Chemical and Pharmaceutical Bulletin p. 988 - 1000 (1998)
Update date:2022-08-04
Topics:
Kizu, Haruhisa
Sugita, Naohiro
Tomimori, Tsuyoshi
From the leaves of Scutellaria repens, sixteen new neoclerodane-type diterpenes named scuterepenins A1, A2, B, C1, C2, D1, D2, E, F1, F2, G1 and G2, and scuterepenosides A1, A2, A3 and A4, have been isolated along with a new 9,11-secoabietane-type diterpene named scuterepenin H. The structures of these compounds have been determined by spectroscopic and chemical methods as follows: scuterepenin A1, (4R,11S,13R)-7β-trans- cinnamoyloxy-4,6α,13-18-tetrahydroxy-11,16:15,16-diepoxy-1-neoclerodanone; scuterepenin A2, cis-cinnamoyl form of A1; scuterepenin B, (4R,11S,13R)- 7β-trans-cinnamoyloxy-2α,4,6α,13,18-pentahydroxy-11,16:15,16-diepoxy-1- neoclerodanone; scuterepenin C1, (4R,11S,13R)-6α-trans-cinnamoyloxy- 7β,13-dihydroxy-4,18:11,16:15,16-triepoxy-1-neoclerodanone; scuterepenin C2, cis-cinnamoyl form of C1; scuterepenin D1, (4R,11S*,13R*)-6α- trans-cinnamoyloxy-1β,7β-diacetoxy-11,16:15,16-diepoxy-18-neoclerodanal; scuterepenin D2, cis-cinnamoyl form of D1; scuterepenin E, (4R,11S*,13R*)-1β-acetoxy-7β-trans-cinnamoyloxy-6α-hydroxy-11,16:15,16- diepoxy-18-neoclerodanal; scuterepenin F1, (4R,11S*,13R*)-1β-O-acetyl- 7β-O-trans-cinnamoyl-18β-O-methyl-6α,18:11,16:15,16-triepoxyneoclerodane- 1,7,18-triol; scuterepenin F2, cis-cinnamoyl form of F1; scuterepenin G1, (4R,7R,11S,13R)-6α-O-trans-cinnamoyl-1,16:4,18:11,16-triepoxyneoclerodane- 6,7,15-triol; scuterepenin G2, cis-cinnamoyl form of G1; scuterepenoside A1, (4R,13S*,16S*)-1β-trans-cinnamoyloxy-6α-(β-D-glucopyranosyloxy)- 16-methoxy-15,16-epoxy-18-neoclerodanal; scuterepenoside A2, cis-cinnamoyl form of A1; scuterepenoside A3, (13S*,16R*)-form of A1; scuterepenoside A4, (13S*,16R*)-form of A2; scuterepenin H, (5S,10R,13S,14S)-13-hydroxy- 7-oxo-9,11-seco-8-abieten-14,11-olide.
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