Dictionary of Natural Products: Volume 11 of Dictionary of Natural Products

622 Pages·1998·24.413 MB·English

by  J. Buckingham (auth.), J. Buckingham (eds.)

Dictionary
of
Natural
Products
FOURTH SUPPLEMENT
Dictionary
of
Natural
Products
FOURTH SUPPLEMENT
VOLUME 11 OF DICTIONARY OF NATURAL ,PRODUCTS
IUIII
SPRINGER-SCIENCE+BUSINESS MEDIA, B.V.
The First Edition of Dictionary of Natural Products in seven volumes published 1994
The First Supplement published 1995
The Second Supplement published 1996
The Third Supplement published 1997
This Fourth Supplement published 1998
© 1998 Springer Science+Business Media Dordrecht
Originally published by Chapman & Hall in 1998
ISBN 978-0-412-60440-9 ISBN 978-1-4899-3314-0 (eBook)
DOI 10.1007/978-1-4899-3314-0
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INTERNATIONAL ADVISORY BOARD
C. Djerassi
Stanford University
J.D. Connolly G.Ourisson
Glasgow University Universite Louis Pasteur, Strasbourg
DJ. Faulkner RA. Raphael
University of California, San Diego University of Cambridge
K. Mori M. Shamma
Science University of Tokyo Pennsylvania State University
K. Nakanishi Ch. Tamm
Columbia University, New York University of Basel
SUBJECT EDITORS
D.C. Ayres J.B. Harborne F.J. Leeper
(lignans) (flavonoids) (polypyrroles)
Formerly of Queen Mary & Reading University University of Cambridge
Westfield College, London E. Haslam R.D.H. Murray
B.W. Bycroft (tannins) (coumarins)
(antibiotics and peptides) Formerly of Sheffield Formerly of
University of Nottingham University Glasgow University
P.M. Collins RA. Hill I. W. Southon
(carbohydrates) (terpenoids and steroids) (alkaloids)
Birkbeck College, London Glasgow University Consultant
F.D. Gunstone D.R Kelly
(lipids) (semiochemicals)
Scottish Crop Research Institute University of Wales,
College of Cardiff
EXECUTIVE EDITOR
J. Buckingham
PROJECT EDITOR
S.H.J. Thompson
ADDITIONAL PRINCIPAL CONTRIBUTORS
R.S. Munasinghe, A.D. Roberts
Fourth Supplement
1. Introduction no necessity for the user to consult the Main Work or
previous supplements.
For detailed information about how to use the Dictionary
of Natural Products (DNP) see the Introduction in
3. Literature coverage
Volume 1 of the Main Work.
In compiling this Supplement the primary literature has
been surveyed to late 1996. The printed supplement con
2. Using DNP Supplements
centrates principally on important new natural products
As in the Main Work volumes, every Entry is numbered isolated during the period in question. A considerable
to assist ready location. The DNP Number consists of a number of amendments have been made during the
letter of the alphabet followed by a five-digit number. review period to entries which have not been
In this Fourth Supplement the first digit is invariably 4. reprinted in the Supplement owing to space limitations.
Cross-references within the text to Entries having All of these can be accessed via the CD-ROM version.
numbers beginning with zero refer to Main Work Entries
and with 1, 2 and 3 refer to the First, Second and Third
4. Indexes
Supplements.
Where a Supplement Entry contains additional or The indexes in the Supplement consist of Name and
corrected information referring to an Entry in the Main Molecular Formula Index and are cumulative for the first
Work the whole Entry is reprinted, with the accom three supplements. No CAS Registry Number Index is
panying statement "Updated Entry replacing ... ". In such included in this supplement, for reasons of pressure on
cases, the new Entry contains all of the information space. A CAS index was published with the Second
which appeared in the former Entry, except for any Supplement and will next reappear as part of the Fifth
which has been deliberately deleted. Therefore there is Supplement.
ix
Contents
Fourth Supplement Entries page 1
Name Index 349
Molecular Formula Index 475
xi
A
9(8 -+ 7)-Abeo-8,13-dinor-11-oxo-6- A-40001 CUH360I0 M 508.564
eremophilen-15-oic acid Constit. of Taxus cuspidata. Amorph. solid. [IX]~ + 79.7
(c, 0.5 in MeOH).
Kobayashi, J. et ai, Tetrahedron, 1996, 52, 5391 (isol, pmr, cmr)
~
19(4 -+5)-Abeo-8(17),14-1abdadien-13-o1 A-40004
8(17),14-Thelopogadien-13-o1
COOH
C H 0 M 222.283
13 1S 3
Me ester: [170473-56-0].
C H 0 M 236.310
I4 20 3
Constit. of Ligularia przewalskii. Gum. [1X]i? + 3.5 (c, 4.5
in CHCI3).
Zhao, Y. et ai, J. Nat. Prod., 1995, 58, 1358 (isol, pmr, emr)
C H 0 M 290.488
20 34
24(23 -+ 22)-Abeo-16,23-epoxy-3,23- A-40002 (4P,13~)-/orm [174756-40-2] Nakamurol A
dihydroxycholesta-5,24-dien-18-al Constit. of Agelas nakamurai. Oil. [IX]~ + 39.1 (c, 1.6 in
CHCI3)·
Shoji, N. et ai, J. Nat. Prod., 1996, 59, 448 (isol, pmr, cmr)
8,13-Abietadiene-11,12-dione A-40005
[86510-12-5]
°
C;7H.~P4 M 428.611
(3P,16p,22rx.H,23rx.)-/orm
3-0-[I X-L-Rhamnopyranosyl-(1 --> 2)-P-D-glucopyranosyl C20H280Z M 300.440
(1 -->2)-P-D-glucopyranoside]: [153005-20-0]. Constit. of Salvia napifolia.
C4sH700lS M 899.037 Ulube1en, A. et ai, Phytochemistry, 1995, 40, 861 (isol, pmr, cmr)
Constit. of Ornithogalum saundersiae (Liliaceae).
3-0-[I X-L-Rhamnopyranosyl-( 1--> 2)-P-D-glucopyranoside]: 8,15-Abietadien-19-o1 A-40006
[173967-24-3].
[178402-85-2]
C:wRfiCPI3 M 736.895
Constit. of O. saundersiae.
3-0-[4-Hydroxybenzoyl-( -->4)-IX-L-rhamnopyranosyl-( 1--> 2)
P-D-glucopyranoside]: [153005-22-2].
C4QH 0 M 857.003
64 15
Constit. of O. saundersiae.
Mimaki, Y. et ai, Tet. Lett., 1996, 37, 1245 (isol, pmr, emr)
11(15-+ 1)-Abeo-2,5,7,9,10,15- A-40003 CH20H
hexahydroxy-4(20),11-taxadien-13-one
C20H3zO M 288.472
Constit. of Vellozia flavicans. Oil.
HO
Pinto, A.C. et ai, Phytochemistry, 1996, 42, 767 (isol, pmr, cmr)
'OH
HO
CwH 0 M 382.453
30 7
(2rx.,5rx.,7p,9rx.,lOfJ)-/orm
2,9,10-Tri-Ac: [175739-44-3]. Taxuspine 0
1
6,8,11,13-Abietatetraene-6,12,14-... - 4-Acetyl-3-methoxy-5-methylbenzoic ... A-40007 - A-40013
6,8,11,13-Abietatetraene-6,12,14-triol A-40007 Alkaloid from the Caribbean sea plume Pseudopterogorgia
[170382-16-8] acerosa. [1X]n +0.44 (c, 2.0 in CHCI3). Closely related to
Tobagolide, T-01505 and Pseudopterolide, P-02044.
Rodriguez, A.D. et ai, Tet. Lett., 1996, 37, 2687 (isol, pmr, cmr,
ms, struet)
5-Acetyl-2,3-dihydro-3-hydroxy-2-[l A-40011
(hydroxymethyl)ethenyl)benzofuran
OH
f
C2oH2803 M 316.439 H3CCO~--'
Enol. Constit. of Salvia napifolia. Amorph.
~O~HPH
Uiubelen, A. et ai, Phytochemistry, 1995, 40, 861 (isol, pmr)
C13HI404 M 234.251
8,1 1, 13-Abietatriene-2,19-diol A-40008
(2R* ,3S*)-form
trans-form
3-0-Angeloyl:
C1sH200S M 316.353
Constit. of Urolepis hecatantha.
de Guttierrez, A.N. et ai, Phytochemistry, 1995,39, 795 (isol, pmr,
ms)
CHPH 3-Acetyl-5, 7- dihydroxy-l (3R) A-40012
C20H3002 M 302.456 isobenzofuranone
2/T.-form [170171-95-6] Acetophthalidin
Constit. of Calceolaria hypericina. [1X]i? + 115.9 (c, 0.5 in
CHCI3) (as di-Ac). COCH
Chamy, M.C. et ai, Phytochemistry, 1995, 40, 1209 (isol, pmr, cmr) H0(G° 3
I
~ °
Aborycin A-40009
OH
RP 71955. Antibiotic RP 71955
C1oHsOs M 208.170
[152835-17-1]
(±)-form
HO-Trp-Phe-Cys-Val-Val-Ala-Tyr Prod. by a fungus isol. from a marine sediment.
i
/Ala-GlY ~GIY Inhibitor of mammalian cell cycle. Powder. Mp 195-
I Phe Cys 205° dec.
S I I Cui, C.-B. et ai, J. Antibiot., 1996, 49, 216 (isol, UV, ir, pmr, emr)
I /Asn-A~p /S
Cys Cys-S 4-Acetyl-3-methoxy-5-methylbenzoic acid A-40013
I I
Ser Leu Macrophomic acid
\ / [100507-74-2]
GIY-I1eGly
C97Hl3IN2PuS4 M 2163.504
Tricyclic peptide antibiotic. Prod. by Streptomyces
griseoflavus and S. sp. SP9440. HIV protease inhibitor.
[IX]~ -72 (c, 1 in MeOH).
HPoetltyenrcakt,, OG.. eett aaii,, AJ.n nAanlteinb,i o1t9.,9 149,79431,4 (6is,o 1l,7 5e6m r(,i smofs) ) CllH1204 M 208.213
Metab. of Macrophoma commelinae. Mp 178.5-182°.
Frechet, D. et ai, Biochemistry, 1994, 33, 42 (props)
Et ester: [80597-52-0].
Aceropterine A-40010 C13H1,04 M 236.267
Cryst. (hexane). Mp 63.1-64.1
0.
COOMe [80597-50-8]
~ Jung, M.E. et ai, Tetrahedron, 1984, 40, 4751 (synth, ester)
Relative Sakurai, I. et ai, Chern. Pharm. Bull., 1985,33, 5141; 1988,36,
1328 (isof)
configuration
Ichihara, A. et ai, Tetrahedron, 1987,43, 5245 (synth, ester)
°
M 431.485
2
l-Acetyl-5-methylcyclopentene - Actinoplanic acid B A-40014 - A-40020
1-Acetyl-5-methylcyclopentene A-40014 Acorientine A-40018
1-(5-Methyl-l-cyclopenten-l-yl)ethanone, 9CI
HO
[54717-25-8] \
COCH
3
H3~
OH
CsHIlO M 124.182
Isol. from the ants Azteca sp., Iridomyrmex discors and I.
purpureus.
Wheeler, J.W. et ai, Science (Washington, D.C.), 1975, 187, 254
(isof) ~OH27N03 M 329.438
Cavill, G.W.K. et ai, Insect Biochem., 1984, 14, 505 (isof) Alkaloid from aerial parts of Aconitum orientale. [IX]D
Cox, M.F. et ai, I. Nat. Prod., 1989, 52, 75 (isol) + 13.5 (c, 0.1 in CHCI3).
U1ube1en, A. et ai, Phytochemistry, 1996, 41, 957 (isol, ir, pmr,
2-Acetyl-l,3,6,8-naphthalenetetrol A-40015 cmr, ms, struct)
2-A cetyl-l ,3 ,6,8-tetrahydroxynaphthalene
Actinoplanic acid A-40019
[159440-19-4]
COOH
OOC~COOH
CIlH100S M 234.208
1,6-Di-Me ether, 3-0-fi-D-apiofuranoside, 8-0-fi-D
glucopyranoside: [170384-73-3]. Cassitoroside COOH
~H32014 M 556.519 OOC~CO
Constit. of the seeds of Cassia tora. Pale yellow needles. ""0
Mp 234-236°.
Choi, 1.S. et ai, Phytochemistry, 1995, 40, 997 (isol, pmr, cmr)
COOH
6-(2-Acetyloxy-4-heptenyl)-5,6-dihydro- A-40016
o
2H-pyran-2-0ne OH
CS1HsoOl6 M 949.183
9Ac ~ Macrolide antibiotic. Prod. by Actinoplanes sp. Potent
inhibitor of Ras famesyl-protein transferase. Gum. [1X]i?
~OAO
+23 (c, 0.1 in MeOH).
C H 0 M 252.310 Singh, S.B. et ai, I.A.C.S., 1994, 116, 11606 (isol, ir, pmr, cmr, ms)
I4 20 4
Constit. of Cryptocarya lati/olia (Lauraceae). Oil. [1X]i,8
+98 (c, 1.4 in CHCI3). Actinoplanic acid B A-40020
Drewes, S.E. et ai, Phytochemistry, 1996, 41, 333 (isol, pmr, cmr) [170661-88-8]
3-Acoren-5-o1 A-40017 COOH
Trichoacorenol OOC~COOH
[167355-55-7]
COOH
OOC~COOH
COOH
C1sHuP M 222.370 o
OH
Metab. of Trichoderma koningii. Amorph. solid. [IX]D - 5.2
(c, 0.12 in CHCI3). CS1H82016 M 951.199
Prod. by Actinoplanes sp. Inhibitor of Ras famesyl-protein
Huang, Q. et ai, Chem. Pharm. Bull., 1995, 43, 1035 (isol, pmr,
transferase. Gum. [lXli? + 16.7 (c, 0.1 in MeOH).
cmr)
Singh, S.B. et ai, 1.D.C., 1995, 60, 7896 (isol, ir, pmr, cmr, ms)
3