Randaiol

New biphenyl derivatives and anti-inflammatory constituents from the stem bark of Magnolia officinalis[Reference: WebLink]

Planta Medica, 2011 , 77 (12):42.

The stem bark of Magnolia officinalis Rehd. et Wils. (Magnoliaceae) has been used as a traditional medicine for the treatment of gastrointestinal disorders, bronchitis, and emphysema, in China, Taiwan, Japan, and Korea [1]. Chemical studies have revealed a variety of neo-lignans and alkaloids as constituents of this plant. Many of these compounds exhibit central depressant effect, muscle relaxation, and antigastric ulcer, antibacterial, antiallergic, vasorelaxant, and neurotrophic activities.
METHODS AND RESULTS:
Investigation on EtOAc-soluble fraction of the stem bark of M. officinalis has led to the isolation of three new biphenyls, 5-allyl-5'-(1-hydroxyallyloxy)biphenyl-2,2-diol (1), 5,5'-diallyl-2'-(allyloxy)biphenyl-2-ol (2), and 5,5'-diallyl-2'-(3-methylbut-2-enyloxy)biphenyl-2-ol (3), together with 12 known compounds, including four neolignans, magnolol (4), honokiol (5), (-)-monoterpenylmagnolol (6), and randainal (7), two norlignans, magnaldehyde D (8) and Randaiol (9), and six steroids, β-sitostenone (10), stigmasta-4,22-dien-3-one (11), β-sitosterol (12), stigmasterol (13), 3β-hydroxystigmast-5-en-7-one (14), and 3β-hydroxystigmasta-5,22-dien-7-one (15). The structure of new compounds (1-3) were determined through spectroscopic and MS analyses. Among the isolates, magnolol (4) and honokiol (5) exhibited potent inhibition against fMLP-induced superoxide production with IC50 values of 4.42±0.24 and 0.68±0.20μg/mL, respectively. In addition, magnolol (4) inhibited fMLP/CB-induced elastase release with an IC50 values of 1.45±0.20μg/mL.

Phytochemistry.1983;22(2):616–617.

Biphenyls from the heartwood of taiwan sassafras.[Reference: WebLink]

Two new biphenyls, randainal and Randaiol, have been isolated from the heartwood of Taiwan sassafras in addition to the known biphenyl magnolol which was found previously in the bark of Magnolia species.
METHODS AND RESULTS:
The two biphenyls were shown to be 2,2′-dihydroxy-5-allylbiphenyl-5′-propenal and 2,2′,5′-trihydroxy-5-allylbiphenyl on the basis of chemical and spectroscopic evidence.

Chinese Traditional & Herbal Drugs, 2013 , 44 (3) :260-264.

Chemical constituents in fractions with vasoactive activity from leaves of Magnolia officinalis[Reference: WebLink]

To study the chemical constituents in the fractions with vasoactive activity from the dried leaves of Magnolia officinalis.
METHODS AND RESULTS:
The compounds were isolated from the chloroform and n-butanol fractions by various chromatographic techniques and identified by spectroscopic methods.Sixteen compounds were obtained and identified as magnolol (1), magnaldehyde B (2), Randaiol (3), syringaresinol (4), 4, 4', 5-trihydroxy-1, 1'-di-2-propenylbiphenyl (5), lariciresinol (6), (7S, 8R) syringoylglycerol (7), coniferin (8), benzylic-β-D-allopyranoside (9), afzelin (10), isorhamnetin-3-O-β-D-glucoside (11), choerospondin (12), 5, 7-dihydroxy chromone-7-O-β-D-glucoside (13), erigeside C (14), tachioside (15), and uridine (16).
CONCLUSIONS:
Compounds 5-8 are isolated from this plant for the first time, and compounds 9-16 are isolated from this genus for the first time.