Studies on the constituents of the crude drug 'Fritillariae Bulbus'. III. On the diterpenoid constituents of fresh bulbs of Fritillaria thunbergii Miq

In addition to trans-communol and trans-communic acid (obtained in the form of the methyl ester), seven new diterpenoids were isolated as non basic constituents from fresh bulbs of Fritillaria thunbergii MIQ. (Liliaceae). Their structures were determined to be isopimaran-19-ol (3), isopimaran-19-oic...

Full description

Saved in:
Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 30; no. 11; pp. 3912 - 3921
Main Authors Kitajima, J, Komori, T, Kawasaki, T
Format Journal Article
LanguageEnglish
Published The Pharmaceutical Society of Japan 1982
Subjects
C-NMR
plant biochemistry
plant physiology
Online AccessGet full text

Cover

Abstract In addition to trans-communol and trans-communic acid (obtained in the form of the methyl ester), seven new diterpenoids were isolated as non basic constituents from fresh bulbs of Fritillaria thunbergii MIQ. (Liliaceae). Their structures were determined to be isopimaran-19-ol (3), isopimaran-19-oic acid [obtained in the form of the methyl ester (4)], ent-kauran-16β, 17-diol (5), ent-kauran-16α, 17-diol (6), ent-16β, 17-epoxy-kaurane (7), ent-16α-methoxy-kauran-17-ol (8), and ent-kaur-15-en-17-ol (9).
AbstractList In addition to trans-communol and trans-communic acid (obtained in the form of the methyl ester), seven new diterpenoids were isolated as non basic constituents from fresh bulbs of Fritillaria thunbergii MIQ. (Liliaceae). Their structures were determined to be isopimaran-19-ol (3), isopimaran-19-oic acid [obtained in the form of the methyl ester (4)], ent-kauran-16β, 17-diol (5), ent-kauran-16α, 17-diol (6), ent-16β, 17-epoxy-kaurane (7), ent-16α-methoxy-kauran-17-ol (8), and ent-kaur-15-en-17-ol (9).
Author Kawasaki, T
Komori, T
Kitajima, J
Author_xml – sequence: 1
  fullname: Kitajima, J
– sequence: 2
  fullname: Komori, T
– sequence: 3
  fullname: Kawasaki, T
BookMark eNplkbtOwzAUhi1UJFpg4gHw1gEl-JLrCBWFSiAGYLYc-7g1CkmxnYEX4XlxCTeJxZaPvv-Tzu8ZmnR9BwidUJJSllXnatuknKS8pmwPTSnPyiRnjE_QlBBSJ4wX_ADNvH8mhOWk5FP0_hAGbcHjvsNhA1j1nQ82DNCFODPjzA0asHbDGs-XzgbbttJZCfhyaJvBz1O8Wq1SfD8atA3gttD1Vv-zGQd-g5sY-3z-kcXo0DXg1tbiO_t6hPaNbD0cf92H6Gl59bi4SW7vr1eLi9tEZUXBklozo5gyNO6TmZJwSbSRvGqaotSVVKpoyrKCvICi5FKy3BDNZK0zYI2idcYP0dnoVa733oERW2dfpHsTlIhdpSJWKjgRu0ojvRzpZx_kGn5Y6YJVLexYWufVjqf0-4zBX2AjnYAuik5HkZG9kGtnvXh6YITy-C01JbzkH_sVj8U
CitedBy_id crossref_primary_10_1016_0031_9422_89_80357_7
crossref_primary_10_3987_COM_18_13891
crossref_primary_10_3390_ijms20071667
crossref_primary_10_1016_0031_9422_94_00982_Y
crossref_primary_10_1080_02773819809349590
crossref_primary_10_1016_S0031_9422_00_97823_3
crossref_primary_10_1016_j_bmc_2003_10_031
crossref_primary_10_1016_j_phytochem_2022_113366
crossref_primary_10_1016_j_fitote_2009_08_014
crossref_primary_10_1007_s10600_016_1571_1
crossref_primary_10_1080_14786419_2018_1477149
crossref_primary_10_1080_10286020500381464
crossref_primary_10_1007_s10600_016_1702_8
crossref_primary_10_1016_0031_9422_95_00816_0
crossref_primary_10_1039_C4NP00063C
crossref_primary_10_3390_molecules17021448
crossref_primary_10_1016_0031_9422_93_85045_S
crossref_primary_10_1016_j_phytochem_2009_06_008
crossref_primary_10_1080_10286020_2020_1737859
crossref_primary_10_1080_14786410310001643885
crossref_primary_10_1002_asia_200900357
crossref_primary_10_1016_0031_9422_88_84109_8
crossref_primary_10_1016_j_phytochem_2007_07_023
crossref_primary_10_1177_1934578X1000500104
crossref_primary_10_1071_DN06014
crossref_primary_10_1016_j_bse_2004_02_009
crossref_primary_10_1016_S0031_9422_00_97822_1
crossref_primary_10_1186_s42269_021_00577_z
crossref_primary_10_1016_S0031_9422_03_00335_2
crossref_primary_10_1016_j_fitote_2019_01_010
crossref_primary_10_1016_0031_9422_90_85139_7
crossref_primary_10_5012_bkcs_2013_34_5_1589
crossref_primary_10_1002_hlca_200390043
crossref_primary_10_1016_j_bse_2012_07_002
crossref_primary_10_3389_fphar_2021_710487
ContentType Journal Article
Copyright The Pharmaceutical Society of Japan
Copyright_xml – notice: The Pharmaceutical Society of Japan
DBID FBQ
AAYXX
CITATION
DOI 10.1248/cpb.30.3912
DatabaseName AGRIS
CrossRef
DatabaseTitle CrossRef
DatabaseTitleList
Database_xml – sequence: 1
  dbid: FBQ
  name: AGRIS
  url: http://www.fao.org/agris/Centre.asp?Menu_1ID=DB&Menu_2ID=DB1&Language=EN&Content=http://www.fao.org/agris/search?Language=EN
  sourceTypes: Publisher
DeliveryMethod fulltext_linktorsrc
Discipline Pharmacy, Therapeutics, & Pharmacology
EISSN 1347-5223
EndPage 3921
ExternalDocumentID 10_1248_cpb_30_3912
article_cpb1958_30_11_30_11_3912_article_char_en
US201302591037
GroupedDBID ---
.55
.GJ
29B
2WC
3O-
53G
5GY
6J9
ABIWU
ABTAH
ACGFO
ACIWK
ACPRK
ADBBV
AENEX
AEQTP
AFRAH
AI.
ALMA_UNASSIGNED_HOLDINGS
BAWUL
BKOMP
CS3
DIK
DU5
E3Z
EBS
EJD
F5P
FBQ
GX1
HH5
JMI
JSF
JSH
KQ8
L7B
MOJWN
OK1
P2P
RJT
RZJ
TKC
TR2
VH1
X7J
X7M
XSB
ZE2
ZGI
ZY4
AAUGY
AAYXX
CITATION
ID FETCH-LOGICAL-c4662-9d2fc2cf10024f703a0dfa38bb67d8acc6b778e56e673aa25f0d2a9d4e2bc1943
ISSN 0009-2363
IngestDate Fri Aug 23 02:36:51 EDT 2024
Thu Aug 17 20:28:01 EDT 2023
Wed Dec 27 19:17:19 EST 2023
IsDoiOpenAccess true
IsOpenAccess true
IsPeerReviewed true
IsScholarly true
Issue 11
Language English
LinkModel OpenURL
MergedId FETCHMERGED-LOGICAL-c4662-9d2fc2cf10024f703a0dfa38bb67d8acc6b778e56e673aa25f0d2a9d4e2bc1943
OpenAccessLink https://www.jstage.jst.go.jp/article/cpb1958/30/11/30_11_3912/_article/-char/en
PageCount 10
ParticipantIDs crossref_primary_10_1248_cpb_30_3912
jstage_primary_article_cpb1958_30_11_30_11_3912_article_char_en
fao_agris_US201302591037
PublicationCentury 1900
PublicationDate 1982-00-00
PublicationDateYYYYMMDD 1982-01-01
PublicationDate_xml – year: 1982
  text: 1982-00-00
PublicationDecade 1980
PublicationTitle Chemical & pharmaceutical bulletin
PublicationTitleAlternate Chem. Pharm. Bull.
PublicationYear 1982
Publisher The Pharmaceutical Society of Japan
Publisher_xml – name: The Pharmaceutical Society of Japan
References 1) J. Kitajima, T. Komori, T. Kawasaki, and H.-R. Schulten, Phytochemistry, 21, 187 (1982) (Basic Steroid Saponins from Aerial Parts of Fritillaria thunbergii) is designated as Part II of this series. A part of the present work was presented at the 26th Annual Meeting of the Japanese Society of Pharmacognosy, Tokyo, November 1979, Abstr., p. 17.
19) J. March, "Advanced Organic Chemistry Reactions, Mechanisms and Structure," McGraw-Hill, Inc., New York, 1968, p. 302.
b) S. Ito, Chem. Pharm. Bull., 11, 1377 (1963
15) a) L.H. Briggs, B.F. Chain, R.C. Cambie, B.R. Davies, P.S. Rutledge, and J.K. Wilmshurt, J. Chem. Soc., 1963, 1345
20) a) L.H. Briggs, B.F. Chain, R.C. Cambie, B.R. Davies, and P.S. Rutledge, J. Chem. Soc., 1962, 1850
b) E. Wenkert and B.L. Buckwalter, J. Am. Chem. Soc., 94, 4367 (1972).
16) J.R. Hanson, M. Siverns, F. Piozzi, and G. Savona, J. Chem. Soc., Perkin Trans. 1, 1975, 114.
6) J. Kitajima, N. Noda, Y. Ida, K. Miyahara, and T. Kawasaki, Heterocycles, 15, 791 (1981) (Steroid Alkaloids of Fresh Bulbs of Fritillaria thunbergii MIQ. and of Crude Drug "Baimo" prepared therefrom) is designated as Part I of this series.
b) N. Masonjoye J.R., E.M. Roberts, R.V. Lawrence, L.J. Gough, M.O. Soffer, and O. Korman, J. Org. Chem., 30, 429 (1965).
4) a) S. Ito, M. Kato, K. Shibata, and T. Nozoe, Chem. Pharm. Bull., 9, 235 (1961
10) R.K. Grant, C. Huntrakul, and J.M. Robertson, Aust. J. Chem., 22, 1265 (1969).
5) K. Kaneko, M. Tanaka, K. Haruki, and H. Mitsuhashi, Chem. Phaym. Bull., 28, 1345 (1980).
b) M. Fukuda, Sci. Report Tohoku Univ., Ser. A, 18, 323 (1929
c) M. Fukuda, Nippon Kagaku Zasshi, 69, 165 (1948).
2) a) M. Fukuda, Nippon Kagaku Zasshi, 50, 74 (1929
12) H. Budzikiewicz, C. Djerassi, and D.H. Williams, "Structure Elucidation of Natural Products by Mass Spectrometry," Vol. II, Holden-Day, Inc., San Francisco, London, Amsterdam, 1964, p. 155.
11) a) E. Wenkert, A. Afonso, P. Beak, R.W.J. Carney, P.W. Jeffes, and J.D. McChemsney, J. Org. Chem., 30, 713 (1965
17) a) S. Mihashi, Y. Yanagisawa, O. Tanaka, and S. Shibata, Tetrahedron Lett., 1963, 1683
b) M.F. Barnes and J. Macmillan, J. Chem. Soc., 1967, 361.
c) S. Shibata, S. Mihashi, and O. Tanaka, Tetrahedron Lett., 1967, 5241.
13) a) E. Breitmaier and W. Voelter, "13C-NMR Spectroscopy," Verlag Chemie GmbH, weinheim/Bergstr., 1974, p. 201
21) T. Kawasaki, T. Komori, and S. Setoguchi, Chem. Pharm. Bull., 16, 2430 (1968).
b) K. Yamasaki, H. Kohda, T. Kobayashi, R. Kasai, and O. Tanaka, Tetrahedron Lett., 1976, 1005.
3) H. Morimoto and S. Kimata, Chem. Pharm. Bull., 8, 302, 871 (1960).
c) S. Ito, Y. Fukuzawa, T. Okuda, and Y. Iitaka, Tetrahedron Lett., 1968, 5373.
9) R.K. Grant, C. Huntrakul, and D.R.J. Sheppard, Aust. J. Chem., 20, 969 (1967).
7) a) B.R. Thomas, Acta. Chem. Scand., 20, 1074 (1966
b) G. Gawdner, J. Polonsky, and E. Wenkert, Bull. Soc. Chim. Fr., 1964, 407
14) V.N. Aiyar and T.R. Seshadri, Tetrahedron, 26, 5275 (1970).
b) D.A.H. Taylor, J. Chem. Soc., (C), 1967, 1360.
18) R. Kuhn, I. Löw, and H. Trischmann, Chem. Ber., 88, 1492, 1690 (1955).
8) H. Erdtman and L. Westfelt, Acta. Chem. Scand., 17, 1826 (1963).
References_xml
SSID ssj0025073
Score 1.3742913
Snippet In addition to trans-communol and trans-communic acid (obtained in the form of the methyl ester), seven new diterpenoids were isolated as non basic...
SourceID crossref
jstage
fao
SourceType Aggregation Database
Publisher
StartPage 3912
SubjectTerms C-NMR
plant biochemistry
plant physiology
Title Studies on the constituents of the crude drug 'Fritillariae Bulbus'. III. On the diterpenoid constituents of fresh bulbs of Fritillaria thunbergii Miq
URI https://www.jstage.jst.go.jp/article/cpb1958/30/11/30_11_3912/_article/-char/en
Volume 30
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
ispartofPNX Chemical and Pharmaceutical Bulletin, 1982/11/25, Vol.30(11), pp.3912-3921
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1Lc9owENaQ9NJLp88J6WM0mUwuxBRk48ep40nCYDLUSYFpevJIstTQg2EIPqQ_pD-yv6IrWfhRemjaiwcLa2Xzfax25d0VQse-60oRuNLyAhccFEKYxVI5sATrMb_P-8TTeyxNPrqjuTO-Gdy0Wj9rUUv5hnX59z_mlfwLqtAGuKos2QcgWwqFBvgM-MIREIbjX2FsggDNgr_efFO9-RcmtEW3rfNUdM7XuVoQIENVwgiAh3sTqvI2y-9AO5BOFEXdTlxIOVdJySuRLRfpjsQhOOe3uqM5LcVB11zHii0WnUl0Xbd5GzUJrm4ba-iN6t9K70ezcBxNQk0u8E3PRuWq7mU8iT9Fml8Xs-n8SzVXhJ_DaXhZfBVPR1FcLWX0A79yedVf4rfxt0Gr8DBjMBuyhhIPLGIbvSgKvW07HvjUReryVrGbFz6GwP2amrYDE7stzGmRpb0znRBHpUjwFevavW7VqVGf26CfwFWqcE9iK69qe4QuSXkBPCCwdg89IqoooQoguC7feIEl6pW7_qmHM7mkcAfva-M3rKc9SZdgOH0DN2IbgqitotlT9MS4MzgsBn-GWiJ7jk7Mj3x_imdVet_dKT7BV1Wl9PsX6IchMF5mGKiH63TDS1m0KQJjRWB8VKcvNvQ9woq8OC4k1Mi7I02TV3czp6UwXJEXA3lfovnwYnY2ssxGIRZ3XJdYQUokJ1yqcsKOhDmM9lJJbZ8x10t9yrnLPM8XA1e4nk0pGcheSmiQOoIw3g8c-xXaz5aZOEBYMtkXYNI61AYbIqDgHqXUsTnlPe7DaG10vAUgWRX1YBLlRwNOigEKd4VTGx0AOAn9CjN1Mp8SHR8wCFRSbht9KBAr-z-UQYf_LeE1eqz-f8VS4hu0v1nn4i0Y1xv2TrPyFz0E0r8
link.rule.ids 315,783,787,4033,27937,27938,27939
linkProvider Colorado Alliance of Research Libraries
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Studies+on+the+Constituents+of+the+Crude+Drug+%22Fritillariae+Bulbus.%22+III.+On+the+Diterpenoid+Constituents+of+Fresh+Bulbs+of+Fritillaria+thunbergii+MIQ&rft.jtitle=Chemical+and+Pharmaceutical+Bulletin&rft.au=KITAJIMA%2C+JUNICHI&rft.au=KOMORI%2C+TETSUYA&rft.au=KAWASAKI%2C+TOSHIO&rft.date=1982&rft.pub=The+Pharmaceutical+Society+of+Japan&rft.issn=0009-2363&rft.eissn=1347-5223&rft.volume=30&rft.issue=11&rft.spage=3912&rft.epage=3921&rft_id=info:doi/10.1248%2Fcpb.30.3912&rft.externalDocID=article_cpb1958_30_11_30_11_3912_article_char_en
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0009-2363&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0009-2363&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0009-2363&client=summon