Studies on nepalese crude drugs. XXIV. Diterpenoid constituents of the leaves of Scutellaria repens. Buch.-Ham. ex D. Don

DOI: 10.1248/cpb.46.988

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 988 - 1000 (1998)

Update date:2022-08-04

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Authors:

Kizu, Haruhisa

Sugita, Naohiro

Tomimori, Tsuyoshi

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Article abstract of DOI:10.1248/cpb.46.988

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.

Full text of DOI:10.1248/cpb.46.988

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