the name shancigusins A, B, C, and D, respectively, and their structures were determined by extensive analyses of their spectroscopic data including 1D-, 2D-NMR, and HR-MS.…”

“…The 1 H-NMR (see Table 1) spectrum of 3 exhibited the resonances of one pair of 4-hydroxybenzyl group, four aliphatic protons due to two benzylic methylenes, and six aromatic protons attributed to the bibenzyl. Among these six aromatic protons, two appeared at d 6.23 and 6.19 (1H each, both d, Jϭ2.0 Hz, H-4, 6) due to two m-coupled protons on A-ring, assignable to H-4 and H-6 from their chemical shifts and splitting patterns; the other four, which appeared at d 7.03 (1H, t, Jϭ8.0 Hz, H-5Ј), 6.57 (1H, br d, Jϭ8.0 Hz, H-4Ј), 6.55 (1H, br s, H-2Ј) and 6.54 (1H, br d, Jϭ8.0 Hz, H-6Ј), deduced the presence of a 1,3-disubstituted aromatic ring (B-ring). These data revealed that the structure of 3 was quite similar to that of 7, 11) except for the absence of the methoxyl group on Aring.…”