Dictionary of Natural Products THIRD SUPPLEMENT Dictionary of Natural Products THIRD SUPPLEMENT VOLUME 10 OF DICTIONARY OF NATURAL PRODUCTS [t1JI 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 This Third Supplement published 1997 © 1997 Springer Science+Business Media Dordrecht Originally published by Chapman & Hall in 1997 ISBN 978-0-412-60430-0 ISBN 978-1-4899-6850-0 (eBook) DOI 10.1007/978-1-4899-6850-0 Apart from any fair dealing for the purposes of research or private study, or criticism or review, as permitted under the UK Copyright Designs and Patents Act, 1988, this publication may not be reproduced, stored, or transmitted, in any form or by any means, without the prior permission in writing of the publishers, or in the case of reprographic reproduction only in accordance with the terms of the licences issued by the Copyright Licensing Agency in the UK, or in accordance with the terms of licences issued by the appropriate Reproduction Rights Organization outside the UK. Enquiries concerning reproduction outside the tcrms stated here should bc scnt to thc publishers at the London address printed on the page. The publisher makes no representation, express or implied, with regard to the accuracy of the information contained in this book and cannot accept any legal responsibility or liability for any errors or omissions that may be made. A catalogue record for this book is available from the British Library Library of Congress Cataloging-in-Publication Data available @ Printedon acid-free text paper, manufactured in accordance with ANSI/NISO Z 39.48-1992 (Permanence of Paper) INTERNATIONAL ADVISORY BOARD C. Djerassi Stanford University J.D. Connolly G. Ourisson Glasgow University Universite Louis Pasteur; Strasbourg D.J. Faulkner R.A. Raphael University of California, San Diego University of Garnbridge K. Mori M. Shamma Science University ofTokyo Pennsylvania State University K. N akanishi Ch. Tamm Colurnbia University, New York University of Basel SUBJECT EDITORS D.C. Ayres J.B. Barborne F.J. Leeper (Jignans) (flavonoids) (polypyrroles) Queen Mary & Westfield College, Reading University University of Garnbridge London E. Haslam R.D.H. Murray B.W. Bycroft (tannins) (coumarins) (antibiotics and peptides) Sheffield University Formerly of University of Notringharn R.A. Hili Glasgow University P.M. Collins (terpenoids and steroids) I. W. Southon (c arbohydrates) Glasgow University ( alkaloids) Birkbeck College, London D.R. Kelly Consultant F.D. Gunstone (semiochemicals) (Iipids) University of Wales, University of St Andrews College of Cardif.f EXECUTIVE EDITOR J. Buckingham PROJECT EDITOR S.H.J. Thompson ADDITIONAL PRINCIPAL CONTRIBUTOR A.D. Roberts Third Supplen1ent 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 Volume 1 of the Main Work. 2. Literature coverage In compiling this Supplement the primary Iiterature has been surveyed to the end of 1995. The printed supple 1. Using DNP Supplements ment concentrates principally on important new natural As in the Main Work volumes, every Entry is numbered products isolated during the period in question. A con to assist ready location. The DNP Number consists of a siderable number of amendments have been made during Letter of the alphabet followed by a five-digit number. the review period to entries which have not been In this Third Supplement the first digit is invariably 3. 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 and 2 refer to the First and Second 3. 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. lX Contents Third Supplement Entries page 1 Name Index 413 Molecular Formula Index 513 xi A AAL Toxin A-30001 7o:-form [157072-23-6] Constit. of Plectranthus hereroensis. Red amorph. solid. OR2 OH Mp 55-60°. [o:m -75.7 (c, 0.111 in CHC13). Batista, 0. et al, J. Nat. Prod., 1994, 57, 858 (isol, pmr) I OH OH 9(10-> 20)-Abeo-7,12-dihydroxy-11,14- A-30004 TA1 R1 = H, R2 = COCH2CH(COOH)CH2COOH dioxo-1,8,10(20),12-abietatetraen-19,6- TA2 R1 = COCH2CH(COOH)CH2COOH, R2 = H olide Prod. by Alternaria alternata f. sp. lycopersici. Host- 0 specific phytotoxin complex. Similar to Fumonisin A1, F-00532. AAL Toxin TA [79367-52-5] 1 C25H47N010 M 521.647 5-Deoxy: [149849-90-1]. AAL Toxin TB 1 C2sH47N09 M 505.648 0 From A. alternata f. sp. lycopersici. Phytotoxin. AAL Toxin TA2 [79367-51-4] Cwll2oÜ6 M 356.374 C25H47N010 M 521.647 (6o:,7o:)-form 5-Deoxy: [149849-91-2]. AAL Toxin TB2 Constit. of Salvia candicans. Orange amorph. solid. [o:]0 C2sH47N09 M 505.648 + 772 (c, 0.036 in CHC13). Related to Anastomosine, A- From A. alternata f. sp. lycopersici. Phytotoxin. 01652. Bottini, A.T. et al, Tet. Lett., 1981, 22, 2723 (isof) Cardenas, J. et al, Phytochemistry, 1995, 38, 199 (iso/, pmr, cmr) Caldas, E.D. et al, J. Agric. Food Chem., 1994, 42, 327 (struct) Boyle, C.D. et a/, J.A.C.S., 1994, 116, 4995 (struct) 11(15-> 1)-Abeo-2,20-epoxy-11-taxene- A-30005 Oikawa, H. et a/, Tet. Lett., 1994, 35, 1223 (synth) 4,5, 7 ,9,10,13,15-heptol Oikawa, H. et a/, Tetrahedron, 1994, 50, 13347 (abs conjig) 12(11-> 10)-Abeo-4-bromo-3-chloro-7,8- A-30002 epoxy-11(13)-chamigren-1-ol [1 16498-63-6] ~-: ~;:~ C2oH320s M 400.468 (2o:,4o:,5o:,7ft,9P,IO/l)-form 9-Benzoy!, 4,7,13-tri-Ac: [167425-73-2]. Taxayunnanine E C15H22BrC102 M 349.694 C33H42012 M 630.688 Constit. of a Laurencia sp. [o:]0 +67 (c, 0.5 in CHC13). Constit. of Taxus yunnanensis. Amorph. powder. [o:]~ Ac: [124019-98-3]. Pinnatifate + 3.3 (c, 0.6 in CHC13). C17H24BrC103 M 391.731 Zhang, H. et al, Phytochemistry, 1995, 39, 1147 (iso/, pmr, cmr) Constit. of L. pinnatifida. [o:)i; +61 (c, 0.6 in CHC13). Bittner, M.L. et al, Phytochemistry, 1985, 24, 987 (isol, pmr, cmr) 14(10-> 1)-Abeo-11-eudesmen-1-ol A-30006 Atta-ur-Rahman, Pure App/. Chem., 1989, 61, 453 (Pinnatifate) 17(15-> 16)-Abeo-7,12-dihydroxy-8,12,16- A-30003 H' ~H O abietatriene-11, 14-dione ii I C15H260 M 222.370 0 (lo:,4fl)-form [166322-01-6] Constit. of Ocotea corymbosa. Oil. [o:]i-;1 -10.5 (c, 0.005 in CHC13). Chavez, J.P. et al, Phytochemistry, 1995, 39, 849 (iso/, pmr, cmr) M 330.423 1 19(10---+ 9}-Abeoeupha-5,24-dien-3-ol - 11(15---+ 1}-Abeo-11-taxene-2,4,5,7,9. .. A-30007 - A-30013 19(10~9)-Abeoeupha-5,24-dien-3-ol A-30007 IP-form [156214-07-2] Constit. of Schaefferia cuneijolia. Gonzalez, A.G. et al, Rev. Latinoam. Quim., 1992, 23, 22 (isol. pmr, cmr) 11(15~ 1)-Abeo-2,5,9,10,15-pentahydroxy- A-30011 4(20),11-taxadien-13-one HO---<~;_, C H 0 M 426.724 30 50 (3 P,8«,9P,10« )-form o~ yj),~J. Boetical Constit. of Euphorbia boetica. Oil. [a]~0 + 30 (c. 0.07 in : H 1; OH CHCI3). HO OH I Ferreira, M.J.U. et al, J. Nat. Prod., 1995, 58, 575 (isol, pmr, cmr) C H 0 M 366.453 20 30 6 (2!7.,5!7.,9oc,10f/)-form 14(10~ 1)-Abeo-10-hydroxy-11-eudesmen- A-30008 2,9-Di-Ac: Taxacustone 3-one CzH 0 M 450.528 4 34 8 Constit. of Taxus cuspidata. Plates (MeOH). Mp 268- 0~ 10-2B71en°.z o[oy:l],i ;' 5--01-4ß.-6D -(gcl,u 0c.o0p7y9r ainn oCsyHl,C 21,39)-. di-Ac: 10-Benzoyl- 5-glucopyranosyltaxacustone C H 0 M 716.778 37 48 14 Constit. ofT. cuspidata. Needles (MeOH). Mp 178-180°. [o:]i;' -92.6 (c, 0.074 in MeOH). C H 0 M 236.353 15 24 2 Tang. X.-J. et al. J. Nat. Prod., 1995, 58, 233 (iso/, pmr, cmr) (1«,4P,10f/)-form [166322-02-7] Constit. of Ocotea corymbosa. Oil. [a]~' + 64.8 (c, 0.003 in CHCIJ 14( 10 ~ 1) -Abeo-1, 10 -seco-11-eudesmene- A-30012 1,10-dione Chavez, J.P. et al, Phytochemistry, 1995, 39, 849 (isol, pmr, cmr) [1 66322-03-8] 25(9~8)-Abeo-3-oxo-4(23)-friedelen-24-al A-30009 [156214-08-3] CISH2402 M 236.353 Constit. of Ocotea corymbosa. Oil. [o:n; -1.48 (c, 0.005 in CHC1,). Chavez, J.P. et al. Phvtochemistry. 1995. 39, 849 (isol, pmr, cmr) 0 11(15~ l)-Abeo-11-taxene- A-30013 C30H,11;02 M 438.692 2,4,5, 7,9, 10, 13, 15,20-nonol Constit. of Schaefferia cuneifolia. Gonzalez, A.G. et a/, Rer•. Latinoam. Quim., 1992, 23, 22 (isol, H~ pH OH pmr, cmr) \_=(o-\r~ -~ 25(9 ~s)-Abeo-3-oxo-4(23)-friedelen-24,1- A-30010 HO· ~I/ 1'' -y/0{ --<i olide -~; H'f\ OH HO OHHo CHzOH C20H3409 M 418.483 (2!7.,4!7.,5oc,7p,9!7.,1 op,l3!7.)-form !0-Benzoy!, 5,7,9,20-tetra-Ac: [160lJ28-37-0]. Yunantaxusin A C35H46Ü14 M 690.740 Constit. of Taxus yunnanensis. Needles (Me,CO). Mp 239-240°. [o:Jn -52 (c, 0.11 in MeOH). 0 Zhang. S et al. J. Nat. Prod .. 1994. 57. 1581 (isol. pmr. cmr) M 452.676 2 19(4 --+ 3)-Abeo-11,12,14-trihydroxy-... - 4-Acetyl-2(3H)-benzoxazolone A-30014 - A-30022 19(4 ---+ 3)-Abeo-11,12,14-trihydroxy- A-30014 ACEinhibitorpeptide C 107 A-30018 4(18),8,11,13-abietatetraen-7-one c 107 [143936-45-2] H-Ala-Leu-Pro-His-Aia-OH C23H37Np6 M 507.589 Isol. from the intestine of the bonito fish. Angiotensin I converting enzyme inhibitor. Matsumura, N. et al, Biosci., Biotechno/., Biochem., !993, 57, 1743 (iso/, struct) C20H2604 M 330.423 ACEinhibitorpeptide C 111 A-30019 12-Me ether: [160896-57-1]. Agastanol C111 C21H2804 M 344.450 [146935-77-5] Constit. of Agaslache rugosa. Pale yellow cryst. Mp 180- 1820. H-Giy-Val-Tyr-Pro-His-Lys-OH 15,16-Didehydro, 12-Me ether: [142182-52-3]. 19(4->3) Abeo-11,14-dihydroxy-12-methoxy-4(18),8,11,13,15- C33H49N908 M 699.806 abietapentaen-7 -one. Dehydroagastanol Isol. from the liver of the bonito fish. Angiotensin I Cz1Hz604 M 342.434 converting enzyme inhibitor. Constit. of A. rugusa. Pale yellow cryst. Mp 158-159°. Matsumura, N. et al, Biosci., Biotechnol., Biochem., 1993, 57, 1743 (iso/, struct) Lee, H.-K. et a/, Saengyak Hakhoechi, 1994, 25, 319; CA, 122, 128601b (isol, pmr, cmr) ACE inhibitor peptide C 112 A-30020 c 9(10---+ 20)-Abeo-11,12,14-trihydroxy-7- A-30015 112 oxo-8, 11 ,13-abietatrien-19, 10 -olide [148162-36-1] H-Ile-Arg-Pro-Vai-Gin-OH C27H49N907 M 611.740 Isol. from the intestine of the bonito fish. Angiotensin I converting enzyme inhibitor. Matsumura, N. et al, Biosci., Biotechnol., Biochem., 1993, 57, 1743 /j (isol, struct) 0 C20H2406 M 360.406 4-Acetoxy-4-methoxy-2-(3,6,9- A-30021 lOft-form tetradecatrienyl)-2-cyclopenten-1-one Constit. of Salvia candicans. Related to lcetexone, I- [156992-93-7] 00023 and Romulogarzone, R-00339. Cardenas, J. et al, Phytochemistry, !995, 38, 199 (isol. pmr, cmr) 0 Musca Accessory gland peptide I A-30016 [ 150302-48-0] MeO OAc H-Leu-Leu-Asn-Aia-Leu-Pro-Leu-Asp-Aia-Leu-Ser-Ser Leu-Thr-Giy-NH2 Cz2H3zÜ4 M 360.492 Constit. of the sea pen Virgularia sp. Unstable oil. [o:Jn C67H117N17021 M 1496.763 + 12.05 (c, 0.9 in CHCI3). Incorrect MF and name in Constit. of the accessory sex gland of the female housefiy CA. Musca domestica. Anjaneyulu, A.S.R. et a/, Indian J. Chem., Sect. B, 1994, 33, 55 Wagner, R.M. et al, Biochem. Biophys. Res. Commun., 1993, 194, (isol, ir, pmr, cmr) 1336 (iso/, struct) 4-Acetyl-2(3H}-benzoxazolone, 9CI A-30022 ACEinhibitorpeptide C 105 A-30017 4-Acetylbenzoxazolin-2-one c 105 [70735-79-4] [144357-25-5] H -Ser-Val-Aia-Lys-Leu-Giu-Lys-OH C34H63N9011 M 773.925 Isol. from the intestine of the bonito fish. Angiotensin I converting enzyme inhibitor. C9H7N03 M 177.159 Matsumura, N. et a/, Biosci., Biotechnol., Biochem., 1993, 57, 1743 Found in kernels of Zea mays (Gramineae). Needles (isol, struct) (Me CO aq.). Mp 217-218°. 2 Fielder, D.A. et al, Tet. Lett, 1994, 35, 521 (iso/. uv, ir, pmr, cmr, ms, cryst struct) Fielder, D.A. et al, J. Nat. Prod., 1995, 58, 456 (synth) 3